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HISAO YAMAMOTO, ATSUKO MISAKI, MITSUO IMANAKA
1968 Volume 16 Issue 12 Pages
2313-2319
Published: December 25, 1968
Released on J-STAGE: March 31, 2008
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When a phenylhydrazine is reacted with phenylacetone or methyl ethyl ketone, the reaction using hydrogen chloride, zinc chloride, ortho-phosphoric acid or boron trifluorideetherate as a condensing agent gives 2-methyl-3-phenylindole or 2, 3-dimethylindole respectively, but the reaction using polyphosphoric acid affords the above-mentioned 2-methylindole derivative as well as 2-benzyl- or 2-ethyl-indole respectively, amount of which product tends to increase with increasing a ratio of phosphorous pentoxide to ortho-phosphoric acid. In reacting a N
1-(p-chlorobenzoyl) phenylhydrazine with phenylacetone, the reaction in the presence of every catalyst gives 2-methyl-3-phenylindole derivatives as a main product, and even when used polyphosphoric acid it is too difficult to yield 2-benzylindole derivative. Several mechanisms on these results are suggested.
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HARUO KITAGAWA, TETSUYA KAMATAKI, SOICHI YOSHIDA
1968 Volume 16 Issue 12 Pages
2320-2323
Published: December 25, 1968
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Effect of high dose administration of pentobarbital and phenylbutazone on the plasma biologic half lives were determined. The remarkable effect on the plasma biologic half life was seen in the pentobarbital administration especially in the mouse, rabbit, cat, dog and monkey. In the case of phenylbutazone administration, however, the prolongation of the half life in the high dose group was seen only in the dog. The liver microsomal pentobarbital and phenylbutazone metabolizing enzyme activities were, in general, in agreement with the plasma biologic half lives.
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YUZO YOSHIDA, HIROSHI KUMAOKA, MASUO AKAGI
1968 Volume 16 Issue 12 Pages
2324-2333
Published: December 25, 1968
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Nitro-reducing systems of rat liver were studied. 1. Rat liver possessed at least two different nitro-reducing systems ; they were distinguished from each other by requirement of hydrogen donor, intracellular localization and sensitivity for phenobarbital induction. 2. Microsomal reduced nicotinamide-adenine dinucleotide phosphate-linked nitro-reducing system was obtained in soluble form by the treatment of microsomes with steapsin, and was partially purified. Some properties of the solubilized system were studied. 3. Evidence was presented that microsomal NADPH-cytochrome c reductase was included in microsomal nitro-reducing system. However, the nitro-reducing system required cofactors. One of them might be flavin mononucleotide interacting weakly with protein. Effect of flavins to the nitro-reducing system was kinetically discussed.
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NOBORU NAKAI, JUNICHI HASE
1968 Volume 16 Issue 12 Pages
2334-2338
Published: December 25, 1968
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1. 2-Methyl-1, 4-naphthoquinone (K
3) reacted with sulfhydryl compound to form a thioether linkage at 3-position of K
3 with an absorption maximum at 420-430mμ. 2. For this reaction, molecular oxygen and alkaline metal ions such as Na
+ and K
+ were essential. One half mole of oxygen was consumed for the reaction of one mole of K
3 with one mole of sulfhydryl compound. 3. The reaction product of K
3 with cysteine was unstable and gradually turned to the insoluble amorphous polymer. By methylation of intermediate, it was identified to be methyl 5-methyl-6-methoxy-3H-naphtho [2, 1-b] [1, 4]-thiazine-2-carboxylate.
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NOBORU NAKAI, JUNICHI HASE
1968 Volume 16 Issue 12 Pages
2339-2342
Published: December 25, 1968
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1. 2-Methyl-1, 4-naphthoquinone (K
3) reacted with sulfhydryl group of protein such as bovine serum albumin and papain to form a thioether linkage at 3-position of K
3 as well as sulfhydryl groups of low molecular compound. 2. K
3 bound to detectable sulfhydryl groups in the active site of native papain with high specificity and its binding was not cleaved by the addition of cysteine.
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KATSUMI KOSHI, MASAO SHIMIZU
1968 Volume 16 Issue 12 Pages
2343-2350
Published: December 25, 1968
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2, 3-Dimethoxy-5-methyl-p-benzoquinone (IV), a synthetic intermediate of ubiquinones was prepared in excellent yield by oxidation of 2, 3-dimethoxy-5-methyl-p-phenylenediamine dihydrochloride (XIV) obtained via 3, 4-dimethoxy-2, 5-dinitrobenzaldehyde (XII) from vanillin. A number of p-benzoquinones related to IV were also synthesized for biological evaluation.
