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Volume 29, Issue 7
Displaying 1-48 of 48 articles from this issue
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MUHAMMAD ISHAQ ALI KHAN, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA1981 Volume 29 Issue 7 Pages 1795-1801
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSDiethanolamine was oxidized by gaseous oxygen to N-(2-hydroxyethyl) glycine in an aqueous solution containing sodium hydroxide over a 0.5% Pd-alumina catalyst in the temperature range of 50-80°C and at ambient pressure in a slurry reactor, and the kinetics was investigated. Under the present experimental conditions, all mass transfer resistances were assumed to be insignificant. The catalyst was very active but its activity decreased rapidly while it was in contact with oxygen. A power-law model was assumed for this reaction. The reaction order was estimated to be 0.37 with respect to diethanolamine concentration and 0.64 with respect to oxygen concentration. The rate was analyzed according to the Hougen-Watson model. It is concluded that the oxidation is mainly controlled by the surface reaction between adsorbed diethanolamine and oxygen in the liquid phase. This reaction is an excellent model for studies of three-phase reaction systems (gas-liquid-solid).View full abstractDownload PDF (593K) -
ISHAQ ALI KHAN MUHAMMAD, YOSHIHISA MIWA, SHUSHI MORITA, JUTARO OKADA1981 Volume 29 Issue 7 Pages 1802-1809
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe oxidation of diethanolamine to N-(2-hydroxyethyl) glycine in alkaline solution was carried out over a Pd-Al2O3 catalyst in a liquid-full reactor, and the effect of mass transfer on the global rate of reaction was studied. Data were taken at 40°C and atmospheric pressure. Experiments were first done to determine the order of reaction with respect to oxygen, which was found to be 0.64 for an assumed tortuosity factor of 3.4 for the catalyst particles. Under the reaction conditions used, the effective mass transfer area between liquid and porous catalyst was found to be less than the outer surface area of the particles. With 0.5% Pd-Al2O3 catalyst, the global rate of reaction was mainly controlled by liquidsolid and intraparticle mass transfers, and the reaction was considered to be completed inside the deactivated outer shell, as the core of the particle still retained high catalyst activity.View full abstractDownload PDF (860K) -
KIYOKO TAKAMURA, ATSUKO MORI, FUMIYO KUSU1981 Volume 29 Issue 7 Pages 1810-1818
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe adsorption behavior of deoxyadenosine-5'-monophosphate (dAMP) on a gold electrode has been studied by specular reflectivity measurement in 0.1 M NaClO4 solutions ranging in concentration from 2.5×10-6 to 2.5×10-4 M. The reflectivity change due to the adsorption of dAMP was suggestive of the formation of two types of adsorbed layer depending on both the bulk concentration and the electrode potential ; one of them, termed the type I layer, appeared at low concentrations at potentials around the point of zero charge (pzc) as well as over the whole concentration range at rather negative potentials, and the type II layer appeared at high concentrations around pzc. The results obtained by analysis of the isotherms corresponding to these layers suggest that the adsorbed molecule is oriented with its adenine moiety nearly flat on the surface in the type I layer, but perpendicular to it in the type II layer. Such a change in orientation was not observed for adenine, deoxyadenosine, or deoxyadenosine-5'-diphosphate or -triphosphate. The characteristics of the adsorption behavior of dAMP were reasonably explained on the basis of its structural effect, i.e., the ease of orientational change of the adsorbed molecules and the resulting mutual interaction between adjacent adsorbates in the type II layer.View full abstractDownload PDF (937K) -
TOHRU KIKUCHI, MINEO NIWA, TOSHIO YOKOI, SHIGETOSHI KADOTA1981 Volume 29 Issue 7 Pages 1819-1826
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRearrangements of the 28-methyl group of pachysonol and pachysandiol-B derivatives in the reaction with methanesulfonyl chloride were examined. It was found that two kinds of methyl-migrated products [(IIa, IIb, and VIIIa) and (IVa, IVb, and Xa)] were formed in addition to normally dehydrated products (IIIa, IIIb, and IX), and their structures were elucidated by chemical and spectroscopic methods.View full abstractDownload PDF (881K) -
TSUYOSHI NAGAYOSHI, SEITARO SAEKI, MASATOMO HAMANA1981 Volume 29 Issue 7 Pages 1827-1831
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTreatment of 1-hydroxy-2-phenylindole (1) with phosphoryl chloride-DMF gave 2-phenylindole-3-carboxaldehyde (2) in 70% yield. The reaction of 1 with quinoline 1-oxide (3) and benzoyl chloride in boiling chloroform produced 1-benzoyloxy-2-phenyl-3-(2-quinolyl) indole (5) and 1-hydroxy-2-phenyl-3-(2-quinolyl) indole (6). In the reaction using tosyl chloride instead of benzoyl chloride, 6 or 2-phenyl-3-(2-quinolyl) indole (8) was formed. These results demonstrate that the enehydroxylamine systems in 1 and 1-benzoyloxy-2-phenylindole (4) can behave as nucleophilic species as a result of enamine-like polarization.View full abstractDownload PDF (559K) -
HARUO OGURA, HIROSHI TAKAHASHI, KAZUYOSHI TAKEDA1981 Volume 29 Issue 7 Pages 1832-1837
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of phenylacetyl isothiocyanate (1a) with diamines afforded 1-substituted 3-phenylacetyl thiourea (3a-d) in good yields. Attempted ring closure of these products under thermal or basic conditions was unsuccessful. However, treatment of 3a with Ac2O-H3PO4 at room temperature gave the cyclized product (5a). Similar reaction of D-gluconyl isothiocyanate (1b) with o-phenylenediamine (2a) or diaminopyrimidines (2b, c, e, f) gave the D-gluco-pentyl benzotriazepine-2-thione (7a) or D-gluco-pentyl pyrimidotriazepine-2-thiones (7b, c, e, f), respectively, in fair yields. Treatment of 1b with ethyl 3-aminocrotonate or 6-amino-1, 3-dimethyluracil afforded D-gluco-pentyl thiopyrimidine (8b) or D-gluco-pentyl pyrimido [4, 5-d] pyrimidine (9b), respectively.View full abstractDownload PDF (566K) -
