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Volume 24, Issue 5
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KENJI INAGAKI, YOSHINORI KIDANI1976 Volume 24 Issue 5 Pages 839-844
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe far-infrared spectra of metal chelates of oxine-like ligands, 2, 3-dimethyl-5-hydroxyquinoxaline, 1-hydroxyphenazine, 6-hydroxybenzo [a] phenazine, 8-hydroxybenzo [a] phenazine and 11-hydroxybenzo [a] phenazine, with divalent metal ions (Co2+, Ni2+, Cu2+, and Zn2+) are investigated. The metal-oxygen stretching bands have been assigned tentatively to the 294-219cm-1. Structure of these metal chelates have been proposed from the magnetic moments, the number of metal-oxygen stretching bands and the spectral pattern in the 600-400 cm-1 region. The structure of copper chelates, except for 11-hydroxybenzo [a] phenazine copper chelate, is trans square planar. The relationship between the M-O stretching band and atomic number of central metal has been discussed.View full abstractDownload PDF (670K) -
HARUNORI YASUO1976 Volume 24 Issue 5 Pages 845-851
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSS-Aminomethylthiamine : N-[(2-Methyl-4-amino-5-pyrimidinyl) methyl]-N-[1-methyl-2-(dialkylaminomethyl) thio-4-hydroxy-1-butenyl] formamide (IIIa-d) were successfully synthesized by the reaction of an alkaline solution of thiamine (I) with chloroform solution of chloromethyldialkylamine (VIa-d), which were freshly prepared from methylenebisdialkylamine (Va-d) and acetyl chloride. The compounds (IIIa-d) were soluble in organic solvents and also soluble in water with the exception of IIIb. When III was dissolved in water, III afforded a small amount of cyclobismethylenethiamine (II) and mostly decomposed to I. The behaviour of IIIa in water was confirmed by means of polarographic technique. N-Hydroxymethylthiamine : 3-[(2-Methyl-4-hydroxymethylamino-5-pyrimidinyl)-methyl]-4-methyl-5-(2-hydroxyethyl) thiazolium chloride (VII) was also prepared from thiamine monochloride (I-Cl) and formalin. Compound VII gave also II in the presence of diethylamine. The formation pathway of II from I was also discussed.View full abstractDownload PDF (812K) -
HARUNORI YASUO, NAOTO YONEDA, YUZO MATSUOKA1976 Volume 24 Issue 5 Pages 852-858
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIt was found that the reaction of S-aminomethylthiamine (II) with acid anhydride afforded the corresponding S-acylthiamine (III) or, O, S-diacylthiamine (IV). Furthermore the reaction of II with anhydrides (VII, IX, XII) of N-benzyloxycarbonyl-or N-t-butyloxycarbonyl-L-amino acid in tetrahydrofuran at -5-5° gave successfully the novel thiamine compounds with amino acid residues : O, S-bis (α-N-benzyloxycarbonyl-aminoacyl) thiamine (VIII) or O, S-bis (α-N-t-butyloxycarbonylaminoacyl) thiamine (X). O, S-Bis (α-aminoacyl) thiamine trihydrochloride (XI·3HCl) was obtained in good yield by the treatment of X with hydrogen chloride in ethyl acetate at -10°. Thiamine activities of VIII·HCl and XI·3HCl in thiamine deficient rats were similar to those of equimolar thiamine chloride hydrochloride (I-Cl·HCl).View full abstractDownload PDF (714K) -
YOSHIHISA KURASAWA, ATSUSHI TAKADA, TAKEO UEDA1976 Volume 24 Issue 5 Pages 859-864
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction product of the coloration of cholesterol in 90% liquefied trichloroacetic acid (conc. TCA) and its mixture with hydrochloric acid were investigated in order to find the relationship between the coloration and the reaction products. It was found that 3, 5-cholestadiene was the main product in all of TCA-containing media and 3, 3'-bis (3, 5-cholestadiene) was the minor product in conc. TCA-HCl (10 : 1) medium, while any of bissteroid was not found in the reaction with conc. TCA-HCl (1 : 1) medium. The colored solution of these compounds showed the similar absorption spectrum to that of cholesterol in the respective medium. Cholesteryl chloride, which developed a red color gradually on dissolving in conc. TCA-HCl (10 : 1) and (1 : 1) media, was also obtained from the colored solution of cholesterol in all of HCl-containing media, and 3, 5-cholestadiene was isolated from the colored solution of cholesteryl chloride. These results suggested that cholesteryl chloride might not be a direct coloring substance but 3, 5-cholestadiene or a coloring intermediate derived from cholesteryl chloride in these media might contribute to the coloration.View full abstractDownload PDF (746K) -