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TOMOKO OKUDA, YOICHI KOBAYASHI, TETSURO IKEKAWA
1968 Volume 16 Issue 12 Pages
2351-2354
Published: December 25, 1968
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Questiomycin A (3-aminophenoxazone-(2)) showed stable ESR spectra in both solid state and organic solvents. The structure of the free radical was discussed by analysis of the hyperfine structure of the radicals produced from questiomycin A and the isotope compounds and simulation using an electronic computor. It was concluded that the spin density of the compound mainly existed in the nitrogen atom of the amino group.
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TAKEO UEDA, YOSHIHISA OKAMOTO, TADAKAZU TSUJI, MASAKO MURAOKA
1968 Volume 16 Issue 12 Pages
2355-2361
Published: December 25, 1968
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For the purpose to examine as to their antiviral activities, 2-acylaminoacetamidine (II) and 3-acylaminopropionamidine hydrochlorides (III) were synthesized from the corresponding nitriles via ethyl imidates. The difference of the reactivity between ethyl 2-acylaminoacetimidates and ethyl 3-acylaminopropionimidates on the course of amidination were postulated. Iminoesterification of dinitrile, (p-cyano) benzamidopropionitrile (XVIII), was discussed by referring the infrared spectrum of a corresponding monocyanomonoester, ethyl p-(N-cyanoethylcarbamoyl) benzoate (XXI). Among the compounds obtained hereof, 3-(p-methyl) benzamidopropionamidine hydrochloride was found to have an inhibitory effect on influenza virus in mice and in membrane culture.
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SHOJI SHIBATA, YOSHIHIRO NISHIKAWA, TADAHIRO TAKEDA, MAMORU TANAKA
1968 Volume 16 Issue 12 Pages
2362-2369
Published: December 25, 1968
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A marked inhibiting effect against implanted sarcoma 180 was shown by the so far unknown glucan of a lichen, Gyrophora esculenta MIYOSHI. The glucan was isolated in a pure state and proved to be a partially acylated β-1, 6-glucan. The antitumour active component of another lichen, Lasallia papulosa (ACH.) LLANO, has been almost established to be identical with that of G. esculenta.
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TSUTOMU MOMOSE, YOSUKE OHKURA, JUNZO SHIOTA
1968 Volume 16 Issue 12 Pages
2370-2375
Published: December 25, 1968
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Four reaction products produced in the color reaction of m-dinitrobenzene with potassium cyanide were separated by a chromatographic technique with alumina. Two of them were determined as 2-ethoxy-6-nitrobenzonitrile and 4, 6-diethoxy-2, 3-benzenedicarbonitrile respectively. Remaining two substances were the main parts of the coloring matters, and their structures were presented as 2, 3-dihydro-4-nitro-3-oxo-1H-indazole-7-carbonitrile or 2, 3-dihydro-6-nitro-3-oxo-1H-indazole-7-carbonitrile and 2, 3-dihydro-6-nitro-3-oxo-1H-indazole-5-carbonitrile respectively. The reaction mechanism was also discussed.
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HIKARU OZAWA, KAZUNOBU SUGAWARA
1968 Volume 16 Issue 12 Pages
2376-2382
Published: December 25, 1968
Released on J-STAGE: March 31, 2008
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The actions and the structure-activity relationship of alkylguanidines on the smooth muscle organs were investigated and the following results were obtained. On guinea-pig hypogastric nerve-vas deferens preparation and trachea preparation, the responses induced by the electrical stimulation of the nerve were potentiated with guanidine (G), methylguanidine (MG), N, N-dimethylguanidine (NN-DMG) and N, N'-dimethylguanidine (NN'-DMG), were not affected with ethylguanidine (EG) and were inhibited with propylguanidine (PG), butylguanidine (BG) and hexylguanidine (HG), in doses of 10
-5-5×10
-3M respectively. Also, the contractions of the vas deferens preparation induced by norepinephrine were potentiated with EG, PG, BG and HG, but the contractions induced by acetylcholine were not potentiated with these compounds. The contractions of the cat nictitating membrane induced by the electrical stimulation of the cervical sympathetic nerve were not affected by all compounds. In anaesthetized cats and rats, G, MG, NN-DMG and NN'-DMG, in dose of 5 mg/kg, produced a rise in the blood pressure. The rising actions induced by these compounds were not abolished with an adrenergic α-blockade. EG, PG, BG and HG, in dose of 5mg/kg, produced a temporary fall followed by a rise. These compounds potentiated the pressor action of norepinephrine and suppressed that of tyramine with the increase of the carbon number. In spinal cats, a temporary fall of the blood pressure induced by these compounds were abolished and only a rise was observed. Also, the fall action in the blood pressure and the increase of the heart rate induced by isoproterenol were suppressed with HG. HG (1%) had local anaesthetic action as potent as procaine, and its action was more lasting than that of procaine.
