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Volume 28, Issue 7
Displaying 1-50 of 53 articles from this issue
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FUMITOSHI HIRAYAMA, KANETO UEKAMA, HIDEOMI KOINUMA1980 Volume 28 Issue 7 Pages 1975-1980
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe molecular dynamics of prostaglandin F2α (PGF2α) and its α- and β-cyclodextrin (α- and β-CyD) complexes in aqueous solution were investigated by means of carbon-13 nuclear relaxation measurements. Some reorientation times calculated for PGF2α in-dicated that the internal motion of the C16-C20 alkyl chain and the overall tumbling motion were predominantly reduced upon binding to α-and β-CyDs, respectively. Upon inclusion of PGF2α, the internal motion of primary alcohol groups slowed down by a factor of 6 in α-CyD and by a factor of 2 in β-CyD, in comparison with the overall motions. The stability of the inclusion complexes is discussed on the basis of dynamic coupling between the molecular motions of the host and guest molecules. Dynamic coupling coefficients of 0.12 and 0.75 were obtained for the PGF2α-α-CyD and PGF2α-β-CyD systems, respectively, indicating a greater dynamic rigidity for the β-CyD complex as compared with the α-CyD complex. On the basis of these observations, different inclusion modes are proposed in the α- and β-CyD complexes.View full abstractDownload PDF (658K) -
YUKO NAKAHARA, TAKASHI TATSUNO1980 Volume 28 Issue 7 Pages 1981-1985
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn alternative synthesis of a fungal metabolite, 12, 13-epoxy-trichothec-9-ene is described. Diels-Alder reaction of methyl coumalate and 2-methoxy-1, 3-butadiene or 2-methyl-3-methoxy-1, 3-butadient is represented.View full abstractDownload PDF (610K) -
KAZUMASA HIRAUCHI, AKIKO FUJISHITA1980 Volume 28 Issue 7 Pages 1986-1991
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA phosphorimetric method for the determination of epinephrine was established. The method is based on measurement of the phosphorescence of the phosphorescent compound formed in the reaction of epinephrine with 2-chloro-5-nitropyridine after isolation of the compound by thin-layer chromatography. The method can be applied to the determination of epinephrine in the concentration range from 2 to 20 μg/ml, and interfering substances such as norepinephrine, tyrosine, metanephrine, normetanephrine, phenylalanine, 3, 4-dihydroxyphenylalanine, and 3-hydroxytyramine are easily removed.View full abstractDownload PDF (605K) -
SHIRO URANO, YUJI HATTORI, SHINJU YAMANOI, MITSUYOSHI MATSUO1980 Volume 28 Issue 7 Pages 1992-1998
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe 13C signal assignments of the aromatic carbon atoms in α-tocopherol were confirmed using [methyl-13C] α-tocopherol. The 13C-NMR spectra of α-tocopherol alkyl ethers and 5-alkyl-2, 5, 7, 8-tetramethyl-2-(4, 8, 12-trimethyltridecyl) chroman-6 (5H)-ones, which are formed in the radical scavenging reaction of α-tocopherol with alkylradicals, were recorded and examined. In α-tocopherol and its alkyl ethers, C-5 is more shielded than nearly equivalent C-7. The chemical shift difference seems to be consistent with the reactivity difference between these carbon atoms, which is known as the"Mills-Nixon effect."View full abstractDownload PDF (720K) -
TOHRU KIKUCHI, MINEO NIWA, MASAHARU TAKAYAMA, TOSHIO YOKOI, TETSURO SH ...1980 Volume 28 Issue 7 Pages 1999-2007
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDownload PDF (853K) -
KEIKO MURAKOSO, YOKO TSUMURA, SHOHEI KAGAWA, AKIRA MATSUOKA1980 Volume 28 Issue 7 Pages 2008-2013
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of alloxan on cultured rat pancreatic endocrine cells was investigated by following changes in the incorporation of UDP-galactose into glycoproteins (chloroform/methanol-insoluble fraction) and glycolipids (chloroform/methanol-soluble fraction). Cultured cells exposed to either alloxan or alloxan plus D-glucose anomers (16.7 mM) at 37° for 5 min, were incubated in a medium containing labeled UDP-galactose for 60 min. Alloxan at concentrations of 1.25 or 6.25 mM had no marked effect on the incorporation of UDP-galactose but 31.2 mM alloxan markedly inhibited the incorporation. The combination of 1.25 mM alloxan and the α anomer of D-glucose significantly reduced the incorporation of UDP-galactose into glycoproteins and glycolipids, while the presence of the β anomer with alloxan had no effect. Incorporation of D-[U-14C] galactose was unaffected by 1.25 mM alloxan or alloxan plus D-glucose anomers (16.7 mM). The present data indicate that cultured rat pancreatic endocrine cells can transfer galactose from UDP-galactose and that the α anomer reinforces the action of alloxan to a greater extent than the β anomer.View full abstractDownload PDF (666K) -
TOHRU KIKUCHI, TOSHIO YOKOI, MINEO NIWA, TETSURO SHINGU1980 Volume 28 Issue 7 Pages 2014-2023
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe homonuclear internuclear double resonance (INDOR) technique in combination with the pseudo-contact shift method was applied to several triterpenes related to friedelin, and the methyl resonances of these triterpenes were assigned. The results suggest that rings D and E of friedelin in solution are in a boat form.View full abstractDownload PDF (931K) -
