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MASATOSHIA. MIYAMOTO, TOMOAKI KIYOTAKI, NAOA. KISOH, TAKAYOSHI MITSUNA ...
1973 Volume 21 Issue 9 Pages
1857-1867
Published: September 25, 1973
Released on J-STAGE: March 31, 2008
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Differential scanning calorimetry was carried out to elucidate the properties of two metastable forms of chloramphenicol palmitate (δ form and sub-α form) and the occurrence and the role of the sub-α form during manufacturing of chloramphenicol palmitate oral suspension. The δ form, a new form, was obtained when the small amount of melted chloramphenicol palmitate was cooled very rapidly to below 0° and it was converted to the sub-α form at 23° on heating. The X-ray diffraction pattern of the δ form was distinguished from that of any other forms reported. The other form, sub-α, was obtained by warming the δ form or directly from the melt by rapid cooling. It was transformed to the α form while liberating heat from about 40° through about 75°. The X-ray diffraction pattern, infrared absorption spectra, the behavior in the hot stage of the polarizing microscope and the differential scanning calorimetric curves suggested that the sub-α form is composed of the crystallites of the α form. Estimated thermodynamic values at the 95% confidence limit were ; ΔH
melt→sub-α=-9.2±0.2kcal/mole, ΔH
melt→δ=-2.8±0.5 kcal/mole, ΔH
δ→sub-a=-2.2±0.7 kcal/mole, and ΔH
sub-α→α=-2.0±0.3 (the sub-α form directly form the melt) and -6.1±0.9 kcal/mole (the sub-α form via the δ form). The supercooled dispersion of chloramphenicol palmitate in the emulsifier solution turned into the suspension while stirring. The first solid state of the chloramphenicol palmitate was estimated to be the sub-α form and it was transformed to the α-form gradually.
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MASAKATSU SHIBASAKI, TADAO SATO, NAOHITO OHASHI, SHIRO TERASHIMA, SHUN ...
1973 Volume 21 Issue 9 Pages
1868-1884
Published: September 25, 1973
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Thermal rearrangements of R(+)-2-(2-carboethoxy-1-phenyl) propyl isocyanide (R(+)-VIII), S(+)-2-(2-methyl-1-phenyl) butyl isocyanide (S(+)-XVI) and R(+)-2-(2-phenyl) butyl isocyanide (R(+)-XXVIII), were carried out under several reaction conditions. Although the reflux of a diphenyl ether solution of R (+)-VIII or heating R(+)-VIII without solvent afforded almost completely racemized cyanide (S (+)-X) (at most 9% retention of configuration) as the sole reaction product in excellent yields, treatment of S (+)-XVI with a procedure similar to that used with R (+)-VIII gave S (+)-cyanide (S (+)-XXIII) with 90% (reflux of a diphenyl ether solution) and 47% (heating without solvent) retention of configuration. The thermal reaction of R(+)-XXVIII gave three different olefins (XXXIV, XXXV, and XXXVI), in addition to the normal reaction product (R(+)-XXIX) with a low retention of configuration (at most 19%). These observations were discussed from various aspects including the effect of asymmetric solvation due to diphenyl ether and the relative stability of the radical intermediates formed.
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SHOJIRO YURUGI, AKIO MIYAKE, MITSUMI TOMIMOTO, HARUKI MATSUMURA, YOSHI ...
1973 Volume 21 Issue 9 Pages
1885-1893
Published: September 25, 1973
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The derivatives of 3-[4-(1-ethoxycarbonyl-1-methylethoxy) phenyl]-5-(3-pyridyl)-1, 2, 4-oxadiazole (I), which showed considerable hypocholesterolemic activities, were synthesized. Among them, 3-[4-(1-ethoxycarbonyl-1-methylethoxy) phenyl]-5-(2-or 3-chlorophenyl)-1, 2, 4-oxadiazole (13, 14) and their amide derivatives (29, 30) showed nearly equal activity to I. Two alternative synthetic routes of I were developed.
