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Volume 29, Issue 10
Displaying 1-50 of 53 articles from this issue
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YUKIHIDE URATA, YUKIO MITSUI, KAZUO NAKAMURA1981 Volume 29 Issue 10 Pages 2737-2742
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA theoretical basis and a program, LSFIT, for attaining optimum spatial fit between the two identical, similar or possibly related (molecular) structures (each described by an arbitrarily chosen coordinate system) are described. It is shown that the six relevant rotational and translational parameters relating the two coordinate systems can be derived by a standard iterative least-squares procedure for non-linear problems. Crystallographic applications and an application to the study of protein structural homology are described.View full abstractDownload PDF (666K) -
TSUNEJI UMEDA, EIZO HIRAI1981 Volume 29 Issue 10 Pages 2743-2752
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dissociation constants (Ka) of the conjugate acids of the p-dimethylaminobenzylidene derivatives (I) of various active methylene compounds (XYCH2) were determined. Alkaline hydrolysis of I was studied kinetically in 30% (v/v) ethanol at 25°C. The rates of nucleophilic attack of a hydroxide ion on the carbon-carbon double bonds of I were linearly correlated with the corresponding pKa values. Thus the pKa values are suggested to be useful parameters to evaluate the relative activating ability of the X and Y groups to support the attack of nucleophiles on compounds of the type XYC=CHAr. In the hydrolysis of structurally similar compounds α-(substituted benzoyl)-p-dimethyl-aminocinnamonitriles, the rates of carbon-carbon bond fission of an uncharged addition intermediate and those of carbon-carbon double bond formation from a carbanion intermediate were also correlated with the dissociation constants (KAMa) of the corresponding substituted benzoylacetonitriles. The pH-rate profile and the relationship between rates and Ka (or KAMa) suggested that the carbon-carbon bond fission of the uncharged intermediate is the rate-determining step in the alkaline hydrolysis of I.View full abstractDownload PDF (1016K) -
TSUNEJI UMEDA, EIZO HIRAI1981 Volume 29 Issue 10 Pages 2753-2761
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrolysis of m- or p-substituted α-benzoylcinnamonitriles (I) was studied kinetically in 30% (v/v) ethanol (pH 2-13) at 25°C. The pH-rate profile showed a maximum at nearly neutral pH and an inflection point at weakly acidic pH. The pH-rate profile and substituent effect suggested that the rate-determining step is the carbon-carbon bond fission of an addition intermediate in the strongly acidic range, and is the nucleophilic attack of water on the carbon-carbon double bond of I in the weakly acidic range. It was also suggested that the hydrolysis of I, except for the compounds with strongly electron-withdrawing substituents, CN and NO2, involves appreciable carbon-carbon bond fission of the addition intermediate at the transition state of breakdown of the intermediate on the basis of the large negative ρ values observed in the alkaline range. Deviation in the cases of the above substituents from the Hammett plots and the enthalpy-entropy relationships appears to show that in these compounds the processes of carbon-carbon bond fission are concerted with deprotonation of the alcoholic hydroxy group of the intermediate.View full abstractDownload PDF (927K) -
SHUNSAKU OHTA, ATSUHIKO TSUJIMURA, MASAO OKAMOTO1981 Volume 29 Issue 10 Pages 2762-2768
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Ketocarboxylic acids including β-ketoglutaric acid half-esters were cyclized by treating them with 1, 1'-carbonyl-diimidazole to give 6-substituted 3-acyl-4-hydroxy-2-pyrones in good yields. 5-Aryl-3, 5-dioxo-1-pentanoic acid and monomethyl malonate gave 6-aryl-4-hydroxy-2-pyrone and dimethyl β-ketoglutarate, respectively, on similar treatment. Anibin, one of the Aniba alkaloids, was synthesized from 5-(3-pyridyl)-4-hydroxy-2-pyrone. In addition, it was confirmed that reaction of magnesium β-ketocarboxylate with acylimidazolide gave the corresponding acyclic β-diketone in excellent yield.View full abstractDownload PDF (876K) -
MINEO SANEYOSHI, HARUMI NISHIZAKA, NOBUYUKI KATOH1981 Volume 29 Issue 10 Pages 2769-2775
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 1, 2 : 5, 6-di-O-isopropylidene-3-amino-3-deoxy-α-D-allofuranose (1) with trifluoroacetic anhydride afforded crystalline 3-trifluoroacetamido derivative (2) in good yield. Selective removal of the 5, 6-O-isopropylidene group of 2 by treatment with 70% acetic acid followed by oxidation with periodate and subsequent reduction with sodium borohydride gave crystalline 1, 2-O-isopropylidene-3-deoxy-3-trifluoroacetamido-α-D-ribofuranose (3) in good yield. p-Nitrobenzoylation of 3 followed by acetolysis afforded crystalline 1, 2-di-O-acetyl-3-deoxy-3-trifluoroacetamido-5-O-p-nitrobenzoyl-β-D-ribofuranose (5). Coupling of the resulting 1-O-acetyl sugar with bis-trimethylsilylated derivatives of N4-acyl-5-fluorocytosines, N4-acylcytosines, 5-fluorouracil and N4-acetyl-5-methylcytosine using SnCl4 afforded the corresponding fully acylated nucleosides (7). Saponification of 7 gave 3-amino-3-deoxy-β-D-ribonucleosides (8a-8d). Alternatively, 2, 4-dimethoxy-5-methylpyrimidine was also coupled with 5 followed by treatment with ammonia to give 8d. The nucleosides (8a-8d) thus obtained were examined for cytostatic effect on mouse leukemic L5178Y cells. The compounds tested were active against this system and their ED50 values were 0.7 μg/ml, 7 μg/ml, 16 μg/ml and 60 μg/ml, respectively.View full abstractDownload PDF (935K) -
KYOKO KOIZUMI, TOSHIKO UTAMURA1981 Volume 29 Issue 10 Pages 2776-2784
