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Volume 24, Issue 11
Displaying 1-50 of 54 articles from this issue
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NOBUTOSHI WATARI, NOBUYOSHI KANENIWA1976 Volume 24 Issue 11 Pages 2577-2584
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSExperiments were made to compare the effect of particle size of sulfonamide on the initial dissolution behaviour in sodium lauryl sulfate solution and in distilled water and the following results were obtained. 1) At agitation speed of 700 rpm, there was no difference of particle size on the initial dissolution in 0.1% and in distilled water but in 1% solution somewhat, and the difference appeared at agitation speed of 300 rpm with decrease in particle size. Results obtained in sodium lauryl sulfate solution showed a similar tendency while the instantly dissolving part increased with decrease in particle size, and this part dissolved instantly at first and the constant rate of dissolution followed in distilled water. 2) Plots of log dissolution rate constants vs. log agitation speed became linear with the same slope irrespective of particle size, when 0.1% and 1% solutions were used. Rank order for the dissolution rates of different particle size of powders was possible even at a relatively low agitation speed of 200 rpm.View full abstractDownload PDF (869K) -
TAKAJI KOYAMA, TOSHIMITSU MOZAI, TAKASHI HIROTA, YOSHIKAZU ISHINO, SHI ...1976 Volume 24 Issue 11 Pages 2585-2588
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSyntheses of tetraazatriphenylenes (II, VI, VIII) from dihydroxynaphthalenes (I, V, VII) with formamide or trisformylaminomethane (Chart 1) are described. Reaction of ethyl 1, 3-hydroxy-2-naphthoate (III) with trisformylaminomethane afforded II and N2-(1, 3-dihydroxy-2-naphthoyl) formamidine (IV). Ammonolysis of III with formamidine acetate gave IV.View full abstractDownload PDF (552K) -
MASAHIRO HAYASHI, TOHRU FUWA, SHOJI AWAZU, MANABU HANANO1976 Volume 24 Issue 11 Pages 2589-2596
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe differences in species for absorption, metabolism and excretion of iodochlorhydroxyquin (I) were investigated by the separate determination method of unmetabolized I (free form) and its conjugated metabolites, i.e., glucuronide (I-G) and sulfate (I-S) in urine and bile. As for urinary excretion ratio in rat, the order of the conjugates was I-S>I-G, while in guinea-pig and rabbit, I-G>I-S, and in man, I-G»I-S. Moreover, the order of biliary excretion ratio in guinea-pig was characteristically I-S»I-G differently from rat, in which it was I-G»I-S. In all cases, unmetabolized I was of trace and neglected. In addition to urinary and biliary excretion, as to blood concentration after oral administration, the complexed absorbability of I was shown. In small animals (rat and guinea-pig), the order of the concentration of unmetabolized I and the conjugates was I-G and I-S> unmetabolized I, but in beagle which was sensitive to the toxicity of I, unmetabolized I>I-G and I-S. Furthermore, the biological stability of the conjugates of I was studied and the conversion of I-G⇋I-S was found to occur in rat. This result shows that the conjugates are hydrolyzed and reconjugation to glucuronide or sulfate occurs in rat.View full abstractDownload PDF (881K) -
NOBUYUKI KITAMORI, SEIZO KAWAJIRI, TAI MATSUZAWA1976 Volume 24 Issue 11 Pages 2597-2602
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe method of particle size evaluation of chloramphenicol suspensions with the Coulter counter has been studied. Using the salt solution, which was supersaturated with chloramphenicol and contained a small amount of polyvinylpyrrolidone to attain a wide range of supersaturation of chloramphenicol, as a diluent, the particle size analysis of chloramphenicol suspensions can be made reproducibly in the size range between 0.7 and 2.0μ. Chloramphenicol suspensions containing different average size particles were administered intramuscularly to rabbits, and it was found that the peak plasma levels obtained were directly related to the reciprocals of the average particle diameters measured by this method.View full abstractDownload PDF (711K) -
MASAHIRO HAYASHI, TOHRU FUWA, SHOJI AWAZU, MANABU HANANO1976 Volume 24 Issue 11 Pages 2603-2609
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSVarious factors affecting the intestinal absorption of iodochlorhydroxyquin (I), which is remarked in relation to SMON (subacute myelo-optico-neuropathy), were investigated. From urinary excretion data in rats, it was found that the excretion ratio to the dose studied was larger in the case of the low dose, but it seemed that the sodium carboxymethyl cellulose (CMC-Na) effect was more effective for the high dose. And from plasma concentration data in rats, the CMC-Na effect at the high dose was also recognized. Therefore considering that the dose dependent effect of CMC-Na was due to that the endogeneous suspending agent in digestive fluid, probably bile component, was enough to suspend I of the low dose, but not of the high dose, the effect of bile on the absorption of I by the method of bile or saline solution infusion into the duodenum of the bile fistula rat was further investigated. The result was that bile was more effective on the absorption than CMC-Na, and so bile could be well regarded as the endogeneous suspending agent. But urinary data of man showed that there were two types of man, sensitive and unsensitive for CMC-Na, and so its effect was not so obvious.View full abstractDownload PDF (844K) -
