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Volume 24, Issue 4
Displaying 1-47 of 47 articles from this issue
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HIROSHI IZUMI, HIKARU OZAWA1976 Volume 24 Issue 4 Pages 555-559
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffects of the 105000g supernatant on adenyl cyclase of rat cerebral cortex have been investigated and following results were obtained. 1) The 105000g supernatant significantly stimulated the activity of the synaptosomal adenyl cyclase in rat cerebral cortex. As the concentration of the supernatant increased, the progressive stimulation was observed with a plateau at a concentration of about 200 μg of protein. 2) This stimulatory effect of the supernatant was completely abolished by a dialysis of the supernatant for 24 hours at 4°. 3) When the enzyme system was incubated with combination of the supernatant and norepinephrine (100 μM), no activation by norepinephrine was observed. 4) Studies on the combined effects of the supernatant and sodium fluoride (NaF) showed that the supernatant additively enhanced NaF stimulated adenyl cyclase activity. 5) Gel filtration indicated that this stimulatory substance (s) in the supernatant had a molecular weight of 1000-1300.View full abstractDownload PDF (641K) -
EIKO OHTSUKA, SHIGEO MORIOKA, MORIO IKEHARA1976 Volume 24 Issue 4 Pages 560-564
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5'-Phosphoryl-N-benzoyldeoxyadenylyl-(3'-5')-N-anisoyl-3'-O-acetyldeoxycytidine (IVa) and 5'-phosphoryl-N-isobutyryldeoxyguanylyl-(3'-5')-N-anisoyl-3'-O-acetyldeoxy-cytidine (IVb) were synthesized by condensation of 5'-O-(N-trityl-p-aminophenyl) phosphoryl-N-benzoyldeoxyadenosine (Ia) or 5'-O-(N-trityl-p-aminophenyl) phosphoryl-N-isobutyryldeoxyguanosine (Ib) with N-anisoyldeoxycytidine 5'-phosphate using triisopropyl-benzenesulfonyl chloride (TPS). The intermediates (III) were isolated by extraction with organic solvents and the N-trityl-p-aminophenyl group was removed by oxidative hydrolysis. The dinucleotides (IV) were obtained without ion-exchange chromatography in yields of 50 to 60% and used for synthesis of the oligonucleotides. The tetranucleotide (VI) was synthesized by condensing V with IVa using TPS and was also isolated from the starting materials by the extraction method in a yield of 49%. The tetranucleotide (VI) was further condensed with the dinucleotides IVa and IVb to yield the hexanucleotide (VII) and the octanucleotide (VIII).View full abstractDownload PDF (623K) -
MORIO IKEHARA, TOKUMI MARUYAMA1976 Volume 24 Issue 4 Pages 565-569
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTriacetyl-8-oxyinosine (Ib) was treated with phosphoryl chloride in diethylaniline or thionyl chloride in dimethyl formamide (DMF) to give only 6-chloro-8-oxy compound (IV). Treating (Ib) with phosphoryl chloride in tri-n-butylamine gave 6, 8-dichloro compound (VII). Compound (VII) was converted to bis (methylmercapto) compound (VIII) and treated successively with dimethylamine and Raney nickel to give N6-dimethyladenosine. Thus, a procedure for eliminating 8-oxy function of purine nucleosides has been substantiated.View full abstractDownload PDF (702K) -
EIKO OHTSUKA, KAZUO FUJIYAMA, MINORU OHASHI, MORIO IKEHARA1976 Volume 24 Issue 4 Pages 570-579
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe pentanucleotide which has the sequence of 8th to 12th base of the 5'-terminus of yeast tyrosine transfer ribonucleic acid (tRNA), UpApm2GpCpC (1) has been synthesized by stepwise addition of properly protected mononucleotides using dicyolohexylcarbodiimide. 5'-O-Monomethoxytrityl-N2-methylguanosine 3'-phosphate was prepared by phosphorylation of the 5'-protected nucleoside to give the 2', 3'-cyclic phosphate and successive hydrolysis with ribonuclease (RNase) St. The isolated yields of the protected ditri, tetra-, and penta-nucleotides were 75, 38, 31, and 21%, respectively. The 5'-terminal tetranucleotide CpUpCpUp (3) corresponding to 1st to 4th nucleotides, was synthesized by condensation of the dinucleotide, Bz-CBz (OBz)-pU (OBz)-p (14) and the anilidate, CBz (OBz)-pU-(OBz)-pNHPh (16b) in a yield of 22%. The trinucleotide CpGpGp (2) spanning 5th to 7th nucleotides from the 5'-end was also prepared by the amidate method from the dinucleotide, MMTrCBz (OBz)-pGBu (OiBu)-p(18) and G1Bu (OiBu)-pNHPhOCH3 (19b) in a yield of 17%.View full abstractDownload PDF (1128K) -
MOTOKO ITO, YOSHIKAZU KONDO, TSUNEMATSU TAKEMOTO1976 Volume 24 Issue 4 Pages 580-583
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe search for spasmolytic principals of Cimicifuga dahurica MAXIM. (Ranunculaceae) with the guidance of the intestinal action resulted in the isolation of two active substances, visamminol and visnagin, in addition to isoferulic acid and norvisnagin. Norvisnagin was first isolated from natural source. Pharmacological estimations using guinea pig jejunum revealed that the spasmolytic actions of visamminol and visnagin were one-third and one-tenth that of papaverine hydrochloride, respectively. Norvisnagin showed inactivity.View full abstractDownload PDF (455K) -