YUKIO MORI, KAZUMI TOYOSHI, SHIGEO BABA1976 Volume 24 Issue 5 Pages 865-870
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe NIH shift during the aryl hydroxylations of the specifically deuterated or tritiated 3'-methyl-4-(dimethylamino) azobenzene (3'-Me-DAB) and 3-methylacetanilide by a rat in vivo or in vitro has been investigated. 3'-Me-4'-OH-DAB was excreted in the bile and 3-methyl-4-hydroxyacetanilide in urine when 3'-Me-DAB [4'-2H] was administered orally and 3-methylacetanilide [4-2H, 4-3H, or 5-2H] intraperitoneally to rats. In in vitro experiments, 3'-Me-DAB [4'-2H or 4'-3H] was incubated at 37° in an aerobic conditions for 1 hr with liver homogenates and 3-methylacetanilide [4-2H, 4-3H, or 5-2H] with liver microsomes. Retention of heavy hydrogen in the 4'-or 4-hydroxylated metabolite was determined by mass spectrometry or radioactivity counting. The NIH shift was observed also during these hydroxylations. In in vitro hydroxylation of 4'-labeled 3'-Me-DAB, tritium was retained 94.1±2.7% and deuterium 43.7±3.4%. Therefore, isotope effect in retention was great in this reaction. In the case of 3-methylacetanilide, such isotope effect was not observed, and heavy hydrogen was retained 19-23% in the 4-hydroxylated metabolite in vivo or in vitro. Isotopic hydrogens at the position adjacent to hydroxylation in both substrates were stable under the employed conditions. It was demonstrated that 3-methylacetanilide belongs to class I substrate and 3'-Me-DAB to class II because of the effect of substituent on their retention of isotopic hydrogen.View full abstractDownload PDF (752K) -
KANJI TAKADA, YUJI TOKUNAGA, SHOZO MURANISHI1976 Volume 24 Issue 5 Pages 871-885
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA new method to investigate the active excretory process of drugs from the hepatocytes into the bile canaliculi has been developed. This method is, briefly speaking, to retrogradely infuse several reagents through a tubing which is cannulated into the common bile duct and the bile-canalicular membrane of the hepatocytes is thought to be mainly solubilized or modified by infusing surfactants, organic solvents, proteases, lipase, metabolic inhibitors and thiol reagents, because both polyacrylamide gel electrophoretical patterns and sodium dodecyl sulfate (SDS) polyacrylamide gel electrophoretical patterns of the bile which was obtained following intrabiliary retrograde infusion of Triton X-100 and SDS display the existance of more proteins than that of normal bile. Moreover, the active excretion of organic anionic dyes, bromphenol blue and uranine, from the hepatocytes into bile was almost inhibited by infusing surfactants retrogradely. The active excretory system is thought to have the following characteristics : it could be solubilized by surfactants and organic solvents, ethanol-ether (3 : 1) and acetone and it is affected by phospholipase D or thiol reagents, p-chloromercuribenzene sulfonic acid and N-ethylmaleimide. A bile-canalicular membrane protein to which the three organic anionic dyes, bromphenol blue, uranine and eosine, are bound has been detected in the Triton X-100 solubilized membrane fraction by polyacrylamide gel electrophoresis and the molecular weight is estimated to be about 80000 by SDS polyacrylamide gel electrophoresis.View full abstractDownload PDF (2591K) -
