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Volume 28, Issue 5
Displaying 1-47 of 47 articles from this issue
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HIROSHI KIWADA, KAZUO TAKAMI, YURIKO KATO1980 Volume 28 Issue 5 Pages 1351-1356
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(α-Bromoisovaleryl) urea has two polymorphic forms (I and II : leaflet crystals and needle crystals, respectively) but another form (III) of fine crystals, which shows different transition and melting properties from the conventional forms, was found in commercial (α-bromoisovaleryl) urea of JP grade. These fine crystals are transformed to parallelogramic plates at about 110° and melt at 142°. Suitable conditions for the preparation of form III were examined and its properties were studied. Form III was obtained as columnar crystals from methanol on standing for 2 days at -20°. The crystals are very fragile and show an X-ray diffraction pattern and infrared spectrum different from those of the conventional polymorphs. The transition and melting properties of these columnar crystals are the same as those of the fine crystals found in commercial (α-bromoisovaleryl) urea. It was found that form III is more stable at 4° or below than the conventional leaflet crystals (form I), though the relative stability of these polymorphic forms is reversed at room temperature.View full abstractDownload PDF (857K) -
FUMIYOSHI ISHIKAWA, YOSHIFUMI WATANABE, JUNJI SAEGUSA1980 Volume 28 Issue 5 Pages 1357-1364
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of aryl-or aralky-substituted 2-amino-3, 4-dihydroquinazolines and related compounds were synthesized. The compounds were evaluated for inhibitory activity towards collagen-and ADP-induced aggregation of rat blood platelet in vitro and ex vivo. A group of 3-benzyl-substituted derivatives had potent activity. The structure-activity relationships are discussed.View full abstractDownload PDF (830K) -
MACHIKO MATSUBARA, HISATORA KURODA1980 Volume 28 Issue 5 Pages 1365-1373
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe compositional changes of free amino acids in germinating conidia of Cochliobolus miyabeanus and the origin of the predominant acid in the conidia were studied. Through all stages of germination, the predominant component in free amino acid pools of the conidia was glutamine. The experimental results on the metabolism of protein and carbohydrate in the conidia suggested that proteolytic products of alkali-soluble protein served as the nitrogen source for glutamine generation, while trehalose, which was consumed rapidly from the commencement of conidial germination, did not provide the carbon skeleton of the accumulated glutamine, but was catabolized to CO2 through the hexose monophosphate pathway and the tricarboxylic acid cycle.View full abstractDownload PDF (934K) -
MASAFUMI FUJIMOTO, YUJI TSUKINOKI, KATSUMI HIROSE, KENTARO HIRAI, TADA ...1980 Volume 28 Issue 5 Pages 1374-1377
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPeptido-aminobenzophenones exhibit potent central nervous system activities similar to those of benzodiazepines in experimental animals, despite their lack of the diazepine skeleton. These compounds have low affinity for benzodiazepine receptors, but are converted into compound (s) having high affinity for the receptors by incubation with crude synaptosomes from rat brains or rat liver homogenates. This conversicn seems to involve an enzymatic process, because it is temperature-dependent and stereospecific. The results suggest that peptido-aminobenzophenones show their pharmacological activities through conversion into benzodiazepine (s) in vivo.View full abstractDownload PDF (477K) -
MASAFUMI FUJIMOTO, YUJI TSUKINOKI, KATSUMI HIROSE, KAZUO KURUMA, RYUSE ...1980 Volume 28 Issue 5 Pages 1378-1386
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn the present work we attempted to detect and quantitate central nervous system (CNS)-active benzodiazepines in rat brain after administration of a peptido-aminobenzophenone. The results can be summarized as follows. 1. Radioreceptorassay (RRA) using 3H-diazepam as the labeled ligand and ratbrain crude synaptosomes was a simple, reliable and sensitive assay method for benzodiazepines. 2. A benzene extract of a rat brain homogenate prepared 15 min after i.p. administration of 2-o-chlorobenzoyl-4-chloro-N-methyl-N'-glycylglycinanilide (1) was subjected to high pressure liquid chromatography (HPLC). By RRA analysis of the eluted fractions, four benzodiazepines having high affinity for benzodiazepine receptors were detected. 3. Changes in the levels of each benzodiazepine in rat brains after i.p. administration of 1 were determined by a combination of HPLC and RRA. The levels can account for the CNS activities of 1. 1 itself could not be detected throughout the experiments. These results strongly indicate that 1 exerts its CNS activities through conversion into CNS-active benzodiazepines in vivo.View full abstractDownload PDF (810K) -