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SHIGEO SENDA, KOSAKU HIROTA, KYOJI MAENO
1973 Volume 21 Issue 9 Pages
1894-1900
Published: September 25, 1973
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Syntheses of 3-substituted 2, 4-dioxo-1, 2, 3, 4, 6, 7-hexahydro-5H-cyclopenta [d] pyrimidines (3-substituents : methyl, cyclohexyl, phenyl) from 2-ethoxycarbonylcyclopentanone were investigated. These compounds were alkylated in 1-position to give 1, 3-disubstituted pyrimidine derivatives (1-substituents : CH
3, CH
2COOR, CH
2CONR
2, CH
2CH
2NR
2). Their acute toxicities and analgetic, antipyretic, and antiinflammatory activities were tested.
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YOSHIO SASAKI
1973 Volume 21 Issue 9 Pages
1901-1905
Published: September 25, 1973
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The ring C-13 nuclear magnetic resonance chemical shifts of 1, 4-and 1, 3-disubstituted benzene derivatives were compared with those of monosubstituted benzene derivatives and the substituent constants σ
i. The slopes of C-1 and C-2 chemical shifts of 1, 4-disubstituted benzene derivatives and also those of C-1 and C-5 of 1, 3-disubstituted series are linear with respect to σ
i. The slopes of other positions have the same characters with those of the corresponding shifts of monosubstituted benzene derivatives.
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TETSUYA KONISHI, SIGEO BABA
1973 Volume 21 Issue 9 Pages
1906-1913
Published: September 25, 1973
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Intracellular distribution and some additional studies of metabolic fate of vitamin K homologs were studied by isotopic tracer with tritium or carbon-14 labeled vitamin K homologs, vitamin K
1, K
2(20) and K
3, to obtain the information about their site of action in the animal tissue. There are several reports on the intracellular distribution of K
1 but no clear result has been obtained about the incorporation site of vitamin K
1 in the animal cell and no report has been found in the case of K
2(20), which is estimated to be a physiologically active type of K homologs in the animal. In our present experiment, K
1 was found to be concentrated in the mitochondrial fraction after a long period of time and K
2(20) was faster incorporated in the liver and heart muscle than K
1 and showed remarkably higher affinity to the mitochondrial fraction. K
3 which is less lipophilic than the other two homologs, was less incorporated into the both tissues and stayed in the supernatant fraction. From these observations, it was revealed that K
1 and K
2 which have a long isoprenoid side chain have a higher mitochondrial affinity like other isoprenoid vitamins and the higher affinity of vitamin K to the mitochondrial fraction suggest the possibility of their function in some regulation process in mitochondria other than blood coagulation protein synthesis.
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YASUO KIKUGAWA, MASASHI KURAMOTO, ISAO SAITO, SHUNICHI YAMADA
1973 Volume 21 Issue 9 Pages
1914-1926
Published: September 25, 1973
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Reductions of 3-substituted pyridines, quinolines and 4-substituted isoquinolines with sodium borohydride were examined. The reduction of the nucleus occurred and the reduction mechanisms were investigated.
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YASUO KIKUGAWA, MASASHI KURAMOTO, ISAO SAITO, SHUNICHI YAMADA
1973 Volume 21 Issue 9 Pages
1927-1937
Published: September 25, 1973
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The reaction of 2-or 4-substituted pyridines and quinolines and 1-or 3-substituted isoquinolines with sodium borohydride was examined. The substituent groups which are usually resistant to reduction with sodium borohydride were reducible through the electronic influence of the heteromatic ring. The solvent effects on the reduction with sodium borohydride were also examined.