SHOJI KISHIMOTO, HIROMU SUGINO, KUNIHIRO TANAKA, ATSUSHI KAKINUMA, SHU ...1976 Volume 24 Issue 4 Pages 584-590
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMicrobiological hydroxylation of 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284), a new potent antiinflammatory agent, with Penicillium concavo-rugulosum IFO 6226 gave 6-chloro-5-(trans-4'-hydroxycyclohexyl) indan-1-carboxylic acid (1), one of the main metabolites of TAI-284 in rats, in 71% yield. From this product two other metabolites, the corresponding 4'-oxo and cis-4'-hydroxy derivatives (4 and 2), were derived chemically. Catalytic hydrogenation of the 4'-oxo compound (4) over PtO2 afforded the unexpected trans alcohol (1), but reduction of 4 with trimethylphosphite and iridium tetrachloride in aqueous isopropanol gave the desired cis alcohol (2) in 69% yield.View full abstractDownload PDF (814K) -
TAKAJI KOYAMA, SUMIO FUKUOKA, TAKASHI HIROTA, JUN MAEYAMA, SHINJI OHMO ...1976 Volume 24 Issue 4 Pages 591-595
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCondensation of 1, 3-cyclohexanedione (I) with formamide gave 9, 10-dihydro-1, 3, 5, 7-tetraazaphenanthrene (II), 1, 2, 3, 4, 5, 6, 7, 8, 9, 10-decahydro-11, 13-diazabenzo [g] chrysene-1, -5-dione (III), 1, 2, 5, 6-tetrahydro-3, 7, 9, 11, 13-pentaazadibenzophenanthrene (IV), and 7, 8, 13, 14-tetrahydro-2, 4, 6, 10, 12-pentaazabenzo [c] chrysene (V). Dehydrogenation of II with sulfur gave 1, 3, 5, 7-tetraazaphenanthrene (VI). To make sure the formation mechanism of IV and V, dimer of I (enol form of VII') was heated with formamide or trisformyl-aminomethane and the formation of IV and V were confirmed.View full abstractDownload PDF (638K) -
TAISEI UEDA, ISOO ITO, YOICHI IITAKA1976 Volume 24 Issue 4 Pages 596-606
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Michael and the Diels-Alder reactions of 1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-benzo [6, 7] thiepino [3, 4-c] pyrazole-3, 4-dione (1) with dimethyl acetylenedicarboxylate (2) were examined, and the fascinating reactions which gave two novel heterocycles were found : dimethyl 1, 2-dihydro-1-methyl-3-oxo-2-phenyl-3H-benzothieno [3, 2-e] indazole-9, 10-dicarboxylate (3) and dimethyl 1, 2-dihydro-4-hydroxy-1-methyl-3-oxo-2-phenyl-3H-[2] benzothiopyrano [4, 3, 2-f, g] indazole-8, 9-dicarboxylate (15). The mechanisms of the formations of 3 and 15 were discussed. For pharmacological evaluation some N, N-dimethylethylenediamine derivatives of 3 and 15 were synthesized.View full abstractDownload PDF (1160K) -
KUNIO SUZUKI, HIDEMICHI FUKAWA, TORU OKUGAWA, MINORU SEKIYA1976 Volume 24 Issue 4 Pages 607-612
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKinetic manner was introduced into mechanistic studies on the formic acid reduction of carbon-carbon double bond adjacent to carbonyl induced by the formate reagent, TEAF, 5HCO2H·2NEt3. Kinetic data obtained by the use of 1, 3-dimethyl-5-benzyli-denebarbituric acid as a representative, the second order kinetics, the large negative entropy of activation, the isotope effect (2.79) and the positive ρ-value (+1.00) of the Hammett equation, suggest one step path, which proceeds by the attack of HCO2-·HN^+Et3 involving the push-pull mechanism of ring system of a transition state.View full abstractDownload PDF (699K) -
CHIKAKO TAKAHASHI, KUNITOSHI YOSHIHIRA, SHINSAKU NATORI, MAKOTO UMEDA1976 Volume 24 Issue 4 Pages 613-620
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolites, compounds A-E, were isolated from a toxic strain of Aspergillus candidus and the structures of the characteristic cytotoxic compounds A (terphenyllin) and E (deoxyterphenyllin) were elucidated to p-terphenyl derivatives (1 and 24) by spectral data, oxidation reactions, and synthesis of compound A trimethyl ether. The cytotoxicity of the compounds and the derivatives was also discussed.View full abstractDownload PDF (1038K) -
KOHICHI AKETA, SHIRO TERASHIMA, SHUNICHI YAMADA1976 Volume 24 Issue 4 Pages 621-631
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to transform an optical integrity of L-lysine (L-5c) into simple piperidine alkaloids in a biomimetic sence, optically active pipecolic acids (D- or L-10c) or their derivatives ((R) - or (S) -11) were chosen as synthetic intermediates. It was found that deamination of L-5c-HC1 with a combination of sodium nitrite and aqueous hydrochloric acid, followed by the treatment with aqueous base, could give D-10c being more than 90% optically active. On the other hand, deamination of L-5c-1/2H2SO4 with sodium nitrite-aqueous sulfuric acid, followed by chlorination with thionyl chloride and pyridine and by cyclization with aqueous base, could afford L-10c which was about 80% optically pure. Precise estimation of retention for optical activity was carried out by isolating formed D- or L-10c as their derivatives ((R) (+)-11a, b or (S) (-)-11b). Exploitations for other synthetic routes to L-10c from L-5c were also undertaken. Based on the above-mentioned experimental results, almost optically pure (S) (+)-coniine, one of the simplest piperidine alkaloids, could be prepared from L-5c-HC1 via D-10c and (R) (+)-11a or b.View full abstractDownload PDF (1394K) -