YASUTAKA NAGAI, KATSUHIKO HINO, HITOSHI UNO, SHINSAKU MINAMI1980 Volume 28 Issue 5 Pages 1387-1393
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe title compounds (19) were synthesized by rearrangement of the 1-ethoxycarbonyl-4-aryl-3, 4-epoxypiperidines (7) to give the 3-aryl-3-formylpyrrolidine derivatives (12) for pharmacological testing. Compound (19b) exhibited moderate central nervous system depressing activity. The mechanism of the rearrangement of 1-substituted 4-aryl-3, 4-epoxypiperidine with boron trifluoride etherate is discussed.View full abstractDownload PDF (793K) -
FUMIYOSHI ISHIKAWA1980 Volume 28 Issue 5 Pages 1394-1402
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-(2, 2-Disubstituted ethenyl-and ethyl)-2-imidazoline derivatives (11, 14) were prepared by direct cyclization of active intermediates, 3, 3-disubstituted acrylimidic ethyl esters (9, 10), with ethylenediamine. The stereoisomers, (Z)-and (E)-3-phenyl-3-pyridylacrylic acid esters (6c-e), nitriles (7c-e) and amides (8c-e), as well as (Z)-and (E)-3-phenyl-3-pyridylacrylimidic acid esters (10c-e), and (Z)-and (E)-2-(2-pyridylethenyl)-2-imidazolines (11c-e), were isolated. Their structures are discussed. Compounds 11 and 14 showed potent hypoglycemic activity.View full abstractDownload PDF (927K) -
SHENGCHIH CHEN, HIROSHI NAKAMURA, ZENZO TAMURA1980 Volume 28 Issue 5 Pages 1403-1407
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAfter oral administration of fluorescein to rabbits and human subjects, the urinary metabolites were examined. Two new metabolites, fluorescin and fluorescin monoglucuronide, were identified in addition to the main metabolite, fluorescein monoglucuronide. In both conjugates, glucuronic acid was found to be linked to a phenolic OH group iva an ether bond.View full abstractDownload PDF (540K) -
SUMIRO ISODA, HITOSHI YAMAGUCHI, YOSHINARI SATOH, TOSAKU MIKI, MIYOSHI ...1980 Volume 28 Issue 5 Pages 1408-1414
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour aza analogs of 4-aminomethylbenzoic acid (1) were prepared as part of a search for new antiplasmin drugs. 5-Aminomethylpyridine-2-carboxylic acid (5) was prepared by the hydrogenation of methyl 5-cyanopyridine-2-carboxylate (4), followed by alkaline hydrolysis. Similarly, 6-aminomethylpyridine-3-carboxylic acid (7) was prepared from ethyl 6-cyanopyridine-3-carboxylate (6). 5-Aminomethylpyrimidine-2-carboxylic acid (12) was obtained from methyl 5-methylpyrimidine-2-carboxylate (8) via the phthalimido derivative (10). 2-Aminomethylpyrimidine-5-carboxylic acid (25) was obtained by the reaction of benzyloxycarbonylaminoacetamidine (22) with ethoxycarbonylmalonaldehyde (18) in acetic acid, followed by deblocking of the protected groups. Treatment of benzoylaminoacetamidine (14) with acetylacetone (15) in acetic acid provided 2-benzoylaminomethyl-4, 6-dimethylpyrimidine (16), whereas in the presence of K2CO3, 2-amino-3-benzoylamino-4, 6-dimethylpyridine (17) was obtained together with a trace of 16. No compound showed more potent antiplasmin activity than tranexamic acid (2), but 5 was more active than 1.View full abstractDownload PDF (800K) -
HARUHISA UEDA, TSUNEJI NAGAI1980 Volume 28 Issue 5 Pages 1415-1421
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA structural study of the inclusion compounds of tolbutamide and chlorpropamide with β-cyclodextrin in aqueous solution was attempted by means of proton nuclear magnetic resonance (1H-NMR) and carbon-13 nuclear magnetic resonance (13C-NMR) experiments. The changes in chemical shift (1H, 13C) and in relaxation times (1H-T1p, 13C-T1) suggested that the drug phenyl moiety was included in the cavity of β-CD mainly by hydrophobic interaction, and that the primary hydroxy side of β-CD was tightly associated with each drug. The binding mechanism and binding sites between the drug molecules and β-CD are discussed in detail.View full abstractDownload PDF (662K) -
HIDENORI IWAMOTO, NORIYOSHI INUKAI, ISAO YANAGISAWA, YOSHIO ISHII, TOS ...1980 Volume 28 Issue 5 Pages 1422-1431
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS16 (S)-Methyl-20-methoxy-PGE2 (YPG-209) (Is), 16 (R)-methyl-20-methoxy-PGE2 (IR) and several analogs, such as 16 (S)-methyl-20-methoxy-PGA2 (XIIIs) and -PGB2 (XIVs), 16-methyl-20-ethoxy-PGE2 (XXVIIa), 16-methyl-20-hydroxymethyl-PGE2 (XXVIa), 16-methyl-17-oxa-ω-dihomo-PGE2 (XXVIIIa) and 20-hydroxymethyl-PGE2 (XXX), were synthesized by Corey's procedure and their biological activities were investigated. Among these derivatives, IS and IR possessed potent oral bronchodilator activity ; the bronchoselectivity of IS was higher than that of IR.View full abstractDownload PDF (1089K) -
