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Volume 89, Issue 5
Displaying 1-25 of 25 articles from this issue
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SADAO BESSHO, SUIICHI TOMIOKA, SHIRO ITO1969 Volume 89 Issue 5 Pages 599-606
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIt is important to consider the pressure transmission in tablet compression designs. Pressure transmission in the two directions, the compression and the die wall direction, were measured for several substances, racked weimhts and compression pressures. The experimental equation in the compression direction is PL=kPU in pressure region 50-4000 kg/cm2, which is usually used in pharmaceutical tablet compression. The presumption equation for pressure transmission ratio, k, in the compression direction is k=exp (-μKCm/A2) theoretically. And the presumption equation for the pressure transmission in mixture and multi-layer compression is PL=k1·k2···.kn·PU. The theoretical pressure transmission equation in the die wall direction is PD=D/4μS·(1-exp (-4μKS/D)) PU, but the fitness is worse experimentally than in the compression direction.View full abstractDownload PDF (861K) -
HIROTAKA OTOMASU, SHIGERU OMIYA1969 Volume 89 Issue 5 Pages 607-609
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS11-Oxo-11H-indeno [1, 2-b] quinoxaline (I) was reduced catalytically with Pd-C to give the corresponding alcohol (II). By the reaction of I with NaOC2H5, the ring-cleavage occured and 2-(3-hydroxy-2-quinoxalinyl) benzoic acid (IV) was obtained. IV was also prepared by the condensation of o-phenylenediamine and phthalonic anhydride. Treatment of IV it H2SO4 or PCl5 gave the dehydrated intramolecular ester (V), which was readily returned to IV with dil. alkali solution. I reacted with PCl5 to give the 11, 11-dichloro derivative (VI) and with hydroxylamine to form its oxine (VII). VII was converted into 6-oxo-5, 6-dihydroisoquino [3, 4-b] quinoxaline (VIII) in good yield by Beckmann rearrangement using PCl5 in CHCl3, and VIII was identical with the condensation product of o-phenylenediamine and phthalonimide by Gabriel method.View full abstractDownload PDF (448K) -
TETSUJI KAMETANI, TSUTOMU SUGAHARA, KEIICHIRO FUKUMOTO1969 Volume 89 Issue 5 Pages 610-616
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe Bischler-Napieralski reactiorx of N-(5-benzyloxy-3, 4-dimethoxyphenethyl)-2-(3-benzyloxy-4-methoxyphenyl) acetamide (VI) gave a mixture of 3, 4-dihydroisoquinolines cyclized in the ortho-and para-position of the 5-benzyloxy group. Without isolation, the mixture was derived to the 1, 2, 3, 4-tetrahydroisoquinoline compounds, and separated into 8-hydroxy (XI) and 6-hydroxy (XII) compounds. The mixture of XI and XII was submitted to the Mannich reaction and the product was methylated with diazomethane to 1, 2, 3, 10, 11-pentamethoxyprotoberberine (XIV). The Bischler-Napieralski reaction of N-(5-benzyloxy-3, 4-dimethoxyphenethyl)-3-(3-ethoxycarbonyl-4-methoxyphenyl) propionamide (XX) also gave a mixture of 3, 4-dihydroisoquinolines which was derived to the 1, 2, 3, 4-tetrahydroisoquinolines and separated into 8-hydroxy (XXIV) and 6-hydroxy (XXV) compounds. Discrimination of 8-and 6-hydroxyisoquinolines was made from infrared and nuclear magnetic resonance spectral data. An attempted synthesis of the so-called 'homocularine' by the phenolic oxidation of the former XXIV, 6, 7-dimethoxy-8-hydroxy-1-(4-hydroxy-3-methoxyphenethyl)-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline, did not materialize.View full abstractDownload PDF (742K) -
TERUYA SEKI, YOSHIAKI WATANABE1969 Volume 89 Issue 5 Pages 617-626
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn continuation of the previous work on analgesics, 10 kinds of 5-substituted 1-(2-diethylaminoethyl)-2-(p-ethoxyphenylthio) benzimidazole were synthesized and tested but none of them showed any marked effect. Some of the previously prepared 5-unsubstituted 1-(2-tert-aminoethyl)-2-(P-substituted phenylthio) benzimidazoles showed a powerful analgesic effect. Comparison of infrared and nuclear magnetic resonance spectra of these two series of compounds showed a distinct difference between them in the absorption considered to be due to CH2 neighboring the nitrogen in diethylaminoethyl group in 1-position, the former showing absorption at around 2800 cm-1 which is absent in the latter. The nuclear magnetic resonance signal of the latter is shifted to a lower magnetic field than that in the former. These evidences suggest a difference in the steric structure of the diethylaminoethyl group in 1-position of the two series of compounds and this difference may be related to their pharmacological effect.View full abstractDownload PDF (917K) -