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe selective acetylation of 6, 6'-di-O-tritylcellobiose (1) and its methyl β-glycoside (5) with 5 molar equivalents of acetyl chloride in pyridine-toluene at 1-4°C has been studied. Acetylation of 1 gave a complex mixture from which α- and β-anomers of three main products, the 1, 2, 2', 3', 4'-pentaacetate (A), the 1, 2, 2', 3'-tetraacetate (B), and the 1, 2, 3', 4'-tetraacetate (C) were isolated by column chromatography. From 5, the 2, 2', 3', 4'-tetraacetate (D, 22.9%), the 2, 2', 3'-triacetate (E, 15.7%), the 2, 3', 4'-triacetate (F, 15.7%), the 2, 3'-diacetate (G, 10.8%), the 2', 3', 4'-triacetate (H, 14.2%), the 2', 3'-diacetate (I, 10.8%), the 3, 3', 4'-triacetate (J, 3.4%), and the 3, 3'-diacetate (K, 5.6%) were obtained. The locations of the unacetylated hydroxyl groups in the partially acetylated compounds were determined by gas chromatography-mass spectrometry after the sequence of methylation (for labeling free hydroxyl groups) with methyl trifluoromethanesulfonate, detritylation, deacetylation, (reduction), methanolysis, and trimethylsilylation and by comparison of acetoxyl signals in 1H-NMR spectra after trideuterioacetylation of free hydroxyl groups in the partially acetylated compounds. From the yields of partially acetylated methyl 6, 6'-di-O-trityl-β-cellobiosides, it was deduced that the order of reactivity of the five secondary hydroxyl groups in 5 is HO-3'>HO-2>HO-2'>HO-4'»HO-3.View full abstractDownload PDF (1001K) -
KYOKO KOIZUMI, TOSHIKO UTAMURA1981 Volume 29 Issue 10 Pages 2785-2790
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe selective acetylation of 6'-O-tritylcellobiose (1), 6-O-tritylcellobiose (3), and their methyl β-glycosides (2 and 4) with 6 molar equivalents of acetyl chloride in pyridinetoluene at 1-4°C has been studied. Acetylation of 1 gave the 1, 2, 6, 2', 3', 4'-hexaacetate (1A) and 1, 2, 6, 2', 3'-pentaacetate (1B), and that of 3 gave the peracetate, 1, 2, 2', 3', 4', 6'-hexaacetate (3A), and 1, 2, 3, 3', 4', 6'-hexaacetate (3B). On the basis of the yields of partially acetylated products from 2, i.e., 2, 6, 2', 3', 4'-pentaacetate (2A, 15.5%), 2, 6, 2', 3'-tetraacetate (2B, 16.2%), 2, 6, 3', 4'-tetraacetate (2C, 10.8%), 6, 2', 3', 4'-tetraacetate (2D, ca. 10.6%), 6, 2', 3'-triacetate (2E, 7.9%), 2, 6, 3'-triacetate (2F, ca. 10.5%), and 3, 6, 2', 3'-tetraacetate (2F', ca. 6.9%), it was deduced that the order of reactivities of the secondary hydroxyl groups in 2 is 3'>2'≃2>4'»3. The partially acetylated products from 4 were separated by column chromatography and semipreparative HPLC to afford the peracetate (17.7%), 2, 2', 3', 4', 6'-pentaacetate (4A, 11.1%), 2, 3, 3', 4', 6'-pentaacetate (4B, 26.0%), and 2, 3, 2', 3', 6'-pentaacetate (4C, 6.5%). It seems likely that the order of reactivities of the secondary hydroxyl groups in 4 toward acetyl chloride is 2, 3'>4'>3>2'. These results suggested that TrO-6' interacts sterically with HO-3 and HO-4', while TrO-6 affects only HO-2'.View full abstractDownload PDF (773K) -
KYOKO KOIZUMI, TOSHIKO UTAMURA1981 Volume 29 Issue 10 Pages 2791-2798
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 1H-NMR spectra of 6, 6'-di-O-trityl-, 6-O-trityl-, and 6'-O-tritylcellobiose peracetates (I-1, II-1, and III-1) showed some of the acetoxyl group resonances at abnormally high fields in CDCl3 and all their acetoxyl group signals were resolved in the region of δ 1.56-2.16. Each individual acetoxyl group signal in the spectra was unambiguously assigned. For this purpose, analogs having trideuterioacetoxyl groups at specific positions were synthesized. The 2'-acetoxyl group exposed to the benzene nuclei of the triphenylmethoxyl group (TrO) at C-6 resonates at the highest field. The large upfield shifts of the 4'- and 3-acetoxyl group signals of the derivatives having TrO at C-6' suggest that there are strong interactions between those acetoxyl groups and TrO. In the spectra of the derivatives which have TrO at C-6, a downfield shift of the 1-acetoxyl group signal was observed.View full abstractDownload PDF (955K) -
EIKO OHTSUKA, KAZUO FUJIYAMA, TOSHIKI TANAKA, MORIO IKEHARA1981 Volume 29 Issue 10 Pages 2799-2806
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA heptadecanucleotide corresponding to the 3'-end (bases 61-77) of the tRNAMetf of E.coli was synthesized by the phosphotriester method involving condensation of protected oligonucleotides with chain lengths of 3 to 6. 2'-O-(o-Nitrobenzyl) derivatives of N-acyl-5'-O-monomethoxytrityl nucleosides were used as the starting materials. To protect the 3'-end of the heptadecanucleotide with phosphorodianilidate during the synthesis, protected AACCAp having 3'-phosphorodianilidate was used as the starting nucleotide block. Condensation of protected CCCCGCp or successive condensations of protected CCCp and CGCp gave the protected undecamer in satisfactory yields. The final condensation of the undecamer to protected UCCGGCp yielded the protected heptadecamer, and the product was deprotected to give the 3'-phosphorylated heptadecanucleotide UCCGGCCCCCGAACCAp. A hexadecanucleotide corresponding to the 3'-end of the same tRNAMetf was also synthesized by the phosphotriester method by condensation of the undecamer with protected CCGGCp. The hexadecamer was deblocked and purified by chromatography on ion-exchange and reverse phase supports. This deprotected hexadecanucleotide CCGGCCCCCGCAACCAp (corresponding to bases 62-77) can be joined to the previously synthesized heptamer corresponding to the eukaryotic loop VI sequences to construct a hybrid tRNA.View full abstractDownload PDF (883K) -
TENJI KONISHI, JUNZO SHOJI1981 Volume 29 Issue 10 Pages 2807-2815
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBesides p-coumaric acid, methyl p-coumarate, β-sitosterol, oleanolic acid and 3-epioleanolic acid, three new phenylpropanoid glycosides, rossicasides B, C and D were isolated from fresh plants of Boschniakia rossica (CHAM. et SCHLTDL.) FEDTSCH. et FLEROV (Orobanchaceae). The structures of rossicasides B, C and D were established as p-hydroxycinnamyl alcohol 1-O-β-D-glucopyranosyl (1→4)-α-L-rhamnopyranosyl (1→3)-β-D-(4-O-caffeyl)-glucopyranoside (1), p-hydroxycinnamyl alcohol 1-O-β-D-glucopyranosyl (1→2)-β-D-(6-O-p-coumaryl)-glucopyranoside (2), and p-hydroxycinnamyl alcohol 1-O-β-D-glucopyranosyl (1→2)-β-D-(4-O-p-coumaryl)-glucopyranoside (3), respectively.View full abstractDownload PDF (1167K) -