AKIRA YAGI, NOBUTAKA TOKUBUCHI, TOSHIHIRO NOHARA, GENICHIRO NONAKA, IT ...1980 Volume 28 Issue 5 Pages 1432-1436
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCompounds I-X were isolated from the water extractive of Cinnamomi Cortex, which shows anti-complement activity. Among them, the structures of I-VI were clarified on the basis of chemical and spectral studies. Compounds I and II were identified as cinnzeylanine and cinnzeylanol, respectively. Compounds III and IV were proved to be dehydrated products of I and II, respectively. Compound V was shown to be 19-hydroxylated IV and was named cinncassiol A. VI was identified as cinncassiol A 19-O-β-D-glucopyranoside.View full abstractDownload PDF (667K) -
TOSHIHIRO NOHARA, TETSUYA KOMORI, TOSHIO KAWASAKI1980 Volume 28 Issue 5 Pages 1437-1448
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA glycoside, mp 209-220° (decomp), [α] D-142°, C47H70O24, named trillenoside A (I), was isolated from the rhizomes of Trillium kamtschaticum PALL (Liliaceae). The structure of its aglycone (designated trillenogenin, II), mp 250-251°, [α] D-198°, C26H36O8, was determined by X-ray crystallographic analysis of the tetraacetyl monobrosyl derivative, mp 242-244° (dec.), [α] D-112°, C40H47BrO14S, and I was characterized as 15-oxo-18-nor-25 R-spirosta-5, 13-diene-1β, 3β, 21, 23α, 24β-pentaol 1-O-β-D-apiofuranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-α-L-arabinopyranoside. I is thus a novel type of steroid glycoside, noteworthy in that the aglycone is an 18-norspirostane derivative having an enone system in the D-ring and hydroxyl groups at C21 and in the F-ring, and also in that the sugar moiety is a branched-chain tetrasaccharide containing apiose.View full abstractDownload PDF (1204K) -
SHIGEYOSHI SAIJO, MASAO WADA, JUNICHI HIMIZU, AKIHIKO ISHIDA1980 Volume 28 Issue 5 Pages 1449-1458
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of (12R, 15S)-(-)-11-deoxy-8-azaprostaglandin E1 ((R)-1a) and three diastereomers ((R)-2a, (S)-1a, and (S)-2a) starting from optically active pyroglutamic acid ((R)-3 and (S)-3) is reported. Esterification of (R)-3 and NaBH4 reduction gave (R)-(-)-5-hydroxymethyl-2-pyrrolidinone ((R)-5). Ethoxyethylation of (R)-5 and Nalkylation with methyl 7-bromoheptanoate, followed by acid treatment, provided (R)-hydroxymethyl pyrrolidinone ((R)-8). The Collins oxidation of (R)-8 gave (R)-(-)-methyl 7-(5-formyl-2-oxo-1-pyrrolidine) heptanoate ((R)-9), which served as a key intermediate. The Wittig reaction of (R)-9 and dimethyl 2-oxoheptylphosphonate gave the (R)-enone ((R)-10a) which was converted to the (12R, 15S)-enol ((R)-11a) and (12R, 15R)-enol ((R)-12a) by NaBH4 reduction. Alkaline hydrolysis of (R)-11a and (R)-12a gave (R)-1a and (R)-2a in high yields. Similarly, the (S)-aldehyde ((S)-9) was prepared from (S)-3 and converted to the (12S, 15S)-acid ((S)-1a) and (12S, 15R)-acid ((S)-2a) by the same sequence of reactions used for the (R)-series. Some (12R, 15S)-acid derivatives ((R)-1b-g) with a modified ω-chain were also synthesized. These analogs ((R)-1b-g) were also prepared from (R)-9 via synthetic sequences similar to that described above.View full abstractDownload PDF (1194K) -
SHIGEYOSHI SAIJO, MASAO WADA, JUNICHI HIMIZU, AKIHIKO ISHIDA1980 Volume 28 Issue 5 Pages 1459-1467
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of 11-deoxy-8, 10-diazaprostaglandin E1 (1a) starting from methyl 3-benzyloxycarbonyl-2-oxo-4-imidazolidinecarboxylate (3a) is reported. Alkylation of 3a with methyl 7-bromoheptanoate and NaH gave methyl 1-benzyloxycarbonyl-3-(6-methoxycarbonyl) hexyl-2-oxo-4-imidazolidinecarboxylate (9), which was converted into the 4-hydroxymethyl-imidazolidine derivative (10). The Moffatt oxidation of 10, and the Wittig reaction of the resulting aldehyde (11) with dimethyl 2-oxoheptylphosphonate provided an enone (12). Reduction of 12, and hydrolysis of a mixture of C15-epimeric alcohols (15) followed by re-esterification afforded 11-deoxy-8, 10-diazaprostaglandin E1 methyl ester (17a). Alkaline hydrolysis of 17a gave 1a as crystals in a good yield. The 10-methyl derivative (2a) was also synthesized. Methylation of 3a with methyl iodide and K2CO3 gave the 1-methylimidazolidine analog (7a), which was converted into methyl 3-(6-methoxycarbonyl) hexyl-1-methyl-2-oxo-4-imidazolidinecarboxylate (20) after debenzyloxycarbonylation and alkylation with methyl 7-bromoheptanoate. Conversion of 20 into 2a was carried out by a synthetic sequence similar to that used for the elaboration of 1a.View full abstractDownload PDF (993K) -
EIICHI IBUKI, SHIGERU OZASA, YASUHIRO FUJIOKA, HIROHIKO KITAMURA1980 Volume 28 Issue 5 Pages 1468-1476