HITOSHI UNO, MIKIO KUROKAWA, KAGAYAKI NATSUKA, YUZURU YAMATO, HARUKI N ...1976 Volume 24 Issue 4 Pages 632-643
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Amidinomethyl- (8), 3-imidazolinylmethyl- (9) and 3-tetrahydropyrimidinylmethyl-1, 2-benzisoxazole (10) were synthesized from 1, 2-benzisoxazole-3-acetonitrile (4) via iminoether (7). 3-Tetrazolylmethyl-1, 2-benzisoxazole (5) and 1, 2-benzisoxazole-3-acetamide oxime (11) were also prepared from 4. 3-Aminoethyl-1, 2-benzisoxazole (25), a tryptamine analogue of 1, 2-benzisoxazole, was synthesized from 3-chloroethyl-1, 2-benzisoxazole (20). The bromination of 1, 2-benzisoxazole-3-acetic acid (1) with one molar equivalent of bromine afforded α-bromo-1, 2-benzisoxazole-3-acetic acid (27), which was decarboxylated to give 3-bromomethyl-1, 2-benzisoxazole (30). The amination of 30 afforded 3-amino-methyl-1, 2-benzisoxazole (31). The bromination of 1 with excess of bromine gave 3-tribromomethyl-1, 2-benzisoxazole (28). N-Substituted 1, 2-benzisoxazolylglycine ester (32) was synthesized from methyl α-bromo-1, 2-benzisoxazole-3-acetate (29) which was obtained by the bromination of methyl 1, 2-benzisoxazole-3-acetate (2).View full abstractDownload PDF (1071K) -
HITOSHI UNO, MIKIO KUROKAWA, HARUKI NISHIMURA1976 Volume 24 Issue 4 Pages 644-647
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrogenation of 1, 2-benzisoxazole-3-acetamide oxime (1) proceeded as follows. At first 1 absorbed one molar hydrogen to give 2-hydroxybenzimidoylacetamide oxime (2) and then 2 was cyclized to 3-amino-5-(2-hydroxyphenyl) isoxazole (4) which absorbed one more molar hydrogen to give 2-hydroxybenzoylacetamidine (3). The alkaline treatment of 2-hydroxybenzoylacetonitrile (11), which was obtained from 1, 2-benzisoxazole-3-acetnitrile (9) by the catalytic reduction and successive hydrolysis, gave 2-coumarinimine (12). The acidic treatment of 2-hydroxybenzimidoylacetamide (13), which was the product of the catalytic reduction of 1, 2-benzisoxazole-3-acetamide (8), afforded 4-aminocoumarin (15), an isomer of 12.View full abstractDownload PDF (550K) -
SHINZO KANO, EIJI KOMIYAMA, YOUKO TAKAHAGI, SHIROSHI SHIBUYA1976 Volume 24 Issue 4 Pages 648-654
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 1-(2-bromo-4, 5-methylenedioxyphenethyl)-1, 2, 3, 4-tetrahydro-6-hydroxy-7-methoxy-2-methylisoquinoline (13) with sodium methylsulfinylmethanide gave the dibenzo [b, g] azecine (14). The 1-benzyl analog possessing a methyl group at the 3-position was transformed to the 6, 13-disubstituted dibenzo [b, f] azonine (33) under the similar conditions. 33 was converted to the corresponding 6, 13-dimethyl derivative (35). Hydrogenolysis of the N-methyl-dibenzo [a, f] quinolizinium iodide (23) over Adams catalyst was also examined to give the dibenzo [b, g] azecine (24).View full abstractDownload PDF (883K) -
TOZO FUJII, KEIJI SAKAMOTO, SATOSHI KAWAKATSU, TAISUKE ITAYA1976 Volume 24 Issue 4 Pages 655-660
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Alkoxy-9-alkyladenines (VIIIa, b, c) have been found to undergo alkylation mainly at the N6-position when treated with alkyl halide in N, N-dimethylacetamide. The structure of the resulting N6-alkylated derivatives (IXa, b, c) has been established by comparison with authentic IXa (X=I, ClO4) and by catalytic hydrogenolysis of IXb, c (X=ClO4) to N4, 9-dialkyladenines (XIb, c). In the case of the benzyl analog (IXc : X=ClO4), removal of the benzyloxy group at the 1-position has also been effected stepwise through the 1-oxide (Xc).View full abstractDownload PDF (775K) -
GENJIRO KUSANO, TSUNEMATSU TAKEMOTO, YOSHIO SATO, DAVID F. JOHNSON1976 Volume 24 Issue 4 Pages 661-666
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical studies have shown that tomatillidine and dihydrotomatillidine, steroidal alkaloids obtained from Solanum tomatillo, are described in revised structures 1a and 2a instead of the old structures 1b and 2b. An isomerization of △22 (N)-22, 26-imino-23-one moiety to △23 (N)-23, 26-imino-22-one is a major topic.View full abstractDownload PDF (752K) -
HARUHIKO TADA, KENICHI TAKEDA1976 Volume 24 Issue 4 Pages 667-671
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy virtue of correlation with pyrethrosin 6a, the structure of laurenobiolide 1, a component of Laurus nobilis L., was confirmed. At least, two races of this plant exist, one of which contains 1 as a major component and the other costunolide 9.View full abstractDownload PDF (613K) -
MORIO IKEHARA, MASAKO MURAOKA1976 Volume 24 Issue 4 Pages 672-682
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe O-cyclonucleosides of hypoxanthine, 6-mercaptopurine, 6-methylmercaptopurine, and purine were synthesized. Cyclonucleosides of hypoxanthine, and 6-mercaptopurine were synthesized i) by the derivatization of corresponding adenine cyclonucleosides and ii) by the cyclization of appropriate 2'-or 3'-TPS-derivatives. Cyclonucleosides of 6-methylmercaptopurine and purine were synthesized from the corresponding 6-mercaptopurine cyclonucleosides by methylation and Raney Nickel desulfurization. Ultraviolet spectrum (UV), nuclear magnetic resonance (NMR), circular dichroism (CD) and Mass spectra of these cyclonucleosides were measured. It was found in the CD spectrum that the purine 8, 2'-cyclonucleoside had a larger magnitude of Cotton effect than its 8, 3'-counterpart, in contrast to the order found in other cyclonucleosides.View full abstractDownload PDF (1264K) -