FUMIYOSHI ISHIKAWA, AKIRA KOSASAYAMA, KUNIO HIGASHI1980 Volume 28 Issue 7 Pages 2024-2028
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Phenyl-substituted 1-methyl tricyclic guanidine (1) having an imidazo- or pyrimido-[2, 1-b] quinazoline ring was easily oxidized at the methine group adjacent to the aromatic rings to give the 5-hydroxy- or 6-hydroxy derivative (2), respectively. Reaction of 2-aminobenzophenone with 2-chloro-2-imidazoline gave the 1-unsubstituted 5-hydroxy-imidazo [2, 1-b] quinazoline derivative (5). The structures of compounds 2 and 5 are discussed. 1-Hydroxy- (13) and 1-amino tricyclic guanidines (16) were prepared by the reaction of 2-chloro-3-(2-chloroethyl)-4-phenyl-3, 4-dihydroquinazoline with hydroxylamine and hydrazine, respectively. Compounds 2, 5 and 13 showed hypoglycemic and platelet aggregation inhibitory activity.View full abstractDownload PDF (642K) -
YOSHIHIRO HARIGAYA, SEIKO TAKAMATSU, HIROKO YAMAGUCHI, TOSHIRO KUSANO, ...1980 Volume 28 Issue 7 Pages 2029-2034
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe compound obtained from the phenacylimide (5) by treatment with p-toluenesulfonic acid and ethylene glycol in benzene is the furoisocarbostyril (7), in contrast to a previous report. Reduction of 5 with sodium borohydride followed by treatment with hydrochloric acid and then hydrogen chloride affords the styrylisocarbostyril (10), photolysis of which provides the benzo [c] phenanthridines (11) and (12), and the amides (13) and (14). The ethylenedioxyimide (8) obtained from 5 affords the styrylisocarbostyrils (18) and (19) by a similar procedure together with enol acetylation. Photolysis of a mixture of 18 and 19 provides the 12-acetoxybenzo [c] phenanthridines (20) and (21).View full abstractDownload PDF (728K) -
YASUJI YAMADA, SUKEJI SUZUKI, KAZUO IGUCHI, HIROYUKI KIKUCHI, YASUMASA ...1980 Volume 28 Issue 7 Pages 2035-2038
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo new epoxy cembranolide diterpenes were isolated from the Japanese soft coral Lobophytum pauciflorum (Ehrenberg). The structures of these diterpenes were elucidated as I and II, mainly on the basis of spectroscopic data. The compound (II) is a possible biogenetic precursor of the 13-membered carbocyclic cembranolides.View full abstractDownload PDF (510K) -
AKIHIRO TADA, RYOJI KASAI, TAMOTSU SAITOH, JUNZO SHOJI1980 Volume 28 Issue 7 Pages 2039-2044
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew homoisoflavonoidal compounds, ophiopogonone A (Va), isoophiopogonone A (VIa), ophiopogonone B (VIIa), desmethylisoophiopogonone B (VIII) and ophiopogonanone A (IXa) were isolated as constitutents of Ophiopogonis tuber (Ophiopogon japonicus KER-GAWLER var. genuinus MAXIM., Liliaceae), and their chemical structures were elucidated as 5, 7-dihydroxy-6-methyl-3-(3, 4-methylenedioxybenzyl) chromone, 5, 7-dihydroxy-8-methyl-3-(3, 4-methylenedioxybenzyl) chromone, 5, 7-dihydroxy-6-methyl-3-(4-methoxybenzyl) chromone, 5, 7-dihydroxy-8-methyl-3-(4-hydroxybenzyl) chromone and 5, 7-dihydroxy-6-methyl-3-(3, 4-methylenedioxybenzyl) chroman-4-one, respectively, by chemical and spectral studies.View full abstractDownload PDF (660K) -
KEIICHI MUNAKATA, SATORU TANAKA, SHOJI TOYOSHIMA1980 Volume 28 Issue 7 Pages 2045-2051
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWith the aim of finding a therapeutic agent for urolithiasis, forty-three new N-(aroyl)-glycinohydroxamic acid derivatives and related compounds were synthesized and examined for urease inhibitory activity. Their urinary excretion in rats was also determined.View full abstractDownload PDF (743K) -
YOSHIKI MINAMOTO, YASUMI YUGARI1980 Volume 28 Issue 7 Pages 2052-2058
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPolymethylglutamate (PMG), a synthetic polypeptide, was used as a carrier to immobilize glucose oxidase (EC 1. 1. 3. 4), uricase (EC 1. 7. 3. 3), peroxidase (EC 1. 11. 1. 7), trypsin (EC 3. 4. 21. 4), chymotrypsin (EC 3. 4. 21. 1), urease (EC 3. 5. 1. 5), and aminoacylase (EC 3. 5. 1. 14) by the azide method. The enzymes could be immobilized covalently on PMG coated on glass beads. The retained activities of all the immobilized enzymes were excellent (more than 90%). The amount of enzyme immobilized on the polymer varied markedly depending on the kind of enzyme (trypsin 30 mg, chymotrypsin 27 mg, urease 5.8 mg, uricase 5.6 mg, aminoacylase 2.3 mg, glucose oxidase 1.8 mg and peroxidase 2.3 mg/100 mg PMG). It was found that the amount of bound enzyme was determined primarily by the molecular weight and secondarily by the content of lysine residues in the enzyme. The heat stabilities of the resulting immobilized enzymes were markedly improved, while the optimal pH and Km values were almost unchanged. The enzymes immobilized on PMG showed improved stability because of both the increased hydrophilicity of the polymer and the multipoint binding mode, including covalent and ionic bonding.View full abstractDownload PDF (795K) -
TETSURO NAGASAWA, TAKAKO YOKOZAWA, YOSHIE NISHINO, HIKOKICHI OURA1980 Volume 28 Issue 7 Pages 2059-2064