SADAO OHKI, YUNOSUKE NAGASE, MOTOYO YOSHINO, TEIKO AZUMA, FUMIKO HAMAG ...1969 Volume 89 Issue 5 Pages 627-632
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe benzoyl compounds (VII and XI) were prepared from 1-ethyl-and 1, 2-dimethyl-3-pyrrolidinecarboxylic chloride (VI and X), and VI and X were reacted respectively with cyclohexyl-and cyclopentyl-magnesium chloride to form 1-ethyl-α-cyclohexyl-and 1-ethyl-α-cyclopentyl-α-phenyl-3-pyrrolidinemethanol (II and III), and 1, 2-dimethyl-α-cyclohexyl-α-phenyl-3-pyrrolidinemethanol (IV).View full abstractDownload PDF (576K) -
SADAO OHKI, TEIKO AZUMA, YUNOSUKE NAGASE1969 Volume 89 Issue 5 Pages 633-637
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to examine pharmacological activities, 1, 2-dimethyl-3-[bis(2-thienyl) methylene] pyrrolidine (I) and 1-[1, 1-bis(2-thienyl)-3-propemyl]-2-methylpyrrolidine were synthesized. I and II are prepared by Grignard reaction between either ethyl 1, 2-dimethyl-3-pyrrolidinecarboxylate (IV) or ethyl 2-methyl-1-pyrrolidinepropionate (XI) and 2-thienylmagnesium bromide, followed by the dehydration. A special examination was made on the novel synthesis of IV from the starting material ethyl 2-cyanomethylacetoacetate.View full abstractDownload PDF (569K) -
TETSUJI KAMETANI, KAZUYA YAMAKI, KUNIO OGASAWARA1969 Volume 89 Issue 5 Pages 638-640
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDiveratryl ether (III), which had been obtained by the Williamson's method or by catalytic hydrogenation, was found to be formed through hydride transfer reduction in case of crossed Cannizzaro reaction. Furthermore, treatment of III with sulfuric acid gave its trimer (VI).View full abstractDownload PDF (399K) -
MASATOMO HAMANA, HIROSHI NODA1969 Volume 89 Issue 5 Pages 641-644
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe reactions of quinoline-, isoquinoline-, pyridine-, lepidine-, 4-chloroquinoline and 4-chloropyridine 1-oxides with morpholine enamine of isobutyraldehyde in the presence of benzoyl- or tosyl-chloride were examined. Both of these reactions at room temperature and under refluxing, afforded 2-(α-heterocyclyl) isobutyraldehydes in rather good yields. The structures of the products were confirmed by the infrared and nuclear magnetic resonance spectra examinations.View full abstractDownload PDF (535K) -
HIDEO IIDA, TOYOHIKO KIKUCHI, KUNIYOSHI SAKURAI, TOKUHIRO WATANABE1969 Volume 89 Issue 5 Pages 645-648
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSCondensation of 5-bromo-3, 4-dimethoxyphenethylamine (II) and methyl ο-benzyloxy-phenylacetate (III) gave the amide (IV). The Bischler-Napieralski reaction of IV gave 3, 4-dihydroisoquinoline compound (V), and reduction of its methiodide with sodium borohydride, followed by debenzylation gave the phenolic base (IX). Intramolecular Ullmann reaction of phenolic base (IX) in the presence of potassium carbonate and cupric oxide in pyridine finally gave the objective 10, 11-dimethoxy-6-methyl-5, 5a, 6, 7, 8-pentahydro [l] benzoxepino [7, 6, 5-i, j] isoquinoline (X) as pale yellow oil, which was characterized as its oxalate of mp 188-190°.View full abstractDownload PDF (465K) -
HIDEHIKO KANEKO, KAGAYAKI NATSUKA1969 Volume 89 Issue 5 Pages 649-659
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSFrom the reaction of 1-aminoisoquinoline with C-ethylated diethyl malonate and/or monoethyl diethylmalonate chloride, 3, 4-dihydro-2, 4-dioxo-2H-pyrimido [2, 1-α] isoquinolines (IIa-c) were obtained which easily converted to the corresponding tetrahydro compounds (IXa-c) by catalytic hydrogenation, while treatment of ethyl α, α-diethyl-1, 2, 3, 4-tetrahydro-1-isoquinolineacetate with cyanic acid, isocyanate, or isothiocyanate afforded the corresponding carbamoyl compounds and thiocarbamoyl compounds (XIXa-f). Intramolecular cyclization of XIXa-f in the presence of sodium ethoxide resulted in formation of the desired products, hexahydro-2, 4-dioxo-2H-pyrimido [6, 1-α] isoquinolines (XXa-f).View full abstractDownload PDF (1102K) -
