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Volume 29, Issue 3
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HITOSHI MATSUMOTO, AKIHIKO ISOBE1981 Volume 29 Issue 3 Pages 603-608
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe emission spectra and the fluorescence quantum yields of psoralens were measured in various solvents. We found that these compounds show a large Stokes shift, which can be explained in terms of intermolecular charge transfer interaction between a solute molecule and a solvent molecule in an excited singlet state. Psoralens have a larger fluorescence quantum yield in hydroxylic solvents than in non-hydroxylic solvents. These were in the following order : TMP≈5-MOP>PS≈8-MOP≈8-iso-AOP. We postulate that the fluorescence quantum yield is increased by the hydrogen bonding between a solute molecule and a solvent molecule in an excited singlet state. In addition, the fluorescence efficiency was enhanced by the presence of an electron-donating substituent group. The peak wavelengths of the phosphorescence spectra were little affected by the different solvents.View full abstractDownload PDF (681K) -
KAZUHIDE KAMIYA, MASAYUKI TAKAMOTO, YOSHIKAZU WADA, MASAO NISHIKAWA1981 Volume 29 Issue 3 Pages 609-615
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSX-ray analysis of cefmenoxime hemihydrochloride was performed. The asymmetric unit of the crystal consists of one chlorine anion and one protonated and one free cefmen oxime molecule. A part of the free molecule is disordered, and conformational differences are observed among the protonated molecule and the two forms of disordered molecules. Intermolecular forces link two independent molecules of cefmenoxime and a chlorine anion and constitute a three-dimensional network in the crystal.View full abstractDownload PDF (614K) -
MASANORI TAKAMATSU, MINORU SEKIYA1981 Volume 29 Issue 3 Pages 616-622
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt has been found that the lithium aluminum hydride reduction of 2, 2, 2-trichloroethylamines occurs to give amines with rearranged carbon skeletons or aziridines, depending on the precise substrate structure.View full abstractDownload PDF (624K) -
MITURU FURUKAWA, MASUMI NISHIKAWA, YASUNOBU INABA, YOSHIHIDE NOGUCHI, ...1981 Volume 29 Issue 3 Pages 623-628
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of sulfinic acid (1) with methanol in the presence of NCS-DMS gave methyl sulfinate (2) and methyl sulfonate (3) in 22% and 45% yields, respectively. Similarly, 1 reacted with morpholine under the same conditions to give the corresponding sulfinamide (5) and sulfonamide (6) in 23% and 50% yields. In these reactions, the disulfone (4) was also obtained as a minor product in some cases. The formation of sulfonic acid derivatives and disulfone was found to proceed through the intermediate formation of the sulfonyl chloride (7). The formation mechanism of sulfinic acid derivatives is also discussed.View full abstractDownload PDF (682K) -
HARUO OGURA, MASAKAZU SAKAGUCHI, KENKO NAKATA, NOBUKO HIDA, HISAKO TAK ...1981 Volume 29 Issue 3 Pages 629-634
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of 6-hydrazino-1, 3-dimethyluracil (1) with aldoses (2a-e), D-fructose, and D-glucuronolactone gave hydrazones (3a-e, 6, and 8) in good yields, and these products were converted to pyrimido [4, 5-c] pyridazine nucleoside analogs (4a-e, 7, and 9) by cyclodehydration. Stereoisomers were isolated from the reaction mixtures of pyrimido [4, 5-c] pyridazine derivatives, and were examined by CD spectroscopy. On the other hand, the hydrazones (11a, b) of 1 with glycolaldehyde or (±)-glyceraldehyde were converted only to acetates (12a, b). Formation of the pyrimido [4, 5-c]-pyridazine derivatives (13a, b) was not observed.View full abstractDownload PDF (713K) -
SHENGCHU KUO, CHUNHSIUNG WU, LIJIAU HUANG, KATSUMI YAMAMOTO, SHIGETAKA ...1981 Volume 29 Issue 3 Pages 635-645
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to investigate the antimicrobial activity of derivatives of methyl 5-nitro-3, 4-diphenylfuran-2-carboxylate, we first studied the optimal conditions for the nitration of methyl 3, 4-diphenylfuran-2-carboxylate. Starting from the nitrofuran methyl ester, various amides, hydrazides, hydrazones, oxadiazoles and thiazoles were synthesized and examined for antimicrobial activity. Most of the derivatives were active against T. vaginalis.View full abstractDownload PDF (1031K) -
KEIJI HEMMI, HIDEKAZU TAKENO, MASASHI HASHIMOTO, TAKASHI KAMIYA1981 Volume 29 Issue 3 Pages 646-650
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of the antibiotics FR-900098 (II) and FR-33289 (III), isolated from Streptomyces rubellomurius, have been established as 3-(N-acetyl-N-hydroxyamino)-propylphosphonic acid and 3-(N-acetyl-N-hydroxyamino)-2 (R)-hydroxypropylphosphonic acid, respectively, on the basis of spectroscopic and chemical evidence and, finally, by synthesis.View full abstractDownload PDF (684K) -
KATSUHIDE MATOBA, EIICHI ISHIGAMI, HIROKI TAKAHATA, TAKAO YAMAZAKI1981 Volume 29 Issue 3 Pages 651-656
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-(2-Oxocyclopentanecarboxamido) quinoline (IVb) was prepared from 5-aminoquinoline (IVa) and 2-carbethoxycyclopentanone (III) and isolated as a crystalline compound. IVb was treated with polyphosphoric acid-xylene to give 4, 11-diazagona-1, 3, 5 (10), 6, 8, 13-hexaen-12-one (I). Two isomers, 4, 11-diazagona-5, 7, 9, 13-tetraen-12-one (II) and 1, 2, 3, 4, 7, 8, 9, 10, 11-nonahydro-4, 11-diazacyclopenta [b] phenanthren-7-one (VI), were synthesized by the reaction of 1, 2, 3, 4-tetrahydro-5-aminoquinoline (Va) and III in the presence of trifluoroacetic acid. 5-(2-Oxocyclopentanecarboxamido)-2-methoxyquinoline (X) could not be cyclized to the expected diazasteroid system under various conditions tested.View full abstractDownload PDF (734K) -