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe major components of ginseng saponins, ginsenoside-Rb1, -Rb2, -Rc, -Rd, -Re, and -Rg1, were isolated from the crude saponin fraction by high-performance liquid chromatography (HPLC), using preparative HPLC on silica gel followed by semi-preparative HPLC on a column packing of Carbohydrate Analysis. This method was rapid and convenient. In addition, ginsenosides could be rapidly analyzed by HPLC on a Carbohydrate Analysis column, which gave excellent resolution.View full abstractDownload PDF (591K) -
KIMIHIRO YOSHIMOTO, YOSHITAKA ITATANI, YOSHISUKE TSUDA1980 Volume 28 Issue 7 Pages 2065-2076
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCMR spectra of all positional isomers of mono-O-myristoyl-α- and β-D-glucopyranoses in pyridine-d5 are reported and discussed in connection with the anomalies of 1α- and 1β-O-acyl derivatives. Calculation of the chemical shifts of some dimyristates using the acylation shifts obtained from monomyristate (Table III) gave values in agreement with the observed values for each compound, confirming the additivity of the acylation shift parameters. The effects of the solvent and the nature of the acyl moiety on the acylation shifts also examined using twenty samples, and it was concluded that the acylation shift parameters are independent of the solvent (s) and the kind (s) of acyl group (s), so that the above shift values obtained for the myristoyl group can be regarded as a universal set of additive parameters for usual di- and tri-acyl derivatives. This additivity rule of parameters was successfully applied to the structure elucidation of two naturally occurring acylglucose derivatives, tuliposide-A and spirarin. The previously reported data for various glucosyl γ-nitropropanoates in acetone-d5 are compared with the values calculated from the above parameters, again showing fair agreement.View full abstractDownload PDF (1176K) -
HIROTERU SAYO, MIKIO HOSOKAWA1980 Volume 28 Issue 7 Pages 2077-2082
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCumene hydroperoxide-supported N-demethylation of aminopyrine catalyzed by catalase has been investigated. The transient free radical of aminopyrine was detected by electron spin resonance at room temperature. 4-Diethylaminoantipyrine was also oxidized to the corresponding free radical. Although another free radical was detected in the absence of aminopyrine in the catalase-cumene hydroperoxide system, this radical is considered not to be the major oxidant of aminopyrine in the catalase-aminopyrine-cumene hydroperoxide system, because its concentration was too low. Cumene hydroperoxide previously added to the catalase solution greatly inhibited the oxidation of aminopyrine, whereas it did not inhibit the catalatic reaction. In contrast, sodium azide significantly inhibited the latter reaction and only slightly inhibited the former reaction. Methanol was not oxidized appreciably in our system. The present study suggests that the active site of catalase for the cumene hydroperoxide-supported N-demethylation of aminopyrine is different from that for the catalatic reaction.View full abstractDownload PDF (687K) -
SHIGERU TANAKA, KAZUYUKI WACHI, ATSUSUKE TERADA1980 Volume 28 Issue 7 Pages 2083-2088
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 1-methyl-3-(3-phenyl-1-triazenyl) pyridinium iodide (2a-e) with base gave triazole derivatives (3 and 4) with expulsion of the pyridine ring. Similarly, the reaction of 1-methyl-3-benzoylpyridinium oxime iodide (10a-c) with base afforded isoxazole derivatives. A possible mechanism for the formation of these reaction products is discussed.View full abstractDownload PDF (561K) -
TSUTAO KURECHI, KIYOMI KIKUGAWA, TETSUTA KATO1980 Volume 28 Issue 7 Pages 2089-2093
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hydrogen donating capabilities of antioxidants, such as butylated hydroryanisole (BHA), butylated hydroxytoluene (BHT), dl-α-tocopherol (Toc), sesamol and ethyl protocatechuic acid (EP), to a stable free radical, 2, 2-diphenyl-1-picrylhydrazyl (DPPH), were investigated. Toc, sesamol and EP donated two hydrogen atoms, BHA donated 0.75-1.2 hydrogen atoms, and BHT donated much less hydrogen. A synergistic effect on hydrogen donation to DPPH was observed with the combinations of Toc+BHT and BHA+BHT. The synergistic effect observed in the reaction between BHA+BHT and DPPH might arise from the regeneration of BHA from its oxidized intermediate, with the loss of BHT.View full abstractDownload PDF (562K) -
MASAKI SHINOGI, KAYOKO FUKUDA, MIYUKI NAKAZAWA, ITSUHIKO MORI1980 Volume 28 Issue 7 Pages 2094-2100
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of standard reference materials (SRM's) i. e. NBS orchard leaves and bovine liver, as multielemental irradiation standards in NAA is discussed. This technique was applied to the analysis of trace elements in various organs of the rat and in cell fractions of the rat liver. Nondestructive neutron activation analysis was carried out to determine 13 elements (As, Br, Co, Cr, Cs, Fe, K, Mn, Na, Rb, Sc, Se and Zn) in each sample. High concentrations of several elements were found in some organs of the rat. In particular, the testes contained many elements at high concentrations, while the contents of all elements were highest in the liver. The mean concentrations of elements in various organs of the rat were classified roughly, and the elemental concentrations in cell fractions of the rat liver are discussed. The cytosol contained the greatest quantities of the elements, with the exception of Mn.View full abstractDownload PDF (656K) -