HIROKO NAKAE, RIE SAKATA, SHOZO MURANISHI1976 Volume 24 Issue 5 Pages 886-893
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe hepato-biliary transport characteristics in vivo and the uptake process by liver slices and by liver cell suspensions were studied in rats using procaineamide ethobromide, its N-acetyl compound and quinine. These organic cations were transported from plasma to liver and from plasma to bile against a concentration gradient, and their biliary excretion was depressed by an administration of the other organic cations in accordance with earlier studies. However the hepatic uptake of quinine was extremely high, 39 of the liver/plasma concentration ratio, as compared with 8.6 of PAEB and 1.7 of APAEB. When taken up by liver slices or liver cell suspensions, PAEB and quinine showed completely different patterns. Slice/medium ratio of PAEB obtained by liver slices attained 3.6 after 4 hours and cell/medium ratio obtained by liver cell suspensions did not attain one. On the other hand, slice/medium and cell/medium ratios of quinine attained about 20 and the high slice/medium ratio was only slightly decreased in an atmosphere of nitrogen or in the presence of DNP. The hepatic high uptake of quinine observed both in vivo and in vitro is mostly explainable by lipid-binding mechanism as the binding to liver lipids showed quite a high value, 77%.View full abstractDownload PDF (951K) -
SHOJI KOJIMA, JUNICHI MIYAKE1976 Volume 24 Issue 5 Pages 894-900
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe effect of K+ on the absorption of acetanilide, salicylamide, sulfisoxazole, and quinine from rat small intestine was studied using principally the in situ perfusion technique. 1) The intestinal absorption of those drugs was considerably reduced by K+. 2) The decrease in the blood flow of the small intestine, which is induced by the depression of cardiac action based on the absorption of K+ from the K or Na-K phosphate buffer solution, markedly inhibits the in situ intestinal absorption of the drugs. 3) It is suggested that the decrease in the intestinal tissue respiration in the presence of K+ produces a depression of functional integrity of the intestinal membrane resulting in the histological changes of the intestinal mucosa, and that a decrease in the absorptive surface area based on the morphological changes in the villi somewhat reduces the absorption of the drugs.View full abstractDownload PDF (986K) -
HIDETOSHI YOSHIMURA, REIKO NATSUKI, SEIU IDA, KAZUTA OGURI1976 Volume 24 Issue 5 Pages 901-906
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSBy substitution reaction with nucleophilic reagents such as lithium chloride and piperidine, morphine-6-conjugates were found to be convertible easily to 6-chloro-6-deoxy-morphine and 8-piperidino-6-deoxy-Δ6-morphine, respectively. The reaction rates of these conjugates were roughly parallel with the analgesic activity, decreasing in the order sulfate>glucuronide≒acetate>phosphate>morphine. Furthermore, in the hope that the similar binding of morphine and its 6-conjugates to nucleophilic sites of the brain macromolecule which is closely related to the analgesic receptor might occur, the binding experiment to rat brain homogenates was conducted using morphine and morphine-6-glucuronide which is known to possess stronger analgesic activity than morphine. As the result, the 6-glucuronide showed greater affinity to rat brain but lesser extent of binding to rat liver and bovine serum albumin than morphine.View full abstractDownload PDF (767K) -
SHIGERU AONUMA, MASARU OKABE, KOJI SUZUKI, KATASHI MATSUMOTO, YUICHI K ...1976 Volume 24 Issue 5 Pages 907-911