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSeven sexiphenyls, including three new isomers, 3, 4, 3', 4'-tetraphenylbiphenyl (Id), 2, 5, 2', 5'-tetraphenylbiphenyl (IIId), and 2, 2'-di (3-biphenylyl) biphenyl (Vd), were synthesized by Ullmann homo-coupling of iodoterphenyl. The characteristic bands of the infrared spectra (675-920 cm-1) and signals of the nuclear magnetic resonance spectra of the sexiphenyls were assigned tentatively and are discussed briefly. Infrared studies indicated that the range 730-770 cm-1, generally accepted as the position of the C-H out-of-plane bending bands of phenyl rings, should be widened slightly to 730-782cm-1. The ultraviolet spectra commonly displayed a intense E-band in the narrow region of 192-207 nm. The prominent K-band above ca. 260 nm of branched sexiphenyls was taken as indicative of the presence of one or more p-linkages, as in the case of linear compounds.View full abstractDownload PDF (1053K) -
AKIHIRO TADA, RYOJI KASAI, TAMOTSU SAITOH, JUNZO SHOJI1980 Volume 28 Issue 5 Pages 1477-1484
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (811K) -
SHOZO KAMIYA, SHOKO SUEYOSHI, MICHIKO MIYAHARA, KIMIE YANAGIMACHI, TOS ...1980 Volume 28 Issue 5 Pages 1485-1490
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Azidoquinoline 1-oxides with methyl, cyano and carbamoyl groups at the 2 position, and chloro and trifluoromethyl groups at the 7 position were prepared. 4-Azidocinnoline 1-oxide and 2-oxide were also prepared. Their antitumor and mutagenic activities were tested in comparison with those of a carcinogenic, carcinostatic and mutagenic compound, 4-nitroquinoline 1-oxide.View full abstractDownload PDF (669K) -
MASATOSHI INOUE, AKIRA INOUE, YOSHIKI MINO, TOSHIMASA ISHIDA, MASAYUKI ...1980 Volume 28 Issue 5 Pages 1491-1496
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCalcium dl-α-glycerophosphate (α-CaG) has three crystal forms (anhydrate, mono-and di-hydrates), and calcium β-glycerophosphate (β-CaG) has two (anhydrate and monohydrate). The X-ray diffraction patterns of these crystals show a characteristic strong peak at a Bragg angle (2θ) of 6° to 8°. This peak is very sensitive to de-and rehydration of the hydrate crystals ; for α-CaG hydrates, the 2θ angle of the peak shifts, while that of β-CaG hydrate does not change, but its intensity changes. Since the dehydrated CaG hydrates recover their original hydrate forms at appropriate relative humidities without any crystal damage, the rate constants of rehydration were measured using the gravimetry and X-ray intensity methods. β-CaG monohydrate has a smaller value of the rate constant than the α-CaG dihydrate, indicating that the dehydrated crystals of the former are more stable than those of the latter, and that water of crystallization in the former may not play as important a role in crystal growth as in the latter. As for α-CaG dihydrate, the rate of rehydration through the incorporation of water into the dehydrated crystal is smaller than the total velocity of water gain (involving water of crystallization and adsorbed water), suggesting that the water molecule is first adsorbed onto the dehydrated crystal and is then incorporated into the crystal. The formation of the different CaG crystals may be a result of differences in the mode of interaction between the water molecules and calcium ions.View full abstractDownload PDF (619K) -
SHIGERU AONUMA, MASARU OKABE, MAKOTO KAWAGUCHI, YUICHIRO KISHI1980 Volume 28 Issue 5 Pages 1497-1502
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe changes of swimming patterns of spermatozoa accompanying capacitation were studied. The spermatozoa were seen to begin activated movement upon capacitation. The sperm activation was inhibited at low temperatures, in the absence of Ca2+, upon addition of Zn2+, and upon addition of Fr. I from guinea-pig spermatozoa which had decapacitation activity against rabbit spermatozoa. However, movement was not inhibited under the same conditions, when the spermatozoa had already acquired activated movement. It was apparent that the activation of spermatozoa was inhibited only when the prccess of capacitation was suppressed. Thus it is suggested that sperm activation is an inherent property of sperm capacitation.View full abstractDownload PDF (882K) -
KATSUHIKO MATSUI, KIYOMI KIKUNO, YUKIO KAMEDA1980 Volume 28 Issue 5 Pages 1503-1508