HARUO OGURA, HIROSHI TAKAHASHI, OSAMU SATO1981 Volume 29 Issue 7 Pages 1838-1842
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of glycosyl isothiocyanate (1a) with thiourea in the presence of Mel-NEt3 gave a di-SMe compound (2a) and a mono-SMe compound (3a). Glycosyl isothiocyanates (1a, b, and c) reacted with amidino compounds (HN=CRNH3 ; R=H, Me, OMe, SMe, NH2) to afforded the corresponding glycosyl isothiobiurets (3a, c, and 6a, b), N-glycosyl-N'-amidino thioureides (4a, b, and 5a, b) or N-glycosyl-N'-guanidyl thioureides (7a and b) in good yields. Treatment of 3a, 6b, or 7a, b with HC (OEt)3 gave the corresponding s-triazine glycosides (8a, 9a, b, and 10b) in fair yields. On the other hand, similar treatment of 4a, b or 5a, b with HC (OEt)3 did not give s-triazine glycosides, but the starting material was recovered. N-Bromosuccinimide oxidation of 4a, b, 5a, b, 3a, c or 7a, b gave the corresponding 5-substituted-1, 2, 4-triazole-3-thiones (11a, b, 12a, b, or 14a, b) in excellent yields.View full abstractDownload PDF (641K) -
HARUO OGURA, HIROSHI TAKAHASHI, OSAMU SATO1981 Volume 29 Issue 7 Pages 1843-1847
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reactions of glycosyl isothiocyanates (1a-c) with diazomethane or ethyl diazoacetate gave the corresponding glycosylamino-1, 2, 3-thiadiazoles (2a-c or 3a, b). Attempted ring transformation of 2 under thermal or basic conditions failed. Similar treatment of D-gluconyl isothiocyanate (1d) with diazomethane afforded D-gluco-pent-1-yl oxathiazolone (5d) in good yield. The reactions of 1a-c with acetoamidine or formamidine hydrochloride under basic conditions gave the corresponding N-glycosyl-N'-acetoamidino-or N-glycosyl-N'-formamidinothiocarboxamides (6a-c ; 7a, c). Subsequent treatment of 6b, c and 7a, c with thionyl chloride under basic conditions afforded the corresponding 1, 2, 4, 6-thiatriazine-S-oxide glycosides (8a-c ; 9a, c) in good yields. Attempted transformation of 8 to 1, 2, 4-triazole glycoside (10) was unsuccessful.View full abstractDownload PDF (534K) -
KOICHIRO YAMADA, NOBUO ITOH, KATSUO IKEZAWA, AKIO KIYOMOTO, TAKEO IWAK ...1981 Volume 29 Issue 7 Pages 1848-1853
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn connection with our previous study on the β-adrenoceptor activities of the positional isomers of trimetoquinol, various 1-arylmethyl-1, 2, 3, 4-tetrahydroisoquinolines (10b-i) were synthesized. The Barbier reaction of the quaternary salt (7) with arylmethyl halides, followed by sodium monoacetoxyborohydride [NaBH3 (OAc)] reduction in a one-pot procedure, gave the tribenzyltetrahydroisoquinolines (9b-i) in excellent yields. Catalytic debenzylation of 9b-i furnished 10b-i. None of the compounds (10b-i) exhibited significant bronchodilating activity.View full abstractDownload PDF (576K) -
AKIRA YOSHIDA, TERUO HAYASHI, NORIKO TAKEDA, SADAO OIDA, EIJI OHKI1981 Volume 29 Issue 7 Pages 1854-1861
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAn N-protected derivative of 4-phenylthio-2-azetidinone (3b) was ethylated to give 3c, which was converted into the phosphorane 5d by the standard procedure. Intramolecular Wittig reaction of 5d afforded 6-ethylpenem esters 8a and 9a which were transformed via manipulation of the side chain to the amino acids 8d and 9d and subsequently to the acetamido derivatives 8e and 9e, which are 1-thia analogs of the antibiotic PS-5.View full abstractDownload PDF (898K) -
MICHIYA KIMURA, TOSHIKI MUTO1981 Volume 29 Issue 7 Pages 1862-1869
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe time courses of the spectral change, decomposition, and consumption of Fe (acac)3, tert-butyl (τBu) hydroperoxide, and cholesteryl acetate, respectively, in the title reaction were followed and the reaction was inferred to be initiated by the active species originating from the interaction of the ferric chelate and the hydroperoxide. Radical processes seem to participate in this reaction, since it was completely inhibited by a radical scavenger (BHT), which was also effective in blocking the further transformation of the intermediary C (7)-τBu-peroxide. The τBuBr-KO2 system generating τBuOO radicals oxidized cholesteryl methylether almost exclusively to an epoxide. The τBuOOH-KO2 system generating τBuO radicals, on the other hand, abstracted the allylic C (7)-hydrogen to give the τBu-peroxide, the alcohol, and the ketone, but no epoxide. The intermediary τBu-peroxide was assumed to be produced also by the nucleophilic attack of τBuOOH on the allylic cation, to which the initially formed C (7)-radical species was further oxidized. A proposed mechanism is presented for the title reaction.View full abstractDownload PDF (829K) -
KIYOSHI OMURA, RYUJI MARUMOTO, YOSHIYASU FURUKAWA1981 Volume 29 Issue 7 Pages 1870-1875
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThree methods for the synthesis of 2-phenylaminoadenosine (1, CV-1808), a potent coronary vasodilator with prolonged action, were exploited. 1) The reaction of 5-amino-4-cyano-1-(β-D-ribofuranosyl) imidazole (7) with phenyl isothiocyanate gave 7-imino-5-phenylamino-3-(β-D-ribofuranosyl) imidazo [4, 5-d] [1, 3]-thiazine (11), which, on alkaline treatment, rearranged to 6-mercapto-2-phenylamino-9-(β-D-ribofuranosyl) purine (12). On methylation, 12 gave the 6-methylmercapto derivative (14), which was converted to 1 by treatment with ammonia. 2) 5-Amino-4-cyano-1-(β-D-ribofuranosyl) imidazole (7) reacted with phenyl cyanamide in methanolic ammonia, giving 1 and 2-aminoadenosine as a by-product. 3) Ethyl 5-amino-1-(β-D-ribofuranosyl)-4-carboximidate (21b) was directly obtained by treatment of 5-amino-1-(2, 3, 5-tri-O-propionyl-β-D-ribofuranosyl) imidazole-4-carboxamide (4) with Meerwein's reagent followed by deacylation, and this was led to 1 by the reaction with phenyl cyanamide.View full abstractDownload PDF (654K) -
KENJIRO TANAKA, MICHIKO INO, YASUOKI MURAKAMI1981 Volume 29 Issue 7 Pages 1876-1886