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TOSHIO NAMBARA, TAKAKO ANJYO, MASAHIRO ITO, HIROSHI HOSODA
1973 Volume 21 Issue 9 Pages
1938-1942
Published: September 25, 1973
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The stereochemistry of hydrogen removal from C-2 during the placental and microbial aromatization of 19-norsteroids has been investigated. The substrates for this purpose, epimeric [2-
3H] estr-4-ene-3, 17-diones (IV, VIII), were prepared along the route which had previously been developed. The tritiated compounds were admixed with an appropriate amount of [4-
14C] estr-4-ene-3, 17-dione and recrystallized until constant isotope ratio was achieved. Each substrate was incubated with the human placental preparation according to the procedure of Ryan. The transformation products, estrone and 1β-hydroxyestr-4-ene-3, 17-dione, and recovered substrate were separated by preparative thin-layer chromatography, diluted with the carrier and then recrystallized to constant isotope ratio, respectively. Estrone formed from the substrate with the label at 2β exhibited a 79% loss, while that from the 2α-labeled substrate lost only 20% tritium. The double-isotope labeled substrate was also incubated with respiring cultures of Bacillus sphaericus. The aromatized product from the 2β-tritiated substrate lost 80% of the label, whereas the 2α-epimer showed only 11% loss. Elimination of hydrogen from C-2 in the aromatization process with human placenta and microorganism is thus stereoselectively β.
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TAKEO HIGASHINO, YOSHIMASA NAGANO, EISAKU HAYASHI
1973 Volume 21 Issue 9 Pages
1943-1953
Published: September 25, 1973
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The reaction of quinazoline 3-oxide (I) with active methylene compound without a base catalyst was carried out and resulted in finding the transformation of I into quinoline derivatives even if the yields of quinoline derivatives were very poor (few percentage). Thus, the reaction with malononitrile gave 2-amino-3-quinolinecarbonitrile (V), with phenylacetonitrile, 2-amino-3-phenylquinoline (VII), with ethyl cyanoacetate, ethyl 2-amino-3-quinolinecarboxylate (IX) and ethyl α-cyano-ο-[N-(2-cyano-2-ethoxycarbonylvinyl) amino] cinnamate (XI), with 1, 3-diphenyl-1, 3-propanedione and 1-phenyl-1, 3-butanedione, 2-phenylquinoline (XII), with 2, 4-pentanedione, methyl 2-methyl-3-quinolyl ketone (XIV) and 4-acetonyl-8-quinolinecarbonitrile (XV), with ethyl acetoacetate, ethyl 2-methyl-3-quinolinecarboxylate (XVII) and 3-acetylcarbostyrile (XVIII), respectively. But in the case of the reaction with diethyl malonate, ethyl 4-quinazolineacetate (XX) was obtained. The possible reaction process for this transformation was also proposed and discussed.
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TOZO FUJII, TOHRU SAITO
1973 Volume 21 Issue 9 Pages
1954-1959
Published: September 25, 1973
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Treatment of 3-ethyladenine (Ia) with carbobenzoxy chloride in a mixture of acetonitrile and aqueous sodium bicarbonate resulted in the cleavage of the imidazole ring to form a compound presumed to be IVa, which was recyclized to 8-hydroxy derivative Va when heated in acetic acid. Carbobenzoxylation of 3-benzyladenine (Ib) under similar conditions gave Vb directly. The 8-hydroxy structure of Va, b was confirmed by hydrogenolysis of Vb leading to 6-amino-8-hydroxypurine (VIII), and the 3-alkyl structure was established by hydrogenolysis of Va to 6-amino-3-ethyl-3H-purin-8-ol (VIa), chlorination of VIa to give 8-chloro derivative VIIa, and hydrogenolysis of VIIa to Ia using hydrogen and palladium-on-charcoal.
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YOSHIAKI KAMANO, SUSUMU KUMON, TOSHIO ARAI, MANKI KOMATSU
1973 Volume 21 Issue 9 Pages
1960-1964
Published: September 25, 1973
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Epimerizations of 14α-artebufogenin (14α-H-15-oxo-bufadienolide, III) and 14β-artebufogenin (14β-H-15-oxo-bufadienolide, V) by acid were examined. From the results of nuclear magnetic resonance and optical rotatory dispersion measurements, the free energy difference between both compounds was calculated to be 0.4 kcal/mole. Therefore the 14β-isomer (C/D cis ring system) was more stable than the 14α-isomer (C/D trans ring system).