KOICHIRO YAMADA, MIKIO TAKEDA, NOBUO ITOH, KATSUO IKEZAWA, AKIO KIYOMO ...1981 Volume 29 Issue 10 Pages 2816-2824
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree methyl derivatives (S-2, S-3, and S-4) of trimetoquinol (TMQ), in which one or both of the ring positions ortho to a phenolic group are substituted by a methyl group, were synthesized and evaluated for bronchodilating activity. They were prepared by NaBH3CN reduction of the Mannich bases (S-6, S-8, and S-23) via the quaternary salts in a one-pot procedure followed by catalytic reduction on 10% Pd-C. A comparison of the 5-methyl derivative (S-2) with TMQ revealed that the duration of bronchodilating effect of S-2 is considerably longer than that of TMQ on intraduodenal administration.View full abstractDownload PDF (1091K) -
MASAHIKO FUJINO, MITSUHIRO WAKIMASU, CHIEKO KITADA1981 Volume 29 Issue 10 Pages 2825-2831
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious multi-substituted benzenesulfonyl protecting groups for the guanidino function of arginine, removable under mild conditions such as with trifluoroacetic acid (TFA)-thioanisole, were studied. Among them, the 4-methoxy-2, 6-dimethylbenzenesulfonyl (Mds) group, the 2, 3, 4, 5, 6-pentamethylbenzenesulfonyl (Pme) group, and the 4-methoxy-2, 3, 6-trimethylbenzenesulfonyl (Mtr) group were found to be useful. Both Mds and Pme show considerable resistance to TFA and, therefore, are suitable for procedures in which the intermediates are deprotected by TFA treatment, while Mtr is the most useful protecting group when TFA treatment is not necessary.View full abstractDownload PDF (893K) -
MASATOSHI YAMATO, YOUICHIRO KUSUNOKI1981 Volume 29 Issue 10 Pages 2832-2836
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactivity of diethyl acetonedicarboxylate (DADC)-magnesium complex (1a, b) was examined. The Michael reaction of 1a, b gave the regioselectively monoalkylated derivative (2 or 3) of DADC. Reaction of 1a with nucleophilic reagents, LiAlH4 or alkylamines, took place at the unchelated ethoxycarbonyl group and gave the single corresponding product (7 or 9) with regioselectivity.View full abstractDownload PDF (645K) -
HIROSHI YAMANAKA, SHOETSU KONNO, TAKAO SAKAMOTO, SETSUKO NIITSUMA, SAY ...1981 Volume 29 Issue 10 Pages 2837-2843
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2- and 4-chloropyrimidines with dimethyloxosulfonium methylide afforded the corresponding pyrimidinylmethylides. Pyrimidine derivatives containing a functionalized side chain such as acetonyl, phenacyl, ethoxycarbonyl, or N-phenylcarbamoyl were synthesized by acylation of the pyrimidinylmethylides followed by desulfurization of the resulting pyrimidinylacylmethylides.View full abstractDownload PDF (802K) -
JUN ZHOU, MINGZHU WU, SHIGENORI TANIYASU, HIROMICHI BESSO, OSAMU TANAK ...1981 Volume 29 Issue 10 Pages 2844-2850
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom Sanchi-Ginseng, roots of Panax notoginseng cultivated in Yunnan, China, two new dammarane-saponins named notoginsenosides-R1 (5) and -R2 (7S) were isolated by means of reverse phase high performance liquid chromatography. The structures of these saponins were established as 20 (S)-protopanaxatriol 6-[O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranoside (5) and 20 (S)-protopanaxatriol 6-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (7S), respectively, mainly by 13C NMR spectroscopy and mass spectrometry. In connection with this study, assignments of carbon signals of ginsenoside-Rf (11), a minor saponin of Ginseng roots, were substantiated by the application of selective deuteration of the sugar moiety as reported by Stuart et al. Besides these saponins, two known saponins, ginsenosides-Rh1 (12) and -Rg2 (13) which have previously been isolated from Ginseng roots, were also isolated and identified.View full abstractDownload PDF (845K) -
YOSHIO OKADA, KOICHI KAWASAKI, SHIN IGUCHI, MASAMI YAGYU, KENJI YAMAJI ...1981 Volume 29 Issue 10 Pages 2851-2855
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tetratriacontapeptide corresponding to sequence 112-145 of the β-subunit of human chorionic gonadotropin (hCG) was synthesized by assembling peptide fragments by the azide procedure, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). New Zealand white rabbits were immunized with the conjugated antigen in Freund's complete adjuvant. Antiserum capable of 30% specific binding of 125I-hCG or 125I-β-subunit of hCG at a dilution of 1 : 5000 was produced.View full abstractDownload PDF (784K) -
MASAYUKI KUZUYA, TAMOTSU USUI, FUMIO MIYAKE, SEIJI ITO, SIGENORI NOZAW ...1981 Volume 29 Issue 10 Pages 2856-2861
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSUpon heating of the leuco triarylmethane dyes (2a) and (2b) with excess phosphoryl chloride under reflux, these compounds underwent a normal chlorination followed by a de-anilination process to give (3a) and (3b), respectively. Replacement of the p-dimethylamino substituent with a p-methoxy substituent on the 4, 4-diaryl groups had a marked effect on the reaction ; only the 1-chlorinated products, (4a) and (4b), were formed even upon heating under reflux for 10 hours. On heating of (2b) in TFA, only 1-trifluoroacetoxylation occurred. Thus, the driving force of this type of de-anilination could be ascribed to a combination of greater orbital interaction between phosphoryl chloride and the HOMO of dimethylaniline, and the aromaticity of the resulting phthalazine molecule, resulting in a special type of carbon-carbon bond cleavage.View full abstractDownload PDF (687K) -
GENICHIRO NONAKA, ITSUO NISHIOKA, TETSURO NAGASAWA, HIKOKICHI OURA1981 Volume 29 Issue 10 Pages 2862-2870
