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Volume 28, Issue 9
Displaying 1-50 of 51 articles from this issue
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YASUYUKI T. NINOMIYA, YOOSUKE YAMADA, MITSUKO ONITSUKA, YUSHIRO TANAKA ...1980 Volume 28 Issue 9 Pages 2553-2564
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour assay systems, i. e. membrane stabilization, inhibition of protein denaturation, and inhibition of collagen- and ADP-induced platelet aggregation, were examined for possible use as in vitro anti-inflammatory screening probes applicable to microbial metabolites. All these systems were simple and reasonably selective for known platelet anti-aggregants or non-steroidal anti-inflammatory agents. As regards sensitivity, detection should be possible at levels of several to several hundred μg/ml for an indomethacin class substance existing in the broth ; such concentrations are attainable in the broth in the case of useful antibiotic production. Each system was hardly disturbed by medium components in the broth and the procedures were successfully applied to actinomycetes cultures. Upon examination of typical non-steroidal anti-inflammatory drugs to determine their effects on these systems, it was found that they could be classified into four distinct types in terms of their mode of action. The correlation of these effects with results in several in vivo models is discussed. Furthermore, the effects of various antibiotics including several types of ionophores on these probes were thoroughly studied.View full abstractDownload PDF (1152K) -
HIROYUKI IMAIZUMI, NAOKI NAMBU, TSUNEJI NAGAI1980 Volume 28 Issue 9 Pages 2565-2569
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn X-ray diffraction method for determination of the degree of crystallinity of indomethacin was established, and the transition rate of indomethacin from amorphous to crystalline form was investigated. The transition of the amorphous form to crystalline form at 20°, 30°and 40°followed first-order kinetics and the Arrhenius plot showed good linearity. The amorphous form was shown to change to form I at 100% relative humidity (RH), to form I or II at 89% RH and to form I at 79% and 69% RH at 30°. The transition rate of the amorphous form to form II at 100% RH was larger than that at 89% RH. A good linear relation was observed between the maximum amount of water absorbed (log scale) and the degree of crystallinity at 100% or 89% RH at 30°. The dissolution rate of the amorphous form was higher than those of forms I and II. The amorphous form showed better tablet-forming properties than the crystalline form.View full abstractDownload PDF (537K) -
RYOHEI KIMURA, SHIZUO MATSUI, SATOSHI ITO, TACHIO AIMOTO, TOSHIRO MURA ...1980 Volume 28 Issue 9 Pages 2570-2579
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe central actions of maltol (2-methylpyromeconic acid, II), previously isolated from the extract of Passiflora incarnata, and its analogs were studied in mice. 2-Butyl-and 2-isobutylpyromeconic acid (IVd) were the most potent depressants of pentetrazoleinduced convulsion among the 2-alkylpyromeconic acids tested. The effect of 2-(1-hydroxy-isobutyl)pyromeconic acid (Vd) was more potent than that of IVd. Methylation on the 3-hydroxyl group of II or replacement of the O atom of the 4-pyrone ring with =NH did not alter the effect on pentetrazole-induced convulsion. Both IVd and Vd also showed depressing effects on the convulsion induced by strychnine or picrotoxin but did not affect the convulsion induced by caffeine. The anticonvulsive effects of IVd and Vd on the maximal electroshock seizure were less potent than that of 2-ethylpyromeconic acid (III). II, III, IVd and Vd depressed spontaneous motor activity, and III and Vd prolonged the hexobarbital-induced sleeping time. The brain levels of these four compounds after subcutaneous injection in mice were not related to their lipid solubilities.View full abstractDownload PDF (862K) -
MINORU KUBOTA, OSAMU NAGASE, HIRO AMANO, HIROSHI TAKAGI, HARUAKI YAJIM ...1980 Volume 28 Issue 9 Pages 2580-2586
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight Met- and Leu-enkephalin analogs substituted with L- or D-Arg at position 2 were synthesized using NG-mesitylene-2-sulfonylarginine. Among them, H-Tyr-D-Arg-Gly-Phe-Met-OH was found to possess an analgesic effect 2.4 times higher than that of morphine on a molar basis, when injected intracisternally. This compound was also found to produce analgesia when administered intravenously.View full abstractDownload PDF (927K) -
FUMIYOSHI ISHIKAWA1980 Volume 28 Issue 9 Pages 2587-2592