TAKAO MURAKAMI, HIDEKI IIDA, NOBUTOSHI TANAKA, YASUHISA SAIKI, CHIUMIN ...1981 Volume 29 Issue 3 Pages 657-662
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Pteris longipes DON two known and five new ent-kaurane type diterpenes were isolated. The structures of the new diterpenes, pterokaurene L1, L2, L3, L4 and pterokaurane L5, were established respectively as ent-9-hydroxy-15-oxo-kaur-16-en-19-oic acid, ent-9, 15α-dihydroxy-kaur-16-en-19-oic acid, ent-9-hydroxy-kaur-16-en-19-oic acid, ent-12α, 15α-dihydroxy-kaur-16-en-19-oic acid and ent-11α, 16α-epoxy-16R-kauranoic acid by spectroscopic methods, some chemical transformations and X-ray crystallographic analysis.View full abstractDownload PDF (773K) -
NOBUTOSHI TANAKA, TAKAO MURAKAMI, YASUHISA SAIKI, CHIUMING CHEN, YOICH ...1981 Volume 29 Issue 3 Pages 663-666
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Pteris purpureorachis COPEL. three new ent-atisane type diterpenes, pteroatisene P1, P2 and pteroatisenoside P1, were isolated. Their structures were elucidated using some chemical transformations, spectroscopic methods and X-ray crystallographic analysis as ent-9-hydroxy-15-oxo-atis-16-en-19-oic acid, ent-9, 15α-dihydroxy-atis-16-en-19-oic acid and ent-9-hydroxy-15-oxo-atis-16-en-19-oic acid-β-D-glucosylester.View full abstractDownload PDF (547K) -
JUTARO OKADA, KOICHI NAKANO, HIROSHI MIYAKE1981 Volume 29 Issue 3 Pages 667-675
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-Chloromethyl-6-ethoxycarbonyluracil (5) was prepared from furo [3, 4-d] pyrimidine-2, 4, 7 (1H, 3H, 5H)-trione (4). Reaction of 5 with some nucleophilic reagents such as secondary amines, alcohols and sodium thiolates afforded 5-(substituted-methyl)-6-ethoxy-carbonyluracils. By treatment of the corresponding esters with methanolic ammonia or ammonia water, 5-(substituted-methyl)-6-carbamoyluracils were prepared. The antitumor activities of the newly synthesized compounds were examined against L-1210 cells in vitro.View full abstractDownload PDF (902K) -
NOBUYUKI OKAMURA, TOSHIHIRO NOHARA, AKIRA YAGI, ITSUO NISHIOKA1981 Volume 29 Issue 3 Pages 676-683
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSZizyphus saponins I, II, III and jujuboside B were isolated from Zizyphi Fructus. On Smith-de Mayo degradation, zizyphus saponins I, II and III yielded jujubogenin as a genuine aglycone. The configuration of the sugar linkages in each saponin was determined on the basis of PMR and CMR examinations and application of Klyne's rule on molecular rotation, and the structures of zizyphus saponins I, II and III were established as (I), (II) and (III), respectively. 6-Deoxy-L-talose was isolated as a sugar component of zizyphus saponins I and III.View full abstractDownload PDF (1030K) -
TAKAKO HORI, CHOSAKU YOSHIDA, SHOHACHI MURAKAMI, RYUKO TAKENO, JOJI NA ...1981 Volume 29 Issue 3 Pages 684-698
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 3-Dioxopiperazine derivatives, which are antitumor agents of a new type, were synthesized and the structure-activity relationship was investigated from the viewpoint of lipophilic-hydrophilic balance. It was found that 1-(4-diethylaminobenzyl)-4-n-hexyl-2, 3-dioxopiperazine (12n) possessed significant in vitro cytotoxicity and in vivo antitumor activity against transplanted tumor, but this in vivo antitumor activity did not reflect the in vitro cytotoxicity. The metabolism of 12n in rats and mice was then studied. It was found that the Et2N-group of 12n was easily metabolized to an AcNH-group in vivo.View full abstractDownload PDF (1360K) -
YASUOKI MURAKAMI, HISASHI ISHII1981 Volume 29 Issue 3 Pages 699-710
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 6-chloro-1, 2, 3, 4-tetrahydrocarbazole (14) with the Vilsmeier-Haack reagent gave 6-chloro-2, 3, 4, 4a-tetrahydrocarbazole-4a, 9-dicarboxaldehyde (16) as a main product, along with 6-chloro-1, 2, 3, 4-tetrahydrocarbazole-9-carboxaldehyde (15) and 6-chloro-1, 2, 3, 4-tetrahydro-1-hydroxycarbazole-9-carboxaldehyde (17). The structures were established by spectral and chemical means. The mechanism of formation of 16 is discussed ; in connection with this, a similar reaction of 6-chloro-1, 2, 3, 4-tetrahydro-1, 1-dimethylcarbazole (37) was carried out and found to yield three products, 6-chloro-1, 2, 3, 4-tetrahydro-1, 1-dimethylcarbazole-9-(38), 5-(39), and 7-carboxaldehyde (40).View full abstractDownload PDF (1329K) -
YASUOKI MURAKAMI, HISASHI ISHII1981 Volume 29 Issue 3 Pages 711-719
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVilsmeier-Haack reaction of 6-chloro-1, 2, 3, 4-tetrahydro-9-methylcarbazole (1b) with 3 mol eq. POCl3 at 70°gave three compounds, 6-chloro-1, 2, 3, 4-tetrahydro-9-methyl-carbazole-1, 1-dicarboxaldehyde (4), 6-chloro-3, 4-dihydro-9-methylcarbazole-1 (2H)-one (5b), and 6-chloro-1, 2, 3, 4-tetrahydro-1-hydroxy-9-methylcarbazole-1-carboxaldehyde (6), while no 4a-formylated product1) was obtained. On the other hand, the reaction of the same compound (1b) with 1.3 mol eq. POCl3 at 100°gave 6-chloro-1, 2, 3, 4-tetrahydro-9-methyl-carbazole-1-carboxaldehyde (20), 5b, 6-chloro-1, 2, 3, 4-tetrahydro-9-methylcarbazole-7-carboxaldehyde (3b), and an aromatized compound, 6-chloro-1, 9-dimethylcarbazole-3-carboxaldehyde (2b). The formation mechanism of the aromatized compound (2b) is considered to involve elimination of a dimethylamino group and formation of 6-chloro-1, 9-dimethylcarbazole (21) as an intermediate.View full abstractDownload PDF (1047K) -