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree new tannin-related compounds (I, II and III), along with lindleyin (IV), (+)-catechin, 3-O-galloyl-(-)-epicatechin, gallic acid, 3, 5, 4'-trihydroxystilbene 4'-O-β-D-(6"-O-galloyl)-glucopyranoside, 3, 5, 4'-trihydroxystilbene 4'-O-β-D-glucopyranoside and 4-(4'-hydroxyphenyl)-2-butanone 4'-O-β-D-glucopyranoside, have been isolated from commercial rhubarb (Rhei Rhizoma). On the basis of spectral and chemical evidence, I, II and III were characterized as 3, 3'-di-O-galloylprocyanidin B-2, 3-O-galloylprocyanidin B-1 and 1, 2, 6-tri-O-galloylglucose, respectively. The occurrence of IV in rhubarb is of great significance, since IV has been reported to have analgesic and anti-inflammatory activities almost equal to those of aspirin and phenylbutanone. Tannins in rhubarb have been partially purified (designated as rhatannin (V)). Thiolysis degradation and enzymatic hydrolysis have shown that V is mainly composed of C4 to C8 linked 3-O-galloyl-(-)-epicatechin units in the extension part (upper part) with either 3-O-galloyl-(-)-epicatechin or (+)-catechin unit in the lower terminal part.View full abstractDownload PDF (985K) -
YOSHIHISA KURASAWA, ATSUSHI TAKADA1981 Volume 29 Issue 10 Pages 2871-2876
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 3-ethoxycarbonylmethylene-2-oxo-1, 2, 3, 4-tetrahydroquinoxaline with the Vilsmeier reagent gave 3-(N, N-dimethylaminocarbonyl) furo [2, 3-b] quinoxaline, which was converted to various quinoxaline derivatives, 3-methyl-2-oxo-1, 2-dihydroquinoxaline, quinoxalinylpyrazolin-5-ones, and pyrazolo [3', 4' : 3, 4] pyridazino [5, 6-b] quinoxalines.View full abstractDownload PDF (724K) -
MASASHI TOMODA, MAEMI YOKOI, KAZUYO ISHIKAWA1981 Volume 29 Issue 10 Pages 2877-2884
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucous polysaccharide, named Plantago-mucilage A, was isolated from the seeds of Plantago major L. var. asiatica DECAISNE (=Plantago asiatica L.). The final preparation was homogeneous as determined by ultracentrifugal analysis, glass-fiber electrophoresis, and gel chromatography. It was readily soluble in water and its solution gave an intrinsic viscosity value of 39.5. It was composed of L-arabinose, D-xylose, D-glucuronic acid, and D-galacturonic acid in the molar ratio of 4.0 : 10.8 : 3.3 : 0.7, and its molecular weight was estimated to be about 1500000. O-Acetyl groups were identified in it and their content amounted to be 4.8%. Reduction of carboxyl groups, methylation analysis, controlled Smith degradation, and partial acid hydrolysis studies showed that the mucilage possesses a main chain composed of β-1→4 linked D-xylopyranose residues having other D-xylopyranose side chains at position 3 and branches composed of O-α-(D-glucopyranosyluronic acid)-(1→3)-α-L-arabinofuranose and of O-α-(D-galactopyranosyluronic acid)-(1→3)-α-L-arabinofuranose at position 2 of the residual D-xylopyranose units.View full abstractDownload PDF (1006K) -
MAKOTO SATO, AKIRA KOSASAYAMA, FUMIHIKO UCHIMARU1981 Volume 29 Issue 10 Pages 2885-2892
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSβ-Phenyl-γ-butyrolactones (IIIa-j) bearing several substituents on the phenyl ring were synthesized. Deamination of 4-amino-3-(2, 4, 6-trimethylphenyl) butyric acid (IV) with nitrous acid gave rearranged compounds, β-(2, 4, 6-trimethylbenzyl)-β-propiolactone (V) and 3-hydroxy-4-(2, 4, 6-trimethylphenyl) butyric acid (VI) together with the required β-(2, 4, 6-trimethylphenyl)-γ-butyrolactone (IIIj). Reaction of 2-phenyloxirane derivatives (IXh-j) with sodium diethylmalonate was found to be a convenient method for the preparation of β-phenyl-γ-butyrolactones (IIIh-j) substituted with electron-donating group on the phenyl ring.View full abstractDownload PDF (912K) -
YUKINOBU IKEYA, HEIHACHIRO TAGUCHI, ITIRO YOSHIOKA1981 Volume 29 Issue 10 Pages 2893-2898
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA procedure for selective cleavage of the methylenedioxyl moiety with lead tetraacetate in dry benzene is described. Piperonylic acid methyl ester (5), 4-nitro-1, 2-methylenedioxybenzene (6), 3, 4-methylenedioxytoluene (7), 2, 3-methylenedioxyanisole (8) and gomisin A (9) afforded protocatechuic acid (12), 4-nitrocatechol (13), 3, 4-dihydroxytoluene (14), 2, 3-dihydroxyanisole (15) and compound 16, respectively. The structure of angeloylgomisin Q isolated from the fruits of Schizandra chinensis BAILL. (Schizandraceae), was elucidated as 1 by using the above reaction.View full abstractDownload PDF (865K) -
AKIRA YOSHIDA, TERUO HAYASHI, NORIKO TAKEDA, SADAO OIDA, EIJI OHKI1981 Volume 29 Issue 10 Pages 2899-2909
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of hydroxyethylazetidinone precursors to 1-thia analogs of thienamycin is described. An N-protected azetidinone 4 was hydroxyethylated via an aldol reaction to give four diastereomers 5-8, which were converted to the diastereomeric pair of racemic 8R and 8S trans azetidinones 9b and 10b. Stereochemical assignment was achieved by correlation of 9b with the optically active azetidinone 16 which was obtained from the hydroxyethylpenicillanate 14a with known stereochemistry. The optically active 8R and 8S azetidinones 16 and 27 were synthesized more efficiently starting from the penicillinderived bromo compound 19 in a series of steps including stereochemical inversion at the C-8 position.View full abstractDownload PDF (1387K) -
HISAYUKI TANIZAWA, YASUYUKI SAZUKA, YOSHIO TAKINO1981 Volume 29 Issue 10 Pages 2910-2914
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe analytical conditions or fluorometric assay of lipoperoxide in the myocardium of mice were investigated in detail. It was found that the reaction of lipoperoxide with thiobarbituric acid (TBA) depended on the acidity of the reaction medium, not on the kind of acid used. The best result was obtained when 2.0 M acetate buffer (pH 3.6) solution was used. In extraction of the fluorescent substance from the reaction medium after the reaction of lipoperoxide with TBA, the addition of one-fifteenth volume of pyridine to n-butanol was suitable to remove the turbidity of the reaction medium. Calibration plots gave a good linear relationship in the range of 0.1-1.0 nmol of malondialdehyde. The TBA aqueous solution was found to decompose and therefore we used the solution within 2 weeks after preparation. This method was used to assay lipoperoxide in the myocardium of mice which had been treated with adriamycin (ADR). Lipoperoxide level in the myocardium was increased from 250.7 nmol/g wet tissue to 674.5 nmol/g wet tissue on the 4th day after ADR administration.View full abstractDownload PDF (586K) -