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis and characterization of tricyclic guanidinium salts and their reduced polycyclic trisaminomethane derivatives are described. N-ω-Chloroalkyl bicyclic guanidines (3) readily gave tricyclic guanidinium salt (4) in a neutral medium. Treatment of the compounds 4 with anion exchange resin caused facile ring cleavage to yield various macrocyclic compounds 6-9. The compounds 6-9 reverted to the parent tricyclic guanidinium salts in acidic and basic media as a result of transannular interactions. The guanidinium salts 4 were reduced with sodium borohydride to polycyclic trisaminomethane derivatives (11). The structures of 6-9 and 11 are proposed on the basis of the spectral data.View full abstractDownload PDF (719K) -
EIJI YUKAWA, KEIKI KOUNO, YUKIO ONO, YO UEDA1980 Volume 28 Issue 9 Pages 2593-2601
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA quantum chemical method for prediction of the specific bond of an aromatic hydrocarbon at which hydroxylation will occur most easily in liver microsomes is presented. The interaction energy changes of a binary system composed of an aromatic hydrocarbon and O2 caused by changes of the mutual spatial arrangement between the hydrocarbon and O2 were calculated by the CNDO/2 method. This method was applied to the hydroxylations of naphthalene, anthracene, phenanthrene, acenaphthylene, indene and 1, 2-dihydronaphthalene. In all cases, the theoretical predictions were found to coincide very well with the reported experimental results.View full abstractDownload PDF (864K) -
TAKASHI TSUCHIYA, MICHIKO ENKAKU, SATORU OKAJIMA1980 Volume 28 Issue 9 Pages 2602-2608
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation of the 1-substituted isoquinoline N-acylimides (3), prepared from isoquinolines (1) by successive N-amination and acylation, brought about a novel photoinduced two-step rearrangement to form the fully unsaturated 1H-1, 3-benzodiazepines (4), which were converted into the indole derivative (10) by treatment with acids via the ring-opened intermediate (8) or into (11) upon irradiation presumably via the tricyclic valence isomer (14).View full abstractDownload PDF (796K) -
TADAO SHIBANUMA, MASARU IWANAMI, MASAHARU FUJIMOTO, TOICHI TAKENAKA, M ...1980 Volume 28 Issue 9 Pages 2609-2613
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEight metabolites (M-1-M-6, M-8, M-9) of 2-(N-benzyl-N-methylamino)ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate hydrochloride (YC-93) were synthesized and the structures of the metabolites were established by comparison with the synthetic compounds.View full abstractDownload PDF (620K) -
HIROAKI TAKAYANAGI, HARUO OGURA, HIKOYA HAYATSU1980 Volume 28 Issue 9 Pages 2614-2617
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe crystal and molecular of N4-aminocytosine was determined by X-ray diffraction. This compound belongs to the monoclinic space group P21/a with four molecules in a unit cell of α=7.950 (2) Å ; b=11.156 (2) Å ; c=6.054 (3) Å ; β=94.59 (2)° ; V=535.2 (3) Å3. The final R value was 0.072 including hydrogen atoms. The present study established that this compound takes the C (4)-amino form rather than the imino form, and is consistent with the report (D. M. Brown, M. J. E. Hewlins and P. Schell, J. Chem. Soc. (C), 1968, 1925 that 1-methyl-N4-aminocytosine takes the amino form in solution.View full abstractDownload PDF (448K) -
KATSUHIKO HINO, KIYOSHI FURUKAWA, YASUTAKA NAGAI, HITOSHI UNO1980 Volume 28 Issue 9 Pages 2618-2622
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-amino-4-phenylquinolines was synthesized and the effects of these compounds on the central nervous system were evaluated pharmacologically in mice. Among these compounds, many 2-(substituted piperazinyl) derivatives exhibited a potent antagonism to hypothermia and catalepsy induced by reserpine, as well as some inhibitory effect on locomotor activity. Some compounds were found to possess activity to inhibit tremorine-induced tremor.View full abstractDownload PDF (580K) -
MASATOSHI YAMATO, JIROH HORIUCHI, YASUO TAKEUCHI1980 Volume 28 Issue 9 Pages 2623-2628
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAcylation of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones (1d, 4, 6, and 7) was attempted. In all cases, the resulting products were not the corresponding acyl derivatives but two types of products (2 or 3 and 5). Heating 1d, the derivative having hydrogen atoms on the N(1) and N(3)-positions of spiro[piperidine-4, 2'-(1', 2', 3', 4'-tetrahydroquinazolin)]-4'-ones with acetic anhydride or benzoic anhydride gave 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (2) or 1-(1-benzyl-1, 2, 5, 6-tetrahydro-4-pyridyl)-2-methyl-1, 4-dihydroquinazolin-4-one (3), respectively. On the other hand, heating 4, the N(1)-substituted derivative of 1d, with acetic anhydride gave 2-benzyl-5-methyl-1, 2, 3, 4, 5, 10-hexahydro-benzo[b]-1, 6-naphthyridin-10-one (5). The N(3)-substituted derivatives (6 and 7) of 1d did not react with acetic anhydride.View full abstractDownload PDF (581K) -
MASARU IWANAMI, TETSUYA MAEDA, MASAHARU FUJIMOTO, YOSHINOBU NAGANO, NO ...1980 Volume 28 Issue 9 Pages 2629-2636