MASATOSHI YAMATO, TADATAKA ISHIKAWA, TOSHIO KOBAYASHI1981 Volume 29 Issue 3 Pages 720-725
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs a part of our studies on the reactions of 1-ethoxyisochroman (1) with nucleophilic reagents, the reaction of 1 with benzylamines was examined. Heating of 1 with benzylamine or its derivatives having an electron-releasing or-attracting group at the 4-position gave 1-benzylaminoisochroman (2) or the corresponding 1-(4-substituted benzylamino) isochromans (6 and 7). Pyrolysis of 2, 6, and 7 gave 4-benzylisoquinoline (3) and 4-(4-substituted benzyl)-isoquinolines (8 and 9), respectively. Compound 3 was also obtained by heating 2-(2-hydroxyethyl) benzaldehyde with benzylamine, or by heating 2-vinylbenzylidenebenzylamine (4), while the reaction of 1 with N-methylbenzylamine afforded 1-(N-methylbenzylamino) isochroman (5) and did not give the 4-benzylisoquinoline derivative at all. The reaction mechanism giving 4-benzylisoquinolines is proposed to be as shown in Chart 3.View full abstractDownload PDF (675K) -
MASANORI SOMEI, SATOMI INOUE, SHOICHI TOKUTAKE, FUMIO YAMADA, CHIKARA ...1981 Volume 29 Issue 3 Pages 726-738
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious 1-hydroxyindoles carrying a nitro, methoxycarbonyl, or benzyloxy group at the 4 position were prepared by the controlled reduction of 6-substituted trans-β-dimethylamino-2-nitrostyrenes with either aqueous titanium (III) chloride or zinc in aqueous ammonium chloride. The stability of 4-substituted 1-hydroxyindoles decreased in the following order : 4-nitro-»4-methoxycarbonyl->4-benzyloxy-1-hydroxyindole. This result clearly indicates that an electron-withdrawing group at the 4-position can stabilize the 1-hydroxyindole structure. It was also found that 4-hydroxy-and 4-benzyloxy-indole were readily accessible by the reduction of 6-benzyloxy-2-nitrophenyl acetaldehyde. A unique route to 4-or 7-aminoindole from cinnoline is also described.View full abstractDownload PDF (1428K) -
YASUMITSU TAMURA, MASANOBU FUJITA, LINGCHING CHEN, KYOJI UENO, YASUYUK ...1981 Volume 29 Issue 3 Pages 739-743
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of the thallium (I) salt of ethyl 1, 4-dihydro-4-oxopyridine-3-carboxylates with alkyl halides was shown to be a useful method for the regioselective N-alkylation of these compounds.View full abstractDownload PDF (585K) -
KOICHIRO YAMADA, MUNEYOSHI IKEZAKI, NORIHIDE UMINO, HISAO OHTSUKA, NOB ...1981 Volume 29 Issue 3 Pages 744-753
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a series of phenylethanolamine β-stimulants, transformation of hydroxyl groups of the catechol type into those of the resorcinol type has been reported to improve the bioavailability. Therefore, five possible positional isomers (1-5) of trimetoquinol (TMQ) with respect to its 6, 7-dihydroxyl groups were synthesized and tested for bronchodilating activity. Among these positional isomers, the 5, 7-dihydroxyl derivative (4) exhibited more potent bronchodilating activity and longer duration of activity than (±)-TMQ and isoproterenol on intraduodenal administration.View full abstractDownload PDF (1224K) -
TOYO KAIYA, NAOHIRO SHIRAI, JINSAKU SAKAKIBARA, YOICHI IITAKA1981 Volume 29 Issue 3 Pages 754-758
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 3, 6-diacetate (3) of grayanotoxin-II (1), a diterpene isolated from Leucothoe grayana, was treated with lead tetraacetate to afford 1, 3, 6-triacetyl-1 (R), 6 (R)-grayanol (4.) The structure of 4 was established by spectroscopic means and X-ray analysis of the ethylidene derivative (5). Alkaline hydrolysis of 4 gave a ketal (7).View full abstractDownload PDF (606K) -
EIKO OHTSUKA, TOSHIAKI WAKABAYASHI, MORIO IKEHARA1981 Volume 29 Issue 3 Pages 759-765
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Protected 2'-O-(o-nitrobenzyl) nucleosides have been used as condensing units with protected nucleoside 3'-phosphates. After formation of the 3'-5'linkage, the 3'-hydroxyl group of the dinucleoside monophosphate was phosphorylated by treatment with ether p-chlorophenyl phosphate plus DCC or p-chlorophenyl phosphoroditriazolide. The dinucleotide was further elongated in the 3'-direction by condensation with the N-and 2'-O-protected nucleosides followed by phosphorylation. Protected C-Gp and C-A-Up were prepared by this procedure. The trimer was used in the synthesis of hexamer C-A-U-A-A-C by condensation with the 3'-O-(o-nitrobenzyl)-containing trimer block. This hexamer corresponds to the bases 35 to 40 of E. coli tRNAMetf, which are located in the anticodon loop. A trimer containing uridine in the middle position has also been synthesized by this method in combination with an extraction procedure for the intermediate to permit rapid isolation.View full abstractDownload PDF (866K) -
TAKASHI HARAYAMA, MUNEO TAKATANI, ATSUO YAMANAKA, HIROKO IKEDA, MIDORI ...1981 Volume 29 Issue 3 Pages 766-772
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRegioselective intramolecular aldol condensations of type I dialdehydes were explored under various reaction conditions, including those of the Woodward and the Corey methods. The results obtained by the use of excess morpholine-camphoric acid are given in Table I in comparison with those obtained by the previous methods. The structure assignments of products by nuclear magnetic resonance analysis are also described.View full abstractDownload PDF (788K) -