HIDEAKI MANITA, HIROMU MORI, MASASHI HASHINO, TAKUMI YANAIHARA, TETSUY ...1981 Volume 29 Issue 10 Pages 2915-2919
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEstrogen levels in the urine of women at various stages of pregnancy were determined semi-quantitatively and quantitatively by the latex agglutination inhibition reaction (LAIR) method. Quantitative processing according to the LAIR method was possible by strictly standardizing the volume of the sample (30 μl) and latex reagents (35 μl), and the rotating speed of the glass slide (30 rpm). The values obtained by the LAIR method were compared with those by gas chromatography-mass spectrometry-selected ion monitoring (GC-MS-SIM) in which deutrated estriol (estriol-2, 4-d2) was used as an internal standard. There was a significant correlation between these values. The correlation coefficient was 0.9865 and the regression line was expressed as y=1.082x-2.10. The results indicate that the estrogen values semi-quantitatively determined by the LAIR method are reliable ones and that this procedure can be used effectively to determine estrogen levels in four ranges, less than 5 μg/ml, 5-10 μg/ml, 10-20 μg/ml, and more than 20 μg/ml, as a clinical screening test for monitoring feto-placental functions. The LAIR method is suitable for routine measurement of urinary estrogens.View full abstractDownload PDF (680K) -
MAMORU SUGIURA, YUICHI IIIZUMI, TETSUO ADACHI, YOSHIMASA ITO, KAZUYUKI ...1981 Volume 29 Issue 10 Pages 2920-2927
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLarge amounts of an esterase that migrated to the γ-globulin region (γ-esterase) upon cellulose acetate electrophoresis were excreted in the urine from patients with renal diseases. The γ-esterase localized in the renal tubules of the kidney in patients with renal tubular diseases was purified and shown to be identical with the urinary esterase that migrated to the γ-globulin region by immunological studies. The esterase has a molecular weight of 66000, an optimum pH of 7.5, and pI values of 7.9 and 8.3.View full abstractDownload PDF (1074K) -
HITOSHI ARITA, KENJI SUGITA, KOSABURO SATO, YASUJI AMANO, JUNICHI KAWA ...1981 Volume 29 Issue 10 Pages 2928-2933
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAddition of phenyl-6-chloro-6-deoxy-β-D-glucopyranoside (PCG) to culture cells before infection with Sendai virus resulted in the production of incomplete virions defective in biological activities as well as infectivity. These noninfectious virions were characterized by chemical and physical methods. Electrophoretic analysis by SDS-PAGE showed differences in the M-protein region between the intaot and incomplete virions, although no morphological differences were observed by electron microscopy.View full abstractDownload PDF (893K) -
HIDEO SAWADA, HITOMI MARUYAMA, HISHIRI SENGOKU, TOSHIHIRO NAKAYAMA1981 Volume 29 Issue 10 Pages 2934-2939
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntibody against purified human prostatic acid phosphatase (orthophosphoric monoester phosphohydrolase, EC 3.1.3.2) was produced in rabbits. The antiserum stabilized the activity of the enzyme against heat treatment, such as incubation at 56°C for 30 min, whereas normal rabbit serum displayed no stabilizing effect. We isolated IgG by ammonium sulfate fractionation and affinity chromatography on a Protein A-Sepharose CL-4B column. the IgG fraction showed a remarkable heat-stabilizing effect on prostatic acid phosphatase (PAPase) and the heat-stabilizing factor was purified 4.2-fold by the IgG isolation method. Complex of PAPase and PAPase specific IgG was separated from a mixture of PAPase and antiserum by a combination of Protein A-Sepharose CL-4B column and Sephacryl S-300 column chromatographies. The immune complex displayed heat stability. IgG which failed to bind PAPase had no heat-stabilizing effect on PAPase. Fab fragments obtained by papain digestion showed a low heat-stabilizing effect, whereas F(ab')2 fragments obtained by pepsin digestion displayed a heat-stabilizing effect comparable with that of the IgG fraction.View full abstractDownload PDF (753K) -
HIROSHI SHIMENO, YOKO FUKUMOTO, AKIHISA TODA, ATSUO NAGAMATSU1981 Volume 29 Issue 10 Pages 2940-2948
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA single administration of dl-3-pyridylalanine (3-PA, 100 mg/kg) significantly increased brain and serum serotonin (5-HT) concentrations without affecting the other tissue 5-HT concentrations (liver, kidney, spleen and small intestine) in male Wistar rats. The increase in brain 5-HT upon 3-PA administration was maintained for a long time (at least 96 h). Chronic administration of 3-PA (100 mg/kg/d) produced no change in brain 5-HT concentration as compared with that found in animals given a single dose of 3-PA. 3-PA decreased liver tryptophan pyrrolase (TP) activity and increased free tryptophan concentration in the serum. 3-PA hardly affected tryptophan 5-hydroxylase, 5-hydroxy-L-tryptophan (5-HTP) decarboxylase and monoamine oxidase (MAO) activities in the brain and liver. These findings suggest that the increase in brain 5-HT concentration upon administration of 3-PA occurs via the inhibition of liver TP, and an increase in free tryptophan concentration in the serum may be the causative factor for the increased brain 5-HT concentration. In contrast with 5-PA, 5-HTP (50 mg/kg, 10 mg/kg) increased the 5-HT concentrations of all tissues studied, and the brain 5-HT concentration fell to control (saline-treated) levels within several hours after the administration of 5-HTP (10 mg/kg, 6 h ; 50 mg/kg, 24 h). 5-HTP decreased brain tryptophan 5-hydroxylase and 5-HTP decarboxylase activities, and increased brain MAO and liver TP activities at 2 h after the administration.View full abstractDownload PDF (935K) -
TAKASHI ABIKO, HIROSHI SEKINO1981 Volume 29 Issue 10 Pages 2949-2955