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KUNITOSHI YOSHIHIRA, SETSUKO SAKAKI, HIDEKO OGAWA, SHINSAKU NATORI
1968 Volume 16 Issue 12 Pages
2383-2389
Published: December 25, 1968
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1, 16-bis (2, 5-Dimethylamino-p-benzoquinon-3-yl) hexadecane (II) was synthesized and proved to be identical with the tetrakis (methylamino) derivative prepared from dihydroardisiaquinone A (IX). The positions of methoxyl groups in ardisiaquinones (Ia-Ic) were confirmed by the examination of the nuclear Overhauser effect. Dealkylation was accompanied in alkylamination of VI and toluquinone. Some observations on nuclear magnetic resonance spectra of alkylaminobenzoquinone derivatives were also reported.
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SHOSHICHIRO KIMOTO, MASAO OKAMOTO, TAKAAKI MIZUMOTO, YASUHIRO FUJIWARA
1968 Volume 16 Issue 12 Pages
2390-2397
Published: December 25, 1968
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The hitherto unknown stereoisomer of trans-2-methyl-1, 2, 3, 4, 4a, 5, 6, 7, 8, 8a-decahydro-7-isoquinolinol (XIIIc) and the known isomer of cis-2-methyl-1, 2, 3, 4, 4a, 5, 6, 7, 8, 8a-decahydro-7-isoquinolinol (XIIIa) were stereoselectively synthesized from 4-hydroxy-1, 2, 3, 4, 5, 6-hexahydrohomophthalic acid 2, 4-lactone (IX). The latter compound (IX) was separated from the reduction product of diethyl 4-hydroxyhomophthalate (II) whose configuration was already decided. Furthermore, another known isomer (XIIId) having trans ring juncture was prepared by different method from the known procedure.
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MOTOHIKO KATO, MASAKO OHNISHI, TOSHIO NAMBARA
1968 Volume 16 Issue 12 Pages
2398-2403
Published: December 25, 1968
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The relationship between Zimmermann reaction and base-catalyzed deuterium exchange reactivity of 16- and 17-oxosteroids together with some simple ketones has been investigated. With regard to the simple ketones such as cyclopentanone (I), cyclohexanone (II) and diethyl ketone (III) the sequential order of the deuterium exchange activity was found to be in qualitative agreement with that of the rate of Zimmermann reaction as follows : I>II≈III. The Zimmermann complex derived from cholestan-3-one, mp178-180°, was isolated and assigned to the structure of 2α-(2, 4-dinitrophenyl) cholestan-3-one on the basis of the nuclear magnetic resonance spectrum. The spectroscopic properties of Zimmermann complexes produced from the cyclic ketones are also described.
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ZENICHI HORII, KAZUO OHKAWA, SANGWON KIM, TAKEFUMI MOMOSE
1968 Volume 16 Issue 12 Pages
2404-2409
Published: December 25, 1968
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Synthesis of 1-hydroxy-3-hydroxymethyl-4-(3, 4-dimethoxyphenyl)-6, 7-methylenedioxy-2-naphthoic acid γ-lactone (I), the structure assigned to diphyllin by T. Murakami in 1961, was carried out by starting from 3, 4-dimethoxy-3', 4'-methylenedioxybenzophenone (III) as shown in Chart 1. Cyclization of benzhydrylsuccinic acid (V) derived from III occurred selectively on the benzene ring bearing no bromo group as expected. Nonidentity of I with diphyllin was confirmed by comparison of melting points, infrared spectra, thin-layer chromatograms and ferric chloride tests.