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MITSURU FURUKAWA, SEISHI TSUIJI, YOKO KOJIMA, SEIGORO HAYASHI
1973 Volume 21 Issue 9 Pages
1965-1970
Published: September 25, 1973
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Sulfenylation of the nucleophilic β-carbon atom of 1-morpholino-1-cyclohexene with several thiosulfonates was attempted. Among these thiosulfonates, the reaction with alkyl alkanethiosulfonates and aralkyl benzenethiosulfonates were unsuccessful, but aryl benzenethiosulfonates in which an electron withdrawing group was substituted in the ortho or para position of the aryl group successfully reacted with 1-morpholino-1-cyclohexene to give the corresponding arylthio derivatives.
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MITSUYA TANAKA, SHIGEHISA KYOSAKA, YUKIKO ITO
1973 Volume 21 Issue 9 Pages
1971-1977
Published: September 25, 1973
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The rates of hydrolysis of some substituted phenyl 2-acetamido-2-deoxy-α-and-β-D-glucopyranosides have been measured in acidic, neutral and alkaline aqueous solutions. In acidic solution, the β-glycosides hydrolyze 2-6 times as fast as the corresponding α-glycosides, and the rates of hydrolysis of the β-glycosides exhibit almost linear ρ-σ relationships (ρ=-0.52 at 61°, -0.54 at 78.2°) whereas those of the α-glycosides show seemingly convex ρ-σ curves, and the tentative calculation on linear relationship shows small ρ values (ρ=-0.16 at 61°, -0.12 at 68.9° and -0.08 at 78.2°). The kinetic parameters for the acid hydrolysis were calculated and discussed in connection with the participation of 2-acetamido group in intramolecular catalysis. The hydrolysis of the glycosides at 120° in neutral buffer solution (pH 6.8) is facilitated by electron-withdrawing substituent (ρ=+0.47 for the α-glycosides, +1.62 for the β-glycosides). The pH-log k
obs profile at 120° for the p-chlorophenyl β-glycoside indicates that the glycoside hydrolyzes at a spontaneous hydrolysis rate. The rate of alkaline hydrolysis of the β-glycosides increases with σ (ρ=+1.69 at 100°, +1.65 at 110°), but the α-glycosides are abnormally alkali-stable.
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ISAO KITAGAWA, TADATO TANI, KIKUYO AKITA, ITIRO YOSIOKA
1973 Volume 21 Issue 9 Pages
1978-1987
Published: September 25, 1973
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The iridoid glucoside composition of Linaria japonica MIQ., a Japanese folk medicine known as a laxative and diuretic, has been clarified to comprise antirride (Ia), antirrhinoside (IIa) and linarioside (IIIa). Linarioside is a new iridoid glucoside possessing a chlorohydrin moiety and the structure has been established as IIIa on the basis of physicochemical evidences and conversion into the corresponding epoxide antirrhinoside (IIa). Antirrhinoside is the major component of the plant and has been revealed to possess a weak and slow laxative property. In addition, the detailed proton magnetic reronance examinations on these glucosides and their derivatives have been presented.
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HIROTERU SAYO, SHIGEKO OZAKI, MASAICHIRO MASUI
1973 Volume 21 Issue 9 Pages
1988-1995
Published: September 25, 1973
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The anodic oxidation of N-monoalkyl and N, N-dialkylhydroxylamines in acetonitrile was studied. These hydroxylamines showed two anodic waves at glassy-carbon electrode. Controlled potential electrolysis of the hydroxylamines at the first wave consumed two electrons per molecule oxidized. N-Alkylhydroxylamines and N, N-dimethylhydroxylamine gave the corresponding nitroso compounds and a nitrone, MeN(O)=CH
2, respectively, while N, N-di-t-butylhydroxylamine gave t-nitrosobutane, t-butanol and isobutene. In the anodic oxidation the peak potentials were linearly related with the second order rate constants for oxidation of the hydroxylamines with DPPH, except in the case of N, N-di-t-butylhydroxylamine and di-t-butylnitroxide.
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KATSUTOSHI KAMEI, MASAYASU MURATA, KAZUKO ISHII, MASAYA NAMEKATA, ATSU ...