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAlanine dehydrogenase of Bacillus natto KMD 1126 is composed of 6 identical subunites each with a molecular weight of 48000 daltons. One cysteine residue per subunit of the enzyme was detected by amino acid analysis, and by titration with p-chloromercuribenzoic acid (PCMB) or 5, 5'-dithiobis (2-nitrobenzoic acid) (DTNB) in the presence of 8M urea. Titration of the sulfhydryl group with PCMB resulted in a linear decrease in activity with a concomitant increase in the absorbance at 250 nm. The loss of activity was restored by the addition of mercaptoethanol. N-Ethylmaleimide (NEM) inhibited the alanine dehydrogenase with pseudo first order kinetics. One mole of S-succinylcysteine per subunit was detected by amino acid analysis of the NEM inactivated enzyme. Some protection against inactivation by NEM was observed by the addition of nicotinamide adenine dinucleotide (NAD+) or its reduced form (NADH). Alanine dehydrogenase was also inhibited by iodoacetamide, and no free sulfhydryl group was detected on titration of the inactivated enzyme with PCMB or DTNB. Gel filtration studies on the binding of NADH to the enzyme revealed that the enzyme contains one coenzyme binding site per subunit.View full abstractDownload PDF (695K) -
AIYA SATO, HIROSHI NOGUCHI, SEIJI MITSUI, ISAO KANEKO, YOKO SHIMADA1980 Volume 28 Issue 5 Pages 1509-1525
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMevalonolactone derivatives were prepared via stereo-and regioselective bromolactonization of γ, δ-unsaturated acids and their structure-activity relationship in connection with their inhibitory activity in vitro against 3-hydroxy-3-methylglutaryl coenzyme A (HMG CoA) reductase, a rate-limiting enzyme in cholesterol biosynthesis, was investigated.View full abstractDownload PDF (1780K) -
HIROSHI YAMANAKA, SHIGERU OGAWA, SHOETSU KONNO1980 Volume 28 Issue 5 Pages 1526-1533
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSKnoevenagel-type condensation and the Mannich reaction were investigated with various pyridine N-oxides having an active methyl group. For example, 6-methyl-4-phenylpyrimidine 1-oxide (Va) readily reacted with benzaldehyde in an aqueous ethanolic solution of potassium hydroxide, while 4-methyl-6-phenylpyrimidine (IVa) failed to react with benzaldehyde under the same conditions. When Va was treated with piperidine hydrochloride and paraformaldehyde, bis piperidinomethylation occurred at the 6-methyl group. The product was transformed into 4-phenyl-6-(2-piperidinoethyl) pyrimidine 1-oxide (XXIIa) by treatment with 5% sulfuric acid at 90°.View full abstractDownload PDF (930K) -
KAZUEI IGARASHI, MAKOTO TANAKA, REIKO HONMA, SEIYU HIROSE1980 Volume 28 Issue 5 Pages 1534-1539
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRat liver isoleucyl-tRNA formation in the presence of more than 0.6mM Mg2+ was inhibited by smooth and rough endoplasmic reticula. The inhibition was partially prevented by ATP, spermine, oligomycin, and Triton X-100. This suggests that microsomal ATPases are responsible for the inhibition of isoleucyl-tRNA formation. Among the microsomal ATPases, an oligomycin-sensitive ATPase was found to be inhibited by spermine. The inhibition of the oligomycin-sensitive ATPase by spermine explains well its partial prevention of the inhibition by endoplasmic reticulum of isoleucyl-tRNA formation.View full abstractDownload PDF (673K) -
KIMIO HIGASHIYAMA, HIROTAKA OTOMASU1980 Volume 28 Issue 5 Pages 1540-1545
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Michael reaction of 3-(carboethoxy-cyano) methyleneoxindole (Ia) or 3-dicyanomethyleneoxindole (Ib) with active methyl groups, e.g., acetophenone and acetone, afforded, the corresponding normal Michael adducts (IIa-c). The reduction of IIa with NaBH4 gave the spiro [oxindole-3, 4'-(2', 3'-dihydro-4'H-pyran)] compound (III), which on reaction with diazomethane afforded two methoxy derivatives (IVa, b) diastereomeric at C-2' of the 2', 3'-dihydropyran ring. The reduction of IIb, c with NaBH4 gave similar spiro compounds (V-VI), which gave similar diastereoisomers, Va, b and VIa, b, respectively. Refluxing of IIc with NH2OH gave the spiro [oxindole-3, 4'-(1', 4'-dihydropyridine)] compound (X). When the same reaction was carried out at 0°, compound (IX), the precursor of X, was obtained.View full abstractDownload PDF (679K) -
MASASHI TOMODA, MAEMI ARAI, YOKO SUZUKI, MASAKO OHMURA, HIROMI TAKAYAM ...1980 Volume 28 Issue 5 Pages 1546-1551
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA representative mucilage, named Abelmoschus-mucilage G, has been isolated from the roots of Abelmoschus glutinotextilis KAGAWA. The final preparation was homogeneous as determined by ultracentrifugal analysis, cellulose acetate membrane electrophoresis, and gel chromatography. Its water solution gave the high intrinsic viscosity value of 52.8. It was composed of acidic polysaccharide and protein in a ratio of approximately 3.9 : 1.0, and its molecular weight was estimated to be 67900. Analysis of component sugars, together with reduction and methylation, and partial degradation studies revealed the structural features of the polysaccharide moiety in the mucilage.View full abstractDownload PDF (702K) -