RYUICHI HIGUCHI, TETSUYA KOMORI, TOSHIO KAWASAKI1976 Volume 24 Issue 11 Pages 2610-2618
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDie aus der Fruchte der Akebia quinata DECNE erhaltenen Oleanolsaure- und Hederagenin-3-O-Glykoside bzw. 3, 28-O-bis-Glykoside sowie Arjunolsaure- und Norarjunolsaure-28-O-Glykoside wurden als Methylat massenspektrometrisch vergleichend untersucht, um einfache Unterscheidungsmethode dieser drei Glykosid-type zu finden.View full abstractDownload PDF (750K) -
KAZUO KAMEI, TAMOTSU KONDO1976 Volume 24 Issue 11 Pages 2619-2623
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPoly (phthaloyl L-lysine) microcapsules were prepared by interfacial polymerization techniques and treated by lecithin. Various mono-, di-, and trivalent cations were found electrophoretically to be bound by both intact and lecithin-treated poly (phthaloyl L-lysine) microcapsules dispersed in aqueous media. In both cases, cation binding was stronger with ions of higher valency and charge reversal of the microcapsules was observed at high concentrations of polyvalent cations. However, the treatment of the microcapsules with lecithin caused appreciable changes in the zeta-potential and cation binding of the microcapsules. That is, the zeta-potential was less negative and the cation concentration needed to produce the charge reversal was lower for the lecithin treated microcapsules than for the intact microcapsules. The zetapotential was converted into the surface charge density by means of a modified Gony-Chapman equation. Finally, the free energy of cation binding was evaluated from the surface charge density as a function of the cation concentration using Stern's adsorption theory.View full abstractDownload PDF (670K) -
RYUJI MARUMOTO, YOSHIO YOSHIOKA, YOSHIYASU FURUKAWA, MIKIO HONJO1976 Volume 24 Issue 11 Pages 2624-2628
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of aristeromycin (I) with acetyl bromide in acetonitrile, followed by treatment with hydrobromic acid afforded 3'β-bromo-3'-deoxyaristeromycin hydrobromide (V) and 2'β-bromo-2'-deoxyaristeromycin hydrobromide (VI). Catalytic reduction of V and VI with palladium on charcoal gave 3'-deoxyaristeromycin (X) and 2'-deoxyaristeromycin (XI), respectively. Treatment of V with sodium alkoxide yielded 2', 3'-anhydroaristeromycin (IV). Two carbocyclic analogs (XII and XV) of inosine and 6-mercaptopurine ribonucleoside, 8-bromoaristeromycin (XVI) and 8-hydroxyaristeromycin (XVII) were also prepared.View full abstractDownload PDF (678K) -
BUNJI SHIMIZU, MASAKATSU KANEKO, MISAKO KIMURA, SHINICHI SUGAWARA1976 Volume 24 Issue 11 Pages 2629-2636
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe synthesis of new 7α-methoxy-7-(2-substituted thio) acetamido derivatives of cephalosporin by nucleophilic displacement of the halogen atom of 7β-(2-halogenoacetamido)-7-methoxy cephalosporanic acid derivatives was described. The in vitro antimicrobial activities were also described.View full abstractDownload PDF (926K) -
YOSHITAKA KIMURA, TERUYUKI MIYAMOTO, JUNICHI MATSUMOTO, SHINSAKU MINAM ...1976 Volume 24 Issue 11 Pages 2637-2643
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA reaction of ethyl α-diazo-β-oxo-5-(4-chloro-2-methylthiopyrimidine) propionate (III) with hydrazine hydrate in ethanol afforded 1, 2-dihydro-4-hydroxy-7-methylthiopyrimido-[4, 5-c] pyridazine-3-carboxamide (VII), of which structure was determined by chemical and infrared, ultraviolet, nuclear magnetic resonance and mass spectral evidences : VII was acetylated to 1, 2-diacetyl-4-hydroxy-1, 2-dihydro-7-methylthiopyrimido [4, 5-c] pyridazine-3-carboxamide (XI) and 4-acetoxy-9-acetyl-1-methyl-7-methylthio imidazo [3', 4' : 2, 3]-pyridazo [6, 5-d] pyrimidin-3 (9H)-one (XII), which were interconvertible. Both XI and XII were converted to 9-acetyl-4-hydroxy-1-methyl-7-methylthioimidazo [3', 4' : 2, 3]-pyridazo [6, 5-d] pyrimidin-3 (9H)-one (XIII). The hydrolyzed product (X) of VII was treated with alkaline permanganate to give 6-methylthio-1H-pyrazolo [3, 4-d] pyrimidine-3-carboxylic acid (XIV), which was subjected to decarbonylation and desulfurization. The formation mechanism of VII was discussed. Treatment of the acid (X) with benzoyl peroxide in ethanol in the presence of triethylamine afforded ethyl 1, 4-dihydro-7-methylthio-4-oxopyrimido [4, 5-c] pyridazine-3-carboxylate (XVII). The corresponding acid (XVIII) is a key intermediate for syntheses of 1, 4-dihydro-4-oxopyrimido [4, 5-c] pyridazine-3-carboxylic acids, which would be expected as antibacterial agents.View full abstractDownload PDF (861K) -
YOSHIO TAKEDA, HIROSHI NISHIMURA, OSAMU KADOTA, HIROYUKI INOUYE1976 Volume 24 Issue 11 Pages 2644-2646
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFrom the fruit of Gardenia jasminoides forma grandiflora, two new glucosides, 10-acetylgeniposide (1) and picrocrocinic acid (2) were isolated and their structures have been established.View full abstractDownload PDF (498K) -
MAMORU SUGIURA, KAZUYUKI HIRANO, HIROKO YOSHIMURA, MASAYASU SUGIYAMA, ...1976 Volume 24 Issue 11 Pages 2647-2650