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCyclizations of [(5-substituted-2-benzimidazolyl) thio] acetic acid (2a-e) to the corresponding thiazolo [3, 2-a] benzimidazol-3 (2H)-one (5 and 6) were successfully carried out by heating 2a-e in Dowtherm A or Ac2O/pyridine, and gave the two possible isomers (5a-e and 6a-e) in a ratio of nearly 1 : 1 in all cases. Separation of 5 and 6 was successfully carried out, and their structures (namely, the direction of cyclization) were suggested on the basis of the NMR spectra. Dowtherm A was more effective than Ac2O/pyridine, particularly for the cyclization of [(5-nitro-2-benzimidazolyl) thio] acetic acid (2a), which had been reported not to be cyclized with other reagents. Similar cyclization of [(4-methyl-2-benzimidazolyl) thio] acetic acid (2f) preferentially gave 8-methylthiazolo [3, 2-a]-benzimidazol-3 (2H)-one (6f).View full abstractDownload PDF (1155K) -
TAKASHI TSUCHIYA, HARUKI SASHIDA1981 Volume 29 Issue 7 Pages 1887-1892
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe thermolysis of the 4-vinyl-1, 2, 5, 6-tetrahydropyridine N-imide (13a) resulted in both [1, 2-]- and [2, 3]-sigmatropic rearrangements to give the tetrahydro-1, 2-diazepine (18) and the 3, 3-divinyltetrahydropyrazole (19), respectively ; this reaction mechanism was confirmed by a deuterium-labelling experiment. In contrast, the thermolysis of both 6-vinyl-1, 2, 5, 6-tetrahydropyridine N-imide (13b) and 2-vinylpiperidine N-imide (17) resulted in only [2, 3] rearrangement with the vinyl group to give nine-membered ring products, the tetrahydro- (21) and the hexahydro-1, 2-diazonine (25), respectively. The starting vinyltetrahydropyridine N-imides (13a, b) were prepared from the corresponding vinylpyridines (10a, b), and 2-vinylpiperidine N-imide (17) was prepared from 1-ethoxycarbonyl-2-vinylpiperidine (14).View full abstractDownload PDF (741K) -
MASAMI MORI, SETSUZO TEJIMA1981 Volume 29 Issue 7 Pages 1893-1899
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSCrystalline 2', 3, 3', 4', 6'-penta-O-acetyl-1, 6-anhydro-β-N-acetylmaltosamine (10) was prepared in 7 steps from 1, 6 : 2, 3-di-anhydro-4-O-(4, 6-O-benzylidene-2-O-tosyl-α-D-glucopyranosyl)-β-D-mannopyranose (3) as follows : benzylation, azidolysis of the oxirane ring, detosylation, debenzylidenation, acetylation, reduction of the azido to an amino group with concomitant debenzylation, and acetylation. Acetolysis of the 1, 6-anhydro-β-ring of 3-O-acetyl-1, 6-anhydro-2-azido-2-deoxy-4-O-(2, 4, 6-tri-O-acetyl-3-O-benzyl-α-D-glucopyranosyl)-β-D-glucopyranose, which is the fifth intermediate in the synthesis of 10 from 3, yielded an anomeric mixture of the corresponding hexaacetates (12). Catalytic reduction of 12 followed by acetylation gave an anomeric mixture of 1, 2', 3, 3', 4', 6, 6'-hepta-O-acetyl-N-acetylmaltosamines (13). De-O-acetylation of 13 gave the title disaccharide 17. The mp and [α] D values of 17 were in fairly good agreement with those of N-acetylmaltosamine synthesized by Sinay et al. [M.A.M. Nassr, J.-C. Jacquinet, and P. Sinay, Carbohydr. Res., 77, 99 (1979)].View full abstractDownload PDF (833K) -
MITSURU KAWADA, YASUHIKO KAWANO, HIROSADA SUGIHARA, SABURO TAKEI, ISUK ...1981 Volume 29 Issue 7 Pages 1900-1911
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA spirocompound, 1'-acetylspiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-one (III-1), was synthesized from anthranilic acid in three steps, which involve the condensation of anthranilic acid with α-bromo-γ-butyrolactone, followed by spiroannelation with acetic anhydride and triethylamine, and subsequent decarboxylation in the presence of sodium chloride to afford III-1 in good yield. Various derivatives (III-2-III-9) were similarly prepared. Some compounds of this series showed an intense fluorescence in solution. The reactivities of III-1 to electrophiles and nucleophiles, as well as its reaction with reducing agents, were investigated.View full abstractDownload PDF (1123K) -
MITSURU KAWADA, HIROSADA SUGIHARA, IWAO MIKAMI, KIYOHISA KAWAI, SEIJI ...1981 Volume 29 Issue 7 Pages 1912-1919
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSpiro [cyclopropane-1, 2'-[2H] indol]-3'(1'H)-ones with various substituents on the benzene ring and at the 1'-position were synthesized. Investigation of their biological activities revealed that significant anti-inflammatory and analgesic activities were exhibited by some compounds of this series. Their structure-activity relationships are discussed.View full abstractDownload PDF (926K) -
TSUYOSHI NAGAYOSHI, SEITARO SAEKI, MASATOMO HAMANA1981 Volume 29 Issue 7 Pages 1920-1926
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS1-Hydroxy-2-phenylindole (1) reacts with tosyl chloride and p-nitrobenzenesulfonyl chloride in DMF-pyridine to give the corresponding 2-phenyl-3-sulfonyloxyindole (2 and 4). Benzoyl chloride is less reactive, and 1-benzoyloxy-2-phenylindole (5) or 3-benzoyloxy-2-phenylindole (6) is formed, depending upon the reaction conditions. 3-Acetoxy-2-phenylindole (7) is also obtained by refluxing 1 with acetic anhydride or with acetyl chloride in DMF-pyridine. Treatment of 1 with tosyl chloride and then with 1-morpholinocyclohexene (9), ethyl acetoacetate (17) and ethyl cyanoacetate (20) in DMF-pyridine at room temperature affords 3-(2-oxocyclohexyl)-2-phenylindole (10), ethyl α-(2-phenyl-3-indolyl) acetoacetate (18) and ethyl α-(2-phenyl-3-indolyl) cyanoacetatc (21) in 23.2, 41 and 61% yields, respectively.View full abstractDownload PDF (765K) -
NOBUTAKA FUJII, HARUAKI YAJIMA1981 Volume 29 Issue 7 Pages 1927-1934
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSRibonuclease (RNase) S' was prepared by the combination of synthetic S-peptide and synthetic S-protein. The S-peptide was synthesized by the azide condensation of three fragments, (1-8), (9-13) and (14-20), followed by deprotection with 1 M trifluoromethanesulfonic acid-thioanisole in trifluoroacetic acid. The same reagent was employed to remove all protecting groups from the protected S-protein. In order to establish the disulfide bonds of the deprotected S-protein, glutathione-mediated air oxidation was performed in the presence of the S-peptide. The product was purified by affinity chromatography followed by ion-exchange chromatography on sulfopropyl-Sephadex to afford RNase S' in 0.5% yield from the protected S-protein.View full abstractDownload PDF (945K) -