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFr. I from guinea-pig spermatozoa which had DF activity against rabbit spermatozoa showed inhibitory effect on respiration and motility of guinea-pig spermatozoa. Measurement of DF activity was attempted in mouse in vitro fertilization system and the potent inhibition of sperm penetration into ova by Fr. I was confirmed, while the addition of anti-Fr. I-immunoglobulin (anti-Fr. I-Ig.) caused disappearance of fertilization inhibitory activity of Fr. I. The DF activity of Fr. I was partially destroyed during incubation at 60° for 2 hours and completely destroyed at 80° for 2 hours. Alkaline and acid treatment of Fr. I caused no effect on the DF activity. The Fr. I did not decrease its DF activity by the digestion with β-amylase. From the enzymatic point of view the inhibition of corona radiata penetrating enzyme by Fr. I was noted.View full abstractDownload PDF (570K) -
KOICHI MATSUMURA, TAKAHIRO SARAIE, NAOTO HASHIMOTO1976 Volume 24 Issue 5 Pages 912-923
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Amino-3, 3-dichloroacrylonitrile (ADAN), a versatile polyfunctional synthetic intermediate, was prepared in 96% yield by addition of HCN to the C-N triple bond of dichloroacetonitrile (11a). The structural proof for ADAN, an enamino nitrile, comes from comparison of the spectral data with those of 2-imino-3, 3, 3-trichloropropionitrile (15), a model compound for α-imino nitrile. Similarly, 2-amino-3, 3-dibromoacrylonitrile (13) was prepared from dibromoacetonitrile (11b) and HCN in 82% yield. ADAN, although relatively unstable in air at room temperature, can be stored without detectable change for a long period in nitrogen or ether vapor atmosphere at low temperatures. 2-Amino-3, 3-bis (substituted mercapto) acrylonitriles (18a-c), mercapto-analogues of ADAN, were prepared from ADAN or its N-acyl derivatives (16, 19) by nucleophilic substitution of the chlorine atoms with mercaptides, and in the latter case, with subsequent hydrolysis of the N-acyl group. Hydrolysis of the cyano group of N-acyl derivatives (16, 21, 22) gave the corresponding carboxamides (23), carboxylic acids (24), and N-t-butylcarboxamides (26) in good yields.View full abstractDownload PDF (1377K) -
KOICHI MATSUMURA, TAKAHIRO SARAIE, NAOTO HASHIMOTO1976 Volume 24 Issue 5 Pages 924-940
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS2-Acetylamino-3, 3-dichloroacrylonitrile (1a) reacted with 2 molar eq. of mercaptides and alkoxides to yield 2-acetylamino-3, 3-bis-(substituted mercapto) acrylonitriles (2) and 2-acetylamino-3, 3, 3-trialkoxypropionitriles (4), respectively, in high yields. In contrast to these results, we found that the reaction of 1a with various aliphatic primary and secondary amines including ammonia and hydrazine gave 2-methyl-5-(substituted amino) oxazole-4-carbonitriles (6) in almost quantitative yields under mild conditions. Reaction of 1a with bifunctional amines such as ethylenediamine and aminoethanethiol generated other types of cyclization products, e.g., imidazolidine and thiazolidine derivatives (8a, b), as major products. Treating 1 or 2-amino-3, 3-dichloroacrylonitrile (ADAN) with various acid anhydrides in the presence of conc. sulfuric acid catalyst resulted in a new one-step synthesis of imidic compounds, 2-acylamino-3, 3-dihalogeno-N-acylacrylamides (21). The reaction of 21 with aliphatic secondary amines yielded 2-substituted-5-(substituted amino) oxazole-4-N-acylcarboxamides (32). The mechanism of the cyclization to oxazoles and the formation of imidic compounds are discussed.View full abstractDownload PDF (1682K) -
KOICHI MATSUMURA, HIROSHI SHIMADZU, OSAMU MIYASHITA, NAOTO HASHIMOTO1976 Volume 24 Issue 5 Pages 941-947
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 2-acetylamino-3, 3-dichloroacrylic-N-acetylamide (1) with aliphatic primary amines gave 2-acetylamino-2-(substituted amino)-3, 3-dichloropropionamides (3) as major products, which differs distinctly from the results of reaction of 1 with aliphatic secondary amines which leads to oxazole derivatives 2. The 3 compounds were also prepared by addition of aliphatic primary and secondary amines to 2-acetylamino-3, 3-dichloroacrylamide (6). Small amounts of 2-methyl-5-(substituted amino) oxazole-4-carboxamides (5) were obtained also. The mechanisms of these reactions are discussed.View full abstractDownload PDF (888K) -