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA hexadecapeptide, H-Tyr-Asn-Ile-Gln-Lys-Glu-Ser-Thr-Leu-His-Leu-Val-Leu-Arg-Leu-Arg-OH, corresponding to the C-terminal sequence 59-74 of bovine ubiquitin, was synthesized in a conventional manner. The synthetic hexadecapeptide was tested for effect on E-rosette forming cells of a patient in the uremic state. After incubation with amounts of the synthetic hexadecapeptide in the range of 200 to 300 μg/ml of uremic blood, recovery of E-rosette forming ability was observed.View full abstractDownload PDF (916K) -
HIDEO NAKAMACHI, YOSHIKAZU WADA, ISAMU AOKI, YOSHIHIKO KODAMA, KOJI KU ...1981 Volume 29 Issue 10 Pages 2956-2965
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of 6-thioxanthine (6TX) on the thermal transformation of 6-mercaptopurine (6MP) crystals was investigated using scanning electron microscopy and X-ray diffraction. The crystal lattice of 6MP and 6TX molecules can include up to 10% of the counterpart molecules to form a solid solution. Monohydrate crystals (form I) of pure 6MP were directly transformed into anhydrate crystals (form II) by heating at 150-220°C, but similar crystals (form ITX) of 6MP containing more than 2% 6TX were converted into another form of anhydrate crystals (form III) via an amorphous state by the same treatment. These phase transformations were kinetically studied and there was a clear difference in mechanism under the present experimental conditions. The transformations of form I into form II and form ITX into an amorphous state were assumed to proceed according to the contracting cube equation whereas that of the amorphous state into form III appeared to follow the Prout-Tompkins equation. The reason for the transformation into different crystal forms, from form I into form II and from form ITX into form III, is discussed on the basis of the experimental results.View full abstractDownload PDF (1619K) -
KATSUHIRO YAMAZAKI, HIROSHI YOKOYAMA, YOSHIKI NUNOURA, CHISAE UMEZAWA, ...1981 Volume 29 Issue 10 Pages 2966-2973
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect on digestive enzymes of stomachic crude drugs that were often compounded in gastrointestinal OTC drugs was investigated. The β-amylase activity of takadiastase was slightly inhibited by cloves and extract of scopolia. Coptis root and extract of scopolia were weak inhibitors of saccharated pepsin. The proteolytic activity of pancreatin was inhibited by 50% in the presence of 5 mg of cinnamon, phellodendron or Japanese prickly ash berry under the conditions used. Cinnamon inhibited trypsin and chymotrypsin, proteases in pancreatin. The inhibitory activity of cinnamon varied from sample to sample ; it was localized in the water-soluble and the residual fractions, and little inhibitory activity was found in the volatile oil fraction. Cinnamic acid, methyl cinnamate, cinnamaldehyde and cinnamyl alcohol were not inhibitory. Antiproteolytic activity was found in both the inner and outer solutions after dialysis of the 25% ethanol extract of cinnamon. Hide powder treatment removed inhibitory activity in the outer solution, while that in the inner solution was unchanged.View full abstractDownload PDF (879K) -
HIDEYA YAGINUMA, TOHRU NAKATA, HARUMASA TOYA, TERUO MURAKAMI, MASARU Y ...1981 Volume 29 Issue 10 Pages 2974-2982
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of non-steroid antiinflammatory (NSAI) drugs on the rectal membrane were studied by measuring the change in the rectal absorption of ampicillin and cephalothin. All the NSAI drugs studied were found to case a remarkable enhancement of the rectal absorption of antibiotics which were not able to permeate readily through the rectal membrane in the absence of NSAI drugs. The optimum concentrations of NSAI drugs as adjuvants in triglyceride suppositories containing 10% ampicillin sodium were 1.5% for indomethacin sodium and diclofenac sodium, 5% for mepirizole, 7.5% for phenylbutazone, and 10% for sodium salicylate. These concentrations of NSAI drugs were used in a study of the promoting efficacy of the drugs as adjuvants for the rectal absorption of antibiotics. The promoting effects of adjuvants in dogs were inferior to those in rabbits. From simultaneous measurements of NSAI drugs and antibiotic, it was found that the absorption of antibiotic started at the early stages after the administration of suppositories and the peak blood level was reached while the blood concentration of NSAI drug was still increasing. From these results, it was suggested that the NSAI drugs made the mucosal barrier leaky to water-soluble antibiotics at the early stages of permeation of the NSAI drugs through the rectal membrane, and that the barrier rapidly recovered its normal properties even while the permeation of NSAI drug was continuing and a considerable amount of antibiotic still remained in the rectal cavity. Alinear correlation between the enhanced absorption of antibiotics and the antiinflammatory activity of NSAI drugs against carrageenan-induced edema was observed.View full abstractDownload PDF (985K) -
KENICHI SHIROTANI, KEIJI SEKIGUCHI1981 Volume 29 Issue 10 Pages 2983-2992
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolvates of cortisone acetate with ethanol, n-propanol and isopropanol were isolated, and their physico-chemical properties were investigated by X-ray powder diffractometry, infrared spectroscopy, differential scanning calorimetry, thermogravimetry, and scanning electron microscopy. Also, the specific surface areas and pore volumes of the desolvated products were measured by the BET method. The combining ratios of the solvates were all determined to be 1 : 1 from the weight change in thermogravimetric curves. From the kinetic analysis of the thermal desolvation, it appeared that the desolvation proceeded in accordance with the mechanism of the two-dimensional growth of nuclei as represented by the Avrami-Erofeev equation. In addition, it was found that the powders recovered by desolvation had fairly large specific surface areas and pore volumes, and were easily divided into fine powders by only slight trituration.View full abstractDownload PDF (1398K) -
YUKIHISA KURONO, KEN IKEDA1981 Volume 29 Issue 10 Pages 2993-3002