1973 Volume 21 Issue 9 Pages
1996-2003
Published: September 25, 1973
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A method using gas chromatography and combined gas chromatography-mass spectrometry techniques for the detection of amphetamine and related amines in urine was investigated. The perfluoroacyl derivatives of these amines have excellent gas chromatographic and mass spectrometric properties. Typical fragmentation processes in their mass spectra were also discussed.
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HIROZUMI INOUE, MIKIO TAKEDA, HIROSHI KUGITA
1973 Volume 21 Issue 9 Pages
2004-2013
Published: September 25, 1973
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Mass, optical rotatory dispersion (ORD) and circular dichroism (CD) spectra of the B/C trans-morphine derivatives have been studied in comparison with the natural (B/C cis) isomers. A characteristic difference between isomers epimeric at C
14 was found in mass spectrum in accord with the reported observation for the cis-and trans-morphinan derivatives. The stereochemistry of C
5 of trans-dihydrocodeinone (V) was established by ORD study and its conversion to trans-dihydrocodeine (VI) by NaBH
4 reduction.
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HARUO OGURA, MASAKAZU SAKAGUCHI
1973 Volume 21 Issue 9 Pages
2014-2018
Published: September 25, 1973
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A simple synthesis of pyrido [2, 3-d] pyrimidine derivatives as an antitumor agent was reported. Reaction of 6-amino- and 6-(substituted) amino-1, 3-dimethyluracil (I) with dimethyl acetylenedicarboxylate in methanol afforded a mixture of 5-oxo- and 7-oxopyrido-[2, 3-d] pyrimidines and an open-chain intermediate. This intermediate was proved to be 5-substituted 6-aminopyrimidine (VIa), and to be cyclized to 7-oxopyrido [2, 3-d] pyrimidine (VIIIa). On the other hand, 5-oxo compounds were obtained from the reaction of I with diketene or ethyl acetoacetate.
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HARUO OGURA, MITSUO KAWANO, TSUNEO ITOH
1973 Volume 21 Issue 9 Pages
2019-2025
Published: September 25, 1973
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Reaction of 2-aminobenzazoles such as 2-amino-benzothiazole, -benzoxazole, and-benzimidazole with acetylene compounds was reported comparing with the condensation product of these benzazoles and ethoxy methylenemalonate. In the former case, 2-oxo compounds were obtained while 4-oxo compounds were the product in the latter condensation. The structure of these products was confirmed from nuclear magnetic resonance and mass spectra.
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HARUO OGURA, KAZUO KUBO, YUMIKO WATANABE, TSUNEO ITOH
1973 Volume 21 Issue 9 Pages
2026-2030
Published: September 25, 1973
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1, 3-Dipolar cycloaddition of aldehyde hydrazones with dimethyl acetylenedicarboxylate without solvent gives rise to dimethyl 1, 3-diphenylpyrazole-4, 5-dicarboxylate, and in some cases trimethyl 1-phenylpyrazole-3, 4, 5-tricarboxylate as a by-product. In case of p-chloro- and p-methoxy-benzaldehyde phenylhydrazone, dimethyl 1-phenyl-3-(p-substitutedphenyl) pyrazoline-4, 5-dicarboxylate is formed. In dimethylformamide as a solvent, the reaction gives the same product in a similar yield. Although, when ethanol is used as a solvent, a small amount of the product is formed.