KOICHI MATSUMURA, OSAMU MIYASHITA, HIROSHI SHIMADZU, NAOTO HASHIMOTO1976 Volume 24 Issue 5 Pages 948-959
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of 2-acylamino-3, 3-dichloroacrylonitriles (1) with various mercaptans in the presence of base gives 2-acylamino-3, 3-bis (substituted mercapto) acrylonitriles (5) or 2-acylamino-3-chloro-3-(substituted mercapto) acrylonitriles (17), each in good yield, depending upon the amount of mercaptans used. Similar nucleophilic substitutions are possible with the corresponding amides (8, 9), N-acylamides (10), esters (7), and acid (11). Treating the 3-mercapto acrylic acid derivatives thus obtained with silver compounds, such as Ag2O, Ag2CO3, and CH3COOAg, gives an excellent new method for synthesizing 5-(substituted mercapto) oxazoles (4). The scope and limitations of this new cyclization are also described.View full abstractDownload PDF (1192K) -
KOICHI MATSUMURA, MASAAKI KURITANI, HIROSHI SHIMADZU, NAOTO HASHIMOTO1976 Volume 24 Issue 5 Pages 960-969
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSchiff bases of 2-amino-3, 3-dichloroacrylonitrile (ADAN) have been prepared in excellent yields by condensation of ADAN with various aldehydes under mild conditions. These Schiff bases (2, 3, 4) are highly reactive polyfunctional compounds and useful synthetic intermediates : the chlorine atoms of Schiff base 2e react with various nucleophiles such as alkoxides, mercaptides, and primary and secondary amines giving the corresponding 3, 3-dialkoxy-, 3, 3-bis (substituted mercapto)-, and 3, 3-bis (substituted amino)-derivatives (7, 8, and 10), respectively. Reduction of Schiff base 2e with zinc powder under mild conditions resulted in formation of the monochloro derivative 5. With anhydrous hydrogen chloride in ether, these Schiff bases underwent smooth cyclization to new 4 (5)-chloro-5(4)-dichloromethylimidazoles 11, which in turn were converted into 4 (5)-chloro-imidazole-5 (4)-carbaldehydes 12 in excellent yields upon hydrolysis.View full abstractDownload PDF (981K) -
YOSHIYASU FURUKAWA, OSAMU MIYASHITA, SHUNSUKE SHIMA1976 Volume 24 Issue 5 Pages 970-978
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 6-amino-1, 3-diethyluracil (Ib) with dimethylformamide-thionyl chloride afforded 5, 7-diethyl-3-dimethylaminoisothiazolo [3, 4-d] pyrimidin-4, 6 (5H, 7H)-dione (IVb) and three minor products (VIb, VIIb, VIIIb). Similar reactions of five 6-aminouracils or 6-amino-1-benzyl-cytosine (XV) with N-formyl-sec-amine-thionyl chloride afforded corresponding 3-aminoisothiazolo [3, 4-d] pyrimidine derivatives (IVa-i or XVI). When 6-amino-1, 3-diethyl-2-thiouracil (Ij) was allowed to react similarly, IVb was obtained as a major product and the yield of the expected 5, 7-diethyl-3-dimethylaminoisothiazolo-[3, 4-d] pyrimidin-4 (5H)-one-6 (7H)-thione (IVj) was very low.View full abstractDownload PDF (902K) -
YOSHIYASU FURUKAWA, SHUNSUKE SHIMA1976 Volume 24 Issue 5 Pages 979-986
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 6-aminouracils (I) with alkyl or aryl isothiocyanates afforded 6-amino-5-substituted thiocarbamoyluracils (II), which were oxidized with bromine or hydrogen peroxide to afford 3-(substituted) aminoisothiazolo [3, 4-d] pyrimidin-4, 6-(5H, 7H)-diones (III). Alkylation of III afforded 3-(N, N-disubstituted) amino derivatives (V). Further oxidation of 1, 3-diethyl-3-dimethylamino-or-3-methylaminoisothiazolo [3, 4-d] pyrimidin-4, 6-(5H, 7H)-dione (Vb or IIIb) with hydrogen peroxide afforded 1, 3-diethyl-5-alkylcarbamoyl-5-hydroxybarbituric acid (Xa or Xb). Treatment of Xa with Raney nickel afforded 1, 3-diethyl-5-dimethylcarbamoylbarbituric acid (XII).View full abstractDownload PDF (850K) -
TAKAKO YOKOZAWA, HIKOKICHI OURA1976 Volume 24 Issue 5 Pages 987-990