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the application of glycerol dehydrogenase from a strain of bacterial Erwinia aroideae, a method of measuring serum aldolase activity is determined. This method is possible to measure 0-50 mU/ml aldolase. Until now, spectrophotometric assay with glycerol-1-phosphate dehydrogenase and colorimetric determination with 2, 4-dinitrophenylhydrazine are available. The former is possible to be affected with serum alkaline phosphatase, the latter needs much serum. Correlation between spectrophotometric assay with glycerol-1-phosphate dehydrogenase and this method using rabbit serum experimentally increased aldolase activity is shown.View full abstractDownload PDF (509K) -
MITSUTAKA NATSUME, MORITAKA WADA1976 Volume 24 Issue 11 Pages 2651-2656
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSStep-wise oxidation of the two double bonds in 1-alkoxycarbonyl-3-cyano-1, 4- or -1, 6-dihydropyridine (6 or 5) was found to be possible and 5-methoxycarbonyl-5-deoxy-dl-xylopiperidinose tetraacetate (18a) was synthesized via 5, 12, 13, and 17 from nicotinonitrile.View full abstractDownload PDF (816K) -
MITSUTAKA NATSUME, MORITAKA WADA1976 Volume 24 Issue 11 Pages 2657-2660
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-O-Methyl-5-benzamido-5-deoxy-dl-idopiperidinose was synthesized from the dihydropyridine derivative (1) by stereoselective introduction of the hydroxyl function.View full abstractDownload PDF (600K) -
NORIYASU HIROSE, SHIZUO KURIYAMA, SHOJI TOYOSHIMA1976 Volume 24 Issue 11 Pages 2661-2667
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-(N-substituted amino) methyl-2, 3-dihydrobenzofurans were synthesized in order to examine the effect of the N-substituent on their analgesic activity. Some of these compounds demonstrated a good analgesic activity when tested by the acetic acid writhing method in mice. 2-(3-Phenylpropylamino) methyl-7-methoxy-2, 3-dihydrobenzofuran (4i) showed the most potent activity in this series.View full abstractDownload PDF (758K) -
TAKEKI OKUMOTO, HIROSHI IMAMURA1976 Volume 24 Issue 11 Pages 2668-2672
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe antitumor activity of improsulfan was examined with respect to an increase in the lifespan of rats bearing ascites tumors when a relatively low dose (5 and 20 mg/kg) was given intraperitoneally in two equal fractions and in a single dose. The fractionated dose schedule, even when given in a time interval of over 24 hr, was more effective against tumors sensitive to alkylating agents, Yoshida sarcoma and AH-272. Against other tumors, the fractionated dose schedule was more effective only when given in an interval of within 3 hr or was equally effective at all of the intervals tested as the single dose schedule. The toxicity of improsulfan to normal healthy rats was severer in a single dose than in two equal fractions of the same total dose, 150 mg/kg. Therapeutic synergism was observed against Yoshida sarcoma when intraperitoneal administration of improsulfan and oral administration of cyclophosphamide were made simultaneously. The pharmacokinetic process in tissue concentrations of alkylating agents like that presumed in the fractionated dose schedule of improsulfan may occur by this combination.View full abstractDownload PDF (607K) -
TADAHIKO KARASAWA, KIYOSHI FURUKAWA, KOUICHI YOSHIDA, MASANAO SHIMIZU1976 Volume 24 Issue 11 Pages 2673-2685
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of 1, 2-benzisoxazole-3-acetamidoxime hydrochloride (PF-257), a novel psychotropic agent possessing the pharmacological properties similar, in some respects, to those of tricyclic antidepressants or monoamine oxidase inhibitors, on the metabolism of brain monoamines were studied in rats. A single large dose or repeated doses of PF-257 caused a slight but significant increase in brain norepinephrine level without affecting the contents of dopamine and serotonin. Like monoamine oxidase inhibitors, PF-257 prevented and reversed the decrease in brain norepinephrine induced by reserpine but it lacked the property to inhibit monoamine oxidase in the brain. Unlike tricyclic antidepressants, the compound was devoid of the capacity to inhibit norepinephrine uptake in vitro. Administration of PF-257 in combination with L-β-3, 4-dihydroxyphenylalanine (L-DOPA) enhanced the increase in brain dopamine without influencing the amount of the amino acid incorporated into the brain. At relatively small doses, PF-257 reduced the rate of decline of brain norepinephrine and dopamine levels following α-methyl-p-tyrosine, a tyrosine hydroxylase inhibitor, and also decreased the levels of brain 3-methoxy-4-hydroxy-phenylethyleneglycol sulfate and homovanillic acid, major metabolites of brain norepinephrine and dopamine, respectively. Thus, it is suggested that the fundamental mechanism underlying the pharmacological and biochemical effects of PF-257 may be its activity to decelerate catecholamine metabolism in the brain without inhibiting the enzymes participating in the metabolic degradation of the amines.View full abstractDownload PDF (1316K) -
YUKIO NOMA, YOSHIKO NOMA, KENJI KIHIRA, MISAO YASUHARA, TAIJU KURAMOTO ...1976 Volume 24 Issue 11 Pages 2686-2691
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe bile alcohol constituents of bullfrog were examined to give four new C26 bile alcohols along with three known bile alcohols, 5α-cyprinol, 5α-ranol, and 5β-ranol. On the basis of the spectral data and the direct comparison with synthetic samples, the structures of the new bile alcohols were established to be four 27-norcholestane-3α, 7α, 12α, 24-tetrols isomeric at C-5 and C-24, (I), (III), (VII), and (VIII).View full abstractDownload PDF (785K) -
KOUKI KITAGAWA, TADASHI AKITA, TOMIO SEGAWA, MASUMI NAKANO, NOBUTAKA F ...1976 Volume 24 Issue 11 Pages 2692-2698