HIROSHI NAKAKIMURA, MORIO KAKIMOTO, SAKAE WADA, KOJI MIZUNO1980 Volume 28 Issue 7 Pages 2101-2104
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPlasma lipid peroxide concentration has been demonstrated to vary with the species, strain, sex and age of laboratory animals as well as with conditions of starvation and stress. Mice showed remarkably high plasma TBA levels as compared with other species of animals, and the ICR and ddY strains of mice, among other strains, may be useful as experimental models, since they proved to have relatively slight interindividual differences. The data obtained indicate that great care in the management and experimental handling of laboratory animals are essential because of the enhancing effect of stress on the plasma TBA level.View full abstractDownload PDF (525K) -
KOICHI KAWASAKI, CHIYE KAWASAKI, MITSUKO MAEDA, YOSHIO OKADA1980 Volume 28 Issue 7 Pages 2105-2115
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo tetradecapeptides, Z-Leu-Gly-Cys (Bzl)-Gln-Ile-Cys (Bzl)-Leu-Thr-Lys (Z)-Ala-Met-Asp (OBzl)-Asn-Met-OH (I) and its benzyl ester (VIII) were synthesized. I was synthesized by the condensation of two heptapeptides [Z-Leu-Gly-Cys (Bzl)-Gln-Ile-Cys (Bzl)-Leu-NHNH2 (II) and Boc-Thr-Lys (Z)-Ala-Met-Asp (OBzl)-Asn-Met-OH (III)], while VIII was synthesized stepwise by the condensation of 4 fragments [Z-Leu-Gly-Cys (Bzl)-Gln-OH (XI), Boc-Ile-Cys (Bzl)-Leu-OH (X), Boc-Thr-Lys (Z)-Ala-NHNH2 (IV) and Boc-Met-Asp (OBzl)-Asn-Met-OBzl (IX)]. Deblocked I and deblocked VIII each formed a chelate with iron and sulfur.View full abstractDownload PDF (1338K) -
TOHRU SUGAWARA, HIROTOMO MASUYA, TAISUKE MATSUO, TAKUICHI MIKI1980 Volume 28 Issue 7 Pages 2116-2128
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-(5-Substituted-1, 3, 4-thiadiazol-2-yl) ceph-3-em derivatives were prepared by oxidative ring closure with 2, 3-dichloro-5, 6-dicyanobenzoquinone directly or after acetylation of 3-thiocarbonylhydrazones, which were obtained from the reaction of 3-formylceph-3-ems and thiocarbonylhydrazines. The antibacterial activity of 7-thienylacetamido-3-(5-substituted-1, 3, 4-thiadiazol-2-yl) ceph-3-em derivatives (4) against gram-positive organisms was similar to that of cephalothin (CET), while the activity against gram-negative organisms was superior to that of CET. A similar oxidative ring closure reaction with other thiocarbonylhydrazones is also discussed.View full abstractDownload PDF (1368K) -
Studies on Ketene and Its Derivatives. CI. Reaction of Diketene with 4-Amino-methylpyridine 1-OxidesTETSUZO KATO, NOBUYA KATAGIRI, MICHIKO TANAKA, AKIHIRO WAGAI, KENZO HA ...1980 Volume 28 Issue 7 Pages 2129-2135
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of diketene with 4-amino-methylpyridine 1-oxides was examined. 4-Aminopyridine 1-oxide (1a) and 4-amino-3-methylpyridine 1-oxide (1c) reacted with diketene in the presence of triethylamine at 0--5° to give the corresponding substituted 2, 6-dimethyl-4-pyrone-3-carboxamides ; i. e., N-(1-oxido-4-pyridyl) (3a) and N-(3-methyl-1-oxido-4-pyridyl) (3c) compounds. The reaction of diketene with 4-aminomethylpyridine 1-oxides (1b, d, and e) afforded 4-acetoacetamindopyridine 1-oxides (2b, d, and e) under the same conditions. However, the reaction of diketene with 4-aminopyridine 1-oxides (1f and g) possessing an ethyl group at the 3-position gave N-(3-ethyl-1-oxido-4-pyridyl)-2-acetyl-3, 5-dimethyl-phenol-4-carboxamides (5f and g), together with N-(3-ethyl-1-oxido-4-pyridyl)-2, 6-dimethyl-4-pyrone-3-carboxamides (3f and g). The mechanism of formation of compounds 5f and g is discussed.View full abstractDownload PDF (707K) -
RIICHI TAWA, SHINGO HIROSE1980 Volume 28 Issue 7 Pages 2136-2143
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidative coupling reaction between the quinonediimine (QDI) of N, N-dimethyl-p-phenylenediamine (DMPD) and aromatic amines was utilized for the simultaneous determination of binary mixtures of aniline and its derivatives by the differential reaction rate method. A mixture of oxidant and DMPD was used instead of QDI because QDI was unstable. The effects of pH and the oxidant (K3Fe (CN)6, K2Cr2O7 and their mixture) on the stability of the first oxidation product of DMPD, semiquinone (SQ), and on the equilibrium among DMPD, SQ and QDI, were investigated. The second-order rate constants of two amines reacting with QDI and the overall pseudo first-order rate constant of a mixture were determined from the slope of the straight line (the concentration of SQ vs. time) and by simplified complementary tristimulus colorimetry. Mixtures of amines down to 1.0×10-4M were determined. Most relative errors were in the range of 0 to 14%. Among the compounds examined for interference, phenols and carbonyl compounds showed serious effects.View full abstractDownload PDF (698K) -
TAISEI UEDA, NORIICHI ODA, ISOO ITO1980 Volume 28 Issue 7 Pages 2144-2147