EISHIN KATO, MASAYUKI OYA, KOZO UDA, TADASHI ISO, TADASHI FUJITA, JUNI ...1981 Volume 29 Issue 7 Pages 1935-1941
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe addition reaction between thiols and adrenochrome at 25°C yielded trans-3a, 4-dihydroadrenochrome-3a-sulfides (3-5), which were treated with hydrazides to give hydrazones (6-10). On the other hand, the reaction of adrenochrome with β-mercaptopropionic acid at 5°C, followed by treatment with benzoylhydrazine, gave cis-3a-(β-carboxyethylthio)-3a, 4-dihydroadrenochrome monobenzoylhydrazone (11) as the main product. These hydrazones were tested for hemostatic effect. The hydrazone with the most potent hemostatic activity was 7.View full abstractDownload PDF (743K) -
ISAO KITAGAWA, TAKAO NISHINO, MOTOMASA KOBAYASHI, TAKAO MATSUNO, HIDEO ...1981 Volume 29 Issue 7 Pages 1942-1950
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo lanostane-type triterpene oligoglycosides designated as holothurin A and holothurin B were isolated from the sea cucumber Holothuria leucospilota BRANDT (=H. vagabnda SELENKA). The chemical structure of holothurin B, which is contained mainly in the body walls, has been established as 3-O-(2'-O-β-D-quinovopyranosyl-β-D-xylopyranosyl)-holothurigenol 4'-O-sodium sulfate (6), on the basis of chemical, physicochemical, and biochemical evidence. The genuine aglycone of holothurin B was designated as holothurigenol (2) and the C-20 and C-22 configurations of 2 and the artifact aglycone 22, 25-oxidoholothurinogenin (1) have been elucidated as S.View full abstractDownload PDF (992K) -
ISAO KITAGAWA, TAKAO NISHINO, MOTOMASA KOBAYASHI, YOSHIMASA KYOGOKU1981 Volume 29 Issue 7 Pages 1951-1956
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe chemical structure of holothurin A, the major lanostane-type triterpene oligoglycoside from the Cuvierian tubules of the sea cucumber Holothuria leucospilota BRANDT (=H. vagabunda SELENKA), has been elucidated to be 3-O-[β-D-3-O-methylglucopyranosyl-(1→3)-β-D-glucopyranosyl (1→4)-β-D-quinovopyranosyl (1→2)-β-D-xylopyranosyl]-holothurigenol 4'-O-sodium sulfate (8), on the basis of chemical, physicochemical, and biochemical evidence. Holothurin A (8) corresponds to the 4"-O-[3'''-O-(β-D-3''''-O-methyl-glucopyranosyl)-β-D-glucopyranoside] of holothurin B (6), which is the major oligoglycoside of the body walls of the same sea cucumber.View full abstractDownload PDF (676K) -
TOYOZO UNO, MIKIO MASADA, KIYOSHI YAMAOKA, TERUMICHI NAKAGAWA1981 Volume 29 Issue 7 Pages 1957-1968
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism and pharmacokinetics of amino-penicillins such as ampicillin (AB-PC), hetacillin (IPAB-PC), talampicillin (TA-PC), amoxycillin (AM-PC) and cyclacillin (AC-PC) in man were investigated. An ion-pair reversed phase high performance liquid chromatographic method was developed for the simultaneous determination of parent penicillins and their metabolites in human urine. The time courses of urinary excretions of unchanged penicillins and metabolites (penicilloic acid (PA) and penamaldic acid (PM)) up to 8 hours after oral administration were determined by using the HPLC method. The moment analysis of urinary excretion rate-time curves gave mean residence times and excretion amounts of the various species. The ratios of excreted amounts to dose (500 mg) at infinite time were estimated to be as follows : (1) AB-PC : 29.4% for unchanged AB-PC, 4.3% for AB-PA and 2.0% for AB-PM (total 35.6%) ; (2) IPAB-PC : 51.8% for AB-PC, 8.7% for AB-PA and 3.9% for AB-PM (total 63.9%) ; (3) TA-PC : 68.8% for AB-PC, 10.2% for AB-PA and 4.5% for AB-PM (total 83.5%) ; (4) AM-PC : 58.9% for unchanged AM-PC, 15.6% for AM-PA and 6.9% for AM-PM (total 81.4%) ; and (5) AC-PC : 76.6% for unchanged AC-PC and 13.4% for AC-PA (total 90.0%). AC-PC gave no detectable amount of penamaldic acid. The rate constants for absorption, metabolism, and urinary excretion were estimated from the moments of the time course curves by using a one-compartment open model. The pharmacokinetic features of amino-penicillins and the prodrugs, are compared and discussed.View full abstractDownload PDF (972K) -
HIROSHI HOSODA, NAHOKO KAWAMURA, TOSHIO NAMBARA1981 Volume 29 Issue 7 Pages 1969-1974
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of the bridge heterologous combination of antiserum and enzyme-labeled steroid on sensitivity in heterogeneous enzyme immunoassay of cortisol has been investigated. The enzyme labeling of cortisol was carried out by the N-succinimidyl ester method. Four cortisol derivatives possessing different bridges at C-4 were covalently linked to β-galactosidase at various molar ratios of steroid to enzyme. The anti-cortisol antisera used were those raised against the conjugates of these haptenic derivatives with bovine serum albumin. The sensitivities obtainable with four homologous and twelve heterologous systems were tested. When thioether derivatives were used for enzyme labeling, the effectiveness of heterology on assay specificity was dependent upon the length of the bridge. It was found that the heterologous system using the steroid-enzyme conjugate obtained from a hapten having a shorter bridge than that used for antibody production resulted in an increase in sensitivity of the assay, whereas the use of a longer bridge was ineffective. This phenomenon can be explained in terms of the steric interaction between antibody and labeled enzyme.View full abstractDownload PDF (757K) -
JUNICHI GOTO, AKIKO SATO, KAZUHIKO SUZAKI, TOSHIO NAMBARA1981 Volume 29 Issue 7 Pages 1975-1980