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HIDEYO SHINDO, TORU KOMAI, KENJI KAWAI
1973 Volume 21 Issue 9 Pages
2031-2038
Published: September 25, 1973
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The rate and mechanism of intestinal absorption of D- and L-isomers of 3, 4-dihydroxyphenylalanine (DOPA) were comparatively investigated in rats by means of in situ ligated loop and in vitro tissue accumulation techniques. L-DOPA was found to be very easily and much more rapidly absorbed from the ligated loop of rat intestine than the D-isomer and the absorption was proved to follow saturation kinetics and to be inhibited competitively by L-alanine and L-phenylalanine, while not by D-phenylalanine and D-DOPA. The in vitro tissue uptake of L-DOPA-
14C revealed an accumulation of radioactivity against the concentration gradient, which was depressed by metabolic inhibitors as DNP and sodium azide. L-DOPA was extensively metabolized in the intestinal tissue to dopamine, its glucuronide and DOPAC, while the D-isomer was not metabolized to any appreciable extent. The rate of absorption and the tissue uptake of L-DOPA-
14C was, however, not affected by inhibition of DOPA-decarboxylase. A saturability of the intestinal DOPA-decarboxylase activity with the substrate was demonstrated by everted sac method with increasing L-DOPA concentration in the incubation medium. From these results, it was concluded that L-DOPA, but not D-DOPA, is absorbed from rat intestine by an active transport mechanism, which proceeds independently from the decarboxylation process. These differences between the two isomers were also discussed in relation to those in their distribution patterns after oral administration to rats.
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Studies on 1-Azabicyclo Compounds. XV. Oxidation of 1, 3, 4, 6, 11, 11a-Hexahydro-2H-pyrazino [1, 2-b] isoquinolin-1-one Derivatives with Mercuric Acetate, and Their Conversion into 1, 2, 3, 4, 5, 6, 7, 8-Octahydro-2-methyl-2, 5-benzodiazecine and Related Compounds
HIDEO KATO, EIICHI KOSHINAKA, YOSHIO ARATA, MIYOJI HANAOKA
1973 Volume 21 Issue 9 Pages
2039-2047
Published: September 25, 1973
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Oxidation of hexahydro-2H-pyrazino [1, 2-b] isoquinolin-1-one (Ia) with mercuric acetate gave the α-aminocarbinol (II), which was characterized as the quaternary ammonium bromide (III). Mercuric acetate oxidation of the diamine (VII), however, afforded the lactam (VIII). Treatment of the methiodides (XIIa, XIIb, and XIIc) with lithium in liquid ammonia yielded the piperazinones (XIIIa, XIIIb, and XIIIc), respectively. On the other hand, reduction of the methiodides (XIIa, XIIb, and XIIc) with sodium amalgam furnished selectively the ten-membered aminolactams (XVIa, XVIb, and XVIc), respectively, in fair yields, which were converted to the corresponding ten-membered diamines (XVIIa, XVIIb, and XVIIc).
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MASAYUKI ONDA, YAEKO KONDA, YOSHITSUGU NARIMATSU, SATOSHI OMURA, TOJU ...
1973 Volume 21 Issue 9 Pages
2048-2050
Published: September 25, 1973
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Pyrindicin isolated from Streptomyces griseofluvus var. pyrindicus is determined to be 5-(trans-1'-butenyl)-3-methyl-3, 4, 6, 7-tetrahydro-2H-1-pyrindine by its chemical reactions and the physico-chemical methods.
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HARUO OGURA, MASARU OGIWARA, TSUNEO ITOH, HIROSHI TAKAHASHI
1973 Volume 21 Issue 9 Pages
2051-2056
Published: September 25, 1973
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Reaction of acetylenic Grignard reagents with 2, 3 : 4, 5-di-o-isopropylidene-aldehydo-D-ribose (I) or 2, 4 : 3, 5-di-o-benzylidene-aldehydo-D-ribose (VII) afforded 3-epimeric heptyne derivatives (II, III and VIII, IX). The configuration of these compounds was determined from nuclear magnetic resonance and mass spectra.
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HIDEO FUKUDA, YUKIKO KAWAKAMI, SHOSHIRO NAKAMURA
1973 Volume 21 Issue 9 Pages
2057-2060
Published: September 25, 1973
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A new method to screen anticholesterol substances produced by microbes was devised and the method was applied for cultured broth of Streptomyces. Only one strain, resembled to be Streptomyces violascens, out of more than 200 Streptomyces was determined to produce an anticholesterol substance by this screening method. Furthermore, a new method to measure the anticholesterol activity was established for fermentation and purification of the active component. The partially purified active component was proved to be a new enzyme which oxidized cholesterol to cholest-4-en-3-one. Nicotinamide adenine dinucleotide or nicotinamide adenine dinucleotide phosphate was not necessary for this enzymatic oxidation. It was found that the enzyme was active against the 3β-hydroxyl group on the steroid skeleton but not against the 3α-hydroxyl group by investigating the substrate specificity of the enzyme.