JUNZO NAKAMURA, YAEKO YOSHIZAKI, MASATO YASUHARA, TOSHIKIRO KIMURA, SH ...1976 Volume 24 Issue 4 Pages 683-690
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAbsorption mechanism of four water-soluble dyes, methylene blue (MB), bromthymol blue (BTB), bromphenol blue (BPB), and phenol red (PR), from the rat small intestine was investigated. Absorptive characteristics of these dyes, highly ionized compounds of very low lipoid solubilities at physiological pH range of the small intestine, varied widely. The percentage net absorption of MB, BTB, BPB, and PR were 46.0±2.9, 14.7±3.7, 2.4±1.1, and 1.2±0.5%, respectively. The degree of binding to the intestinal mucosa preparation determined in vitro was correlated to the disappearance from the intestinal lumen and the accumulation in tissue rather than net absorption. The binding to brush borders, the first step of intestinal absorption, was paralleled to the tendency of uptake by isolated epithelial cells. These results suggest that binding to the mucosa, especially to the brush borders (microvilli) as the first step, is important in the process of absorption of these water-soluble dyes from the rat small intestine. The poor absorbability of PR is due to its very low affinity to the intestinal mucosa in addition to poor lipoid solubility.View full abstractDownload PDF (905K) -
JUNZO NAKAMURA, YAEKO YOSHIZAKI, MASATO YASUHARA, TOSHIKIRO KIMURA, SH ...1976 Volume 24 Issue 4 Pages 691-697
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRole of membrane components in the absorption from the rat small intestine of four water soluble dyes, methylene blue (MB), bromthymol blue (BTB), bromphenol blue (BPB), and phenol red (PR) was investigated. Uptake by the isolated epithelial cells, binding to the brush borders, and uptake by the everted sac of BTB and BPB, anionic dyes, were significantly reduced by digestion with papain, but in PR on effect was found. Binding of the dyes to the components released by the cellulose papain complex digestion from the brush borders was examined using the method of equilibrium dialysis. More MB and BTB bound to the components than BPB and PR, poorly absorbable dyes. These results suggested that membrane component contributing to the dye binding to the brush borders may be glycocalyx (surface coat). Lipids, other major membrane components, were extracted from rat intestinal mucosa and separated to neutral lipid (NL), glycolipid (GL), phosphatidylcholine (PC), and phosphatidylethanolamine (PE) fractions. Each fraction was dissolved in chloroform and partitioning behavior of the dyes was examined using a non-emulsifying system. Extent of transfer of the dyes from aqueous phase into chloroform containing GL and total lipid (TL) was well correlated to the extent of net absorption and tissue accumulation respectively.View full abstractDownload PDF (927K) -
KAZUYA KAMIJO, TAKAKO WATANABE1976 Volume 24 Issue 4 Pages 698-704
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe report here is the study as for the effects of NH2OH on the enzymic reaction of monoamine oxidase (MAO) using rat liver mitochondria. In the short-term reaction (1 min) by MAO, NH2OH decreased the MAO activity by either tyramine or benzylamine as substrate. In the long-term reaction (60 min), there was an increased activity in the MAO reaction by tyramine and an decreased one in that by benzylamine under various concentrations of NH2OH. In the long-term reaction, Km-values for tyramine and benzylamine were 1.82×10-3.0M and 2.50×10-2.0M, respectively, which were consistent with those in the presence of NH2OH. Pursuing the changes of MAO activities by various concentrations of NH2OH using the tyramine substrate at intervals of 1, 10, 30, and 60 min, there was a decrease of MAO activity accompanying an increased concentration of NH2OH after 1 min period, a partial increase after 10 min, and an entire increase in extensive concentrations of NH2OH after 30 min. In the other substrates such as tryptamine, amylamine, hexylamine, and β-phenylethylamine, the effects of NH2OH on MAO were similar to those in tyramine. In the butylamine substrate, NH2OH caused as inhibitory effects as shown in the benzylamine substrate. These results suggest the existence of a complex of MAO enzymes corresponding to monoamine substrates. The multiplicity of MAO enzyme is further discussed in the text.View full abstractDownload PDF (860K) -
TOMIHIKO OHSAWA, HIROMITSU MIZUNO, TOSHIO TAKIZAWA, MASAYOSHI ITOH, SH ...1976 Volume 24 Issue 4 Pages 705-715