TAKAO MURAKAMI, NOBUTOSHI TANAKA, HIDEKI IIDA, YOICHI IITAKA1981 Volume 29 Issue 3 Pages 773-778
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of two isomeric diterpenes, pterokaurene L2, [I], and pteroatisene P2, [III], isolated from Pteris longipes and Pteris purpureorachis, respectively, were elucidated by X-ray crystallographic analysis. The crystal structures were determined by the direct method. The crystal data are : I ; tetragonal, space group P4322, a=12.510 (5), b=12.510 (5), c=22.923 (10) Å, V=3587.5 Å3, z=8, Dx=1.239 g cm-3, III ; orthorhombic, space group P212121, a=14.370 (7), b=20.205 (10), c=12.808 (6) Å, V=3718.8 Å3, z=8, Dx=1.227 g cm-3. The structures of I and III were established to be ent-9, 15α-dihydroxykaur-16-en-19-oic acid and ent-9, 15α-dihydroxyatis-16-en-19-oic acid, respectively.View full abstractDownload PDF (645K) -
MASAHIRO NAGAI, KAZUO IZAWA, SEIJI NAGUMO, NOBUKO SAKURAI, TAKAO INOUE1981 Volume 29 Issue 3 Pages 779-783
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the aerial parts of Gynostemma pentaphyllum MAKINO (Cucurbitaceae), two glycosides were isolated, namely gynosaponin TN-1 (III), C36H62O9·3/2H2O, mp 168-173°, [α]D+34.5°and gynosaponin TN-2 (IV), C42H72O13·1/2H2O, mp 236-240°, [α]D+11.6°. On acid hydrolysis, gynosaponin TN-1 (III) yielded glucose as its sugar moiety and 2α-hydroxypanaxadiol (II), C30H52O4 as an artificial genin, while gynosaponin TN-2 (IV) afforded rutinose and II. The structure of II was elucidated to be 20, 25-epoxydammarane-2α, 3β, 12β-triol on the basis of its mass spectrum, molecular optical rotation and nuclear magnetic resonance (NMR) spectra (1H, 13C) in comparison with those of panaxadiol (I). Carbon 13 NMR spectra of III and IV indicated that their aglycone moiety has a (20S)-dammar-24-en-20-ol partial structure. Their chemical structures were established as (20S)-dammar-24-ene-2α, 3β, 12β, 20-tetraol 20-O-β-D-glucopyranoside (III) and (20S)-dammar-24-ene-2α, 3β, 12β, 20-tetraol 20-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (IV).View full abstractDownload PDF (698K) -
HIROKAZU TANIGUCHI, TOMOHIKO YOSHIDA, TSUNEO KOBAYASHI, SABURO NAKANO1981 Volume 29 Issue 3 Pages 784-788
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA sensitive fluorometric method for the determination of primary aromatic amines is described. The procedure consists of diazotization of the amino group followed by coupling with 4-methoxy-m-phenylenediamine (MPD), and reaction of the resulting azo compound with ammoniacal cupric sulfate. By this reaction, primary aromatic amines are derivatized to intensely fluorescent compounds, and a method for the determination of p-aminobenzoic acid (PABA) was established. A linear relationship was observed between the PABA concentration and the fluorescence intensity in the range of 0.001-1.0 μg/ml. The proposed method is applicable to the determination of other primary aromatic amines.View full abstractDownload PDF (562K) -
JUNKO SEKI, YOSHIHIRO ARAKAWA, KAZUHIRO IMAI, ZENZO TAMURA, SHOHEI YOS ...1981 Volume 29 Issue 3 Pages 789-795
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple, accurate and reliable method for the simultaneous measurement of L-3, 4-dihydroxyphenylalanine (L-DOPA) and its metabolites, dopamine (DM), 3, 4-dihydroxyphenylacetic acid (DOPAC) and homovanillic acid (HVA), excreted in the urine after oral administration of L-DOPA was developed. The method consists of the addition of internal standards to urine samples, high-performance liquid chromatography for 50 min on a column of sulfonated polystyrene, detection of DOPAC, p-hydroxyphenylacetic acid (an internal standard) and HVA by UV absorbance measurements and detection of DOPA, 3, 4-dihydroxybenzylamine (an internal standard) and DM by measurements of fluorescence generated by the reaction with o-phthaldialdehyde. L-DOPA was administered to patients with Parkinson's disease, control patients and normal subjects, and urine samples were collected 0, 2, 4 and 6 hr later. DOPA and metabolites were measured by this method. The excretion patterns in control patients and normal subjects were quite similar to each other and the maximum excretions of these compounds were observed mostly in 0-2 hr urine, whereas in patients with Parkinson's disease the patterns varied and the excretions of all the compounds were delayed in 11 out of 13 patients.View full abstractDownload PDF (734K) -
HIROSHI MIYAZAKI, MASATAKA ISHIBASHI, KOUWA YAMASHITA, MAKOTO YAKUSHIJ ...1981 Volume 29 Issue 3 Pages 796-803
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-Methoxytyramine, dopamine, norepinephrine, epinephrine and 6-hydroxydopamine were derivatized to their N-trifluoroacetyl-O-dimethyl-n-propylsilyl ether or 2'-O-methyl-N-trifluoroacetyl-O-dimethyl-n-propylsilyl ether derivatives by treatment with trifluoroacetic anhydride, methanol and then dimethyl-n-propylsilyl imidazole. These derivatives could be separated completely by gas chromatography (GC) on a non-polar liquid stationary phase such as OV-101. In addition, these derivatives were very stable in benzene and ethyl acetate, and showed excellent stability during silica gel column chromatography in comparison with the corresponding trimethylsilyl ether derivatives. In GC-mass spectrometry (MS) of these derivatives, ammonia chemical ionization (CI)-MS provided the ion [M+NH4]+ as the base peak or an intense peak. The detection limit of the dopamine derivative in the CI mode with ammonia was 2 pg with S/N at 2 : 1.View full abstractDownload PDF (794K) -