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe abilities of four β-glucuronidase preparations, Helix pomatia, Patella vulgata, Escherichia coli, and beef liver, to hydrolyze bile acid glucuronides were determined as a function of pH and time. The substrates included 3-glucuronides of free, glycine- and taurine-conjugated lithocholate, chenodeoxycholate, deoxycholate, and cholate. In general, the optimal pH for β-glucuronidase-catalyzed hydrolysis of these substrates was more acidic in the case of nonbacterial β-glucuronidase preparations than in the case of the E. coli enzyme. It was also dependent upon the number of hydroxyl groups on the steroid nucleus, but not upon the side chain structure. No evidence was obtained of any overall superiority of any one enzyme preparation in hydrolyzing bile acid glucuronides.View full abstractDownload PDF (663K) -
ATSUO NAGAMATSU, KAZUNARI ABE, SHINJI SOEDA1981 Volume 29 Issue 7 Pages 1981-1985
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFollowing the activation of hog kidney cortex homogenate with acetone, kallikrein was purified about 317-fold by diethylaminoethyl-cellulose adsorption, acetone precipitation and chromatography on Sephadex G-75, diethylaminoethyl-Sephadex A-50 and Sephadex G-100, and affinity chromatography on Trasylol-Sepharose 4B. The final purified preparation of hog renal kallikrein had a kinin-forming activity of 35.1 μg bradykinin eq/min/mg, and appeared to be homogeneous in polyacrylamide gel electrophoresis. This enzyme was a glycoprotein with a molecular weight of 50000 as determined by gel filtration on a column of Sephadex G-100. The hog renal kallikrein had an optimum pH of 9.5 and was stable at pH 8.0. This enzyme was hardly inhibited by soybean trypsin inhibitor, but was moderately sensitive to ovomucoid and more sensitive to Kunitz inhibitor. These properties were compared with those of hog pancreatic kallikrein.View full abstractDownload PDF (587K) -
TERUO MURAKAMI, HIROMU TAMAUCHI, MASARU YAMAZAKI, KAZUYOSHI KUBO, AKIR ...1981 Volume 29 Issue 7 Pages 1986-1997
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnamine derivatives of ampicillin, amoxicillin and cephalexin were prepared by reacting the drugs with ethyl acetoacetate under mild conditions. The enamine structures of these compounds were determined by measurements of the nuclear magnetic resonance (NMR) spectra. The compounds were easily hydrolyzed in vitro in aqueous solution and the rate accelerated as the pH was lowered. The determination of Rf and rate of migration of the enamine derivatives showed that the enamine derivatives were more lipophilic than the corresponding parent drugs. The bioavailabilities of these prodrugs were studied following oral and rectal administrations in rabbits. The bioavailabilities of the parent antibiotics were not improved by the oral administration of the corresponding enamine prodrugs. However, the bioavailabilities of ampicillin and amoxicillin were markedly improved by rectal administration of the corresponding enamine prodrugs. The improved bioavailabilities exceeded those of the parent drugs following oral administration in rabbits. The enamine prodrug of ampicillin was found to promote the rectal absorption of ampicillin upon coadministration of these two drugs. Thus, enamine derivatives of amino acid-like β-lactam antibiotics appear to be interesting candidates for possible clinical use as prodrugs for rectal administration.View full abstractDownload PDF (1141K) -
TERUO MURAKAMI, NOBORU YATA, HIROMU TAMAUCHI, JUNKO NAKAI, MASARU YAMA ...1981 Volume 29 Issue 7 Pages 1998-2004
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSEnamine derivatives of amino acids were synthesized and their promoting efficacies for the rectal absorption of β-lactam antibiotics were studied in rabbits. Ethyl acetoacetate (EtAA) enamine derivatives were preferentially studied because of the low toxicity of EtAA generated by the hydrolysis of the enamine moiety in the rectum and blood stream. The EtAA enamine of sodium D-phenylglycine (PG EtAA Na) was found to have remarkable promoting efficacy for the rectal absorption of sodium ampicillin, cephalothin, cephapirin, cefazolin and cephaloridine. Other enamine derivatives of amino acids also showed promoting efficacy for the rectal absorption of penicillins and cephalosporins which could not permeate alone due to their poor lipid affinity. The promoting efficacy of PG EtAA Na for the rectal absorption of antibiotics increased with decrease in their partition coefficients. The present results suggest that the enamine derivatives of amino acids are clinically applicable for use in rectal delivery preparations of penicillins and cephalosporins which cannot permeate unaided through the rectal membrane.View full abstractDownload PDF (800K) -
KOICHI AKIMOTO, ISAO SUGIMOTO1981 Volume 29 Issue 7 Pages 2005-2011
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe stability of (+)-cyanidanol-3 in aqueous solution was investigated. Two degradation products were found at pH 1.4 by TLC. These were assumed to be epicatechin and the dimer. In the basic pH region, the main product was found to be epicatechin. It was most stable at about pH 3 and was labile in strongly acidic and basic solutions. The effect of oxygen in the head space of the container was remarkable, especially in basic solution. In strongly acidic solution, the degradation of (+)-cyanidanol-3 appeared to occur by simultaneous apparent 1st-order (epimerization) and 2nd-order (dimerization) reactions. The rate constants were calculated by a new method. In the neutral and basic pH regions, the reverse reaction between (+)-cyanidanol-3 and epicatechin took place and the rate constants were obtained.View full abstractDownload PDF (719K) -
AKIRA KAMADA, TOSHIAKI NISHIHATA, SUNI KIM, MIDORI YAMAMOTO, NOBORU YA ...1981 Volume 29 Issue 7 Pages 2012-2019
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFour phenylglycine enamines were synthesized by reacting sodium phenylglycinate and β-diketones, ethyl acetoacetate, and diethyl ethoxymethylenemalonate, ethoxyethyl acetoacetate, and 3-acetylbutyrolactone (abbreviated as PG-EtAA Na, PG-DEMM Na, PG-EthoxyEtAA Na, and PG-AcBu Na, respectively). Increase in the immunoreactive serum insulin levels and decrease in the serum glucose levels were observed in rabbits and dogs following the rectal administration of insulin suppositories in the presence of most PG-enamines. However, PG-AcBu Na failed to promote the rectal absorption of insulin or inulin. The ability of PG-enamines to interact with Ca2+ was found to be closely correlated with their promoting efficacies on the rectal absorption of insulin in terms of the maximum response to glucose levels and on the rectal absorption of inulin in terms of the AUC value of serum levels. The lack of promoting efficacy of PG-AcBu Na was explained on the basis of its poor ability to interact with Ca2+.View full abstractDownload PDF (832K) -