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA novel intramolecular rearrangement of isothiazolethioacetamides into 1, 3-dithietanecarboxamides is described, together with the synthesis of a new cephamycin derivative (YM-09330) having a 1, 3-dithietane structure at the 7β-position. This compound showed strong antibacterial activity, especially against gram-negative organisms.View full abstractDownload PDF (846K) -
HIROFUMI TAKEUCHI, YOSHIHISA MIWA, JUTARO OKADA1980 Volume 28 Issue 9 Pages 2637-2641
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVapor-phase synthesis of benzyl cyanide from 2-phenylethanol and ammonia was studied over Ni-Cu-SiO2 catalyst in the presence of hydrogen. Experiments were carried out in a flow reactor system under atmospheric pressure at 300°. The main product was benzyl cyanide, and toluene and phenethylamine were also produced. The Ni-Cu-SiO2 catalyst (Ni/Cu=3/1) gave the best selectivity for benzyl cyanide, 80%. The deactivation of this catalyst was negligible. By kinetic analysis, the rate of loss of 2-phenylethanol was found to show a first order dependency on the partial pressure of 2-phenylethanol, and was not affected by the partial pressures of ammonia and hydrogen. The experimental data were well interpreted by a model in which phenethylimine was produced as an intermediate and was then dehydrogenated to benzyl cyanide.View full abstractDownload PDF (523K) -
SHOICHIRO TAGAMI1980 Volume 28 Issue 9 Pages 2642-2646
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMeprobamate decomposes into NH4Cl, CO2, and a diol compound on heating in 20% HCl, and the NH3 evolved at pH above 11 can be determined using the NH3 selective electrode without separation from the decomposition solution. A linear calibration plot was obtained within the concentration range of 1×10-5-1×10-2M meprobamate. Volatile amines and the Hg ion, which forms a metal complex with NH3, are known to interfere with the electrode measurements.View full abstractDownload PDF (565K) -
SHIGEO UKAI, CHIHIRO HARA, TAKASHI KIHO, KAZUO HIROSE1980 Volume 28 Issue 9 Pages 2647-2652
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new type of mannan (T-2-HN) has been isolated as a neutral homoglycan from the aqueous 70% ethanol extract of the fruit bodies of Dictyophora indusiata FISCH., which grows in China. T-2-HN was homogeneous as judged by gel filtration (Sepharose 2B) and Tiselius-type electrophoresis. It was composed of D-mannose and a trace of glucose in a molar ratio of 100 : 1, and contained O-acetyl groups in the proportion of about one acetyl group per two sugar residues. Its highly positive specific rotation, [α]20D+116°(c=0.1, H2O), and the presence of an absorption band at 820 cm-1 (type 2a) in the infrared spectrum suggested that most of the glycosidic linkages in this mannan are of α-D configuration. Structural analysis indicated that T-2-HN has a linear chain composed largely of α-1→3 linked D-mannosyl residues, but the linear chain also contains traces of 1→6 linked D-mannopyranosyl (and/or glucosyl) residues. In addition, trace amounts of branching points are present at position 2 or 4 on each of the 1→3 linked D-mannose residues.View full abstractDownload PDF (823K) -
CHISAKO YAMAGAMI, MAKIKO SUGIURA, KAZU TAMURA, NARAO TAKAO1980 Volume 28 Issue 9 Pages 2653-2657
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe behavior of several N-substituted-4-piperidones in methanol has been studied by 13C nuclear magnetic resonance (NMR) spectroscopy. All the piperidones studied were found to be equilibrium with their hemiacetals in methanolic solutions. The features of N-acyl derivatives were different from those of N-alkyl derivatives and the differences could be accounted for by electronic factors. The chemical shifts of the acetals were also determined and a procedure for distinguishing between hemiacetal and acetal is proposed.View full abstractDownload PDF (578K) -
SHIGEHISA KYOSAKA, SANAE YAMASHIRO, MITSUYA TANAKA1980 Volume 28 Issue 9 Pages 2658-2664
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPorcine kidney β-acetylhexosaminidase A was purified to electrophoretic homogeneity by procedures involving ammonium sulfate precipitation, gel filtration and column chromatography on diethylaminoethyl cellulose, octyl Sepharose CL-4B and ε-aminohexanoyl β-acetylglucosaminylamine-Sepharose 4B. Analysis by sodium dodecyl sulfate-gel electrophoresis suggested that the enzyme consists of three subunits with molecular weights of 61000, 31000 and 9000. The molecular weight of the intact enzyme as determined by gel filtration was 129000 at pH 8.0 and 302000 at pH 5.0. Kinetic analysis with mixed substrates as well as inhibition studies with various substrate analogs, indicated that the enzyme hydrolyzes both β-N-acetylglucosaminide and β-N-acetylgalactosaminide at the same active site. Among hexoses tested for inhibitory effect, only mannose was an effective competitive inhibitor. A comparison of mannosides with N-acetylglucosaminides with respect to binding ability to the enzyme in terms of K1 or Km values implied the presence of a site for mannose other than the active site. On the other hand, kinetic studies with mixed inhibitors indicated that mannose competes with N-acetylgalactosamine, N-acetylglucosamine and acetamide.View full abstractDownload PDF (820K) -