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Anilino (or amino) antipyrines (Ia, b) were transformed into 5-anilino (or amino)-4 (3H)-pyrimidones (IIa, b) in the presence of bases such as sodium hydride, sodium amide, sodium hydroxide, or sodium ethoxide in refluxing xylene. Treatment of IIa with hydrazine hydrate gave 4-anilino-5-hydroxy-3-methyl pyrazole (V). However, the reaction of IIb with hydrazine hydrate gave 3, 5-diamino-6-methyl-4 (3H)-pyrimidone (VI) and 4-(5-oxo-3-methyl-pyrazolinyliden) amino-5-hydroxy-3-methyl pyrazole (VII).View full abstractDownload PDF (543K) -
JUNICHI MATSUMOTO, HIRONORI SOGO, SHINSAKU MINAMI1980 Volume 28 Issue 7 Pages 2148-2153
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEthyl 4-oxopyrimido [1, 6-α] pyrimidine-3-carboxylates (4) were prepared by the thermal cyclization of diethyl N-(4-pyrimidinyl) aminomethylenemalonates (3) in which no substituent was present at position 2. Some of the compounds 4 readily afforded stable covalent hydrates which proved to be ethyl 6, 7-dihydro-6-hydroxy-4-oxopyrimido-[1, 6-α] pyrimidine-3-carboxylated (9) formed by the addition of a molecule of water across the 6, 7 C=N bond in 4. This hydration was affected by the electronic character of the substituent at position 8 in the 4H-pyrimido [1, 6-α] pyrimidine ring.View full abstractDownload PDF (691K) -
KAZUHITO WATANABE, IKUO YAMAMOTO, KAZUTA OGURI, HIDETOSHI YOSHIMURA1980 Volume 28 Issue 7 Pages 2154-2157
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo carboxylic acids were isolated as the major metabolites from the liver of rats injected with 11-hydroxy-Δ8-tetrahydrocannabinol (11-OH-Δ8-THC). One of the metab-olites was identified as Δ8-THC-11-oic acid, and the other was assumed to be 7-hydroxy-Δ8-THC-11-oic acid. The effects of SKF 525-A, cobaltous chloride and phenobarbital on the contents of these metabolites in the rat liver were studied. Pretreatment with SKF 525-A and cobaltous chloride resulted in significant decreases of the contents of these metabolites (by 73 and 70% for Δ8-THC-11-oic acid, and by 91 and 89% for 7-hydroxy-Δ8-THC-11-oic acid, respectively). On the other hand, the level of 7-hydroxy-Δ8-THC-11-oic acid was increased, but that of Δ8-THC-11-oic acid remained unchanged by pretreatment with phenobarbital. These results suggest that the metabolism of 11-OH-Δ8-THC to Δ8-THC-11-oic acid and 7-hydroxy-Δ8-THC-11-oic acid is mediated in part by the microsomal monooxygenase system in vivo.View full abstractDownload PDF (512K) -
MOTOAKI KUWAYAMA, SOHACHIRO MIYAKE, KOHEI NISHIKAWA1980 Volume 28 Issue 7 Pages 2158-2165
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple and rapid fluorodensitometric method for the simultaneous determination of 1, 4-dimorpholino-7-phenylpyrido [3, 4-d] pyridazine (DS-511) and its metabolites in urine and bile was established. The biological specimens containing DS-511 and its metabolites were separated into lipophilic and hydrophilic layers by extraction with ethyl acetate. The hydrophilic layer was incubated at 37° for 24 hr with β-glucuronidase and arylsulfatase, then separated again into two layers by a similar extraction procedure. The lipophilic layers were purified by two-dimensional thin-layer chromatography with chloroform-methanol (10 : 1) and ethyl acetate-benzene (3 : 2). The hydrophilic layer was passed through a column of Amberlite XAD-2 (100-200 mesh), eluting with ethanol, and the eluate was purified by stepwise thin-layer chromatography with ethyl acetatebenzene (3 : 2) and chloroform-methanol (2 : 1). After moistening the air-dried chromatogram with 1-butanol, the fluorescent spots were quantitatively determined with a spectrodensitometer in the fluorescence mode. The recoveries and the coefficients of variation (c. v.) with this method were 89-116% (c. v. 6-14%) for lipophilic compounds and 93.0-95.0% (c. v. 5-6%) for hydrophilic compounds at concentrations between 0.1-1.0 μg/ml in biological specimens. This method could be used to analyze biological specimens from rats and dogs after administration of DS-511 and should also be applicable to human specimens.View full abstractDownload PDF (777K) -
HIROYUKI AKITA, TAKANOBU NAITO, TAKESHI OISHI1980 Volume 28 Issue 7 Pages 2166-2171
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLarge scale syntheses of (±)-isodrimenin (4) and (±)-confertifolin (5) were achieved starting from β-ionone via the tricyclic furan derivative (16). Oxidation of this intermediate (16) with lead tetraacetate followed by pyrolysis afforded (±)-confertifolin (5) as a main product. Conversion of the lead tetraacetate oxidation product (17) into (±)-winterin (19) followed by NaBH4 reduction produced (±)-isodrimenin (4) as a main product.View full abstractDownload PDF (732K) -
TADASHI NAKATA, HIROYUKI AKITA, TAKANOBU NAITO, TAKESHI OISHI1980 Volume 28 Issue 7 Pages 2172-2177
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA total synthesis of (±)-warburganal has been completed starting from (±)-isodrimenin and other drimane-type compounds. 11, 12-Diacetoxy-drim-8-ene (9), which can be readily obtained from the above starting compounds, was converted to the 7-oxo derivative (7). Treatment of 7 with 30% H2O2 followed by NH2NH2·H2O promoted reductive opening of the resulting keto epoxide group to afford the trialcohol (11). Selective silylation of the allylic primary alcohol in 11 with tert-butyldimethylsilyl chloride followed by protection of the α-glycol with N, N'-carbonyldiimidazole afforded the carbonate (14). Desilylation of 14 and subsequent oxidation of the allyl alcohol moiety afforded 16. Protection of the aldehyde followed by base-induced deprotection of the glycol afforded 18, which was subjected to Moffatt oxidation to give 19. Treatment of 19 with p-TsOH-acetone afforded (±)-warburganal.View full abstractDownload PDF (744K) -