YOSHINOBU NAKAI, SHINICHIRO NAKAJIMA, KEIJI YAMAMOTO, KATSUHIDE TERADA ...1980 Volume 28 Issue 5 Pages 1552-1558
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGround mixtures of aspirin, benzoic acid and p-acetoxydiphenyl were prepared with tri-O-methyl-β-cyclodextrin (methyl-CD). An apparent amorphous state of methyl-CD and the medicinals after grinding was indicated by X-ray diffraction analysis. Infrared analysis also indicated that the medicinal molecules were monomolecularly dispersed in the methyl-CD ground mixtures. The infrared solution spectra of medicinals in CCl4 were compared with the solid state infrared spectra in the carbonyl stretching absorption region. It was found that in the ground mixture of aspirin with methyl-CD, the hydroxyl group of aspirin was hydrogen-bonded with the methoxyl group of methyl-CD, while the acetoxyl group of aspirin was in a free state.View full abstractDownload PDF (664K) -
KAZUTAKE SHIMADA, TOSHIO NAMBARA1980 Volume 28 Issue 5 Pages 1559-1562
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe occurrence of a new type of bufotoxin, in which L-glutamine replaces the arginine residue of hitherto known"bufotoxin, "in the skin of the North American toad, Bufo americanus, is reported. Two novel bufotoxins, 3-suberoyl-L-glutamine esters of marinobufagin and telocinobufagin, were separated by column chromatography on silica gel, high-performance liquid chromatography and gel chromatography on Sephadex LH-20, and their structures were elucidated by degradative and synthetic studies.View full abstractDownload PDF (576K) -
SHOICHIRO UYEO, HISAO ONA1980 Volume 28 Issue 5 Pages 1563-1577
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTotal syntheses of several types of racemic 1-carbacephem derivatives, 30, 32, 35, 37, 39, 45, 46, 50, 56, 57, 58, 65, and preliminary biological results are described. Addition of azidoacetyl chloride to the Schiff base 10 in the presence of triethylamine gave cis-azetidinones 11a, b which were converted to the racemic key intermediate 5. By applying sequences of reactions developed in 1-oxacephem syntheses, various kinds of 1-carbacephems were prepared from 5. Among twelve derivatives prepared, 50 showed the highest antibacterial activity.View full abstractDownload PDF (1526K) -
SHOICHIRO UYEO, HISAO ONA1980 Volume 28 Issue 5 Pages 1578-1583
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA total synthesis of 1, 2-dehydro-1-carbacephalosporin 2 (R2=CH3) is described. The azido-azetidinone 8, prepared from the Schiff base 5, azidoacetyl chloride and triethylamine, was converted to the ylide 13 via 10. Conjugate addition of benzenethiol to 13 followed by an intramolecular Wittig reaction gave the 1-carbacephem derivatives 16, which were transformed to the sulfoxides 17. Treatment of 17 with triethylamine yielded the 1, 2-dehydro derivative 18. The carboxylic acid derivatives 19, and 23, prepared from 18, did not show antibacterial activity.View full abstractDownload PDF (776K) -
YOSHIHISA MIZUNO, TAKESHI ENDO, YASUKO INOUE, HAJIME TAMPO, AKIRA TAKA ...1980 Volume 28 Issue 5 Pages 1584-1589
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWe have developed a new method for the synthesis of 2-formyl-thiazole 3-oxide and 2-formyl-4-methylthiopyridine 1-oxide. Several new p-tosylhydrazones of pyridine, thiazole and imidazole derivatives were prepared. It was found that some of the hydrazones of the pyridine 1-oxides series were active in vivo against ascites sarcoma 180, whereas p-tosylhydrazones of the azole-N-oxide series were less active or inactive.View full abstractDownload PDF (691K) -
KOTARO TAKAHASHI, MASAKO TAKANI, YOSHIKAZU WADA1980 Volume 28 Issue 5 Pages 1590-1596
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of a new alkaline degradation product of 1-dihydrousnic acid was elucidated as 5-acetyl-1, 2, 3, 3a, 7, 7a-hexahydro-2, 6-dihydroxy-1, 2, 3a-trimethyl-4-oxo-4H-inden-3, 3-dicarboxylic acid (I) by chemical and spectral studies, together with X-ray analysis. The mechanism of formation of I from 1-dihydrousnic acid is discussed.View full abstractDownload PDF (667K) -
YASUMITSU TAMURA, SAIDMOHAMAD BAYOMI, MASAZUMI IKEDA, MASAHIRO KISE1980 Volume 28 Issue 5 Pages 1597-1603
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe ring expansion reactions of 2, 2-dimethyl-2, 3-dihydrobenzo [b] thiophene N-(p-toluenesulfonyl) sulfilimine (5) were investigated. Refluxing 5 in benzene gave the dihydrobenzo [b] thiophene 7 (60%) and the unsymmetrical dimer 13 (18%) as major products. Refluxing 5 in acetic acid gave a mixture of the dihydrobenzo [b] thiophene 8 and the thiochroman 11 in 76% total yield (ratio 2.6 : 1), while refluxing 5 in methanol afforded the dihydrobenzo [b] thiophene 9 and the thiochroman 12 in 58% total yield (ratio 1 : 5). The reaction of 5 with 2-mercaptobenzothiazole in refluxing toluene afforded exclusively the dihydrobenzo [b] thiophene 10. These results were rationalized in terms of the intermediacy of the sulfenamide 15 and thiiranium ion 16.View full abstractDownload PDF (771K) -