YOSHIHISA MATSUDA, TOSHIKO ITOOKA, YOSHIKO MITSUHASHI1980 Volume 28 Issue 9 Pages 2665-2671
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dependence of the photostability of indomethacin on the capsule shell thickness and on the concentration of titanium dioxide used as an opacificient was investigated using gelatin films prepared by casting as models of hard gelatin capsules. The film thickness and concentration of opacificient were varied in the ranges of 50-150μm and 0-1.5% of the amount of dried films, respectively. Films and indomethacin tablets were exposed to a 400 W mercury vapor lamp for 120 min, then coloration of the enclosed indomethacin was measured by tristimulus colorimetry, and evaluated as Hunter's color difference. The chemical stability of the drug was determined by following the ultraviolet spectrophotometric change of a solid sample. There was a good linear relationship between color difference values and the square root of exposure time at all concentrations and thicknesses. The coloration rate constants calculated from the slopes of these lines were affected by both parameters, and decreased significantly as the film thickness was increased at every concentration of opacificient. However, the effect of concentration seemed to disappear above 1% addition. The coloration rate was directly dependent on the average transmittance of films over the wavelength range relating to the photostability of indomethacin. Degradation of indomethacin followed apparently sequential first-order kinetics. Apparent conversions after 120-min exposure as determined from the UV spectra were also affected by both parameters and were below 3% at thicknesses above 80μm at every opacificient concentration tested ; this represents excellent protection of indomethacin.View full abstractDownload PDF (719K) -
YOSHIKAZU MATSUSHIMA, SETSURO SUGATA, YUKO SAIONJI, MINORU TSUTSUI1980 Volume 28 Issue 9 Pages 2672-2675
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSmeso-Tetra[5-(8-hydroxyquinolyl)]porphine was synthesized by the Rothemund method as a model of porphyrin with metal chelating groups in the peripheral region. The presence of three kinds of copper (II) complexes was demonstrated ; free base porphyrin with metal chelated 8-quinolinol groups and metalloporphyrin with metal chelated and unchelated 8-quinolinol groups. In dimethylformamide solution, reaction of the compound with excess copper (II) perchlorate occurred in two steps ; rapid metal chelation of the 8-quinolinol moiety and subsequent slow Cu (II) incorporation into the porphine moiety. Reaction with excess aluminum (III) nitrate under similar conditions gave free base porphyrin with Al (III) chelated 8-quinolinol groups.View full abstractDownload PDF (476K) -
Studies on Diazepines. XIII. Photochemical Behavior of Pyrazine, Pyrimidine, and Pyridazine N-ImidesTAKASHI TSUCHIYA, JYOJI KURITA, KAZUKO TAKAYAMA1980 Volume 28 Issue 9 Pages 2676-2681
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhotolyses of various diazine N-ethoxycarbonylimides (3, 9, and 19), prepared from the corresponding diazines (1, 8, and 17), resulted in the formation of the pyrazole derivatives (4 and 10) from pyrazine and pyrimidine N-imides, and of the pyrrole derivatives (20) from pyridazine N-imides. These photolyses may proceed by rearrangement to diaziridine intermediates, followed by ring expansion to the corresponding 1, 2, 5-, 1, 2, 4-, or 1, 2, 3-triazepines (6, 12, or 22), which then undergo isomerization to the triaza[3.2.0]bicycloheptadienes (7, 13, and 23), followed by elimination to give the products (4, 10, and 20, respectively).View full abstractDownload PDF (681K) -
TOSHIHIRO NOHARA, NOBUTAKA TOKUBUCHI, MIHOKO KUROIWA, ITSUO NISHIOKA1980 Volume 28 Issue 9 Pages 2682-2686
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCompounds 7-13 were isolated from the water extractive of Cinnamomi Cortex (the dried bark of Cinnamomum cassia BLUME, "Toko Keihi"in Japanese, Lauraceae), which shows anti-complement activity. Among them, the compounds 7 and 8 were characterized by chemical and spectral means and named cinncassiol B and cinncassiol B 19-O-β-D-glucopyranoside, respectively.View full abstractDownload PDF (532K) -
YOSHIKI MINO, NAGAYO OTA, SHIGERU SHIMOMURA, SHIGERU SHIMOMURA1980 Volume 28 Issue 9 Pages 2687-2691