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid treatment in acetic anhydride of blocked cyclohexadienone derivatives (6a) and (6b) obtained from l-abietic acid (1) gave 14 and 16, respectively, through Wagner-Meer-wein rearrangement of the angular methyl group. On the other hand, under similar conditions, 6c and 6d were transformed into 18 and 20, respectively, as the result of an abnormal dienone phenol rearrangement, namely, aromatization of the B-ring with concomitant cleavage of C-C bond.View full abstractDownload PDF (1393K) -
SHIGERU KOBAYASHI, MASARU KIHARA, TOSHIHIRO HASHIMOTO, TETSURO SHINGU1976 Volume 24 Issue 4 Pages 716-723
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of deoxytazettine neomethine (I), derived from tazettine (III) via 5 steps, was confirmed by synthesis of its optically active and racemic forms. A key step in the synthesis, conversion of 2'-bromomethyl-4', 5'-methylenedioxy-2-biphenylcarbal-dehyde (VI) to 7-cyano-5, 7-dihydro-2, 3-methylenedioxydibenz [c, e] oxepin (VII), was achieved by employing a novel method which had been developed for synthesis of 5-cyano-5, 7-dihydrodibenz [c, e] oxepin (V). The nuclear magnetic resonance spectra of the neomethine (I) and its synthetic intermediates were discussed.View full abstractDownload PDF (918K) -
HIROMICHI SAEKI, NORIKO TAKEDA, YOSHIKAZU SHIMADA, EIJI OHKI1976 Volume 24 Issue 4 Pages 724-730
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 3-p-toluenesulfonate (4) of methyl 2, 6-dibenzyloxycarbonylamino-2, 6-dideoxy-α-D-glucopyranoside was treated with sodium borohydride in dimethyl sulfoxide, giving 3-deoxy-and 4-deoxy-α-D-ribo-hexopyranosides (10 and 11) in a ratio of 1 : 5. On the other hand, analogous treatment of the 4-p-toluenesulfonate (5) afforded the allo-3, 4-epoxide (19). Further, related study was described.View full abstractDownload PDF (1032K) -
NORIAKI FUNASAKI, SAKAE HADA, KEIZO SUZUKI1976 Volume 24 Issue 4 Pages 731-735
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe relations between the surface tension and the concentration of the aqueous solutions of triacetin, tripropionin, tributyrin, tricaproin, and tricaprylin were determined at 37°. The solubilities and the adsorbed amounts of triglycerides were obtained from these results. Since the solubilities of tricaproin and tricaprylin were extremely low, the corrections for adsorption at the interfaces were necessary to obtain their solubilities. The linear relationship between the logarithm of solubility and the total surface area of hydrophobic groups in a triglyceride molecule which could contact maximally with the water, was found to hold. The smallness of the slope of this straight line in comparison with those of hydrocarbon and alcohol, was interpreted as showing that three hydrophobic chains in a triglyceride molecule may aggregate intramolecularly with one another in the water; threefifths of the total surface area of hydrophobic group are in contact with water and the two-fifths are in contact with hydrophobic group. Moreover, from the molecular area occupied at the air-water interface, it was suggested that the hydrophobic chains in adsorbed monolayer of triacetin might correspond to the "tune-forming" conformation like the β-form crystal of triglyceride; the chains in 1-and 3-position were directed toward the air and the chain in 2-position was directed toward the water.View full abstractDownload PDF (615K) -
YOSHIO BAN, NAOMASA TAGA, TAKESHI OISHI1976 Volume 24 Issue 4 Pages 736-751
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe total synthesis of the entitled four alkaloids, which were oxindole alkaloids of Uncaria species and Mitragyna species, has been completed through several steps starting from the condensation of 2-hydroxytryptamine hydrochloride (IV) with 3, 3-dimethoxy-propionaldehyde (V). The condensation product (XV) was submitted to the Michael addition with methyl vinyl ketone, followed by acid treatment to give the α, β-unsaturated ketones (XIVa, b) as two stereoisomers. The isomer (XIVb) was condensed with methyl malonate to yield the ester (XXb), which was hydrogenated with Adams' catalyst to XXIb. The compound (XXIb) was treated with dil. sulfuric acid to give the lactones (XXIIa, b) as two spiro-iso-mers, the isomer (XXIIa) of which in turn, was heated with the aminal ester, then stirred with 5% MeOH-HCl, refluxed with aq. dioxane and heated with PPA to afford (±)-for-mosanine (IIIa) and (±)-isoformosanine (IIIb). Similarly, the lactone (XXVa) which was obtained from (XXb) by reduction with NaBH4 and hydrolysis with acid, gave (±)-mitraphylline (IIa) and (±)-isomitraphylline (IIb).View full abstractDownload PDF (1778K) -
TAMOTSU SAITOH, TAKESHI KINOSHITA, SHOJI SHIBATA1976 Volume 24 Issue 4 Pages 752-755
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew compounds were isolated from the root of Glycyrrhiza glabra L. (Leguminosae) and named glabridin and glabrol, whose structures were determined to be an isoflavan (I) and a flavanone (VI), respectively.View full abstractDownload PDF (531K) -
YOSHIHIRO NISHIKAWA, KIMIHIRO YOSHIMOTO, MIDORI OKABE, FUMIKO FUKUOKA1976 Volume 24 Issue 4 Pages 756-762