CHIAKI MORIWAKI, HIROYUKI FUJIMORI1981 Volume 29 Issue 3 Pages 804-809
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe influence of hog pancreatic kallikrein and kinin on the transport of amino acids or glucose across the rat small intestine was further examined by the in vitro everted sac method and by the in situ mesenteric perfusion technique. Absorption of methionine and glucose into the vascular system was significantly enhanced, as was that of valine, by intra-luminal administration of kallikrein. Transport of methionine, valine and glucose was also enhanced by addition of bradykinin to the serosal fluid of the everted intestine, but no enhancement of glutamic acid transport was observed under the same conditions. The stimulation of in vitro valine transport by kallikrein was inhibited by aprotinin. Valine transport was not affected by addition of trypsin, plasmin or kallikrein to the serosal side, whereas it was significantly increased by addition of 0.01 KU of kallikrein together with 10 μg of kininogen to the serosal side. Valine transport was reduced under anaerobic conditions or by removal of the intestinal epithelial layer. Ouabain or 2, 4-dinitrophenol also inhibited the intestinal transport of valine. Under these conditions (except for ouabain treatment), valine transport was not enhanced by addition of bradykinin to the serosal side. In ouabain-treated intestine, however, bradykinin increased valine transport approximately 1.5 times compared with the control, but the transport was not restored to the normal level. Meanwhile, valine absorption was decreased to about 40% of the normal value by in situ infusion of 1.0 mM ouabain into the mesenteric vascular system, and the rate was restored to the normal level by intra-luminal administration of kallikrein.View full abstractDownload PDF (694K) -
MASAMI ISHIDA, YOSHIHARU MACHIDA, NAOKI NAMBU, TSUNEJI NAGAI1981 Volume 29 Issue 3 Pages 810-816
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe present study was intended to develop a new oral mucosal dosage form with a view to solving the problems of the administration of insulin by injections. We prepared a potentially suitable dosage form and tested it in beagle dogs. The new oral mucosal dosage form of insulin consists of the core-base, which contains cacao butter, insulin and additive, and the peripheral-base, which contains a mixture of hydroxypropyl cellulose-H (HPC) and Carbopol-934 (CP). The suitable mixing ratio of HPC and CP in the peripheral-base was chosen as 1 : 2 on the basis of experimental results concerning the stickiness, dissolution properties, viscosity and fracture resistance. This dosage form could stick tightly to the oral mucosa of beagle dogs for 6 hr. The change of blood sugar and plasma insulin levels in beagle dogs was investigated by the three-way crossover method with group A as a reference, group B given insulin alone and group C given insulin and sodium glycocholate. Absorption of insulin was recognized only in group C, indicating that sodium glycocholate effectively promoted the absorption of insulin from the oral mucosa. The percentage absorbed of insulin in this dosage form was about 0.5% compared with the amount absorbed upon intramuscular injection of insulin.View full abstractDownload PDF (843K) -
KOICHIRO HIRANO, TERUHISA ICHIHASHI, HIDEO YAMADA1981 Volume 29 Issue 3 Pages 817-827
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe absorption characteristics and kinetics of practically water-insoluble drugs following intramuscular injection of their aqueous suspensions were investigated by the local clearance method in the m. gastrocnemius of the rat. The plot of the cube root of the residual fraction of the drug in the injection site versus time gave a good straight line. Between the absorption rate constant (j) and the initial drug concentration (C0) or injection volume (V0), the relationship j∝C0g V0h was observed experimentally (g=-0.55 and h=-0.32). Comparison of j values among various compounds having different solubilities in saline (Cs') but similar colloidal properties (particle size distribution and sedimentation volume) showed that a plot of log j against log Cs'gave a linear relationship with a slope close to 0.5. The absorption rate constant (j) increased with decreasing particle size on condition that the other colloidal properties changed little. This increase was remarkable in the region of mean particle diameter (Dss) less than 2-3 μm, while it was gradual or slight in the region above this. The results could be explained by a kinetic model in which the dissolution (diffusion) process from the particle agglomerate formed by injection was assumed to be a rate-limiting step for the drug absorption. The effect of the type or concentration of the macromolecular dispersing agent was also examined in detail.View full abstractDownload PDF (1219K) -
YASUYUKI TAKAHASHI, NAOKI NAMBU, TSUNEJI NAGAI1981 Volume 29 Issue 3 Pages 828-833