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFlameless atomic absorption spectrometry combined with solvent extraction was developed for the determination of germanium in medicinal plants. A wet oxidation procedure using only nitric acid was suitable for ashing plant samples. Carbon tetrachloride and water were used as solvents for extraction and back-extraction. Measurements were carried out after preparing sample solutions in 0.5 M sodium hydroxide in order to enhance the sensitivity. This high sensitive method (detection limit, 1 ppb) was applied to the determination of germanium in some medicinal plants. The analytical results obtained indicate that medicinal plants contain small amounts of germanium ; it appeared that there was no connection between the pharmacological effects of medicinal plants and their germanium contents.View full abstractDownload PDF (601K) -
KOICHI KAWASAKI, CHIYE KAWASAKI, YUKO TSUDA, MITSUKO MAEDA, YOSHIO OKA ...1980 Volume 28 Issue 9 Pages 2692-2698
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA hexadecapeptide, H-Arg-Leu-Pro-Gly-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH, corresponding to the C-terminal sequence 132-147 of hCG-β proposed by Carlsen et al., was synthesized stepwise by fragment condensation, assembling five fragments [Z-Arg(NO2)-Leu-Pro-NHNHBoc, Z-Gly-Pro-Pro-NHNHBoc, Z-Asn-Thr-Pro-NHNHBoc, Z-Ile-Leu-Pro-NHNHBoc, and Z-Gln-Ser-Leu-Pro-OBut].View full abstractDownload PDF (855K) -
KOICHI KAWASAKI, CHIYE KAWASAKI, YUKO TSUDA, MASAMI YAGYU, YOSHIO OKAD ...1980 Volume 28 Issue 9 Pages 2699-2706
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA dotriacontapeptide, H-Gln-Asp-Ser-Ser-Ser-Lys-Ala-Pro-Pro-Pro-Ser-Leu-Pro-Ser-Pro-Ser-Arg-Leu-Pro-Gly-Pro-Pro-Asn-Thr-Pro-Ile-Leu-Pro-Gln-Ser-Leu-Pro-OH, corresponding to the C-terminal sequence 116-147 of hCG-β proposed by Carlsen et al. was synthesized by stepwise fragment condensation, linking five fragments [Z-Gln-Asp(OBzl)-OH, Z-Ser(Bzl)-Ser-Ser-Lys(Boc)-NHNH2, Z-Ala-Pro-Pro-Pro-NHNHBoc, Z-Ser(Bzl)-Leu-Pro-NHNHBoc, and Z-Ser(Bzl)-Pro-Ser-NHNH2] to the hexadecapeptide reported in the preceding paper.View full abstractDownload PDF (1017K) -
YOSHIO OKADA, SHIN IGUCHI, MASASHI MIMURA, KOICHI KAWASAKI, KENJI YAMA ...1980 Volume 28 Issue 9 Pages 2707-2713
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hexadecapeptide corresponding to sequence 130-145 of the β-subunit of human chorionic gonadotropin (hCG) according to the amino acid sequence proposed by Morgan et al. was synthesized by successive azide condensation of 4 peptide fragments, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). Antiserum produced against this conjugate did not bind with 125I-hCG.View full abstractDownload PDF (828K) -
YOSHIO OKADA, SHIN IGUCHI, MASAMI YAGYU, KOICHI KAWASAKI, KENJI YAMAJI ...1980 Volume 28 Issue 9 Pages 2714-2719
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe triacontapeptide corresponding to sequence 116-145 of the β-subunit of human chorionic gonadotropin (hCG) according to the amino acid sequence elucidated by Morgan et al. was synthesized by successive azide condensation of 5 peptide fragments, followed by TFA treatment and catalytic hydrogenation. This peptide was conjugated with bovine serum albumin (BSA). A 1% binding of 125I-hCG was observed with the antiserum produced against the conjugate obtained above at a 1 : 500 dilution.View full abstractDownload PDF (779K) -
MITSUHIKO MANO, TAKUJI SEO, KINICHI IMAI1980 Volume 28 Issue 9 Pages 2720-2733
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2(1H)-Pyrazinone 4-oxide (emimycin) and its 1- and 6-substituted derivatives were synthesized by the reaction of a variety of 2-(hydroxyamino)acetamides with glyoxals.View full abstractDownload PDF (1044K) -
MITSUHIKO MANO, TAKUJI SEO, TOSHINORI HATTORI, TATSUHIKO KANEKO, KINIC ...1980 Volume 28 Issue 9 Pages 2734-2747
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 1-, 3-, 5- and 6-substituted 2(1H)-pyrazinone 4-oxides were synthesized and tested for anticoccidial activity. Of the compounds tested, 1-(β-D-ribofuranosyl)-(22), 1-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl)-(21) and 1-(2, 3, 5-tri-O-acetyl-β-D-ribofuranosyl)-2(1H)-pyrazinone 4-oxides (24) showed high activity.View full abstractDownload PDF (1181K) -
KIYOMI TSUCHIDA, KAZUYOSHI IKEDA, YOSHIHISA MIZUNO1980 Volume 28 Issue 9 Pages 2748-2752
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS3-(2-Amino-2-carboxyethyl)uracil (racemic isowillardiine) was synthesized by the use of a four-component (aldehyde, amine, isocyanide, and carboxylic acid) condensation as the key reaction. Thus, 1-(2-picolyl 1-oxide)-3-(formylmethyl) uracil was allowed to react with 2-picolylamine 1-oxide and cyclohexyl isocyanide or 2-picolyl isocyanide 1-oxide in the presence of acetic acid in methanol to afford the corresponding condensation product, which after deblocking, gave (±)-isowillardiine in fair yield.View full abstractDownload PDF (671K) -
HIKARU OKABE, YUMI MIYAHARA, TATSUO YAMAUCHI, KAZUMOTO MIYAHARA, TOSHI ...1980 Volume 28 Issue 9 Pages 2753-2762