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntitumor activity of some unsaturated fatty acids and the ester derivatives was tested with Ehrlich ascites carcinoma in mice. The compounds examined were A) 10-undecenoic, elaidic, oleic, linoleic, and linolenic acids, B) methyl esters of oleic, linoleic, and linolenic acids, C) 1-O-acyl-β-D-glucopyranose tetraacetates derived from oleic, linoleic, and linolenic acids, and D) sucrose monoesters prepared from the fatty acids belonging to group A. The agent to be tested was administered to mice by intraperitoneal injection, and the effect was evaluated with total packed cell volume ratio on the 7th day after tumor implantation. The free fatty acids having 18 carbon atoms were all highly active, but 10-undecenoic acid proved to show no activity. All members of groups B and C were completely ineffective. The sucrose monoelaidate, in particular, and the sucrose monooleate exerted strong effect, whereas other sucrose monoesters exhibited only slight or negative activity. Some basic properties of the two types of carbohydrate esters employed are also described.View full abstractDownload PDF (855K) -
HISASHI MIYAZAKI, KEIKO NAMBU, YASUO MINAKI, MASAHISA HASHIMOTO, KIYOS ...1976 Volume 24 Issue 4 Pages 763-769
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1) After intravenous treatments of mice with equimolar doses of 14C-labeled β-dimethylaminoethanol (DMAE*) or its p-chlorophenoxyacetate [MF (DMAE*)], brain levels of DMAE* were found to be much higher in the latter treatment, due to the better penetration of the ester derivative, followed by hydrolysis. 2) DMAE* in the brain administered in either form of drugs was gradually phosphorylated to yield DMAE*-P, which was in turn converted to ptd-DMAE*, seemingly the end metabolite of DMAE* in the brain. 3) Acid-soluble and lipid cholines derived from DMAE* and MF (DMAE*) were also found in the brain. However, methylations of DMAE or its ester were attributed to occur in organs other than the brain, such as the liver, as revealed by relative incorporations of a labeled methyl group into lipid choline in the brain and liver after the treatment of methionine-methyl-14C.View full abstractDownload PDF (763K) -
YASUO MAKISUMI, SUSUMU TAKADA1976 Volume 24 Issue 4 Pages 770-777
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new, general method was developed for the synthesis of 3-(substituted-methyl)-indoles from N-propargylanilines. The method involves oxidation of the aniline with m-chloroperbenzoic acid and subsequent treatment with a suitable nucleophilic reagent under mild conditions in a single flask. The possible pathway was indicated to be (a) formation of an N-oxide, (b) [2, 3] and [3, 3] sigmatropic rearrangements of a propargyl group, (c) formation of a 3-methylideneindolenine intermediate, and (d) an attack of a nucleophilic reagent on the methylidene function. The process was quite general and provided a new route for synthesizing 3-(substituted-methyl) indoles-for example, indole-3-acetonitriles, 3-phenylthiomethylindoles, 3-azidomethylindoles and their derivatives.View full abstractDownload PDF (917K) -
TOSHIO NAKAGAWA, KATSUTOSHI AONO1976 Volume 24 Issue 4 Pages 778-781
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has been suggested by dermatologists that boron compounds of chlorpromazine are promising agents for neutron capture therapy of malignant melanoma. The compounds are desired to have a high boron content, good stability, and sufficient solubility in water. To fulfil these requirements, chlorpromazine undecahydrododecaborate and nonahydrodecaborate have been synthesized starting from 2-chloro-10 (3-bromopropyl) phenothiazine and ammonioundecahydrododecaborate or 2-ammoniononahydrodecaborate, respectively.View full abstractDownload PDF (522K) -
HIROTAKA OTOMASU, TAE TANAKA, MIDORI AOYAGI1976 Volume 24 Issue 4 Pages 782-787
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA spiro-heterocyclate, pyrazole-ring combined at the position-3 of indolin-2-ones was examined. 3-Phenacylideneindolin-2-ones (Ia-d) reacted with hydrazine hydrate to give the corresponding spiro [indoline-3, 3'-(5'-pyrazolin)]-2-ones (IIa-d). The reaction of 3-phen-acylidene-(Ia) and 3-acetonylideneindolin-2-one (If) with diazomethane afforded 4' benzoyl-(Va) and 4'-acetyl-spiro [indoline-3, 3'-(1'-pyrazolin)]-2-one (Vb), respectively. The decomposition of 1-pyrazolines (Va-b) by thermolysis or by reacting with HCI gave spiro [cyclopropane-1, 3'-indolin]-2'-ones (VIa and VIb), whereas during chromatography on alumina changed into 3-(α-benzoyl)-(VIIa) and 3-(α-acetyl) ethylideneindolin-2-one (VIIb), respectively. In addition, 3-(α-nitro) ethylideneindolin-2-one (VIII) reacted with diazomethane to give 1, 4'-dimethyl-4'-nitro-spiro [indoline-3, 3'-(1'-pyrazolin)]-2-one (IX), which being chromatographed on alumina gave 1, 4'-dimethyl-spiro [indoline-3, 3'-(3'H-pyrazol)]-2-one (X).View full abstractDownload PDF (702K) -
MAMORU SUGIURA, MUTSUKO SUZUKI, MASANORI SASAKI, TOKIKO SHIMOMURA1976 Volume 24 Issue 4 Pages 788-793