KENICHI YAKUSHIJIN, MASAMICHI KOZUKA, HIROSHI FURUKAWA1980 Volume 28 Issue 7 Pages 2178-2184
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3, 4-Diphenyl-2-furylcarbamoyls (IIIa-e) react with oxygen in benzene at room temperature and in the absence of catalysts or bases to give 3, 4-diphenyl-5-hydroxy-3-pyrrolin-2-ones (Va-e) as main products. Under the same conditions, treatment of 3, 4-diphenyl-2-furyl isocyanate (II) with an excess of various amines resulted in a clean autoxidation reaction to give Ve-h and diphenylmaleimides (XIIa-d) in a ratio of about 1 : 1. 3-Hydroxyphenanthro [9, 10-c] pyrrolin-1-ones (XIIIa-e) were prepared by the photocyclization of Va-e.View full abstractDownload PDF (918K) -
NOBUTOSHI TANAKA, TSUYOSHI KIMURA, TAKAO MURAKAMI, YASUHISA SAIKI, CHI ...1980 Volume 28 Issue 7 Pages 2185-2187
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Protowoodsia manchuriensis (HOOK.) CHING a new sesquiterpene was isolated and its structure elucidated as 6β-hydroxy-isodrimenin by spectroscopic investigations and chemical transformations.View full abstractDownload PDF (420K) -
TOYOHISA TSUKAMOTO, SHUSHI MORITA, JUTARO OKADA1980 Volume 28 Issue 7 Pages 2188-2193
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidation of glucose to gluconic acid in aqueous alkaline solution on a platinumcarbon catalyst was chosen as a model reaction to study the liquid-solid contacting efficiency in trickle-bed reactors. The global rates of dissipation of oxygen were measured for both liquid-full and trickle-bed reactors under conditions of negligible liquid-solid mass transfer effects. The liquid-solid contacting efficiency was evaluated from the rates for both reactors, which were measured under the same conditions of temperature, oxygen concentration and liquid flow rate using the same catalyst. Under the range of experimental conditions used (catalyst particle sizes ; 0.110 and 0.242 cm, superficial liquid velocity ; 0.0236 to 0.337 cm/sec), the liquid-solid contacting efficiency was nearly constant. The average value was 0.91. Data were taken in a gas-continuous flow regime and showed no significant change in the rate of reaction with change in superficial gas (oxygen) velocity.View full abstractDownload PDF (725K) -
HIDEO KATO, EIICHI KOSHINAKA, NOBUO OGAWA, KAGARI YAMAGISHI, KAZUYA MI ...1980 Volume 28 Issue 7 Pages 2194-2206
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a search for new antispasmodics, we have synthesized N-alkyl 2- and 1-diarylmethyleneindolizidinium bromides (6-13), which can be regarded as conformationally rigid derivatives of prifinium bromide (14) or the basic compound (15) of the pyrrolidine antispasmodics. Condensation of ethoxycarbonylindolizidines (20 and 26) with phenyllithium or 2-thienylmagnesium bromide, followed by dehydration, afforded diarylmethyleneindolizidines (23, 24, 29 and 30). Quaternization of the 2-substituted derivatives (23 and 24) with methyl bromide afforded two isomeric methobromides, the trans-(6a and 7a) and the cis-methobromides (6b and 7b), while the 1-substituted derivatives (29 and 30) afforded only the cis-methobromides (10 and 11). The stereochemistries of these methobromides were confirmed by the chemical shifts of the N+-methyl signals in the 1H- and 13C-NMR spectra. The stereochemistries of 2- and 1-diarylhydroxymethylindolizidines (21, 22, 27 and 28) were also determined from the IR spectra and by X-ray analysis. The quaternary ammonium salts (6-13) exhibited anticholinergic activity more potent than that of 15, and the activities of several compounds were equal to that of 14. The structure-activity relationships of these compounds are discussed.View full abstractDownload PDF (1216K) -
MICHIHARU NAKANO, KAZUTAKA TANIZAWA, MASAYUKI NOZAWA, YUICHI KANAOKA1980 Volume 28 Issue 7 Pages 2212-2216
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe kinetic properties of esters derived from guanidinophenol and aminomethylphenol were investigated with trypsin. These compounds, in which the site-specific groups (positive charge) are of the inverse type compared with normal substrates, were demonstrated to be specific substrates, like amidinophenyl esters. The behavior of these"inverse substrates"with trypsin and pseudotrypsin was also compared. A dramatic decrease in the efficiency of hydrolysis of the"inverse substrates"by pseudotrypsin as compared to that by trypsin was observed, which was comparable in extent to that observed for specific normal-type substrates. All these observations confirm the view that specific interaction between the positive charge at the leaving moiety of"inverse substrates"and the anionic site of the trypsin active center is an essential feature of the catalysis, just as in the case of normal-type substrates.View full abstractDownload PDF (646K) -
SHUNSUKE KAZAMA, EIJI SATO, MAMORU KAMIYA, YUKIO AKAHORI1980 Volume 28 Issue 7 Pages 2216-2220