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA detailed account of the synthesis of bovine neurotensin was presented. This tridecapeptide was synthesized in a conventional manner, after deprotecting three different protecting groups employed (Tos, Z and Bzl) by trifluoromethanesulphonic acid.View full abstractDownload PDF (962K) -
KIYOSHI OMURA, NORIO TADA, MITSUMI TOMIMOTO, YOSHIRO USUI, YOSHIKAZU O ...1976 Volume 24 Issue 11 Pages 2699-2710
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA variety of 7, 8-disubstituted 1, 4-dimorpholinopyrido [3, 4-d] pyridazine derivatives were synthesized in connection with the structure-activity relationships on diuretic activity. 1, 4-Dipolar cycloaddition of 4-alkyl- and 4-benzyl-5-ethoxyoxazoles with dimethyl maleate afforded dimethyl 6-alkyl- and 6-benzyl-5-hydroxy-pyridine-3, 4-dicarboxylate (3), which were alkylated to give the corresponding 5-alkoxypyridine derivatives (4). The cycloaddition of 5-alkyl- or 5-benzyl-4-phenyloxazole (9) with N-phenylmaleimide gave an adduct (10), heating of which under acidic condition effected dehydration to give 5-alkyl- or 5-benzyl-N, 6-diphenylpyridine-3, 4-dicarboximide (11). Reactions of 4 and 11 with hydrazine gave pyrido [3, 4-d] pyridazine-1, 4 (2H, 3H)-dione derivatives (5 and 12), chlorination of which followed by substitution with morpholine afforded 7-alkyl- and 7-benzyl-8-alkoxy-pyrido [3, 4-d] pyridazine derivatives (7a-k) and 8-alkyl- and 8-benzyl-7-phenyl derivatives (14a, 14b, and 14c). Also prepared were 8-methyl-7-substituted phenyl (14d and 15), 8-chloro- (19 and 21), 8-alkoxy-7-phenyl (26a, 26b, and 26c), and 7-methyl-8-phenyl (43) derivatives. Stereochemistry of the adduct (8) obtained by the 1, 4-cyclo-addition reaction of 4-phenyloxazole and N-phenylmaleimide was discussed.View full abstractDownload PDF (1298K) -
KUNIHIRO NINOMIYA, TAKAYUKI SHIOIRI, SHUNICHI YAMADA1976 Volume 24 Issue 11 Pages 2711-2715
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of penicillin sulfoxides with diethyl phosphorocyanidate (DEPC) was investigated. Treatment of benzylpenicillin (S)-sulfoxide methyl ester (4a) with a slight excess of DEPC in N, N-dimethylacetamide gave the 3-cephem (5a), the 2-cephem (6a). and the 3-methylenecepham (7a) in 22, 4, and 4% yields, respectively. Increase of the quantity of DEPC to a three or five fold excess increased the yield of the 3-cephem (5a). Phenoxymethylpenicillin (S)-sulfoxide methyl ester (4b) also afforded the 3-cephem (5b) and the 3-methylenecepham (7b) under analogous reaction conditions as above, while phthalimidopenicillin (R)-sulfoxide methyl ester (8) furnished the 3-cephem (9) and the isothiazolones (10 and 11).View full abstractDownload PDF (729K) -
MASAHIRO NAKANO, YOSHIKO ARAKAWA, KAZUHIKO JUNI, TAKAICHI ARITA1976 Volume 24 Issue 11 Pages 2716-2722
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS5-Fluorouracil and its derivative, 1-(2-tetrahydrofuryl)-5-fluorouracil (THFFU) were studied as to their permeability through cellophane, collagen, and silicone membranes. 5-Fluorouracil permeated through cellophane and collagen membranes slightly faster than THFFU. 5-Fluorouracil, however, permeated through the silicone membrane much more slowly than THFFU. Although the solubility of THFFU in silicone oil was much smaller than that in water, propylene glycol, or macrogol 400, its permeation rates through the silicone membrane from suspensions in these media were similar. The permeation rate of 5-fluorouracil through the silicone membrane from suspension in water was slightly greater than that in macrogol 400 in spite of smaller solubility in water. The permeation rate of THFFU from aqueous solutions through the silicone membrane was accelerated by the presence of sodium chloride and sodium sulfate whereas it was decelerated by sodium iodide. Permeation studies of THFFU through the silicone membrane at various pH values revealed that only the unionized form of the drug permeated through the membrane. The effect of temperature on permeability and flux of THFFU through the silicone membrane was also studied.View full abstractDownload PDF (762K) -
KUKYUN SHIN, HIDEO NAKAGAWA, SUSUMU TSURUFUJI1976 Volume 24 Issue 11 Pages 2723-2727
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA significant inhibition of desoxyribonucleic acid (DNA) synthesis in rat granuloma cells was brought about by 6 repeated administrations (250 mg/kg) of hydroxyurea at 12 hr intervals from day 5 to day 7 after carrageenan injection. The suppressive effect of hydroxyurea on the amount of DNA in granulomatous tissue began to appear on day 8 (12 hr after the last injection of hydroxyurea), and then a maximum inhibition was attained on day 9. The inhibitory effect on the amount of collagen, on the other hand, was disclosed on day 9 with the retardation of around one day to the appearance of suppressive effect on DNA. The cellular activity for collagen synthesis in the hydroxyurea-treated group was gradually elevated accompanying coincidental suppression of DNA synthesis, suggesting that mature cells synthesized collagen more actively than newly formed cells. Suppression of cell proliferation by hydroxyurea seems to result in decrease in the number of mature cells with the retardation of time required for maturation of newly formed cells.View full abstractDownload PDF (609K) -
KUNIO KAWAI, SHIGEO BABA1976 Volume 24 Issue 11 Pages 2728-2732