OSAMI TSUZUKI, HIDEAKI AKIYOSHI, YASUHIRO TANAKA, KIMIHIKO KOHNO1981 Volume 29 Issue 7 Pages 2020-2026
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of carbachol on the absorptions of caffeine, aminopyrine and salicylic acid in the rat small intestine was studied, using an in situ recirculating perfusion method. Carbachol, either added to the perfusate or injected intravenously, remarkably reduced drug absorption. Upon the addition of carbachol, the perfusate volume of intestine decreased markedly and there was a positive correlation between the perfusate volume and the drug absorption rate. No physicochemical interaction, as determined by measurement of the partition coefficient between isoamyl acetate or benzene and phosphate buffer (pH 7.0), was noted between the drugs and carbachol in solution. Our results suggest that the carbachol-induced decrease in drug absorption is due to a reduction in the perfusate volume in the intestine upon recirculating perfusion.View full abstractDownload PDF (714K) -
KIYOSHI NAKABAYASHI, TAKUO TSUCHIDA, HIROYUKI MIMA1981 Volume 29 Issue 7 Pages 2027-2034
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn order to predict the shelf lives of solid dosage forms whose active ingredients are susceptible to damage by moisture and heat, the stabilities of aspirin aluminum tablets packaged in a press-through pack and a glass bottle were investigated in a storehouse. The degradation was found to follow apparent zero-order kinetics. Predictions of the stabilities of aspirin aluminum tablets in these packages were carried out by an iterative calculation over a time interval through a mathematical model in which the kinetic parameters of stability were combined with the moisture permeabilities of the packages. In this study, for the purpose of improving the reliability of shelf-life prediction, the effects of moisture and heat on aspirin aluminum stability were analyzed by a multiple regression technique on the basis of the Carstensen equation. The variation of the degradation rate constants was estimated to obtain their confidence limits with a certain probability. It was found that there was a good agreement between the observed data and the predicted values of the aspirin aluminum contents in the packaged tablets, and that the confidence limits of the degradation rate constants gave reliable shelf lives with the expected probability.View full abstractDownload PDF (802K) -
TADAAKI RIKIHISA, TOSHIAKI OHKUMA, MUTSUHIRO MORI, MINEZO OTSUKA, TOKU ...1981 Volume 29 Issue 7 Pages 2035-2042
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhole-body autoradiography was used to investigate the influence of the route of administration and dose on the distribution of drugs in the rat. Propranolol and imipramine were used as model drugs with a relatively high hepatic extraction ratio, and salicylic acid and antipyrine were used as model drugs with a relatively low hepatic extraction ratio. Each drug was administered at the same radioactivity level to rats by intravenous infusion or portal venous infusion over 30 s, regardless of the total dose and route of administration. An autoradiogram obtained 3 min after portal venous infusion was compared with that obtained 3 min after intravenous infusion. The radioactivity of propranolol that reached the systemic circulation was highly dependent on both the route of administration and dose, while that of imipramine was dependent only on the route in the dose range studied. The radioactivity of salicylic acid and antipyrine was distributed in the whole body independently of the route of administration and dose. The two drugs having a higher hepatic extraction ratio showed an uneven distribution in the liver after portal venous administration, but the two drugs having a lower hepatic extraction ratio did not. It was shown that the technique of portal venous administration for whole-body autoradiography is useful to visualize differences in drug distribution depending on the route of administration and dose and to study hepatic tissue binding in the first-pass extraction of drugs.View full abstractDownload PDF (1116K) -
KUNIO MIMURA, SHIGEO BABA1981 Volume 29 Issue 7 Pages 2043-2050
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe metabolism of paeonol (2-hydroxy-4-methoxyacetophenone : I) in man was studied by a stable isotope tracer technique. For the qualitative analysis of metabolites, an aliquot of 24 h urine from a man who had recived orally an equimolar mixture of I and I [methoxy-d3, acetyl-13C2] was investigated by mass chromatography. Paeonol, 2, 5-dihydroxy-4-methoxyacetophenone (II) and resacetophenone (III) were identified as free, β-glucuronide, sulfate and enzyme-resistant conjugate form metabolites in the urine. In addition, by comparing the ion intensities of fragment ions of II and II-13C2d3 and those of III and III-13C2, an isotope effect in the process of metabolism was found. This isotope effect was explained in terms of the metabolic switching phenomenon. By dilution analysis using I [methoxy-d3], II [methoxy-d3] and III [acetyl-13C2] as internal standards, the amounts of metabolites in the urine were determined. The excretion of this drug was very rapid ; the total amount of metabolites excreted in the urine within 24 h reached 78.8% of the dose (II 50.2%, III 21.0%, I 7.6%). Predominant metabolites were the β-glucuronide of II (28.8% of dose) and an enzyme-resistant conjugate form of II (23.9%).View full abstractDownload PDF (885K) -
KIYOSHI NAKABAYASHI, TSUGIO SHIMAMOTO, HIROYUKI MIMA, JUTARO OKADA1981 Volume 29 Issue 7 Pages 2051-2056