AKIRA TANAKA, TOSHINAO USUI1980 Volume 28 Issue 5 Pages 1604-1611
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSα-Substituted β-(5-nitro-2-furyl) ethanediones, α-substituted β-(5-nitro-2-furyl)-ethanedione β-oximes, α-substituted α-chloro-β-(5-nitro-2-furyl) vinyls, and 2-substituted 3-(5-nitro-2-furyl)-4-methylquinolines were prepared from aryl or 2-furyl 5-nitro-2-furfuryl ketones, which were easily obtained by the hydrolysis of α-aryl-or α-(2-furyl)-β-(5-nitro-2-furyl) vinylamines. α-Substituted β-(5-nitro-2-furyl) ethanedione β-oximes exhibited moderate antibacterial activity in vitro against gram-negative and gram-positive organisms.View full abstractDownload PDF (715K) -
EMAKO SUZUKI, MINORU IIYOSHI, MASASHI OKADA1980 Volume 28 Issue 5 Pages 1612-1618
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNuclear magnetic resonance (NMR) spectra of a series of N-alkyl-N-(ω-carboxyalkyl)-nitrosamines and their methyl or p-bromophenacyl esters have been obtained. The (E)-and (Z)-conformers of the esters were separated by high-pressure liquid chromatography (HPLC) and thin-layer chromatography. Conformer ratios of the N-nitrosamines and their esters were determined by NMR spectrometry and HPLC.View full abstractDownload PDF (714K) -
MASAICHIRO MASUI, YOSHIYUKI KAMADA, SHIGEKO OZAKI1980 Volume 28 Issue 5 Pages 1619-1622
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe anodic oxidation of ephedrine was reexamined in aqueous buffer solution at pH 10. Cleavage of the (α) C-(β) C bond occurs predominantly in the initial chemical process to give benzaldehyde, rather than the usual C-N bond fission such as that observed in the simple aliphatic amines. A revised scheme for the anodic oxidation is proposed.View full abstractDownload PDF (504K) -
KOOHEI NOZAWA, SHOICHI NAKAJIMA, MIKIKO YAMADA, KENICHI KAWAI1980 Volume 28 Issue 5 Pages 1622-1625
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe racemate of 5-chloro-3, 4-dihydro-8-hydroxy-6-methoxy-3-methylisocoumarin (I), a fungal metabolite of Periconia macrospinosa, was synthesized from 6-chloro-3, 5-dimethoxyhomophthalic acid (III) via compounds IV, VI, VII and VIII. Catalytic hydrogenation of V resulted in dechlorination, yielding 6-methoxy-8-hydroxy3-methylisocoumarin (II), another natural product from Streptomyces mobaraensis.View full abstractDownload PDF (549K) -
HIROSHI TAKAKU, KAZUO TSUBUHARI, YOICHI NAKAJIMA1980 Volume 28 Issue 5 Pages 1626-1629
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found that mixed diesters of phosphoric acid and pyrophosphates were obtained in good yields when alcohols and arylphosphates, respectively, were allowed to react with 4-methoxyphenyl N-(2-aminophenyl) phosphoramidate in the presence of cupric chloride.View full abstractDownload PDF (515K) -
TAKASHI ABIKO, IKUKO ONODERA, HIROSHI SEKINO1980 Volume 28 Issue 5 Pages 1629-1633
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn acidic tripeptide was isolated from neurotoxic dialysate by ultrafiltration with an Amicon Centriflo DM-5 membrane, followed by gel filtration on Sephadex G-15 and Sephadex G-10, and ion-exchange chromatography on DEAE-Sephadex A-25. The tripeptide thus obtained was identified as H-Glu-Asp-Gly-OH by amino acid analysis, Edman degradation, and measurement of physical constants and analytical data in comparison with those of the authentic tripeptide. This tripeptide inhibited LDH activity.View full abstractDownload PDF (634K) -
HIDEAKI UMEYAMA1980 Volume 28 Issue 5 Pages 1633-1636
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA molecular orbital study on the donor-acceptor complex of (CH3)2O-BH3 was performed, in comparison with the (CH3)2N-BH3 complex. The driving force for (CH3)2O-BH3 complex formation was electrostatic interaction energy. The interaction energy between (CH3)2O and BH3 was smaller than that between NH3 and BH3 by 10.5 kcal/mol due to a difference between the electrostatic terms. In the optimized structure of (CH3)2O-BH3, the distance γ (OB) was 1.65412 Å. The angle∠BOY, where Y is a point on the C2V axis of (CH3)2O, was 152.8°. The results are in agreement with the electron diffraction analyses of (CH3)2O-BF3 reported by Shibata and Iijima.View full abstractDownload PDF (514K) -
SADAO NISHIGAKI, YUKAKO KANAMORI, KEITARO SENGA1980 Volume 28 Issue 5 Pages 1636-1641