YOSHIHIRO NITTA, YOSHIAKI IKEDA, YASUYUKI SHIRAKI1969 Volume 89 Issue 5 Pages 660-668
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIntroduction of 2-hydroxyethyl group into the nitrogen in 1-phenyl-2-aminoethanol derivative (III-1-3), and dl-and l-ephedrine hydrochlorides afforded dihydroxy compounds (IV-1-4 and VIII) which were chlorinated into a nitrogen mustard-type dichloro compounds (V-1-4 and IX), and the latter were reacted with primary amine (VI) to obtain 2-phenylpiperazine derivatives (VII-1-19 and X-1-2), (+)-1-(p-chlorobenzyl)-2-phenyl-3, 4-dimethylpiperazine (X-1) was prepared by the chlorination of l-ephedrine hydrochloride to L-(+)-threo-chloro compound (XI), its reaction with a primary amine to obtain(+)-diamino compound (XII), and treatment of XII with dibromoethane. The compounds so obtained were tested for increasing the coronary and peripheral (femoral artery) blood flow using dogs. Some nine of the compounds tested were found to increase coronary blood flow, more than three times that of aminophylline used as the control. Some considerations were also made on the relationship between chemical structure and pharmacological activity.View full abstractDownload PDF (925K) -
YOSHIAKI IKEDA, YOSHIHIRO NITTA, KIYOSHI YAMADA1969 Volume 89 Issue 5 Pages 669-676
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSPiperazinoalkylbarbituric acid derivatives (VIII, IX, and X) were prepared by the introduction of phenobarbital and allobarbital into 1-and 1, 3-position of substituted piperazines with ethylene, propylene, and β-hydroxypropylene as the bonding bridge. These derivatives were obtained by the reaction of barbituric acid with unsymmetrically 1, 4-disubstituted piperazines having a functional group in the ω-position. Phenobarbital series compounds with ethylene as the bonding bridge were obtained by the reaction of 1-(2-bromoethyl)-5-ethyl-5-phenylbarbituric acid (VII) and monosubstituted piperazines. The compounds so obtained were tested for prolonged duration of hexobarbital sodium anesthesia, using mice, and general symptoms in mice was tested with two compounds by their intraperitoneal administration. Correlation between chemical structure and pharmacological activity was examined from these results.View full abstractDownload PDF (895K) -
YOSHIAKI IKEDA1969 Volume 89 Issue 5 Pages 677-688
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSIn order to examine their pharmacological activity on the circulatory system, some piperazinoalkyltheophylline derivatives (X, XI, XIV, XV) were synthesized. X, XI, and XIV were obtained by the reaction of 7-(ω-halogenoalkyl) theophyllines (VIII, IX) and 7-(2, 3-epoxypropyl) theophylline (XII) with monosubstituted piperazines (I), and also by the reaction of theophylline with unsymmetrically 1, 4-disubstituted piperazines (II, III, IV, V) with a functional group in ω-position. Application of 0.5 equivalent of VIII and XII to piperazine afforded 7-piperazinoalkyl-(and 2-hydroxypropyl)-theophyllines (XVI and XVII) which were reacted with halogenide (XXI) to form X and XIV. XVI and XVII were obtained by the hydrolysis of X and XIV having a carbonyl-containing substituent in the 4-position of piperazine, and subsequent application of hydrogen bromide. Reaction of piperazine with 2 equivalents each of VIII and XII afforded the corresponding bis compounds (XVIII and XIX).View full abstractDownload PDF (1159K) -
YOSHIRO USUI1969 Volume 89 Issue 5 Pages 689-698
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESS3-Aminothiazoline-2-thiones, 4H-1, 3, 4-thiadiazine-2-thiols, and their derivatives were synthesized, and structure of their reaction intermediates was elucidated. It has been found that 3-arylideneamino-4-phenylthiazoline-2-thiones tend to decompose into aromatic nitriles and 4-phenylthiazole-2-thiol when heated to above their melting point. New synthetic method for nitriles from aldehydes that utilizes this thermal decomposition is described.View full abstractDownload PDF (955K) -