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to develop a practical technique useful for metabolic studies in man by the use of drugs labeled with a stable isotope, l-ephedrine-d5 was administered to man and the urinary metabolites were quantitatively determined by mass spectrometry. In this method, unlabeled compounds were used as carriers and internal standards for deuterated metabolites of interest. It was thereby found that 75.1% of the administered l-ephedrine was excreted unchanged, 3.6% as norephedrine, and 3.5% as hippuric acid.View full abstractDownload PDF (648K) -
AKIRA MIZUTANI, TAKAHARU MIZUTANI, POFENG KUO1976 Volume 24 Issue 11 Pages 2733-2738
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMolecular weight determinations were carried out on a hypocalcemic protein purified from bovine parotid gland by sedimentation equilibrium, gel chromatography on Sepharose 6B in 6 M guanidine hydrochloride (Gun HC1), and viscometry in 6 M Gun HC1 0.1 M mercaptoethanol, and the values obtained were 45000, 47000, and 45700, respectively. These results agreed well with the result (48000) from sodium dodecyl sulfate polyacrylamide gel electrophoresis. The optical rotatory dispersion and circular dichroism spectra of the purified hypocalcemic protein showed that the contents of α-helix, β-structure, and random coil were 54, 26, and 20%, respectively. It was found that this protein contains large amounts of α-helix and thereby has a rigid structure.View full abstractDownload PDF (702K) -
TENGK. LIN, YIEW. CHIEN, HITENDRAB. DESAI, PETERK. YONAN1976 Volume 24 Issue 11 Pages 2739-2743
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA model has been proposed to explain and determine biological response to antiarrhythmic compounds. A series of compounds was administered to mongrel dogs and tested for their ability to correct the induced arrhythmias. This drug response is shown to be a function of lipophilicity, IR-absorption and electrostatic interaction. Frontier electron density is shown as a good parameter in the comparison of electrostatic interaction between different molecules and is significantly correlated with biological activity. This parameter is shown as a possible explanation for the observation that compounds with a high value of lipophilicity and low value of electrostatic factor may show good ventricular antiarrhythmic activity but fail to show atrial antiarrythmic activity.View full abstractDownload PDF (585K) -
MASASHI TOMODA, SACHIKO KANEKO, CHIEKO OHMORI, TOMOKO SHIOZAKI1976 Volume 24 Issue 11 Pages 2744-2750
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA mucous polysaccharide, named Lilium-La-glucomannan, has been isolated from the bulbs of Lilium lancifolium THUNB. It was homogeneous on glass-fiber paper electrophoresis and by ultra centrifugal analysis. The component sugars of it were D-mannose and D-glucose in the molar ratio of 5 : 2, and its molecular weight was measured at 417000. The O-acetyl groups in the polysaccharide were identified and determined as the content of 1.2%. They are located in positions 2, 3, and 6 of a part of D-mannose units. Methylation, periodate oxidation and partial acetolysis studies suggested that the polysaccharide is mainly composed of β-1→4 linked aldohexopyranose residues and it contains about thirty aldohexose units per one end group on the average. D-Mannose units occupy non-redncing terminal positions and branch points linked through positions 2 and 3.View full abstractDownload PDF (1033K) -
KENYA KAWASHIMA, YASUHIKO KAWANO1976 Volume 24 Issue 11 Pages 2751-2760
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Simmons-Smith reaction of 5H-dibenz [b, f] azepine (4) and 5-methyl-5H-dibenz-[b, f] azepine (5) yielded 1, 1a, 6, 10b-tetrahydro-6-methyldibenzo [b, f] cycloprop [d] azepine (6), which represents synthesis of a novel condensed ring system. 6 was demethylated via the formamide derivative 7 to give 1, 1a, 6, 10b-tetrahydrodibenzo [b, f] cycloprop [d]-azepine (8), which was converted into pharmacologically active 6-dialkylaminoalkyl (9) and 6-carbamoyl (17) derivatives. Cyclopropanation of 5-(3-halopropyl)-5H-dibenz [b, f] azepines (11) with the Simmons-Smith reagent, however, led to additional reactions in the side chain to yield 12, 13, 14, and 15.View full abstractDownload PDF (1195K) -
KENYA KAWASHIMA, EIJI MIZUTA1976 Volume 24 Issue 11 Pages 2761-2768
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDetailed inspection of the nuclear magnetic resonance spectra of 1, 1a, 6, 10b-tetrahydrodibenzo [b, f] cycloprop [d] azepines (1) in CDCl3 solutions has revealed that the state of conformational equilibrium falls into the following five categories according to the nitrogen substituent Z : 1) There exists a slow equilibrium between conformers I and IV, conformers II and III being either involved in a fast process or not involved at all. 2) Thre eexists a slow (much slower than category 1) equilibrium between conformers I and IV, conformers II and III being either involved in a fast process or not involved at all. 3) Conformer I is the sole one that is present, conformer III being either involved in a fast process or not involved at all. 4) Conformer IV (≡II) is the sole one that is present. 5) There exists a fast equilibrium between conformers I and IV, conformers II and III being either involved in a fast process or not involved at all.View full abstractDownload PDF (816K) -
YOSHIKI HAMADA, ISAO TAKEUCHI1976 Volume 24 Issue 11 Pages 2769-2774