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effects of moisture and temperature on tablet disintegration time were investigated on a tablet containing gelatin as a binder under accelerated conditions. The higher the ambient temperature was and the more moisture the tablet contained during storage, the longer the disintegration time became. Among several kinetic models investigated, a half-order reaction model was found to be most suitable, when the ratio of the disintegration time of the aged samples to that of the initial ones was taken as a variable to be predicted. The effects of moisture and heat on the disintegration time ratio were analyzed by a multiple regression technique on the basis of the Carstensen equation. In order to estimate the effect of aging on the disintegration time ratio, tablets in several kinds of moisture-semipermeable packages, including an overwrapped package, were examined in artificial climate laboratories. The effect of aging could be predicted by an iterative calculation through a mathematical model in which the kinetics of the increase in the disintegration time ratio was combined with the moisture permeabilities of the packages. It was found that the simulated values could represent the observed data fairly well, though the confidence intervals of the predicted values were rather wide owing to the variances of the experimental data obtained.View full abstractDownload PDF (603K) -
KIYOSHI NAKABAYASHI, SHINJI HANATANI, TSUGIO SHIMAMOTO1981 Volume 29 Issue 7 Pages 2057-2061
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe shelf lives of prednisolone tablets in a moisture-semipermeable package and a glass bottle were examined in relation to the in vitro dissolution rate. The effects of moisture and heat on the tablet dissolution rates, which were obtained by use of the Kitazawa equation, were investigated under various temperature-humidity conditions. Retardation of the dissolution rate was found to be caused by increasing moisture content at ambient temperature. The dependence of the reduction in the dissolution rate on moisture and heat was analyzed by a multiple regression technique on the basis of the Carstensen equation. Predictions of the reduction in the dissolution rates for packaged tablets kept under various conditions were performed by an iterative calculation over a time interval through a mathematical model which combined the multiple regression function with the moisture permeabilities of the packages. There were good agreements between the predicted values and the observed data. The prediction procedure utilizing the rate constants together with their confidence limits gave reliable estimates of the shelf lives of the packaged tablets.View full abstractDownload PDF (609K) -
MASAZUMI IKEDA, KAZUNORI OHNO, KOICHI HOMMA, HIROYUKI ISHIBASHI, YASUM ...1981 Volume 29 Issue 7 Pages 2062-2068
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIrradiation of 3-(3-butenyloxy)- and 3-(4-pentenyloxy)-5, 5-dimethyl-2-cyclohexen-1-ones resulted in an intramolecular cycloaddition to give the corresponding 2-oxabicyclo-[n.2.0] alkanes rather than the 2-oxabicyclo [n.1.1] alkanes. Similarly 3-(N-acetyl-N-3-butenylamino)- and 3-(N-acetyl-N-4-pentenylamino)-5, 5-dimethyl-2-cyclohexen-1-ones afforded the 2-azabicyclo [n.2.0] alkanes. Some of the ring opening reactions of these photoadducts are also described.View full abstractDownload PDF (778K) -
MANKI KOMATSU, ICHIRO YOKOE, YOSHIAKI SHIRATAKI1981 Volume 29 Issue 7 Pages 2069-2072
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new 2-arylbenzofuran, named sophorafuran A (I), mp 145-146°C, C16H12O6, and a new coumestan, named sophoracoumestan B (II), mp over 300°C, C17H10O7, together with (-)-3-hydroxy-4-methoxy-8, 9-methylenedioxypterocarpan (III) were isolated from the root of Sophora franchetiana DUNN (Leguminosae). The structures of I and II were established to be 2-(2', 4'-dihydroxy-3'-methoxyphenyl)-5, 6-methylenedioxybenzofuran and 3-hydroxy-4-methoxy-8, 9-methylenedioxycoumestan, respectively, on the basis of chemical and spectral evidence.View full abstractDownload PDF (461K) -
TOHRU KIKUCHI, SHIGETOSHI KADOTA, SAYAKA HANAGAKI, HISASHI SUEHARA, TS ...1981 Volume 29 Issue 7 Pages 2073-2078
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSChemical constituents of Nervilia purpurea SCHLECHTER and Nervilia aragoana GAUD. were examined. Phytol, a glycerin ester, cycloeucalenol, stigmasterol, linolic acid, linolenic acid, and L-norleucine were identified.View full abstractDownload PDF (706K) -
SANSEI NISHIBE, KAZUKO OKABE, SUEO HISADA1981 Volume 29 Issue 7 Pages 2078-2082
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new lignan 1 and two phenolic compounds, scopoletin and vanillic acid, were isolated from the stems of Trachelospermum asiaticum NAKAI var. intermedium NAKAI (Apocynaceae). The structure of 1 was elucidated as (2R, 3R) 2-4"-hydroxy-3"-methoxybenzyl-3-3', 4', 5'-trimethoxybenzylbutyrolactone by analysis of the carbon-13 nuclear magnetic resonance, mass and circular dichroism spectra.View full abstractDownload PDF (570K) -
SANSEI NISHIBE, HIROKI TSUKAMOTO, SUEO HISADA, SAKAE YAMANOUCHI, MICHI ...1981 Volume 29 Issue 7 Pages 2082-2085
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo 2, 3-dibenzylbutyrolactone lignans containing a secondary hydroxyl group at one of the benzylic positions, 5-hydroxyarctigenin (I) and 5-hydroxytrachelogenin (XI), were transformed to phenyltetralin lignans, α-conidendrin monomethyl ether (II) and 3-hydroxy-α-conidendrin monomethyl ether (XII), respectively, by acid treatment. The hemiacetal lignan, (1S, 2R, 3S, 3aR) 6, 7-dimethoxy-3-hydroxy-2-hydroxymethyl-1-3', 4'-dimethoxyphenyl-1, 2, 3, 4-tetrahydronaphthalene-3-carboxylic acid lactol (XV), was obtained in addition to isoolivil dimethyl ether (XIV), the normal reduction product, when 3-hydroxy-α-conidendrin dimethyl ether (XIII) was treated with lithium aluminum hydride, and a mechanism is proposed for this reaction.View full abstractDownload PDF (544K) -
YOSHIHIRO ARAKAWA, KAZUHIRO IMAI, ZENZO TAMURA1981 Volume 29 Issue 7 Pages 2086-2089