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HIROMICHI SAEKI, TADAHIRO IWASHIGE, EIJI OHKI
1968 Volume 16 Issue 12 Pages
2410-2415
Published: December 25, 1968
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Treatment of methyl 2, 3-di-O-benzyl-α-L-arabino-pentodialdo-1, 4-furanoside (1) with nitromethane in the presence of sodium methoxide afforded an epimeric mixture of methyl 2, 3-di-O-benzyl-6-deoxy-6-nitro-α-L-altro-(2c) and -β-D-galactofuranoside (3c) in a ratio of 2.5 : 1. On the other hand, the analogous treatment of 3-O-benzyl-1, 2-O-isopropylidene-α-D-xylo-pentodialdo-1, 4-furanose (7b) with nitromethane gave 3-O-benzyl-6-deoxy-1, 2-O-isopropylidene-6-nitro-α-D-glucofuranose (8b) predominantly.
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HIROMU MORI, KENYU SHIBATA, KIYOSHI TSUNEDA, MASANOBU SAWAI
1968 Volume 16 Issue 12 Pages
2416-2425
Published: December 25, 1968
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22-Isoecdysone (XXIX) was synthesized from 22α
F-hydroxy-3, 6-dioxohomo-5α-cholan-25-oic acid 25→22-lactone (II) by 14 steps. Novel methods of synthesis of 2β, 3β-dihydroxy and 14α-hydroxy-6-oxo-7-ene function reported in this series of papers could be used very efficiently.
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TADAHIKO OTAKA, MITSURU UCHIYAMA, SEIICHI OKUI, TSUNEMATSU TAKEMOTO, H ...
1968 Volume 16 Issue 12 Pages
2426-2429
Published: December 25, 1968
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The insect-metamorphosing steroids (ecdysterone, inokosterone and cyasterone) and the related substance (rubrosterone) isolated from Achyranthes and Cyathula (Amaranthaceae) were assayed in terms of their ability to stimulate protein synthesis in mouse liver. High stimulation was introduced by all steroids, administered intraperitoneally, in which cyasterone showed the highest activity. Oral administration of ecdysterone produced similar activation. Ecdysterone stimulated protein synthesis not only in male mice but also in female mice.
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TOSHIO KAWASAKI, TETSUYA KOMORI, SHINRO SETOGUCHI
1968 Volume 16 Issue 12 Pages
2430-2435
Published: December 25, 1968
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Three nonsteroidal compounds, named diosbulbins A, B and C, were isolated from the root tubers of Dioscorea bulbifera L. forma spontanea MAKINO et NEMOTO (a wild type of D. bulbifera L.) in which scarcely steroid sapogenin was found. Diosbulbin A, C
20H
24O
7, mp 265°(decomp.), [α]
20D+26.7°, B, C
19H
20O
6, mp 285°(decomp.), [α]
20D+92.0°and C, C
19H
22O
7, mp 247-250°(decomp.), [α]
20D+64.7°, all having bitter taste, were assigned the partial structural formulae III, I, II, respectively, and regarded as a series of novel type of furanoid norditerpenes. These are first terpenoids reported in Dioscoreaceae and first furanoid diterpenoids in Monocotyledoneae.
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JOHN CARRICK, K.C. CHAN, H.T. CHEUNG
1968 Volume 16 Issue 12 Pages
2436-2441
Published: December 25, 1968
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Reported here (Table II) are the results of screening of Malayan plants from 82 families, representing 169 genera and 226 species, for presence of alkaloids, saponins, and steroids and triterpenes. Results of ensuing detailed chemical investigations on some plants are summarized (Table I), and the potentials of others discussed.
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YO UEDA, JUNICHI UCHIDA, JUNKO KUROKI, KUNIKO TOYONAGA, YOSHIKO WATANA ...
1968 Volume 16 Issue 12 Pages
2442-2446
Published: December 25, 1968
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The chemical structures of the color reaction products (Ib and Ic) obtained from butyl-and p-tolyl-urea with diacetyl monoxime and glucuronolactone in phosphoric acid were elucidated by their physical properties. Ib develops immediately a red color in phosphoric acid and is thought to be one of the main reaction product or one of the main reaction intermediate responsible for the color reaction. Ib gave two kinds of diacetate, and their structures were also established.
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SHUJI TAKAHASHI
1968 Volume 16 Issue 12 Pages
2447-2450
Published: December 25, 1968
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A bicyclic primary alcohol was isolated from vetiver oil. The structure was elucidated to be I, a member of the eremophilane series, by corelation with α-vetivone (isonootkatone).