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4, 6-Phenanthroline 6-oxide (II), 4-oxide (IV), and 4, 6-dioxide (III) were synthesized from 4, 6-phenanthroline by various methods. The reaction of II, III, and IV with phosphoryl chloride gave some chlorinated compounds (V to IX), and the reaction of II with acetic anhydride gave 4, 6-phenanthrolin-5 (6H)-one (X) and 6-(5'-4', 6'-phenanthrolinyl)-4, 6-phenanthrolin-5 (6H)-one (XI). These results were compared with the same reaction of 1, 6-phenanthroline.View full abstractDownload PDF (730K) -
KEIICHI FUKUYAMA, TOMITAKE TSUKIHARA, YUKITERU KATSUBE, MASAAKI KATAI, ...1976 Volume 24 Issue 11 Pages 2775-2780
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stereochemistry of pieristoxin G, C20H32O8, has been established by the X-ray diffraction method. The compound crystallized in the space group P212121, with a=13.668, b=6.567, and c=21.516 A. The structure was solved by the direct method and refined to R=0.050 for 1409 reflections. The conformations of the rings A, C, and D are envelope, distorted chair, and half-chair respectively. The junctions of the rings of A/B, B/C, and C/D are trans, cis, and cis respectively.View full abstractDownload PDF (656K) -
YOSHIRO MORI, HARUAKI YAJIMA1976 Volume 24 Issue 11 Pages 2781-2787
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe heptadecapeptide amide corresponding to the C-terminal portion of porcine cholecystokinin-pancreozymin (CCK-PZ) was synthesized in the protected, but unsulfated form.View full abstractDownload PDF (1008K) -
YOSHIRO MORI, KANAME KOYAMA, YOSHIAKI KISO, HARUAKI YAJIMA1976 Volume 24 Issue 11 Pages 2788-2793
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hexadecapeptide corresponding to the N-terminal portion of porcine cholecystokinin-pancreozymin (CCK-PZ) was synthesized by the successive azide condensation of four peptide fragments.View full abstractDownload PDF (912K) -
HARUAKI YAJIMA, YOSHIRO MORI, KANAME KOYAMA, TAKAYOSHI TOBE, MOTOICHI ...1976 Volume 24 Issue 11 Pages 2794-2802
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe tritriacontapeptide amide, [27-Tyr]-CCK-PZ, was synthesized by successive azide condensation of 4 peptide fragments, (1-5), (6-11), (12-16), and (17-33), followed by exposure to hydrogen fluoride to remove all protecting groups. Though the CCK-PZ activity of synthetic peptide was only 1/250 of the standard from the natural source, it was smoothly labeled with radioactive iodine. Chain length activity relationship of CCK-PZ was also discussed.View full abstractDownload PDF (1163K) -
TAEKO ADACHI, KAZUO OTSUKI1976 Volume 24 Issue 11 Pages 2803-2809
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSN, N-Dibromobenzenesulfonamide (II) was reacted with propenylbenzene (Ib), p-methoxypropenylbenzene (Ic), m-methoxypropenylbenzene (Id), 3, 4-dimethoxypropenylbenzene (Ie), and 4-benzyloxy-3-methoxypropenylbenzene (If), in various molar ratios in dichloromethane. 1-Benzenesulfonamido-2-bromo-1-phenylpropane (IIIb), 1-benzenesulfonamido-2-bromo-1-(4'-methoxyphenyl) propane (IIIc), 3'-bromo-substituted analog of IIIc (IVc), 1-benzenesulfonamido-2-bromo-1-(3'-methoxyphenyl) propane (IIId), 6'-bromo-substituted analog of IIId (IVd), 1-benzenesulfonamido-2-bromo-1-(3', 4'-dimethoxyphenyl) propane (IIIe), 6'-bromo-substituted analog of IIIe (IVe), N-benzenesulfonyl-3, 4-dimethoxyaniline (V'e), 6-bromo-substituted analog of V'e (Ve), 1-benzenesulfonamido-2-bromo-1-(4'-benzyloxy-6'-bromo-3'-methoxyphenyl) propane (IVf), and N-benzenesulfonyl-6-bromo-4-benzyloxy-3-methoxyaniline (Vf) were produced as main products, respectively. Formation of the side-chain eliminated compounds (such as V'e, Ve, and Vf) has been found when reacted in a ratio of I : II of less than 1 : 1, starting from 3, 4-dialkoxypropenylbenzene, and the sulfonamido group substituted in the position from which the side chain was eliminated.View full abstractDownload PDF (793K) -
KOJI YAMAKAWA, KIYOSHI NISHITANI1976 Volume 24 Issue 11 Pages 2810-2817
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical transformations of α-santonin (V) into arsantin (IIIa) and arsanin (IVa) isolated from Artemisia santolina by Sidyakin, et al. were described. α-Epoxyketone (IX) was prepared from α-tetrahydrosantonin (VI) via three steps. Reductive ring-opening of IX with zinc dust in methanol in the presence of a small amount of acetic acid afforded arsantin (IIIa). IIIa was not coincident with the reported natural atsantin, which was probably identical with a dimorph of arsanin (IVa). β-Epoxy compound (XVI) was prepared from 1-en-3β-ol (XIVa) by Sharpless' procedure. Reductive ring-opening of β-epoxyketone (XVIII) by a method similar to described for arsantin gave 1β-hydroxyketone (IVa). The mp, nuclear magnetic resonance and infrared spectra of IVa were identical with those of natural arsanin.View full abstractDownload PDF (1059K) -
YASUO SHIBATA, TOMOKO NOZAKI, TOKUHIKO HIGASHI, SHUICHI SANADA, JUNZO ...1976 Volume 24 Issue 11 Pages 2818-2824
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSGinsenosides Rb1 and Rc purified from the ethanol extract of a root of Panax ginseng were administered into rats at the dose of 5 mg/100 g of body weight. After 3 hours of the administration, biosynthesis of rat serum protein was stimulated at 2 times and more than the control, in 1 hour 14C-amino acid incorporation experiment. From the analyses of serum proteins by salting-out, electrophoresis and NaBr flotation, apoproteins of chylomicrons and very low density lipoprotein showed mostly stimulated synthesis by the treatment with ginsenosides. This coincided with the stimulation of cholesterol synthesis reported previously, and a possible relationship between the synthesis of lipids and that of apo-lipo-proteins was discussed.View full abstractDownload PDF (818K) -