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo triterpene glycosides, momordicosides A and B, were isolated from the seeds of Momordica charantia L. (Cucurbitaceae). Their structures were determined on the basis of spectral and chemical evidence and by X-ray analysis as the 3-O-β-gentiobioside and 3-O-β-D-xylopyranosyl (1→4)-[β-D-glucopyranosyl(1→6)]-β-D-glucopyranoside, respectively, of cucurbit-5-ene-3β, 22(S), 23(R), 24(R), 25-pentaol.View full abstractDownload PDF (1182K) -
YUKUO EGUCHI, AKIKO SUGIMOTO, MASAYUKI ISHIKAWA1980 Volume 28 Issue 9 Pages 2763-2769
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-Hydroxymethyl-1(2H)-phthalazinone derivatives were synthesized and assayed for their inhibitory effects on platelet aggregation and edematous arterial reaction. Among the tested compounds, 7-ethoxycarbonyl-4-hydroxymethyl-1(2H)-phthalazinone showed the highest potency in these pharmacological tests. The structure-activity relationship of phthalazinone derivatives and related compounds is discussed.View full abstractDownload PDF (820K) -
MASAYUKI ISHIKAWA, YUKUO EGUCHI, AKIKO SUGIMOTO1980 Volume 28 Issue 9 Pages 2770-2778
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTo enhance the biostability of the ester linkage of 7-ethoxycarbonyl-4-hydroxymethyl-1(2H)-phthalazinone, which has potent biological activities, the corresponding tert-butyl ester (1e) and 7-ethoxycarbonyl-4-hydroxymethyl-6, 8-dimethyl-1(2H)-phthalazinone (EG 626) (6) were prepared. The synthesis and inhibitory effects on platelet aggregation and edematous arterial reaction of these and other closely related compounds were investigated. EG 626 appears to be a potentially effective antithrombotic and antiatherosclerotic agent.View full abstractDownload PDF (1153K) -
SEIICHI INAYAMA, YUKIKO TOKUNAGA, EIKICHI HOSOYA, TERUO NAKADATE, TETS ...1980 Volume 28 Issue 9 Pages 2779-2782
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN-Carboxymethylmethamphetamine, a derivative of methamphetamine, was prepared through a new synthetic pathway from ephedrine. Specific antiserum was obtained by immunization of rabbits with the conjugate of N-carboxymethylmethamphetamine with bovine serum albumin. A radioimmunoassay procedure was established using this antibody (specific for methamphetamine) and a 125I-methamphetamine derivative. A high degree of specificity of the antibody was confirmed by testing for cross-reaction with several methamphetamine analogs, and the sensitivity was found to be 1 ng/tube. The present micro method using radioimmunoassay is highly sensitive, rapid, simple and may be useful as a micro-scale primary screening test for methamphetamine excreted in human urine, for forensic and medical purposes.View full abstractDownload PDF (584K) -
KAGARI YAMAGISHI, EIICHI KOSHINAKA, NOBUO OGAWA, KAZUYA MITANI, TOMOYA ...1980 Volume 28 Issue 9 Pages 2783-2795
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of a search for new antispasmodics, we have synthesized N-alkyl 6- and 7-diarylmethyleneindolizidinium bromides (1-8), which might be expected to exhibit potent anticholinergic activities due to the rigid piperidine ring structure, by analogy with N-alkyl 2- and 3-diarylmethylenequinolizidinium bromides (I). Treatment of ethoxycarbonylindolizidines (13 and 22) with phenyllithium or 2-thienylmagnesium bromide, followed by dehydration, afforded diarylmethyleneindolizidines (25, 26, 29 and 30). Quaternization of the 6-substituted derivatives (25 and 26) with methyl bromide afforded two isomeric methobromides, the trans- (1a and 2a) and the cis-methobromides (1b and 2b), and the 7-substituted derivatives (29 and 30) also afforded the corresponding trans- (5a and 6a) and cis-methobromides (5b and 6b). 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 6- and 7-diarylhydroxymethylindolizidines (23, 24, 27 and 28) were also determined from their IR and 13C-NMR spectra.View full abstractDownload PDF (1125K) -
KAZUHIKO SAGARA, SADAO KAKIZAWA, KOHJI KASUYA, TETSUO MISAKI, HIROSHI ...1980 Volume 28 Issue 9 Pages 2796-2799
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new simple gas chromatographic method for the simultaneous determination of capsaicin, dihydrocapsaicin and nordihydrocapsaicin in capsicum fruit was developed. The three components extracted from capsicum fruit could be completely separated on a 3% Apiezon grease L column. Quantitative analysis could be achieved by the peak area ratio method using methyl arachidate as an internal standard. The results obtained by this method were in good accord with those obtained by mass chromatography.View full abstractDownload PDF (544K) -
TOSHIHIRO HASHIMOTO, YOSISIGE KATO, YUKIYO NAGAOKA, TOMOMI OHTA, DAISU ...1980 Volume 28 Issue 9 Pages 2799-2803