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method for the synthesis of 3-O- and 4-O-sulfoconjugates of norepinephrine and epinephrine was developed by the reduction of the corresponding sulfates of noradrenalone and adrenalone. Simultaneous separation of the six kinds of sulfoconjugates of catecholamines was achieved by thin-layer chromatography and high-performance liquid chromatography.View full abstractDownload PDF (499K) -
SUSUMU ISHIMITSU, SADAKI FUJIMOTO, AKIRA OHARA1981 Volume 29 Issue 7 Pages 2089-2092
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen phenylalanine was treated with the ascorbic acid-hydrogen peroxide system in acetate buffer (pH 4.0), o-tyrosine, m-tyrosine and p-tyrosine were identified as hydroxylated products. The hydroxylation of phenylalanine in the ascorbic acid-hydrogen peroxide system was prevented by radical scavengers, e.g., potassium iodide, potassium bromide, sodium thiocyanate, sodium formate, mannose, ethyl alcohol, superoxide dismutase and Tiron. The possibility is discussed that the active species responsible for the hydroxylation of phenylalanine in the ascorbic acid-hydrogen peroxide system is the hydroxyl radical.View full abstractDownload PDF (509K) -
NAOKI NAMBU, TSUNEJI NAGAI1981 Volume 29 Issue 7 Pages 2093-2096
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAdsorption of nicotinic and isonicotinic acid derivatives from aqueous solution by hydroxyapatite (HAP), the main component of tooth enamel, was investigated, and the effects of various factors on the adsorption were studied. These nicotinic and isonicotinic acid derivatives are similar in chemical structure to nicotine which is contained in tobacco, and which might be adsorbed by teeth during smoking. The amounts adsorbed at pH 6.0 and 7.0 at 37°C were determined by measurement of concentration differences (before and after adsorption). Six compounds, that is, nicotinic acid, isonicotinic acid, nicotinamide, isonicotinamide, nicotinic acid hydrazide, and isonicotinic acid hydrazide were used as drugs. All the drugs used were determined by ultraviolet absorption spectrophotometry. Adsorption isotherms were essentially of almost Langmuir type for every drug. The order of the amount adsorbed was 10-6 mol/g, and this value was smaller than that of chlorhexidine adsorption by HAP reported previously. It is suggested that the size of adsorbate molecules affects the adsorbability. The amounts adsorbed of isonicotinic acid derivatives were larger than those of the corresponding nicotinic acid derivatives. The order of the amounts adsorbed for both nicotinic and isonicotinic acid derivatives was as follows : acid>amide>hydrazide. This order was opposite to that of the solubility. The adsorption behavior of HAP was different from that of carbon black, a hydrophobic adsorbent. The amount adsorbed decreased upon addition of sodium chloride and sodium fluoride.View full abstractDownload PDF (473K) -
MAMORU SUGIURA, MASAYUKI KUROBE, SUMIHIRO TAMURA, SHINICHI IKEDA1981 Volume 29 Issue 7 Pages 2096-2100
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe procedure for predicting digestive enzyme stability in the solid state was further investigated by utilizing the Weibull distribution function, which needs two mathematically meaningful parameters, m and k. These parameters could be estimated by graphic calculation. If the parameter m is independent of temperature, the Arrhenius plots of (1/m) 1nk versus 1/T are linear since k1/m is proportional to the inactivation rate constant. The parameter k could be estimated by extrapolating to the desired temperature in the Arrhenius plots and the activation energy could be determined from the slope of this line. These parameters, m and k, made it possible to predict the inactivation ratio of enzymes in the solid state. By comparing the predicted value of the inactivation ratio with the observed value under controlled conditions, it was shown that the proposed method is accurate and useful for studies on enzyme stability in the solid state.View full abstractDownload PDF (563K) -
Synthesis of 12α and 12β-Carboxyestradiol Derivatives via the Thermal Elimination of β-KetosulfoxideTAKAO KUROSAWA, MASAHIKO TOHMA, YUJI OIKAWA, OSAMU YONEMITSU1981 Volume 29 Issue 7 Pages 2101-2103
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe unsaturated keto ester (3) prepared from the β-ketosulfoxide (2) by the mild thermal elimination was condensed with 2-methylcyclopentane-1, 3-dione to give the trione (4), which was converted into the novel title compounds (14) and (15).View full abstractDownload PDF (444K) -
EIICHI IBUKI, SHIGERU OZASA, YASUHIRO FUJIOKA, HIROSHI MIZUTANI1981 Volume 29 Issue 7 Pages 2103-2106
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNew stable cis and trans rotational isomers of 1, 8-di (1-naphthyl) naphthalene were prepared by the Kharash-type Grignard cross-coupling of 1-naphthylmagnesium iodide and 1, 8-diiodonaphthalene in the presence of N, N'-bis (1-methyl-3-oxobutylidene) ethylene-diaminatonickel (II). Thermoanalytical and proton magnetic resonance spectral studies indicated that both rotamers are stable in the solid state as well as in a solution, but are interconversible at temperatures above their melting points. A convenient method, obtaining pure trans rotamer from the equilibrium mixture of both rotamers, is also presented.View full abstractDownload PDF (507K) -
YOSHIFUMI MATSUDA, KYOSUKE MIYAZAKI, HIROSHI MORIYA, YUKIO FUJIMOTO1981 Volume 29 Issue 7 Pages 2106-2108
Published: July 25, 1981
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSHuman renal kallikrein (HRK, E.C. 3.4.21.8) was purified about 540-fold by using chromatographic techniques with an overall yield of 4.6% from crude preparation of HRK being prepared with acetone activation of human kidney cortex extract. The activities of this kallikrein were 3.2 KU/A280 of vasodilator and 0.27 μmol/min/A280 of TAME esterolytic activities. This purified HRK was observed to be nearly single band with faint subband on disc gel electrophoresis. The approximate molecular weight of HRK was estimated to be 4.7 to 4.9×104 by gel filtration on Sephadex G-100 and G-150 columns.View full abstractDownload PDF (394K)
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