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MASAHIRO NAGAI, NOBUTOSHI TANAKA, OSAMU TANAKA, SACHIKO(MIYAHARA) ICHI ...
1973 Volume 21 Issue 9 Pages
2061-2065
Published: September 25, 1973
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A new triterpene named now betulafolientriol oxide I (IV), mp 237-240°, [α]
22D+2.6° (CHCl
3), was isolated from the leaves of Betula platyphylla SUKATCHEV var. japonica HARA in addition to betulafolientriol (I), hydroxyhopanone (II), and dammar-24-ene-12β, 20(S)-diol-3-one (III). The isolation of III was the first example of its occurrence in nature. The chemical and spectrometric investigation of IV and its derivatives showed that IV is a derivative of I, having a modified side chain of a substituted tetrahydrofuran ring. The oxidation of betulafolientriol (I) with perbenzoic acid gave betulafolientriol oxide I (IV) along with its C-24-epimer (XIV). The structure of XIV including its all stereochemistries was clarified by the derivation of XIV from 25-bromo-20 (S), 24 (S)-epoxy-dammarane-3α, 12β-diol (XV). Accordingly, the structure of betulafolientriol oxide I (IV) was established as 20 (S), 24 (R)-epoxy-dammarane-3α, 12β, 25-triol. The achievement of chemical conversion of IV into ocotillone II (XII) showed that the stereochemistry at C-24 of ocotillol II (VIII) and its derivatives is expressed in term of (R) configuration (the methyl at C-20/ the hydroxyisopropyl at C-24 : trans).
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YOSHIRO KOBAYASHI, ITSUMARO KUMADAKI, HARUO SATO, CHIHIRO YOKOO, TSUTO ...
1973 Volume 21 Issue 9 Pages
2066-2067
Published: September 25, 1973
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N-Oxides of quinoline, isoquinoline, and benzo [f] quinoline were methylated with sodium methylsulfinylmethylide. Methyl group was introduced into the α-position to the N-oxide group in each case, regardless of the charge densities. Reaction mechanism is proposed upon these results.
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HIROSHI TAKAKU, YOSHIFUSA SHIMADA, KATSUHARU AOSHIMA
1973 Volume 21 Issue 9 Pages
2068-2070
Published: September 25, 1973
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YOICHI TANIGUCHI, HIDEFUMI KATO
1973 Volume 21 Issue 9 Pages
2070-2073
Published: September 25, 1973
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AKIRA KAMADA, NOBORU YATA, KAZUYOSHI KUBO, MASATO ARAKAWA
1973 Volume 21 Issue 9 Pages
2073-2076
Published: September 25, 1973
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YURIKO KATO, MOTOHARU IWAZURU, YUZABURO HIROOKA
1973 Volume 21 Issue 9 Pages
2077-2082
Published: September 25, 1973
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SHOICHI NAKAJIMA
1973 Volume 21 Issue 9 Pages
2083-2085
Published: September 25, 1973
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TAEKO NAKAYAMA, TERUMI NAKAJIMA, HIROFUMI SOKABE
1973 Volume 21 Issue 9 Pages
2085-2087
Published: September 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
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MITSUAKI SANO, ISAO TOMITA, TATSUO OZAWA, TETSURO IKEKAWA, MITSUKO TAN ...
1973 Volume 21 Issue 9 Pages
2090-2092
Published: September 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL
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ITIRO YOSIOKA, YOSHINOBU MORII, ISAO KITAGAWA
1973 Volume 21 Issue 9 Pages
2092-2094
Published: September 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS
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KIYONORI SANO, ITIRO YOSIOKA, ISAO KITAGAWA
1973 Volume 21 Issue 9 Pages
2095-2097
Published: September 25, 1973
Released on J-STAGE: March 31, 2008
JOURNAL
FREE ACCESS