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe inhibition parameters of various drugs (inhibitor, I) for the reaction of p-nitrophenyl acetate (substrate, S) with human serum albumin (HSA) could not be directly determined, because HSA has two esterase-like active sites for S (i.e. R and T sites) and three drug binding sites (i.e. R, T and U sites) [Ozeki et al., Chem. Pharm. Bull., 28, 525 (1980)]. In the present study, the dissociation constants between I and the individual binding sites on HSA, KI, R, KI, T and KI, U, were determined by analog computer simulation of the inhibition. Clofibric acid, ibuprofen and dansylsarcosine were found to bind solely to the R site, and their KI, R values were determined. Flufenamic acid, ethacrynic acid and salicylic acid bind primarily to the R site and then to the T site, and their KI, R and KI, T values were estimated. The KI, U and KI, R values for phenylbutazone and sulfinpyrazone were also determined, and their KI, U values were smaller than their KI, R values. It is likely that warfarin binds primarily to two binding sites unconcerned with the esterase-like activities and then to the R site of HSA, and these three dissociation constants were estimated. Since this kinetic method distinguishes the drug binding sites on HSA and gives the dissociation constants for the individual sites, it is very useful for studies on drug interaction with HSA.View full abstractDownload PDF (890K) -
KIYOMI KIKUGAWA, YASUKO MACHIDA, MASA KIDA, TSUTAO KURECHI1981 Volume 29 Issue 10 Pages 3003-3011
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReactions of malonaldehyde (MA), a secondary product of lipid peroxidation, with amino acids and related compounds were performed under mild conditions. Thus, mixtures of 200 mM MA-50 mM amino acid (or related compound) were treated at around pH 7 at 37°C. The major fluorescent products IG, IGE and IH were isolated as crystals from the reaction mixtures of glycine, its ethyl ester and n-hexylamine, respectively, and their structures were established to be 1-substituted 4-methyl-1, 4-dihydropyridine-3, 5-dicarbaldehyde (I). The compounds showed fluorescence with λexmax 365, 403 nm and λexmax 440-460 nm. The reaction mixtures of MA and amino acids except for L-tryptophan, crysteamine and L-cysteine exhibited the same fluorescence spectra. The reactions of MA with cysteamine and L-cysteine produced a different type of fluorescent products. Under the reaction conditions employed here, formation of conjugated Schiff bases (III) as described by Chio and Tappel (Biochemistry, 8, 2821 (1969)) could not be detected. The fluorescence spectrum of I resembled those of lipofuscin pigments extracted from the tissue homogenates.View full abstractDownload PDF (1049K) -
TSUTAO KURECHI, TETSUTA KATO1981 Volume 29 Issue 10 Pages 3012-3018
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCombination effects of butylated hydroxyanisole (BHA), butylated hydroxytoluene (BHT) and their analogs on hydrogen donation to 2, 2-diphenyl-1-picrylhydrazyl (DPPH) were investigated. A synergistic effect was observed when 2, 6-di-tert-butylphenol derivatives were combined with 4-methoxyphenol derivatives such as BHA and 4-methoxyphenol. This effect might arise from the regeneration of 4-methoxyphenol derivatives from possible intermediates formed from DPPH and these phenols, with enhanced loss of the 2, 6-di-tert-butylphenol derivatives. The formation of the cross coupling compound from a pair in combination might decrease the regeneration of the phenols and thus influence the synergistic effect.View full abstractDownload PDF (820K) -
SHOJI TAKEMURA, YASUYOSHI MIKI, MARIKO HOSHIDA, MAYUMI SHIBANO, ARITOM ...1981 Volume 29 Issue 10 Pages 3019-3025
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree types of compound, quinuclidine-3-spiro-2'-dioxolane (A), piperidine-4-spiro-2'-dioxolane (B), and piperidine-4-spiro-2'-(4'-oxodioxolane) (C) and their methiodides were synthesized. The cholinomimetic activities of these compounds were examined to investigate the relationship between the activities of these compounds, which have rigid skeletons, and those of known muscarinic agents.View full abstractDownload PDF (695K) -
SHOJI TAKEMURA, YASUYOSHI MIKI, MASAMI UONO, KAZUYUKI YOSHIMURA, MASAY ...1981 Volume 29 Issue 10 Pages 3026-3032
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDimethyl quaternary salts of cis- and trans-piperidine-3, 4-diol acetonides (9 and 15) were prepared from readily available intermediates, 1-benzoyl and 1-ethoxycarbonyl derivatives of 1, 2, 5, 6-tetrahydropyridine (4a and 4b). The activity of 9 was examined and the presence of the rigid skeleton was shown to markedly decrease the cholinomimetic effect compared with the partially opened skeleton. The relationship between 9 and known potent muscarinic agents is discussed.View full abstractDownload PDF (785K) -
YOSHIAKI SHIRATAKI, MANKI KOMATSU, ICHIRO YOKOE, AKIHIKO MANAKA1981 Volume 29 Issue 10 Pages 3033-3036
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new flavanone, named euchrestalfavanone A (I), mp 145-147°C, C25H28O5, was isolated from the root of Euchresta japonica HOOK. f. ex REGEL (Leguminosae) together with l-maackiain, medicagol and trifolirhizin. The structure of I was established to be 6, 3'-di-γ, γ-dimethylallyl-5, 7, 4'-trihydroxyflavanone on the basis of chemical and spectral evidence.View full abstractDownload PDF (524K) -
KAZUYUKI KIZUKI, HIROSHI MORIYA1981 Volume 29 Issue 10 Pages 3037-3041
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSShimeji kininase intravenously administered almost completely suppressed the pulmonary edema in rats induced by L-epinephrine. This observation suggested that kinin might be involved in the genesis of this edema because this enzyme maintained its kininase activity in the rat body for a fairly long time and was able to block the kinin action in the body. However, no inhibitory effect was observed when Shimeji kininase was intraperitoneally administered. The reason for this was probably that the amount of Shimeji kininase that entered into the vascular system was small, and the concentration of Shimeji kininase in the plasma was therefore inadequate. On the other hand, attempts to determine whether the kallikrein-kinin system was really activated or not in this pathogenetic state were unsuccessful because L-epinephrine present in plasma interfered with the quantitative determination of components related to the kallikrein-kinin system in plasma. At present, the mechanism of the activation of the kallikrein-kinin system in this pathogenetic state is not clear, although the marked suppression of the pulmonary edema by Shimeji kininase strongly suggested the involvement of the kallikrein-kinin system in this pathogenetic state in rats.View full abstractDownload PDF (588K) -