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInteractions between phenothiazines and pectin in aqueous solution were studied by the equilibrium dialysis method, in order to investigate the relation between binding parameters and drug properties. Scatchard plots were not linear for water-soluble drugs such as promazine hydrochloride, triflupromazine hydrochloride, and so on, and thus the number of binding sites of pectin was considered to be more than two. On the other hand, it was impossible to obtain the γ value (mol of drugs bound per mol of pectin) on Scatchard plots for such slightly soluble drugs as levomepromazine maleate, perazine dimaleate and prochlorperazine dimaleate at higher concentrations. Therefore the data were analyzed simply by assuming that they gave a linear plot. The maximum binding number was significantly larger than the values already reported. A good positive correlation was observed between the binding parameters and adsorption parameters related to hydrophobicity. Among drugs having the same side chain at the 10-position but different substituents at the 2-position, the maximum binding number increased with the bulkiness of the substituents. The micelle formation of phenothiazines was shown to be related to the interaction and also to the formation of coprecipitate.View full abstractDownload PDF (663K) -
KOICHIRO HIRANO, TERUHISA ICHIHASHI, HIDEO YAMADA1981 Volume 29 Issue 3 Pages 834-843
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe intramuscular absorption characteristics and kinetics of practically water-insoluble drugs, which were solubilized in water with nonionic surfactants, were studied by the local clearance method in the m. gastrocnemius of the intact rat. The solubilized drugs were absorbed approximately according to 1st order kinetics. Their absorption rates were controlled by the distribution coefficient (K, micellar phase/water phase) as well as the injection volume (V0) and the surfactant concentration (Cs0), but depended little on the vehicle viscosity under the present experimental conditions. A model, based on the assumptions that the drug is distributed instantaneously between the micellar and water phases in the depot and that the drug molecules in both phases are transported into the vascular systems by diffusion at different rates, was proposed to account for the kinetic features of the process. It predicted that the plot of the 1st order absorption rate constant (k) against 1/Cso or 1/K would be approximately linear when the injection volume was fixed, the surfactant absorption was very slow, and the contribution of the drug entrapped in micelles to the absorption was much smaller than that of the free drug. The experimental results agreed well with these predictions, except for the systems of very high surfactant concentration. Experimentally, k was inversely proportional to V01/3 and this was explained reasonably by the model.View full abstractDownload PDF (1025K) -
TOSHIO SUZUKI, ETSUKO SATO, KOZO GOTO, YUKO KATSURADA, KATSUO UNNO, TO ...1981 Volume 29 Issue 3 Pages 844-848
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMitomycin C, daunomycin and adriamycin, three potent cancer chemotherapeutic agents, were linked to immunoglobulins by the cyanogen bromide method and the conjugates were separated on Sepharose 6B. The most suitable conditions for binding of the drug to the antibody, while retaining both antibody and drug activity, included the use of 25-50 mol of cyanogen bromide per mol of IgG at pH 11 for the activation of immunoglobulin. The extent of substitution in this preparation was about 1 mol of drug per mol of IgG. This conjugate might be considered as a sustained release form of the antitumor agent.View full abstractDownload PDF (597K) -
SHIRO MORIMOTO, NORIFUMI NAKAMURA, ATSUKO FUKUHARA, RYOKO ABE, YASUO M ...1981 Volume 29 Issue 3 Pages 849-854
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA centrifugation study was carried out to investigate the subcellular localization of renin in the mouse kidney cortex. Renin activity was radioimmunoassayed and found mainly in the heavy mitochondrial fraction, with very little in the microsomal fraction, by differential centrifugation. Upon discontinuous sucrose density gradient centrifugation, renin granules were recovered mainly in the fraction corresponding to 1.5 м sucrose, while most of the mitochondria, lysosomes and microsomes equilibrated in the upper fractions. This renin granular fraction contained 53% of the total granular renin activity and had a specific activity 3.2 times that found in the unfractionated homogenate. After recentrifugation of the renin granular fraction, most of the renin activity was recovered in the sediment. Repeated freezing and thawing of this fraction resulted in an increase of renin activity, showing structure-linked latency. On the basis of these findings, it is assumed that renin in the mouse kidney cortex is located in granules which have a higher density than other subcellular particulates such as mitochondria, lysosomes and microsomes.View full abstractDownload PDF (778K) -
SHUICHI MIYAURA, YOSHIFUMI MATSUDA, KEIKO YAMAGUCHI, HIROSHI MORIYA1981 Volume 29 Issue 3 Pages 855-860
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAntiserum against purified human urinary kallikrein (HUK) found to be a homogeneous preparation by disc electrophoresis was produced in rabbits. However, this antiserum was found to react slightly with some serum protein components, such as albumin or albumin-like protein, as well as HUK. It is conceivable that some small amount of serum protein detectable only by the immunochemical method was contained in the electrophoretically homogeneous HUK. Although a trace amount of serum protein contained in the purified HUK could not be completely removed by physicochemical procedures, highly purified homogeneous HUK was successfully obtained by the application of affinity absorption treatment using anti-human whole serum. Both in immunodiffusion and in immunoelectrophoresis, antiserum against this preparation gave only one line of precipitin with the crude or the finally purified HUK and no line with human whole serum. Our antiserum was found to be immunochemically monospecific.View full abstractDownload PDF (1014K) -