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSolvent effects on the dimerization of 16, 17-dehydrodigitoxigenin 3-acetate (I) were investigated. Heating of I in less polar solvents, such as toluene, xylene, dioxane or tetrahydrofuran, gave the dimer III as the main product, in similar yields. The reaction in slightly basic media, such as toluene containing sodium acetate or dimethylformamide, afforded an isomeric dimer IV preferentially. The structure of IV was established on the basis of its spectral data and anhydration reaction in contrast to those of III. A mechanism is proposed for the formation of IV from I.View full abstractDownload PDF (560K) -
MAMORU SUGIURA, TSUTOMU OIKAWA1980 Volume 28 Issue 9 Pages 2803-2806
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSLipoprotein lipase (glycerol ester hydrolase ; EC 3.1.1.3) from Pseudomonas fluorescens was oxidized with N-bromosuccinimide at 37°. One mol of tryptophan residue per mol of enzyme was oxidized, but the enzymatic activity was unaffected. The enzyme was inactivated by photooxidation in the presence of methylene blue, and the inactivation was pH-dependent. In addition, the decrease in the enzymatic activity was accompanied by the loss of a histidine residue. It appears that the histidine residue in involved in the catalytic activity of the enzyme.View full abstractDownload PDF (538K) -
KANJI TAKADA, MIDORI YAMAMOTO, HIROKO NAKAE, SHOZO ASADA1980 Volume 28 Issue 9 Pages 2806-2808
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of a sulfonic acid dye and a surfactant on the pulmonary absorption of fluorescein isothiocyanate-labelled dextran (FITC-dextran), a model macromolecular compound (MW=150000) which is not absorbed after pulmonary administration, were studied. Bromphenol blue, a sulfonic acid dye, did not show an enhancing effect. However, sodium glycocholate (SGC) considerably enhanced the pulmonary absorption of FITC-dextran. Therefore, SGC may be a useful additive to increase the systemic availability of macromolecular compounds administered as aerosol dosage forms.View full abstractDownload PDF (433K) -
TADAO SHIBANUMA, MASARU IWANANI, KOUHEI OKUDA, TOICHI TAKENAKA, MASUO ...1980 Volume 28 Issue 9 Pages 2809-2812
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS(+)- and (-)-2-(N-benzyl-N-methylamino)ethyl methyl 2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3, 5-dicarboxylate (6) (nicardipine) were synthesized from (-)- and (+)- 1-ethoxymethyl-5-methoxycarbonyl-2, 6-dimethyl-4-(m-nitrophenyl)-1, 4-dihydropyridine-3-carboxylic acid (3), respectively. Resolution of 3 was carried out using cinchonidine and cinchonine as resolving agents. The vertebral vasodilating activity of (+)-YC-93 (the hydrochloride of (+)-(6)) was about 3 times that of (-)-YC-93.View full abstractDownload PDF (547K) -
SHENGCHIH CHEN, HIROSHI NAKAMURA, ZENZO TAMURA1980 Volume 28 Issue 9 Pages 2812-2816
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA simple method for the fluorometric determination of fluorescein and fluorescein monoglucuronide in urine was developed. Free fluorescein was determined by measuring its native fluorescence at 494 nm excitation and 516 nm emission. The conjugate was determined as fluorescein after hydrolysis at 37°for 20 min with β-glucuronidase. This method was applied to investigate the glucuronidation function of Wistar rats with liver injury in comparison with that of normal rats.View full abstractDownload PDF (578K) -
MEGUMI ITOH, MASAHIRO NAKANO1980 Volume 28 Issue 9 Pages 2816-2819
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe use of ethylcellulose microcapsules possessing a reservoir system to achieve sustained release of sulfamethizole or 5-fluorouracil was examined in vitro. As a first step, the drugs were dispersed in cellulose acetate matrices, then the matrices were microencapsulated by means of coacervation-phase separation of ethylcellulose from diethyl ether solution by nonsolvent addition. The surfaces of microcapsules were rounded, whereas the milled matrices were sharp-edged. In microcapsules of both drugs, longer release half-lives were obtained than with the corresponding matrices.View full abstractDownload PDF (695K) -
TAISUKE ITAYA, KAZUO OGAWA, HIROO MATSUMOTO, TOMOKO WATANABE1980 Volume 28 Issue 9 Pages 2819-2824
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHeating N, N-diethyl-3, 9-dialkyladeninium halides (Ig-j) in aqueous sodium hydroxide gave 1-alkyl-5-(alkylamino)imidazole-4-carboxamides (IV) together with minor amounts of 1-alkyl-5-(alkylamino)imidazole-4-carbonitriles (III), which were converted into IV on further heating. N, N-Dimethyl-3, 9-dialkyladeninium halides (Ia-d) underwent hydrolysis more rapidly to provide IV selectively in 90-94% yields.View full abstractDownload PDF (751K) -
Significance of Stomach-Emptying-Controlled Rabbits for GI Absorption Studies of Water-Soluble DrugsTADAO MAEDA, HIROSHI TAKENAKA, YOSHIYA YAMAHIRA, TAKESHI NOGUCHI, TETS ...1980 Volume 28 Issue 9 Pages 2824-2826