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid β-galactosidase I and II (β-D-galactoside galactohydrolase, EC 3. 2. 1. 23) from Sclerotium tuliparum were purified by column chromatography with DEAE-cellulose, SP-Sephadex C-50, Sephadex G-200 and by isoelectric focusing (pI, 4.5 and 4.4, respectively). The purified β-galactosidase I and II were homogeneous in disc electrophoresis. The enzymes were most active at pH 2.0 and stable over a pH range from 3.0 to 6.0 at 37° for 3 hr. Optimum temperatures of β-galactosidase I and II were 53° and 47°, respectively, and the thermal stability of β-galactosidase I was slightly higher than that of β-galactosidase II. Both enzymes were completely inactivated by N-bromosuccinimide at 0.01 mM. Km of β-galactosidase I and II were 1.4 mM and 1.2 mM for o-nitrophenyl β-D-galactopyranoside (ONPG) and 20 mM and 19 mM for lactose, respectively, and Vmax of β-galactosidase I and II were 433 μmoles·min-1·mg-1 and 480 μmoles·min-1·mg-1 for ONPG and 139 μmoles·min-1·mg-1 and 149 μmoles·min-1·mg-1 for lactose, respectively.View full abstractDownload PDF (752K) -
MAMORU SUGIURA, MUTSUKO SUZUKI, MASANORI SASAKI, TOKIKO SHIMOMURA1976 Volume 24 Issue 4 Pages 794-799
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcid β-galactosidase (EC 3. 2. 1. 23) was purified from the culture filtrate of Macrophomina phaseoli by column chromatography using DEAE-cellulose and Sephadex G-200, and isoelectric focusing (pI, 3.6). The purified enzyme was homogeneous on disc electrophoresis. The enzyme is considered to be a glycoprotein, because the mobility of the protein band coincided with that of sugar one in disc electrophoresis, and because sugar content was not varied before and after isoelectric focusing of the purified enzyme. The sugar content of the enzyme was estimated to be 12% with phenol-sulfuric acid method. The enzyme was most active at pH 5.0 and 60°, and stable over a pH range from 4.0 to 8.0 and below 55°. The enzymatic activity was completely inactivated only by N-bromosuccinimide at 0.1 mM. Km value was determined to be 0.45 mM for o-nitrophenyl β-D-galactopyranoside (ONPG) and 15 mM for lactose, and Vmax was calculated to be 93.6 μmoles·min-1·mg-1 for ONPG and 54.5 μmoles·min-1·mg-1 for lactose.View full abstractDownload PDF (688K) -
NORIO TAKAMURA, SHUN-ICHI YAMADA1976 Volume 24 Issue 4 Pages 800-803
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Substituted α-diazoesters (I), readily prepared from α-amino acid esters, were reduced with various reductants to give corresponding α-hydrazinocarboxylic acids (II) and their derivatives. Several investigations were also undertaken in order to synthesize α, α-disubstituted α-hydrazinocarboxylic acid derivatives (VII) from I.View full abstractDownload PDF (621K) -
YOSHIAKI TANAKA, MITSUJI SANO1976 Volume 24 Issue 4 Pages 804-807
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism of mepirizole (I) in human urine was studied by labeling the drug with a stable isotope, deuterium. An equimolar mixture of the deuterium labeled mepirizole (II) and its protium counterpart (I) was administered orally to a man. The metabolites were extracted from the pooled urine with CH2Cl2, treated with diazomethane and applied to GC-MS. The ion clusters in the mass spectra were used for detection of the urinary metabolites of I in man. By this technique, three metabolites, 1-(4-methoxy-6-methyl-2-pyrimidinyl)-5-methoxy-3-hydroxymethylpyrazole (III), 1-(4-methoxy-6-methyl-2-pyrimidinyl)-5-methoxypyrazole-3-carboxylic acid (IV) and 1-(4-methoxy-6-carboxy-2-pyrimidinyl)-5-methoxy-3-methylpyrazole (V) were identified in human urine.View full abstractDownload PDF (508K) -
YOSHIAKI TANAKA, YOSHIO ESUMI, MITSUJI SANO1976 Volume 24 Issue 4 Pages 808-812
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHighly sensitive techniques for the quantitative determination of mepirizole (I) and its metabolites are described. The compounds were first extracted from rat serum with dichloromethane, and they were converted to their respective trifluoroacetyl derivatives in isopropyl ether, which could be detected by a gas chromatograph equipped with an electron capture detector. The approximately linear relationships existed between the quantities of these compounds and the sensitivities to electron capture detector in the range of the serum levels as low as several hundred ng. The structures of the trifluoroacetylated derivatives of the metabolites were identified by gas chromatography-mass spectrometry.View full abstractDownload PDF (602K) -
KUNIO SUZUKI, MINORU SEKIYA1976 Volume 24 Issue 4 Pages 813-815
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reductive fission, previously realized at one of the centered β-carbon bond of alkylidenebisketones by the formate, triethylammonium formate, has been mechanistically revealed to be initiated by retro-Michael addition and followed by reduction of the resulting α, β-unsaturated carbonyl compound.View full abstractDownload PDF (457K) -
MUNEHISA ARISAWA, NAOKATA MORITA1976 Volume 24 Issue 4 Pages 815-817
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKanzakiflavone-1 (III), C17H12O7, mp 291-293°, a new flavone, has been isolated from the rhizomes of Iris unguicularis POIR. (Japanese name : Kanzakiayame) together with irigenin (I) and iristectorigenin A (II). The structure of kanzakiflavone-1 (III) has been determined as 5, 8-dihydroxy-4'-methoxy-6, 7-methylenedioxyflavone by chemical and spectral means.View full abstractDownload PDF (484K) -