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSInvestigations were carried out to determine whether the nutritional status of an animal changes the effect of ginseng extract. Incorporation of 14C-acetate into total lipid and the glycogen content in the liver were determined 4 hr after the intraperitoneal administration of ginseng extract (fraction 4) to rats. The results indicated a striking stimulation of metabolism in rats fed a fat-free diet.View full abstractDownload PDF (591K) -
TAKESHI KINOSHITA, TAMOTSU SAITOH, SHOJI SHIBATA1976 Volume 24 Issue 5 Pages 991-994
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe structures of a new isoflavone glabrone (I) and the corresponding isoflavene, glabrene (IV), isolated from the roots of Glycyrrhiza glabra (Leguminosae), have been determined by spectroscopic analysis and by chemical method.View full abstractDownload PDF (492K) -
HIROYUKI AKITA, AKIRA TAHARA1976 Volume 24 Issue 5 Pages 995-1001
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe reaction of the deisopropyl phenacylidene ester (6) gave the rearranged deisopropyl phenacylidene ester (7), as a major product, in company with the γ-lactone (8) in the same manner as the phenacylidene ester (2). On the other hand, the reaction of the deisopropyl-10α-phenacylidene ester (9), which has steric hindrance due to 1, 3-diaxial relations between 4-methoxycarbonyl group and 10-methyl group, afforded a large portion of the starting material (9) in company with a small amount of the rearranged deisopropyl phenacylidene ester (10). Next, the reaction of the enol acetate (32) gave only the enol compound (33) in the accompany of deacetylation.View full abstractDownload PDF (883K) -
MIKIO TAKEDA, HIROZUMI INOUE, KATSUYUKI NOGUCHI, YASUSHI HONMA, MASATO ...1976 Volume 24 Issue 5 Pages 1002-1012
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSAs part of studies on azabicycloalkanes as analgetics with narcotic antagonist activity, 1-phenyl-6-azabicyclo [3, 2, 1] octane derivatives have been synthesized. Bromination of the keto amide (IXa, b) followed by treatment with sodium methoxide gave the bicyclic keto lactam (XIa, b) respectively. A number of drivatives bearing various substituents on nitrogen and C7 have been prepared from (XIa, b) for pharmacological evaluation. 6, 7-endo-Dimethyl-1-(3-hydroxyphenyl)-6-azabicyclo [3, 2, 1] octane (XXc) and its dextro isomers exhibited analgetic activities on the order of meperidine and morphine, respectively. They also had narcotic antagonist activity with a low grade of abuse potential.View full abstractDownload PDF (1248K) -
KOICHI SHUDO, TOSHIHIKO OKAMOTO1976 Volume 24 Issue 5 Pages 1013-1015
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPhenanthrene-9, 10-imine tosylate was prepared from phenanthrene-9, 10-oxide. The chemical behavior was descrived.View full abstractDownload PDF (431K) -
KAZUYASU NAKAYA1976 Volume 24 Issue 5 Pages 1016-1020
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe circumstances in which monomers and dimers of eukaryotic small and large ribosomal subunits occur were examined by measuring the sedimentation profiles of each subunit with glutaraldehyde fixation. When small ribosomal subunits were prepared from rat liver ribosomes in the medium containing 50mM Tris-HCl (pH 7.6), 880mM KCl, 12.5mM MgCl2, 10mM mercaptoethanol and 0.1mM puromycin, about 41.4% of the preparations sedimented as a monomer and the other as a dimer in T10K20M5 (10mM Tris-HCl, pH 7.6 ; 80mM KCl ; 5mM MgCl2) buffer. There were no difference in the monomer content of small ribosomal subunits from free and membrane bound ribosomes from rat liver. Moreover, small ribosomal subunits from the muscle of normal and diabetic rats contained just the same proportion of the monomer and dimer particles when assayed under the same ionic conditions. The proportion of the monomer and the dimer of the small ribosomal subunits changed with change in the concentration of potassium