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe usefulness of stomach-emptying-(SE-) controlled rabbits for GI absorption studies of relatively water-soluble drugs was investigated, employing aminopyrine and sulfisoxazole as model drugs. When aminopyrine was administered, similar plasma level-time curves were obtained in both SE-controlled and conventionally fasted rabbits. In the case of sulfisoxazole, the time required to reach the peak plasma level was much longer in conventionally fasted rabbits than in the SE-controlled group. It was concluded that use of conventionally fasted rabbits for GI absorption studies should be limited to work on water-soluble drugs.View full abstractDownload PDF (442K) -
HARUHISA KIZU, TSUYOSHI TOMIMORI1980 Volume 28 Issue 9 Pages 2827-2830
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour triterpenoid prosapogenins tentatively named CP1, CP3, CP4 and CP5 were isolated from the alkaline hydrolysate of the crude saponin obtained from the root of Clematis chinensis OSBECK. On the basis of chemical and physicochemical evidence, they were characterized as follows : CP1 (I), hederagenin 3-O-α-L-arabinopyranoside ; CP3 (II), oleanolic acid 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP4 (VI), oleanolic acid 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside ; CP5 (VIII), hederagenin 3-O-β-D-xylopyranosyl-(1→3)-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranoside.View full abstractDownload PDF (588K) -
ICHIZO OKABAYASHI, NORIKO IWATA1980 Volume 28 Issue 9 Pages 2831-2835
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Chloroxanthone (2) was obtained by cyclization of 2-chloro-6-phenoxybenzoic acid (10) prepared from 2-nitro-6-phenoxybenzoic acid (8) via 2-amino-6-phenoxybenzoic acid (9). Similarly, 1, 5-dichloroxanthone (14a) and 1, 7-dichloroxanthone (14b) were obtained from 2-(2-chlorophenoxy)-6-nitrobenzoic acid (11a) and 2-(4-chlorophenoxy)-6-nitrobenzoic acid (11b), respectively. Furthermore, 2, 6-dichloroxanthone (19) was prepared by cyclization of 4-chloro-2-(4-chlorophenoxy)benzoic acid (18). Dichloroxanthone B, obtained by cyclization of 5-chloro-2-(3-chlorophenoxy)benzoic acid (16) and reported by Nargund et al. as 1, 7-dichloroxanthone, could not be separated into 1, 7-(14b) and 2, 6-dichloroxanthone (19) by recrystallization, column chromatography or thin-layer chromatography, but was proved here to be a mixture of 14b and 19 by gas chromatography.View full abstractDownload PDF (641K) -
SATOSHI MINEO, HARUO OGURA, KUNIO NAKAGAWA1980 Volume 28 Issue 9 Pages 2835-2838
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of 6-amino-5-benzylideneamino-1, 3-dimethyluracils (Ia-e) with nickel peroxide (Ni-PO) in dimethylsulfoxide (DMSO) afforded 8-substituted theophyllines (IIa-e) and dimethylsulfone. Ni-PO oxidation of the Schiff base acetate (V) of 5, 6-diamino-1, 3-dimethyluracil with D-glucose did not give a nucleoside analog ; in stead, 1, 3, 7, 9-tetramethyl-2, 4, 6, 8-(1H, 3H, 7H, 9H)pyrimido[5, 4-g]pteridinetetrone (VI) and penta-O-acetylgluconic acid were obtained. The reaction mechanisms of Ni-PO and the Schiff bases (Ia-e, V) are discussed.View full abstractDownload PDF (478K) -
KENJI OKAMOTO, KOICHI YASUMURA, SHINICHI SHIMAMURA, SHIGETADA NAKANISH ...1980 Volume 28 Issue 9 Pages 2839-2842
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe dodecapeptide corresponding to γ-melanotropin, a newly found amino acid sequence in bovine corticotropin-β-lipotropin precursor protein, was synthesized in a conventional manner. The synthetic peptide exhibited weak melanocyte-stimulating activity, but failed to show any significant steroidogenic and lipolytic activities.View full abstractDownload PDF (577K) -
NOBUTOSHI TANAKA, SACHIKO NAGASE, KYOKO WACHI, TAKAO MURAKAMI, YASUHIS ...1980 Volume 28 Issue 9 Pages 2843-2845
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fronds of Dennstaedtia scandens (BLUME) MOORE a new acylglucose was isolated and identified as 1, 4-di-O-p-coumaroyl-β-D-glucose. As further extractives, the following compounds were isolated : p-hydroxybenzoic acid, methyl p-coumarate, pinocembrin-7-O-β-D-glucoside, vitexin and isovitexin.View full abstractDownload PDF (501K) -
AKIRA TANAKA, TOSHINAO USUI, MASAJI SHIMADZU1980 Volume 28 Issue 9 Pages 2846-2849
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-(2-, 3-, 4-Substituted phenoxy)-2-furancarbaldehydes were prepared by the reaction of various phenoxides with 5-nitro-2-furancarbaldehyde via replacement of the nitro group.View full abstractDownload PDF (425K) -
MAKOTO NISHIZAWA, TAKASHI YAMAGISHI, GENICHIRO NONAKA, ITSUO NISHIOKA1980 Volume 28 Issue 9 Pages 2850-2852
Published: September 25, 1980
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe gallotannins (polygalloylglucoses) were isolated homogeneously from Paeoniae Radix and their structures were elucidated by 13C-nuclear magnetic resonance spectroscopy.View full abstractDownload PDF (417K)