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSElectron spin resonance (ESR) spectra of the anion radicals of 10 (9H)-xanthene-9-ylidene-9 (10H)-anthracenone, 10-diphenylmethylene-9 (10H)-anthracenone, 9-diphenylmethylene-9H-xanthene, 9, 9'-bixanthene and diphenylfulvene were measured. These compounds, except for diphenylfulvene, are thermochromic ethylenes. On the basis of calculation of the spin densities by McLachlan's method and h. f. s. analysis of the ESR spectra, the anion radicals were found to be substantially twisted about the central double bond.View full abstractDownload PDF (492K) -
NOBUTOSHI WATARI, MANABU HANANO, NOBUYOSHI KANENIWA1980 Volume 28 Issue 7 Pages 2221-2225
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of the particle size of sulfadimethoxine on its in vitro and in vivo dissolution rates and on bioavailability were examined using rabbits. The particle size significantly affected the rate and extent of bioavailability, and the in vivo dissolution, which was calculated by the deconvolution method. A good correlaion between in vitro and in vivo dissolution rates was obtained.View full abstractDownload PDF (593K) -
HAJIME KATAYAMA, MITSUKO OHKOSHI, MASAITI YASUE1980 Volume 28 Issue 7 Pages 2226-2228
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Acetyl- and N-formyl-1, 2-dihydroquinoline were conveniently prepared by reductive acylation of quinoline without isolating the labile 1, 2-dihydroquinoline. This method was also applied to isoquinoline to prepare N-acetyl-1, 2-dihydroisoquinoline.View full abstractDownload PDF (467K) -
TSUTAO KURECHI, KIYOMI KIKUGAWA, TETSUTA KATO, TOSHIKO NUMASATO1980 Volume 28 Issue 7 Pages 2228-2232
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reduction of ferric ions by phenolic antioxidants was investigated by the Emmerie-Engel method. Diphenolic and triphenolic compounds reduced 2-2.5 and 5 molar equivalents of ferric ions, respectively. Monophenolic compounds reduced different amounts of ferric ions : BHT, 0.6 ; tocopherol, 2 ; BHA, 3 and sesamol, 4 molar equivalents. When two compounds were used in combination, the reducing potency was enhanced or decreased depending on the antioxidants used. The combination of BHA and BHT produced 1.5 times more ferrous ions than the calculated amount, and the combination of BHA and PG produced only 0.75 times the calculated amount of ferrous ions. In the combined use of BHA and BHT, BHT was more rapidly lost than it was in the reaction of BHT alone, probably due to some interaction of the two compounds.View full abstractDownload PDF (614K) -
BANRI YAMANOHA, KEIJIRO SAMEJIMA1980 Volume 28 Issue 7 Pages 2232-2234
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSynthetic decarboxylated S-adenosylmethionine and six analogs were tested in a decarboxylating system based on rat liver S-adenosylmethionine decarboxylase. All the compounds inhibited the putrescine-activated decarboxylase activity and were competitive with respect to S-adenosylmethionine. Among the compounds tested, S-5'-deoxyadenos-yl-(5')-2-methylthioethylamine was the most potent inhibitor. The Ki value of the inhibitor was seven times lower than that of decarboxylated S-adenosylmethionine.View full abstractDownload PDF (433K) -
KENJI MIZOJIRI, ETSUKO YAMAMOTO, YOSHITSUGU NAKAJIMA, HIROSHI OKABE, K ...1980 Volume 28 Issue 7 Pages 2235-2239
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAfter a single administration of perisoxal citrate to rats (21 mg/kg, i. v.), rabbits (15 mg/kg, i. v.) and humans (200 mg/man, p. o.), urinary excretion of the unchanged drug and its phenolic metabolites and the glucuronide forms of all these compounds was determined by a newly developed specific and simultaneous GC method. Generally, in all the species examined, excretion of the free forms of perisoxal and hydroxyperisoxals (m- and p-) was low or even undetectable, but that of the glucuronide forms was high. Neither the free nor the glucuronide form of o-hydroxyperisoxal was detected. The proportion of total m-hydroxy metabolites to total p-hydroxy metabolites varied in different species, being about 3 in rats, about 0.4 in rabbits and less than 0.1 in humans.View full abstractDownload PDF (579K) -
FUSAO KAIHO, YOSHIAKI GOTO, YURIKO KATO1980 Volume 28 Issue 7 Pages 2240-2243
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of crystalline conversion from the anhydrous form of prednisolone (A-PD) to its hydrated form (C-PD) on prednisolone (PD) release from o/w type ointment was studied in vitro at 37° and 5°, by using a diffusion cell and X-ray diffractometer. The conversion of A-PD in the ointment (A-PD ointment) into C-PD started on incubation for 4 days at 37° and the A-PD was entirely converted into C-PD after about 18 days. The longer the time of storage of the A-PD ointment at 37°, the less the release of PD from the ointment. On the other hand, A-PD was entirely converted into C-PD in the ointment in only one day at 5° ; the amount of PD released from the ointment was not dependent upon the time of storage and showed a constant release pattern. The crystalline conversion from A-PD to C-PD in the ointment is apparently due to the deterioration of the o/w type emulsion (in the ointment) with the passage of time. When the emulsion deteriorates, the A-PD dissolves in water released from the emulsion, and accordingly hydrated prednisolone (C-PD) is deposited in the ointment to an increasing extent. The reduction of PD release from the ointment stored at 37° is apparently due to the different solubilities of A-PD and C-PD in water. It is suggested that emulsion type ointment should be stored under suitable conditions.View full abstractDownload PDF (456K) -