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TETSUJI KAMETANI, ISAO NOGUCHI
1968 Volume 16 Issue 12 Pages
2451-2455
Published: December 25, 1968
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Phenolic oxidation of 1, 2, 3, 4-tetrahydro-7-hydroxy-1-(2-hydroxy-4, 5-methylenedioxybenzyl)-6-methoxy-2-methylisoquinoline (Ib) afforded the dienone (IIb) in 3.2% yield, which was characterized by its microanalysis and spectral determination.
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ZENICHI HORII, SHIRO YAMAMURA, HIDEO HAKUSUI, TAKAKO NISHIKADO, TAKEFU ...
1968 Volume 16 Issue 12 Pages
2456-2462
Published: December 25, 1968
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A convenient synthesis of 6-ethyl-1-naphthol (I) and its conversion into 4-bromo-6-ethyl-1-naphthol (VI) are described. Chromium trioxide oxidation of 6-ethyltetralin gave predominantly 6-ethyl-1-tetralone (IX), which was dehydrogenated with palladized charcoal to I. Bromination of I afforded VI, a starting material in the synthesis of bisanhydrodaunomycinone (V). Structuers of VI and IX were confirmed by alternative syntheses as shown in Chart 3.
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YASUO INUBUSHI, TAKASHI HARAYAMA, MITSUHIRO AKATSU, HISASHI ISHII, YUJ ...
1968 Volume 16 Issue 12 Pages
2463-2470
Published: December 25, 1968
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The structures of two new lycopodium alkaloids, serratine and serratanidine, which have been isolated from Lycopodium serratum THUNB. var. serratum f. serratum (=L. serratum THUNB var. Thunbergii MAKINO) were studied. From the chemical and spectroscopic evidence, the structures of these alkaloids were established as serratine (VI) and serratanidine (VII), respectively.
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HIROMICHI SAEKI, EIJI OHKI
1968 Volume 16 Issue 12 Pages
2471-2476
Published: December 25, 1968
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Syntheses of methyl 2, 3-di-O-benzyl-5, 6-dideoxy-5, 6-epimino-α-L-altrofuranoside (4a) and 3-O-benzyl-5, 6-dideoxy-5, 6-epimino-1, 2-O-isopropylidene-β-L-idofuranose (11a) were described. It was found that an attack of nucleophiles in these epimines occurs exclusively in the terminal position with epimine ring opening.
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HIROMICHI SAEKI, EIJI OHKI
1968 Volume 16 Issue 12 Pages
2477-2481
Published: December 25, 1968
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Lithium aluminum hydride reduction of 6-azido-3-O-benzyl-6-deoxy-1, 2-O-isopropylidene-β-L-idofuranose (5b) afforded 3-O-benzyl-5, 6-dideoxy-5, 6-epimino-1, 2-O-isopropylidene-α-D-glucofuranose (1a). Its acetate (1b) was treated with acetic acid to give an 5-acetamido-6-O-acetyl-5-deoxy-derivative (6) which was transformed into a monosaccharide antibiotic, nojirimycin (2) which was produced by some strains of Streptomyces and showed activity against Sarcina lutea and Xanthomonas oryzae.
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HIKARU OZAWA, KAZUHIKO IWATSUKI
1968 Volume 16 Issue 12 Pages
2482-2487
Published: December 25, 1968
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1-Phenyl-4-guanylpiperazine sulfate [PGP] and its derivatives were synthesized. The effects of these compounds on blood pressure, the nictitating membrane and the action of sympathomimetic amines such as tyramine and norepinephrine were examined in spinal cats. The effects of these compounds on MAO activity were also examined using the rat liver enzyme preparation in vitro. The results obtained were briefly summarized as follows : 1) PGP derivatives caused a rise in blood pressure and a contraction of the nictitating membrane in spinal cats. 2) PGP derivatives potentiated a pressor effect and a contraction of the nictitating membrane induced by tyramine and norepinephrine in spinal cats. 3) Reserpine caused a long-lasting hypertension and contraction of the nictitating membrane in spinal cats, when the animals were pretreated with PGP. 4) PGP derivatives showed a property to inhibit monoamine oxidase (MAO) activity. 5) PGP inhibited the restoration of the pressor effect of tyramine by a slow intravenous infusion of norepinephrine.