and magnesium at which ribosomal subunits were prepared ; the content of the monomer decreased with lowering the ratio of magnesium concentration and was only 10.1% when the preparation was conducted in the medium containing 880 mM KCl and 3mM MgCl2. The addition of poly U to the small subunit preparations caused the conversion of the dimer into the monomer. Large ribosomal subunits dimerized gradually at low temperature even in high potassium concentration but the dimers of the large subunits dissociated easily into their monomers by incubation at 30°.View full abstractDownload PDF (694K) -
RYUICHI HIGUCHI, TOSHIO KAWASAKI1976 Volume 24 Issue 5 Pages 1021-1032
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSTwo free triterpenoids and twelve triterpenoid saponins were isolated from the fresh pericarps of Akebia quinata DECNE. (Lardizabalaceae). Ten saponins, PA-G, PJ2, PJ3 and PK, of the above twelve were characterized as follows : PA (I), hederagenin (hederag.) 3-O-α-L-ara·pyranoside ; PF (II), hederag. 3-O-β-D-glc·pyr-(1→2)-α-L-ara·pyranoside ; PB (III), oleanolic acid (ol. acid) 3-O-α-L-rha·pyr-(1→2)-α-L-ara·pyranoside ; Pc (VI), hederag. 3-O-β-D-xyl·pyr-(1→3)-α-L-ara·pyranoside ; PD (IX), hederag. 3-O-α-L-rha·pyr-(1→2)-α-L-ara·pyranoside ; PE (XI), ol, acid 3-O-β-D-glc·pyr-(1→2)-α-L-ara·pyranoside ; PG (XIII), hederag. 3-O-β-D-xyl·pyr-(1→3)-α-L-rha·pyr-(1→2)-α-L-ara·pyranoside ; PJz (XV') 3-O-α-L-ara·pyranosyl-hederag. 28-O-α-L-rha·pyr-(1→4)-β-D-glc·pyr-(1→6)-β-D-glc·pyranoside ; PJs (XIX'), 3-O-α-L-rha·pyr-(1→2)-α-L-ara·pyranosyl-ol. acid 28-O-α-L-rha·pyr-(1→4)-β-D-glc·pyr-(1→6)-β-D-glc·pyranoside ; PK (XXI), 3-O-α-L-rha·pyr-(1→2)-α-L-ara·pyranosyl-hederag. 28-O-α-L-rha·pyr-(1→4)-β-D-glc·pyr-(1→6)-β-D-glc·pyranoside. VI, XI and XV'are new members of the group of hederagenin and oleanolic acid oligoglycosides. It is noted that they all have the common unit, 3-O-α-L-ara·pyranoside, and that XV', XIX'and XX, having the same trisaccharide combined with the 28-carboxyl group of the aglycone, are corresponding to I, III and IX, respectively.View full abstractDownload PDF (1388K) -
MASAYASU TOMIE, HIDEKI SUGIMOTO, NAOTO YONEDA1976 Volume 24 Issue 5 Pages 1033-1039
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOptically active prenylamine was synthesized from natural (-)-norephedrine, through the aziridine derivatives. The absolute configuration of (+)-prenylamine was confirmed to have (S)-configuration by the synthesis. Further, the pharmacological activity was examined.View full abstractDownload PDF (852K) -
HIROSHI KOHDA, OSAMU TANAKA, KOZABURO NISHI1976 Volume 24 Issue 5 Pages 1040-1044
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe leaves of Stevia paniculata (Compositae) which are not sweet unlike the leaves of S. rebaudiana, were shown to contain several glycosides. The enzymatic hydrolysis of the crude glycosides fraction of the leaves gave four aglycones A (II), B (XVI), C (XV) and D (IV). It was proved that II and IV were identical with the known diterpene acids, ent-15α-hydroxykaur-16-en-19-oic acid and ent-16α, 17-dihydroxykauran-19-oic acid, respectively. On the basis of the chemical and physical investigation as well as the comparison of the known kaurene-type diterpenes, XV and XVI could be formulated as ent-11α, 15α-dihydroxykaur-16-en-19-oic acid and its 15-oxo derivative, respectively. From the ether-soluble fraction, taraxasterol and its acetate were also isolated and identified.View full abstractDownload PDF (653K) -
MIYOJI HANAOKA, NOBUO OGAWA, YOSHIO ARATA1976 Volume 24 Issue 5 Pages 1045-1049