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 1, 3-dimethyl-5-nitro-6-styryluracils (IIa-e) with sodium dithionite in formic acid afforded the corresponding 8-aryl-9-deazatheophyllines (IVa-e). The reaction of IVa with phosphorus oxychloride gave 6-chloro-6-deoxy-8-phenyl-9-deazatheophylline (XIII), while the reaction of IVa with phosphorus oxychloride in the presence of arylamines provided the corresponding 6-arylamino-6-deoxy-8-phenyl-9-deazatheophyllines (XIV-XVI) in a single step.View full abstractDownload PDF (570K) -
SHOJI HARA, NOBORU FUKASAKU, TOKUHIRO WATANABE, AKIHIRO OHTA1980 Volume 28 Issue 5 Pages 1641-1644
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to eliminate the tedious, multi-step isolation process commonly used in the synthesis of aromatic amine oxides employing hydrogen peroxide and acetic acid, a direct chromatographic fractionation procedure was developed. The polar reagents were found to be flushed out, while the N-oxide was retained by a reversed-phase column packed with styrene-divinylbenzene copolymer gel or octadecylsilanized silica gel as the stationary phase, and using methanol-water as the mobile phase. By stepwise elution, clean-up of the reagents and direct fractionation of the N-oxide from the crude reaction mixture were simultaneously accomplished.View full abstractDownload PDF (555K) -
MAKOTO SUNAGAWA, HIROMI SATO, JUNKI KATSUBE1980 Volume 28 Issue 5 Pages 1644-1647
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudies on the structure-activity relationship of 9-γ-methylaminopropyl-9, 10-dihydro-9, 10-bridged anthracene antidepressants led us to synthesize 9-γ-methylaminopropyl-9, 10-dihydro-9, 10-propanoanthracene (3). The key intermediates, 9-β-propenyl-9, 10-dihydro-9, 10-propanoanthracene derivatives (8 and 9), were successfully synthesized by nitrous acid deamination of the ethanoanthracene derivative (7).View full abstractDownload PDF (516K) -
NORIO MINAMI, SHIZUMASA KIJIMA1980 Volume 28 Issue 5 Pages 1648-1650
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2, 3-Dimethoxy-5-methyl-p-benzoquinone (3), an important intermediate in the synthesis of ubiquinones (1), was synthesized from 3, 4, 5-trimethoxysalicylic acid (6) or 2, 3, 4-trimethoxybenzaldehyde (9). 6 was reduced via the ethoxycarbonyl derivative (7) to 6-methyl-2, 3, 4-trimethoxyphenol (8) with sodium borohydride, and then 8 was oxidized to 3 in high yield with ferric chloride. On the other hand, 2, 3, 4-trimethoxyphenol (10) was obtained from 9 by the Baeyer-Villiger reaction or treatment with hydrogen peroxide under acidic or basic conditions, and then converted into 8 by reductive methylation. Sodium borohydride reduction of the Mannich base (11) of 10 also gave 8.View full abstractDownload PDF (463K) -
ISAO KITAGAWA, TATSUYA INAMOTO, MASAKO FUCHIDA, SHINJI OKADA, MOTOMASA ...1980 Volume 28 Issue 5 Pages 1651-1653
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOn the basis of chemical and physicochemical evidence, the structures of two antifungal oligoglycosides, echinoside A and B from the sea cucumber Actinopyga echinites (JAEGER), have been elucidated as 5 and 3, respectively.View full abstractDownload PDF (425K) -
SUSUMU ISHIMITSU, SADAKI FUJIMOTO, AKIRA OHARA1980 Volume 28 Issue 5 Pages 1653-1655
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIncubation of L-phenylalanine with rat brain homogenate in the presence of a pteridine co-factor and 2-mercaptoethanol gave rise to three hydroxylated products which were identified with high-performance liquid chromatography as p-tyrosine, m-tyrosine and o-tyrosine.View full abstractDownload PDF (439K) -
MASAHIKO FUJINO, CHIEKO KITADA, MITSUHIRO WAKIMASU, OSAMU NISHIMURA, T ...1980 Volume 28 Issue 5 Pages 1655-1658
Published: May 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFirst synthesis of a nonacosapeptide corresponding to the entire amino acid sequence of salmon endorphin, Ac-Tyr-Gly-Gly-Phe-Met-Lys-Pro-Tyr-Thr-Lys-Gln-Ser-His-Lys-Pro-Leu-Ile-Thr-Leu-Leu-Lys-His-Ile-Thr-Leu-Lys-Asn-Glu-Gln-OH, and its des-acetyl derivative was described. Toward the synthesis of this hormone, five fragments, 1-7, 8-15, 16-18, 19-24 and 25-29, were prepared and the fragments were served as the building blocks for the final construction of the entire amino acid sequence of the hormone. The final deprotection of the fully protected peptide was achieved by treatment with trifluoroacetic acid and the purification of the synthetic peptides was effected by a column chromatography on CM-cellulose and then Sephadex LH-20. The synthetic acetylated nonacosapeptide was compared with purified natural salmon endorphin by means of chromatography, electrophoresis and also enzymatic digestion and found to be indistinguishable from natural isolated salmon endorphin. The opiate activity of the synthetic salmon endorphin and des-acetyl salmon endorphin was also described.View full abstractDownload PDF (538K)
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