SHIGEO TANAKA, KANETO UEKAMA, KEN IKEDA1976 Volume 24 Issue 11 Pages 2825-2831
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of cyclodextrin (CyD) on the alkaline hydrolysis of various ethyl cinnamates was investigated. The inclusion by χ-CyD retarded the hydrolysis in all cases but that by β-CyD accelerated for esters bearing electron withdrawing substituents. Stability constant, Kc, and rate constant, kc, of the complexes were determined kinetically on the basis of 1 : 1 complexation. To elucidate the reaction mechanism the hydrolysis rates of para substituted ethyl benzoates, ethyl phenylacetate, ethyl phenylpropionate, and ethyl phenylbutyrate in the presence of β-CyD were examined. Results showed that the effect of the inclusion primarily could be attributed to the magnification of electrostatic effect in hydrophobic cavity of CyD, i.e. "microsolvent effect", rather than complex stability.View full abstractDownload PDF (663K) -
SHIKIFUMI KITAZAWA, IKUO JOHNO1976 Volume 24 Issue 11 Pages 2832-2840
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of alloxan-induced diabetes on the relation between transmucosal fluid movement and its effect on sulfanilamide absorption were studied with the in situ recircurating perfusion method using the small intestine of rats with perfusion solution having three different tonicities which were adjusted to hypertonic (1.2%), isotonic (0.9%), and hypotonic (0.6%) solution with sodium chloride, respectively. Sulfanilamide absorption in both of control and diabetic rats was increased with increasing the apparent transmucosal fluid movement. The regression lines obtained from both of them were almost overlapped in a wide range of drug absorption on the horizontal axis and fluid movement on the vertical axis. The transmucosal fluid movement using the entire small intestine in diabetic rats were always significantly greater than in control animals. On both the wet- and the dry-weight basis, the fluid movement was also significantly greater with the diabetics. The total drug absorption was significantly increased in the diabetics than in the controls. The drug absorption in the diabetics was also significantly incresaed than in the controls when compared on the dry-weight basis. The increased drug absorption in the diabetics might be based on the increase of fluid inflow rather than increased transport activity per unit weight of the intestine, since the drug absorption was increased only the increased portion of fluid inflow in the diabetics along the regression line of the controls. These evidences and findings so far obtained might allow us to conclude that the effect of transmucosal fluid movement on the drug absorption was the same characteristic in nature indifferent to the induced mechanisms which were due to artificial and natural devices.View full abstractDownload PDF (1111K) -
AKEMI YAMASAKI, HIROMI TERAUCHI, SHOJI TAKEMURA1976 Volume 24 Issue 11 Pages 2841-2849
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of N, N-dibromo-, and dichlorobenzenesulfonamides (DBBS and DCBS) and N, N-dichlorourethan (DCU) with dienes were examined. Reactions of DBBS or DCBS with 1, 5-hexadiene, 1, 4-pentadiene, and 1, 4-diphenyl-1, 3-butadiene caused cyclic additions to give pyrrolidine derivatives in some extent accompanying with open-chain adducts whereas DCU gave no cyclic adduct but only mixtures of open chain-adducts. The reactions of N, N-dihaloamides with 1, 4-cyclohexadiene also gave acyclic adducts.View full abstractDownload PDF (956K) -
REIMEI MOROI, KENJI ONO, TADASHI SAITO, MITSUJI SANO, TAKESHI AKIMOTO1976 Volume 24 Issue 11 Pages 2850-2858
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism of budralazine in rats was investigated. Ten urinary metabolites were detected and identified after oral administration. Major metabolites were 3-methyl-s-triazolo [3, 4-a] phthalazine and 1-(s-triazolo [3, 4-a] phthalazine-3-carboxy)-β-D-glucopyranosiduronic acid. Comparison of the metabolic pattern obtained in spontaneously hypertensive rat and normotensive Wistar-strain rat was also discussed. But no significant difference was observed for the time course of biotransformation rate between them.View full abstractDownload PDF (922K) -
NARAO TAKAO, KINUKO IWASA, MIYOKO KAMIGAUCHI, MAKIKO SUGIURA1976 Volume 24 Issue 11 Pages 2859-2868
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSince dl-cheilanthifoline (2) was converted in Corydalis incisa plants into corynoline (3) and protopine (4), it was shown that 2 was the intermediate between scoulerine (15) and stylopine (10). Corycavine (9) was shown to be biosynthesized in Corydalis incisa plants from dl-mesotetrahydrocorysamine (7) and dl-tetrahydrocorysamine (8) via their α-N-methosalts (7α and 8α). Protopine (4) is shown to be formed in vivo from the α-N-methosalt of dl- or l-stylopine (10α). Incorporation of the β-N-methosalts (10β and 8β) into 4 and 9 might be absent or negligible. These results imply that α-N-methosalts of tetrahydroprotoberberines are stereospecifically converted into protopine-type alkaloids. Sanguinarine (13) and chelidonine (14) were shown to be biosynthesized in Chelidonium majus plants from α-N-methosalt of dl- or l-stylopine (10α) via protopine (4). This shows that protopine-type alkaloid is the intermediate between tetrahydroprotoberberine-type and benzo [c] phenanthridine-type alkaloids.View full abstractDownload PDF (1045K) -