TETSUZO KATO, MASAYUKI SATO, MASAKI NODA, TETSUO ITOH1980 Volume 28 Issue 7 Pages 2244-2247
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCondensation of acetoacetamide (1) with acetone in polyphosphoric acid (PPA) gave 4, 6-dimethyl-2 (1H)-pyridone (2a) in 32% yield. Similarly, the amide 1 was condensed with 2-butanone, 2-pentanone, 3-pentanone, cyclopentanone, cyclohexanone, cycloheptanone, acetophenone, and propiophenone to give the corresponding pyridone derivatives (2b-i) in 13-76% yields. Condensation of the amide 1 with acetylacetone and ethyl acetoacetate gave 3-acetyl-4, 6-dimethyl-2 (1H)-pyridone (5) and ethyl 4, 6-dimethyl-2 (1H)-pyridone-5-carboxylate (6), respectively. Self-condensation of the amide 1 in PPA gave 3-acetyl-4-hydroxy-6-methyl-2 (1H)-pyridone (7).View full abstractDownload PDF (506K) -
HIDENOBU OHMORI, SHIRO NAKAI, MASAICHIRO MASUI1980 Volume 28 Issue 7 Pages 2247-2250
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSControlled potential electrolyses of triphenylphosphine (TPP) in acetonitrile containing an excess of N-hydroxy compounds such as ketoximes, aldoximes, and hydroxamic acids were examined : subsequent treatment of the products under mild conditions gave amides, nitriles, and ureas, respectively. Electrolyses under conditions where the amounts of TPP were equal to or larger than those of the N-hydroxy compounds did not give satisfactory results.View full abstractDownload PDF (556K) -
ICHIRO YASUDA, KOICHI TAKEYA, HIDEJI ITOKAWA1980 Volume 28 Issue 7 Pages 2251-2253
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structure of the pungent principle spilanthol isolated from the aerial part of Spilanthes oleracea JACQUIN (Compositae) was elucidated as (2E, 6Z, 8E)-N-isobutyl-2, 6, 8-decatrienamide by comparing its proton and carbon-13 nuclear magnetic resonance spectra with those of all-trans spilanthol.View full abstractDownload PDF (438K) -
YOSHIO OKADA, YUKO TSUDA, MASAMI YAGYU1980 Volume 28 Issue 7 Pages 2254-2258
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStudies on the rate of Curtius rearrangement of acyl amino acid and peptide azides were carried out by means of IR (infrared) spectrophotometry at 25°. It was found that Z-Gly-N3 and Z-Pro-N3 were more stable than the other acyl amino acid azides. The reactivity of isocyanates derived from azides with side chain functional groups of various amino acids or additives was also studied. It was found that isocyanates thus obtained were decomposed in the presence of triethylamine, its hydrochloride or 1-hydroxy-benzotriazole at 25°.View full abstractDownload PDF (612K) -
HIDEO BANDO, TAKASHI AMIYA, ETSUKO SATO, HIROSHI MITSUHASHI1980 Volume 28 Issue 7 Pages 2258-2260
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new polyoxypregnane derivative, 5α, 6α-epoxycaudatin, was isolated from Cynanchum caudatum MAX. and its structure was elucidated on the bases of physical data and chemical reaction. This compound is a probable intermcdiate in the biosynthesis of 5, 6-glycolic compounds. Kidjoranin was also isolated from this plant for the first time.View full abstractDownload PDF (440K) -
SHOZO MIYAZAKI, TANEKAZU NADAI1980 Volume 28 Issue 7 Pages 2261-2264
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFibrin film prepared from human plasma was evaluated as a new biodegradable carrier for drug delivery. Two steroidal compounds, prednisolone and prednisone, were used in this evaluation. The drug permeability of the fibrin film and the release characteristics of the drug/fibrin film system were investigated using in vitro test models. The high permeability of the fibrin film to drugs suggests that it may be available as a unique vehicle for drug delivery. The possible use of fibrin film in the control of drug release is also discussed.View full abstractDownload PDF (502K) -
MASAHARU TAKEYAMA, KANAME KOYAMA, HARUAKI YAJIMA, MOTOYUKI MORIGA, MIT ...1980 Volume 28 Issue 7 Pages 2265-2269
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of Glu8-vasoactive intestinal polypeptide (porcine VIP) is described. A 1 M solution of trifluoromethanesulfonic acid-thioanisole (1 : 1 equiv.) in TFA was found to cleave all the protecting groups employed, Z, Z (OMe), Bzl and Mts, suppressing the acid-catalyzed aminosuccinimide formation of the Asp residue (position 3) with the free carboxyl group. The activity of Glu8-VIP was 1/7-1/8 of that of synthetic porcine VIP.View full abstractDownload PDF (640K) -
KEIICHI FUKUYAMA, YUKITERU KATSUBE, HIROSHI ISHIDO, MIKIO YAMAZAKI, YU ...1980 Volume 28 Issue 7 Pages 2270-2271
Published: July 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDesacetyl derivative of austin has newly been isolated from Emericella nidulans var. dentata. The X-ray difraction analysis has revealed that the absolute configuration of this compound is antipodal to that of austin previously reported.View full abstractDownload PDF (346K)