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TOSHIMITSU UJIIE
1968 Volume 16 Issue 12 Pages
2488-2494
Published: December 25, 1968
Released on J-STAGE: March 31, 2008
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In order to obtain some information on the action mechanism of 2-(2-hydroxyphenyliminomethyl)-4-n-hexylphenol (II) as a possible anticancer agent a series of experiments were performed, in which the influence of II on macromolecular synthesis and energy metabolism was examined employing B. subtilis in vitro. As the results, net synthesis of RNA was fairly inhibited by II at the level of 10μM, though DNA and protein syntheses were less affected under the same conditions. Both respiration and anaerobic glycolysis of the bacterial cell were suppressed at the concentration of 33.3μM or more of II. Then, it might be postulated that depression of RNA synthesis in one hand and suppression of respiration and anaerobic glycolysis in the other are responsible for the inhibition of the bacterial growth. Additionally, experimental data suggest that metal chelating ability of II might be contributing to the antibacterial action, because the inhibition of bacterial growth by II could be almost completely reversed by either Fe
2+, or Fe
3+, or Mn
2+.
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KEIJI SEKIGUCHI, ISAMU HORIKOSHI, IKUZO HIMURO
1968 Volume 16 Issue 12 Pages
2495-2502
Published: December 25, 1968
Released on J-STAGE: March 31, 2008
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In order to find the limit of size reduction by the method of solvation and desolvation, the effect of repeated solvation and desolvation of CHCl
3 on the specific surface area of griseofulvin particles was investigated by the BET gas adsorption method. It was found that the antibiotics was effectively pulverized by a single application of the method. The applicability was also tested with several substances forming solvates and hydrates and the specific surface areas were all found to be 2-3m
2/g, unless a solution was formed during the desolvation process. The heat of solvation of griseofulving with CHCl
3 and the heat of activation of the desolvation reaction were estimated to be 6.4±0.5 and 20±1 kcal/mole by the differential scanning calorimetry and gas evolution analysis.
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KOICHI NAKAZAWA
1968 Volume 16 Issue 12 Pages
2503-2511
Published: December 25, 1968
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Permethylated 3-nitrobisflavonyl ether (XXIV), the key-intermediate for the synthesis of the proposed structure (XXX), was prepared by the condensation of 8-hydroxy-4', 5, 7-trimethoxyflavone (XX) with 4'-iodo-3'-nitro-5, 7-dimethoxyflavone (XXIII) in DMSO in the presence of K
2CO
3 at 110°for 1 hr. The nitro ether was reduced by Na
2S
2O
4 in aq. DMF, diazotized and decomposed with 50% H
3PO
2 to give XXVII, which proved to be different from pentamethyl ether of natural hinokiflavone. An alternative bisflavone with 4', 6''-coupling positions has now been synthesized in a similar route described above. XXXIV was condensed with XXIII to 3'-nitro ether (XXXV), which was reduced, diazotized and decomposed to give permethylated ether (XXXVIII), identical with permethyl ether of natural hinokiflavone. The synthesized methyl ether was finally demethylated by means of HI·Ac
2Oat 130-140° for 3 hr to give 4''', 5, 5'', 7, 7'-pentahydroxy-4', 6''-bisflavonyl ether (XLII) identical with natural hinokiflavone. 4', 8''-Bisflavone (XXVII) was converted into a bisflavone (XLII) identical with natural hinokiflavone, when heated with HI·Ac
2O as above (Wessely-Moser rearrangement).
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TSUTOMU FURUYA, KEISUKE ARAKI
1968 Volume 16 Issue 12 Pages
2512-2516
Published: December 25, 1968
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Two pyrrolizidine alkaloids, symphytine (I), a new compound, and echimidine (II) have been isolated from the dried roots of Symphytum officinale. Both have a retronecine nucleus esterified on the 7-hydroxyl group with angelic acid. The other esterifying acid of symphytine is l-viridifloric acid (III), identical with the authentic sample. The structure of symphytine, a diastereoisomer of echiumine (retronecine esterified with angelic acid and trachelanthic acid), has been confirmed. A large amount of allantoin has also been isolated from the dried roots and leaves.
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TAKASHI TATSUNO, MAMORU SAITO, MAKOTO ENOMOTO, HIROSHI TSUNODA
1968 Volume 16 Issue 12 Pages
2519-2520
Published: December 25, 1968
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HIDEO INATOMI, FUMITO INUGAI, TAKAO MURAKAMI
1968 Volume 16 Issue 12 Pages
2521
Published: December 25, 1968
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KOJI HAYASHI, HIROSHI MITSUHASHI
1968 Volume 16 Issue 12 Pages
2522-2524
Published: December 25, 1968
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HIDEKO ISHIHARA, OTOHARU ISHIZAKA
1968 Volume 16 Issue 12 Pages
2524-2525
Published: December 25, 1968
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