KAZUKO KIDO, YASUO WATANABE1981 Volume 29 Issue 3 Pages 861-862
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of N-[α-(3, 4-dimethoxybenzyl)-3, 4-dimethoxybenzyl] aminoacetal (1) or its oxalate with chlorosulfonic acid at low temperature gave isopavine (3) in extremely good yield.View full abstractDownload PDF (347K) -
TETSUZO KATO, TAKUO CHIBA, TAKESHI SHIMIZU, HITOSHI TAKAHASHI1981 Volume 29 Issue 3 Pages 862-866
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of diketene with cyanamide gave 2-amino-6-methyl-4H-1, 3-oxazin-4-one, which was transformed to 6-methyluracil by refluxing it in acetic acid. Diketene also reacted with monosubstituted cyanamides to give 1, 3-oxazin-4-one derivatives, which could be similarly converted into 1-substituted 6-methyluracils. The reaction of diketene with dicyanodiamide afforded 2-guanidino-6-methyl-4H-1, 3-oxazin-4-one, which, on treatment with ammonia, afforded 2-guanidino-4-hydroxy-6-methylpyrimidine.View full abstractDownload PDF (615K) -
TAKAO MURAKAMI, TSUYOSHI KIMURA, HIROSHI WADA, NOBUTOSHI TANAKA, YASUH ...1981 Volume 29 Issue 3 Pages 866-868
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Polystichum tripteron (KUNZE) PR. a new norcarotenoid glycoside was isolated and shown to be (6R, 7E, 9R)-9-hydroxy-megastigma-4, 7-dien-3-one-9-O-β-D-glucoside. The fronds of Dennstaedtia wilfordii (MOORE) CHRIST. contain the same glucoside.View full abstractDownload PDF (488K) -
KOZO ISHIZAKI, NARIKO SHINRIKI, AKIRA IKEHATA, TOHRU UEDA1981 Volume 29 Issue 3 Pages 868-872
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe degradation of nucleobases, ribonucleosides and ribonucleotides with ozone was examined as a model of the action of ozone on nucleic acids. The degradation rates of nucleobases were in the following order : G, T>U>C>A. Nucleosides and nucleotides were degraded in the same order as in the corresponding nucleobases. The ribose moiety was degraded more slowly than the base portion in nucleosides and nucleotides except in the cases of adenosine and AMP. The degradation of D-ribose and D-ribose-5-phosphoric acid (R5P) was also examined, and it was found that R5P resisted the attack of ozone. Inorganic phosphate was liberated after the degradation of the ribose moiety.View full abstractDownload PDF (635K) -
TSUNEO SADANAGA, KOZO HIKIDA, KATSUNOBU TAMETO, MICHIO NAKANISHI, YOSH ...1981 Volume 29 Issue 3 Pages 872-874
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple high-performance liquid chromatographic method for the determination of sulthiame, N-(4'-sulfamoylphenyl)-1, 4-butanesultam, in plasma is described. The method permits the accurate determination of the drug in plasma at concentrations as low as 150 ng/ml and is suitable for monitoring the drug in the therapeutic dose range and for investigation of the bioavailabilities of preparations of the drug.View full abstractDownload PDF (432K) -
SHINYA SHIBUTANI, TETSURO NAGASAWA, HIKOKICHI OURA, GENICHIRO NONAKA, ...1981 Volume 29 Issue 3 Pages 874-878
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIntraperitoneal administration of the extract from Paeoniae Radix decreased the urea-nitrogen (BUN) concentration in rat serum. An attempt was made to extract and purify the active components, monitoring the BUN-decreasing activity. The acetone fraction from Paeoniae Radix decreased BUN concentration. After partition between ethyl acetate (EtOAc) and water, BUN-decreasing activity was detected in the EtOAc fraction. Further purification was carried out by Sephadex LH-20 column chromatography, and 1, 2, 3, 4, 6-penta-O-galloyl glucose, (+)-catechin, and gallic acid were purified from the EtOAc fraction. (+)-Catechin and gallic acid showed no activity. It became clear that one of the BUN-decreasing components from Paeoniae Radix was 1, 2, 3, 4, 6-penta-O-galloyl glucose, which is a typical tannin of the gallotannins.View full abstractDownload PDF (570K) -
YOSHIHIRO NISHIKAWA, KIMIHIRO YOSHIMOTO, MASANORI OHKAWA1981 Volume 29 Issue 3 Pages 878-880
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAnomerically pure, synthetic 1-O-lauroyl-α-and-β-D-glucopyranoses exhibited strong plant growth inhibiting activity in the Avena coleoptile straight growth test at a final concentration of 500/3 ppm. The growth inhibition ratios obtained with α-and β-anomers were 94.2% and 81.6%, respectively. Under the same conditions, 2-O-and 4-O-lauroyl-D-glucopyranoses and the mono-, di-, and poly-substituted products obtained by selective lauroylation of maltose were all found to be ineffective. In view of these results, the presence of a lauroyl function, either axial or equatorial, at the C-1 position of a monosaccharide unit appears to be important for this biological activity.View full abstractDownload PDF (470K) -
YOSHIHIRO NISHIKAWA, KIMIHIRO YOSHIMOTO, KUMIKO ASHIZAWA, TETSURO IKEK ...1981 Volume 29 Issue 3 Pages 880-883