MASATAKA ICHIKAWA, CHIYUKI YAMAMOTO, TAKUZO HISANO1981 Volume 29 Issue 10 Pages 3042-3047
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVinylpyridines were utilized for protection of the benzimidazole N-H bond to give 1-(2-pyridylethyl)-benzimidazoles. The reaction was found to progress smoothly when glacial acetic acid was used as a catalyst. In the alkylation of 5- or 7-substituted-2-arylbenzimidazoles with vinylpyridines, the yield decreased with increasing electronattracting effect of the substituent groups in the benzimidazole ring. On the other hand, the removal of pyridylethyl groups by the use of aluminum chloride as a catalyst was kinetically examined ; a large excess of sodium hydroxide was used for decomposition of the intermediate adduct of aluminum chloride. The rate increased somewhat when electron-releasing substituent groups were present in the benzimidazole ring. 1-[2-(2-Pyridyl) ethyl]-2-arylbenzimidazoles were resistant to removal of their (2-pyridyl) ethyl groups. 4-Vinylpyridine can be used more efficiently as a protecting agent.View full abstractDownload PDF (648K) -
KEIZO MATSUO, TOSHIYUKI KINUTA, KUNIYOSHI TANAKA1981 Volume 29 Issue 10 Pages 3047-3050
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-Malyngolide, which is an antibiotic isolated from a marine blue-green alga, was synthesized starting from 2-ethoxycarbonylcyclopentanone.View full abstractDownload PDF (570K) -
TATSUO YAMAUCHI, FUMIKO ABE, MASAKATSU TAKI1981 Volume 29 Issue 10 Pages 3051-3055
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSProtoplumericin, 13-O-(β-D-glucopyranosyl-p-coumaroyl)-plumieride (IV), was isolated from the polar fraction of the MeOH percolate of Allamanda neriifolia HOOK by means of several column chromatographies and droplet counter current chromatography. Enzymatic and alkaline transformations of IV into plumericin (I) and plumieride (III), respectively, were carried out.View full abstractDownload PDF (690K) -
MASATOSHI YAMATO, JIROH HORIUCHI, YASUO TAKEUCHI1981 Volume 29 Issue 10 Pages 3055-3059
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 1, 2, 3, 4-tetrahydroquinazoline-2-spirocyclohexan-4-one (1b) with acetic anhydride and pyridine gave 1-(1-cyclohexenyl)-2-methyl-1, 4-dihydroquinazolin-4-one (3b). Compound 3b gave 3-acetyl-1-(1-cyclohexenyl)-2-methyl-1, 2, 3, 4-tetrahydroquinazolin-4-one (8b) upon reduction with NaBH4 followed by acetylation with acetic anhydride. The position of the acetyl group of 8b was determined by comparison of its NMR spectrum with those of related compounds (9, 10, 11, 12, and 13).View full abstractDownload PDF (584K) -
KOSAKU HIROTA, YOSHIHIRO YAMADA, TETSUJI ASAO, YUKIO KITADE, SHIGEO SE ...1981 Volume 29 Issue 10 Pages 3060-3063
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-Amino-1, 3-dimethyl-6-(substituted amino) methyluracils (3a-d) prepared by the reduction of 1, 3-dimethyl-5-nitro-6-(substituted amino) methyluracils (2a-d) were treated with triethyl orthoformate to give the corresponding 7-substituted pyrimido [5, 4-d] pyrimidines (7a-d) in good yields. Treatment of 3a with dimethylformamide dimethyl acetal afforded a 5-dimethylaminomethylenamino intermediate (6), which cyclized to 7a on heating in toluene.View full abstractDownload PDF (509K) -
YASUNORI KANAHO, TAKASHI SATO, TATSUZO FUJII, YOZO IWANAMI, TSUKASA IW ...1981 Volume 29 Issue 10 Pages 3063-3066
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of the following compounds (most of which had been proved to inhibit mitotic progression of pollens) on the shape of the membrane of human erythrocytes were tested : myrmicacin (3-hydroxydecanoic acid) and its derivatives, even-numbered C4-10 fatty acids, and some C10 diols. They all induced a shape change of the membrane-exvagination (crenation) type at pH 7.4 to different extents, depending on their structures, but not at pH 6.0. The shape change induced was reversible. The structure-activity relationship and the mode of action were compared with those for the action of these compounds on pollen growth.View full abstractDownload PDF (532K) -
SHOZO MIYAZAKI, KUNIAKI ISHII, TANEKAZU NADAI1981 Volume 29 Issue 10 Pages 3067-3069
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe suitability of chitin and chitosan for use as vehicles for the sustained release of drugs was examined. Indomethacin and papaverine hydrochloride were used as model drugs in this evaluation. Sustained release of the drugs from the dried gels was obtained. Drugs dispersed in the chitosan gels were released at a constant rate (zero order). Chitin and chitosan could be useful vehicles for the sustained release of drugs.View full abstractDownload PDF (413K) -
KEIZO MATSUO, KUNIYOSHI TANAKA1981 Volume 29 Issue 10 Pages 3070-3072
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(±)-Malyngolide, which is an antibiotic isolated from a marine blue-green alga, was synthesized stereoselectively in four steps starting from 2-ethoxycarbonylcyclopentanone.View full abstractDownload PDF (388K) -
YOSHIO SASAKI, TATSUYA TAKAGI, YOKICHI YAMAZATO, AKIHIRO IWATA, HIDEKO ...1981 Volume 29 Issue 10 Pages 3073-3075
Published: October 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSValues of the substituent entropy constants σso for monosubstituted methane and benzene derivatives were determined from the standard entropy of the 3rd law of thermodynamics. This parameter is orthogonal to σt or σπ, and seems preferable to π, Es, MR, Mw, Pr and Vw. Two examples of QSAR are successfully analysed in terms of σso.View full abstractDownload PDF (383K)