YOSHIRO USUI, TOGO YAMANO1969 Volume 89 Issue 5 Pages 699-701
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSComparative examinations were made on the activities against several fungi using 3-aminothiazoline-2-thiones, 4H-1, 3, 4-thiadiazines, and their derivatives synthesized in earlier work, 1) and relationship between their structure and activity has been discussed.View full abstractDownload PDF (394K) -
The Constituents of Chrysosplenium Plants in Japan. : Structure of Chrysosplenin and ChrysosplenetinMINEO SHIMIZU, NAOKATA MORITA1969 Volume 89 Issue 5 Pages 702-704
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSChrysosplenin, a flavonoid glicoside from C.japonicum (MAXIM.) MAKINO (japanese name "Yamanekonomeso"), had been assumed to be 3, 5, 4'-trihydroxy-6, 7, 3'-trimethoxyflavone monoglucoside.3) Using paper partition chromatography, however, chrysosplenin was revealed to be a mixture of I and II. I, mp 226-228°, C25H28O13·2H2O, was identified as chrysospenoside B4) and II, mp 163-165°, C24H26O13, was determined to be 5, 3', 4'-trihydroxy-6, 7, 3-trimethoxyflavone 4'-monoglucoside. We proposed the names chrysosplenoside D and chrysospenol D for the glycoside and its aglycone, respectively.View full abstractDownload PDF (478K) -
MUNEHISA ARISAWA, TASHICHIRO NAKAOKI1969 Volume 89 Issue 5 Pages 705-706
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSThe fresh lieves of Sorbaria stellipila SCHNEID. (=Sorbaria sorbifolia A.Br.var.stelipila MAXIM.) was extracted with methanol and the methonolic extract was extracted with ether. The insoluble part was further extracted with ethyl acetate and the latter extract afforded a new flavonoid glycoside as pale yellow needles, mp 256-257°, in 0.3% yield. This glycoside corresponded to the molecular formula of C21H20O10·H2O. Its hydrolysis with conc.hydrochloric acid afforded one mole each of scutellarein (5, 6, 7, 4'-tetrahydroxyflavone) and rhamnose. This is a new glycoside and was named sorbarin. Hydrolysis of the thoroughly methylated compound of sorbarin gave an aglycone of mp 197°, which was identified with scutellarein 5, 6, 4'-trimethyl ether, mp 198°, obtained by hydrolysis of the thoroughly methylated compound of pectolinarin. Consequently, sorbarin was determined as scutellarein 7-momorhamnoside.View full abstractDownload PDF (383K) -
SETSUO KIRYU, SADAO IGUCHI1969 Volume 89 Issue 5 Pages 707-711
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSTo obtain basic data on crystallization of the molecular compound of aminopyrine and barbital from aqueous solution, the diagram of the ternary system, aminopyrine-barbital-water, was studied in the temperature range 0° to 98°. It was observed that lower critical temperature of layering of the aminopyrine-water system decreases with addition of barbital, that concentration ranges of aminopyrine and barbital in the solution which is in equilibrium with the molecular compound crystals, are narrowed with decrease of temperature and that concentration of barbital decreases more rapidly than that of aminopyrine. Therefore the best conditions to obtain the molecular compound are as follows : 1) excess amount of aminopyrine, 2) crystallization from concentrated solution, and 3) crystallization at high temperature. Furthermore, crystals of the molecular compound were examined by X-ray diffraction measurement; they belong to monoclinic system and the unit cell dimensions are : a 11.92, b 26.92, c 7.20 Å, β 97.3, with Z=4, space group is P21/c.View full abstractDownload PDF (619K) -
KEIJIRO TAKAGI, MADOKA SHIBATA1969 Volume 89 Issue 5 Pages 712-720
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSCrude saikosides are crude saponin fraction extracted from Bupleurum falcatum L. some pharmacological properties, particularly the acute toxicity ana the central depressant action of this fraction were described. Crude saikosides showed a strong toxic effect by intraperitoneal administration but low toxicity by oral route. High hemolytic value was obtained with this crude saponin. Crude saikosides had potent sedative, analgesic, hypothermic and antipyretic effect. Furthermore they had a potent antitussive effect. On the other hand they did not show any anticonvulsant activity nor reduction of muscle tone using the grip strength test. From these findings it may be concluded that crude saikosides have a strong central depressant action.View full abstractDownload PDF (982K) -