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-O-, 3-O-, and 6-O-acyl-D-glucopyranoses carrying capryloyl, lauroyl, myristoyl, palmitoyl, and stearoyl functions were tested for their in vivo and in vitro antitumor effects against Ehrlich ascites carcinoma in mice and a leukemia cell line L-5178Y by the total packed cell volume method and the tissue culture method, respectively. In the in vivo bioassay, the 1-and 3-myristate and the 6-stearate were moderately effective, while all other compounds exhibited little or no effect. These samples inhibited the growth of the cultured leukemia cells to various extents : relatively lower ID50 values were obtained with the 1-laurate, 1-myristate, 1-palmitate, 3-myristate, and 6-laurate. On the basis of these findings, the monoesters of monosaccharide appear to be less promising as antitumor agents than the analogous derivatives of disaccharide.View full abstractDownload PDF (567K) -
SHOZO MIYAZAKI, MIDORI OSHIBA, TANEKAZU NADAI1981 Volume 29 Issue 3 Pages 883-886
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dissolution properties of hydrochloride, sulfate, and iodide salts of berberine were compared. The apparent solubility and dissolution rate of the hydrochloride salt were less than those of the sulfate salt in media resembling GI fluids with respect to pH. The common ion effect on the solubility of berberine hydrochloride was also investigated.View full abstractDownload PDF (504K) -
HISASHI ICHIBAGASE, YORISHIGE IMAMURA, KAZUNORI SHIOZU1981 Volume 29 Issue 3 Pages 887-891
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of diphenhydramine on the intestinal absorption of sulfisomidine was investigated in rabbits. Diphenhydramine significantly reduced the mean blood sulfisomidine concentrations at 0.5 and 1.0 hours. In addition, diphenhydramine altered the maximum blood concentration (Cmax) and the time taken to reach the maximum blood concentration (Tmax) of sulfisomidine from 103.6±3.2 to 87.2±7.5μg/ml and from 1.1±0.2 to 2.1±0.5 hour, respectively. However, diphenhydramine was found to have little effect on the area under the blood concentration-time curve (AUCo-∝) or on the elimination half-life (t1/2) of sulfisomidine. Diphenhydramine also increased the amount of phenol-red remaining in the rabbit stomach from 26.8±4.1 to 46.5±4.5%. These results indicate that diphenhydramine decreases the rate but not the extent of sulfisomidine absorption by delaying the gastric emptying.View full abstractDownload PDF (615K) -
Some Structure-Activity Relationships for Bactobolin Analogs in the Treatment of Mouse Leukemia P388TOMOHIKO MUNAKATA, TAKEKI OKUMOTO1981 Volume 29 Issue 3 Pages 891-894
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBactobolin, (3S, 4R, 4aR, 5R, 6R)-4-(L-alanylamino)-3-(dichloromethyl)-3, 4, 4a, 5, 6, 7-hexahydro-5, 6, 8-trihydroxy-3-methyl-1H-2-oxa-1-naphthalenone, is an antitumor antibiotic produced by Pseudomonas. In the present studies, 14 bactobolin analogs with or without substituents on the amino group attached to the 4 position of the bactobolin nucleus were synthesized and evaluated for activity against mouse leukemia P388. These compounds were given intraperitoneally to mice bearing ascitic leukemia P388. Compounds with the L-seryl group and some L-alanine derivatives on the amino group were found to possess antileukemic activity, but at the dose levels tested, they were neither more effective nor more potent than bactobolin which increased the lifespan of leukemic mice by 110% over the control at an optimal dose of 2.5 mg/kg/day. The other analogs examined were found to be ineffective and nonlethal for mice at doses of 10 mg/kg/day or less. The structure-activity relationships for bactobolin analogs are discussed.View full abstractDownload PDF (540K) -
ICHIRO YOKOE, KYOKO HIGUCHI, YOSHIAKI SHIRATAKI, MANKI KOMATSU1981 Volume 29 Issue 3 Pages 894-898
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation of flavonols (1) in methanol gave 3-arylphthalides (3) which were formed via the diketones (4). Metal ions (Cu2+, Ni2+, Fe3+, Co2+ and Be2+) inhibited this rearrangement.View full abstractDownload PDF (540K) -
JUNICHI GOTO, SAKAE KOMATSU, NOBUHARU GOTO, TOSHIO NAMBARA1981 Volume 29 Issue 3 Pages 899-901
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new sensitive derivatization reagent for use in liquid chromatographic separation of hydroxyl compounds has been developed. A suitable reagent for this purpose, 4-dimethylamino-1-naphthoyl nitrile, was readily prepared from the corresponding acid chloride by the exchange reaction with trimethylsilyl cyanide. Condensation of a hydroxyl compound with the reagent was effected in the presence of triethylamine under the mild condition. The resulting ester was highly responsible for a fluorescence detector with a detection limit of 200 pg.View full abstractDownload PDF (456K) -
TAKESHI IMANISHI, AKIRA NAKAI, NORIYUKI YAGI, MIYOJI HANAOKA1981 Volume 29 Issue 3 Pages 901-903
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel and convenient total synthesis of (±)-cleavamine (1) starting from ethyl 1, 6-dihydro-3 (2H)-pyridinone-1-carboxylate (2) is described.View full abstractDownload PDF (424K) -
SUGURU TAKATSUTO, BAIPING YING, MASUO MORISAKI, NOBUO IKEKAWA1981 Volume 29 Issue 3 Pages 903-905
Published: March 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS28-Norbrassinolide (2α, 3α, 22R, 23R-tetrahydroxy-B-homo-7-oxa-5α-cholestan-6-one), which is an analog of the plant growth promoting steroidal lactone, brassinolide, was synthesized via 22R, 23R-dihydroxycholesterol. Syntheses of the other C-22, 23 stereoisomers of 22, 23-dihydroxycholesterol were also described.View full abstractDownload PDF (425K)
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