TOSHIO NAMBARA, NORIMASA TAKIZAWA, JUNICHI GOTO, KAZUTAKE SHIMADA1976 Volume 24 Issue 11 Pages 2869-2870
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSConvenient synthesis of phenolphthalein β-glucuronide (IV), which is widely used for the assay of β-glucuronidase activity as a substrate, has been described. Koenigs-Knorr reaction of phenolphthalin methyl ester (I) with methyl acetobromoglucuronate in the presence of cadmium carbonate as a catalyst provided the monoglucuronide acetatemethyl ester (II) which on oxidation with 2, 3-dichloro-5, 6-dicyanobenzoquinone was led to the phenolphthalein derivative (III). Elimination of protecting groups with methanolic sodium hydroxide afforded the desired compound (IV) in a satisfactory yield.View full abstractDownload PDF (389K) -
MITSUHIKO MANO, TAKUJI SEO, TOSHIMI MATSUNO, KINICHI IMAI1976 Volume 24 Issue 11 Pages 2871-2876
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA series of 2-amino-5-aryl-1, 3, 4-oxadiazoles, 5-alkoxy-3-aryl-1H-1, 2, 4-triazoles, and 3-aryl-⊿2-1, 2, 4-triazolin-5-ones were prepared and their anticoccidial activity was tested. Among them, 5-(3, 4-dichlorophenyl)- and 5-(2, 4, 5-trichlorophenyl)-2-amino-1, 3, 4-oxadiazoles, 3-(3, 4-dichlorophenyl)- and 3-(2, 4-dichlorophenyl)-5-ethoxy-1H-1, 2, 4-triazoles, and 3-(4-bromophenyl)-, 3-(4-chlorophenyl)-, and 3-(2, 4-dichlorophenyl)-⊿2-1, 2, 4-triazolin-5-ones showed moderate anticoccidial activity.View full abstractDownload PDF (660K) -
JUN ADACHI, KEIICHI NOMURA, SHINICHI YAMAMOTO, KEMMOTSU MITSUHASHI1976 Volume 24 Issue 11 Pages 2876-2880
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS6-Acetamido-5, 6, 7, 8-tetrahydroquinoline N-oxide (VI) was derived to the 8-oxo derivative (IX) via the acetoxy compound (VII). Introduction of carboxymethyl group by a Witting reaction of IX and catalytic hydrogenation afforded the amido ester (XI). The title compound (XVI) was synthesized from the amino acid ester (XII) by intramolecular cyclization and the subsequent lithium aluminum hydride reduction of the resulting lactam.View full abstractDownload PDF (686K) -
KATSUHIKO NAGAHARA, KANAME TAKAGI, TAKEO UEDA1976 Volume 24 Issue 11 Pages 2880-2882
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of ethoxymethylenemalononitrile (EMMN) with hydrazine hydrate in the presence of ethanol at room temperature gave 3-amino-4-cyanopyrazole (I) and a novel pyrazole derivative, 3-amino-4-cyano-2-hydrazonomethylpyrazole (II). When this reaction was carried out under reflux, II was not obtained. The result of various solvents for the preparation of II was found at present acetonitrile as a solvent most suitable. The reaction of EMMN with hydrazine hydrate in water at room temperature gave I in good yield. On the other hand, the reaction of hydrazine hydrate with excess EMMN afforded 7-amino-3, 6-dicyanopyrazolo [1, 5-a] pyrimidine.View full abstractDownload PDF (413K) -
TADAO SAKAI, MASAHIRO TSUBOUCHI1976 Volume 24 Issue 11 Pages 2883-2886
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA singly charged tetrabromophenolphthalein ethyl ester (TBPE) was found to be extracted with quinine ethylcarbonate as a 1 : 1 complex in 1, 2-dichloroethane. Among various solvents, TBPE-1, 2-dichloroethane system gives the red colored species for alkaloids and amines, while in the absence of alkaloids and amines, the organic phase shows pale yellow color. In this way, the spectrophotometric method was investigated for the determination of a small amount of quinine ethylcarbonate by solvent extraction. Quinine ethylcarbonate is determined by measuring absorbance of the extracts over the range of 2×10-6 M to 1.6×10-5 M (0.793-6.34μg/ml) at 555 nm. From the electric conductivity measurements, the extracts with TBPE are classified into four categories as follows ; (1) blue ; dissociated ion-pair complexes (2) blue ; associated ion-pair compounds (3) red ; associated charge transfer complexes (4) yellow ; associated H·TBPE.View full abstractDownload PDF (531K) -
HIKARU OKABE, TATSUO YAMAUCHI1976 Volume 24 Issue 11 Pages 2886-2888
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new cardiac trioside was isolated from the seeds of Mallotus japonicus MUELL. ARG. (Euphorbiaceae) and it was identified as corotoxigenin β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl-(1→4)-α-L-rhamnopyranoside.View full abstractDownload PDF (514K) -
MASANORI SAKAMOTO, MICHIKO SHIBANO, KYOKO MIYAZAWA, MICHIKO SUZUKI, YO ...1976 Volume 24 Issue 11 Pages 2889-2890
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-(1-Pyrrolidinyl) cyclohexene reacts with 2-(p-nitrobenzylideneamino) benzoxazole and 2-(p-nitrobenzylideneamino) benzimidazole, affording new Diels-Alder type adducts respectively.View full abstractDownload PDF (327K) -
NOBUTOSHI TANAKA, MASAAKI HASEGAWA, TAKAO MURAKAMI, YASUHISA SAIKI, CH ...1976 Volume 24 Issue 11 Pages 2891-2892
Published: November 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAus den oberirdischen Teilen von Microlepia marginata (HOUTT.) C. CHR. wurden zwei neue Diterpen-glykoside, Microlepin und 16-epi-Microlepin, isoliert und jeweils als ent-16β, 17, 19-Trihydroxy-kauran-19-β-4-O-methyl-D-glukosid (I) und ent-16α, 17, 19-Trihydroxy-kauran-19-β-4-O-methyl-D-glukosid (II) identifizierte.View full abstractDownload PDF (355K)