TETSUJI KAMETANI, ISAO NOGUCHI1969 Volume 89 Issue 5 Pages 721-725
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSTreatment of 7-benzyloxy-1-(3-benzyloxy-4, 5-dimethoxybenzyl)-6-methoxy-1, 2, 3, 4-tetrahydroisoquinoline (III) with acetic acid and 37% formaldehyde solution resulted in the progress of the Mannich reaction and protoberberine bases (VI and VII) were obtained. These bases were identified with the authentic sample obtained by the treatment of the hydrochloride of III with 37% formaldehyde solution. Debenzylation of VI and VII gave the phenolic bases, X ((±)-O-demethylstepharotine) and XI, and their methylation with diazomethane gave the same (±)-O-methylstepharotine (XII). XI was also obtained by debenzylation of III to IX and its Mannich reaction. The Eschweiler-Clarke reaction of III gave VI and VII accompanied by a small amount of 7-benzyloxy-1-(3-benzyloxy-4, 5-dimethoxybenzyl)-6-methoxy-2-methyl-1, 2, 3, 4-tetrahydroisoquinoline (VIII) which was identified with an authentic specimen.View full abstractDownload PDF (614K) -
RIITIRO IWAKI, JUNITI ISHIKO, YOSHITAKA KUDO, TSUTOMU IRIKURA1969 Volume 89 Issue 5 Pages 726-729
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSEffect of 15 kinds of pharmaceutics acting on the circulatory system, including ATP, nitroglycerin, 4, 4'-diethylaminoethoxyhexostrol, and adrenaline, was examined by their intra-arterial and intravenous injection, to see their effect on the amount of blood flow in coronary circulation, brain, kidneys, intestine, and hind leg circulation system, and systemic blood pressure. Results are listed in Table I.View full abstractDownload PDF (578K) -
KIYOSHI TAKIURA, MINORU YAMAMOTO, NOBUKO TSUJIMOTO1969 Volume 89 Issue 5 Pages 730-733
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSUronic acid forms a complex salt with molybdic acid in acetic acid and this complex shows rotatory dispersion curve with a maximum rotation value at 345 mμ. When molybdic acid is added to uronic acid lactone, a considerable time is required until the optical rotation reaches a constant value. There is a proportional relation between the degree of optical rotation at 345 mμ and concentration of uronic acid, and uronic acid can be determined by using this relationship.View full abstractDownload PDF (434K) -
YOSHIRO MASADA, KEIJI HASHIMOTO, TAKEHISA INOUE, TOKUNOSUKE SAWADA1969 Volume 89 Issue 5 Pages 734-736
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSQuantitative determination of glucose and fructose in honey was carried out by gas chromatography. This new method was found to be much more rapid and simple than the existing colorimetry, gravimetry, or microbiological assay, and would be of advantage in the quality control of honey. Trimethylsilylation of glucose and fructose was examined by using trimethylchlorosilane, hexamethyldisilazane, N, O-bis (trimethylsilyl) acetamide, and N-trimethylsilylimidazole.View full abstractDownload PDF (398K) -
MASAO TOMITA, TOKUNOSUKE SAWADA, MUTSUO KOZUKA, DAISUKE HAMANO, KATSUM ...1969 Volume 89 Issue 5 Pages 737-740
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSLaurolitsine (II) was isolated from the root of a Lauraceous plant, Lindera strychnifolia (SIEB. et ZUCC.) F.VILL. (Japanese name "Tendai -uyaku"). Launobine (V) was isolated from the bark and wood of Lindera umbellata THUNB. (Japanese name "Kuromoji").View full abstractDownload PDF (600K) -
TSUKINAKA YAMANA, YUZO MIZUKAMI, AKIRA TSUJI, FUJIO ICHIMURA1969 Volume 89 Issue 5 Pages 740-744
Published: May 25, 1969
Released on J-STAGE: May 30, 2008
JOURNAL FREE ACCESSDegradation of hydrochlorothiazide (I) and N, N'-dimethylhydrochlorothiazide (IV) at pH 1.5-11.5 in aqueous solutions at 90° and 60° was examined. The pH rate profiles with bell-shaped curves at neutral pH region were obtained from the kinetic measurements. I and IV were found to be most stable at pH 2.5 and 8.0, respectively.View full abstractDownload PDF (491K)
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