KIKUKO HONMA, AKIRA HAMADA1976 Volume 24 Issue 4 Pages 818-820
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSApplication of the Helferich method to the preparation of thioglycosides was performed in dichloroethane at room temperature by use of SnCl4 as catalyst. The reaction gave 1-thio-β-D-glucopyranoside from penta-O-acetyl-β-D-glucopyranose and thiophenol in good yield. However, the similar reaction with methyl 1, 2, 3, 4-tetra-O-acetyl-β-D-glucopyranuronate and thiophenol gave an unpredicted product, 3, 4-di-O-acetyl-6-methoxy 6-thiophenyl-α-D-glucopyranose 1, 2-(phenylthio orthoacetate). The structure was confirmed by analytical and spectral data.View full abstractDownload PDF (474K) -
NORIYOSHI INUKAI, HIDENORI IWAMOTO, TOSHINARI TAMURA, ISAO YANAGISAWA, ...1976 Volume 24 Issue 4 Pages 820-822
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe α-position of active methylene compounds which were activated by the carbonyl group was halogenated using metal halides in the presence of peroxides.View full abstractDownload PDF (448K) -
HISASHI MIYAZAKI, KEIKO NAMBU, MASAHISA HASHIMOTO1976 Volume 24 Issue 4 Pages 822-825
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEffect of meclofenoxate against subacute anoxia in mice was tested in view of the fact that dimethylaminoethanol derived in the brain was sequentially metabolized from free alcohol to phospholipid. Some other agents were also tested to examine the test system used and to clarify the nature of meclofenoxate effect. Chlordiazepoxide, hexobarbital and meclofenoxate (either 20 min or 4 hr after intravenous administration) produced tolerance against anoxia, whereas methamphetamine exerted the opposite effect. An equimolar mixture of dimethylaminoethanol and p-chlorophenoxyacetic acid, the constituents of meclofenoxate, was ineffective in this system. Chlordiazepoxide enhanced the effect of methamphetamine, whereas hexobarbital and meclofenoxate (20 min after administration) diminished the methamphetamine effect. The results were discussed in relation to the disposition of meclofenoxate in central nervous systems.View full abstractDownload PDF (578K) -
YOSHINORI FUJIMOTO, NOBUO IKEKAWA1976 Volume 24 Issue 4 Pages 825-828
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFive steroidal allylic alcohols were treated with lithium aluminum hydride-titanium tetrachloride in comparison with lithium aluminum hydride-aluminum chloride. The former reagent was found to be useful for the hydrogenolysis of allylic alcohols, especially for tertiary ones.View full abstractDownload PDF (518K) -
HARUO SAKAMOTO, MOTOHIKO KATO1976 Volume 24 Issue 4 Pages 828-831
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe partial synthesis of (20R)-17α, 20, 21-trihydroxypregna-1, 4-dien-3-one (its Dring moiety is identical with that of cortisone) from androsta-1, 4-diene-3, 17-dione is described. This conforms a model experiment for the synthesis of adrenal steroid compounds from the latter compound without affecting its A-ring moiety.View full abstractDownload PDF (526K) -
MASAHIRO NOBUHARA, HIDEO TAZIMA, KOICHI SHUDO, AKIKO ITAI, TOSHIHIKO O ...1976 Volume 24 Issue 4 Pages 832-834
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a fungal metabolite isolated from Trichoderma sp. was determined.View full abstractDownload PDF (439K) -
TORU KOIZUMI, YOSHIKO KOBAYASHI, EIICHI YOSHII1976 Volume 24 Issue 4 Pages 834-835
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA stereochemical study of the acid-catalyzed methanolysis of N-cyclohexyl methyl-phenylphosphinamide shows that the reaction proceeds by almost pure A-2 mechanism irrespective of the acidity of the reaction medium.View full abstractDownload PDF (381K) -
YASUHIRO YAMANE, HIDEKI FUKINO, MASAYOSHI IMAGAWA1976 Volume 24 Issue 4 Pages 836-837
Published: April 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMale rats were given subcutaneous injection of mercuric chloride (0.018 mmole/kg/day) and oral administration of zinc acetate (3.0 mmoles/kg/day). Mercury and zinc were administered at the same time, once every 24 hr for 5 days. Only 1 of 10 rats given mercury alone survived for 3 days, and this one rat died on the 4 th day. In the animals given mercury and zinc at the same time, all the 10 animals were alive on the 5 th day, indicating the marked effect of zinc in suppressing the toxicity of mercury. Based on such a marked effect of zinc. examinations were made to see whether biosynthesis of metallothionein would occur by the presence of zinc or mercury from the incorporation of 14C-cysteine into the metallothionein fraction. High rate of incorporation of radioactivity into the metallothionein in the rat liver was observed by the administration of zinc but the incorporation was not so marked by the administration of mercury. This fact seems to suggest that the biosynthesis of metallothionein by zinc is responsible for the suppressive effect of zinc on the toxicity of mercury.View full abstractDownload PDF (331K)
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