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe first total synthesis of one of the cis-quinolizidine Lythraceae alkaloids, vertaline (IV), was described. The Mannich reaction of isopelletierine (V) with 6-bromoveratraldehyde (VI) in tetrahydrofuran in the presence of aqueous sodium hydroxide gave the cis-and trans-quinolizidine (VII and VIII) in the ratio of 5 : 2. Reduction of VII with sodium borohydride afforded the axial alcohol (IX) along with the equatorial alcohol (X). The Ullmann condensation of the acetyl derivative (XI) from IX with methyl 3-(4-hydroxyphenyl) propionate furnished the biphenyl ether (XIII). Hydrolysis of XIII and lactonization of the resulting hydroxy-acid (XV) provided (±)-vertaline (IV).View full abstractDownload PDF (698K) -
NORIO SUZUKI, SHIZUO KADOYA, RENZO DOHMORI1976 Volume 24 Issue 5 Pages 1050-1058
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSA method of synthesizing for 3, 6-disubstituted 2, 9-dioxo-2, 3, 6, 9-tetrahydrothiazolo-[5, 4-f] quinoline-8-carboxylic acids via the thiazolium salts was studied and proved to be practical. The reactions of the thiazolium salt with various nucleophilic reagents afforded several new derivatives. Gould-Jacobs reaction of the benzothiazole-2-ones and benzothiazole-2-thione derivatives were also carried out.View full abstractDownload PDF (989K) -
YASUO KIKUGAWA1976 Volume 24 Issue 5 Pages 1059-1063
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSodium anilidoborohydrides were synthesized from sodium borohydride and anilides in pyridine or in α-picoline, and these compounds were found to be useful reagents for facile reduction of both esters in α-picoline and aldehydes or ketones in dichloromethane. The structure of sodium acetanilidoborohydride was discussed.View full abstractDownload PDF (630K) -
HIROSHI IZUMI, HIDEKO OYAMA, HIKARU OZAWA1976 Volume 24 Issue 5 Pages 1064-1067
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSWhen the 105000g supernatant from rat brain cerebral cortex was fractionated using chromatography on a Sephadex G-25 Superfine, similar low molecular factors activated adenyl cyclase and adenosine 3', 5'-monophosphate (cyclic AMP) phosphodiesterase in rat brain synaptosomes. Therefore a comparative study of the effects of these factors with those of sodium fluoride (NaF) or imidazole was carried out. These factors additively enhanced NaF stimulated adenyl cyclase and did activate the particulate (synaptosomal) cyclic AMP phosphodiesterase but not soluble enzyme. These results suggest that these factors act on a distinctly different site from that of NaF and imidazole.View full abstractDownload PDF (527K) -
KATSUJIRO UENO, REIMEI MOROI, MASAYUKI KITAGAWA, KOHACHIRO ASANO, SEII ...1976 Volume 24 Issue 5 Pages 1068-1072
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSReaction of 1-hydrazinophthalazine (1) with mesityl oxide gave five crystalline compounds, including hydrazones and their cyclization products. Isomerization of the hydrazones which were elucidated to be two geometrical isomers was discussed briefly. Structures of several products obtained by reactions of 1 with acetylacetone, tiglic aldehyde were also discussed on the basis of their spectral properties.View full abstractDownload PDF (666K) -
ISOO ITO, NORIICHI ODA, TAISEI UEDA, SHINICHI NAGAI, SHIGEYUKI KUME1976 Volume 24 Issue 5 Pages 1072-1075
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the studies on modification of mesembrine (II), N-methyl-2-[8-(3, 4-dimethoxyphenyl)-1, 4-dioxaspiro [4, 5] decan-8-yl] ethylamine (I) was synthesized from 1, 4-dioxaspiro [4, 5] decan-8-one (III) : the Cope reaction of III with ethyl cyanoacetate gave 1, 4-dioxaspiro [4, 5] decan-8-ylidene cyanoacetate (IV), whose Grignard reaction with 4-halogeno-1, 2-dimethoxybenzene afforded ethyl 8-(3, 4-dimethoxyphenyl)-1, 4-dioxaspiro-[4, 5] decane-8-cyanoacetate (V). Hydrolysis of V followed by decarboxylation gave 8-(3, 4-dimethoxyphenyl)-1, 4-dioxaspiro [4, 5] decane-8-acetonitrile (VIII), which was reduced with LiAlH4 to obtain 2-[8-(3, 4-dimethoxyphenyl)-1, 4-dioxaspiro [4, 5] decan-8-yl]-ethylamine (IX). Treatment of IX with ethyl chloroformate followed by reduction with LiAlH4 furnished I.View full abstractDownload PDF (608K) -
SHIGEHO INABA, MITSUHIRO AKATSU, TOSHIYUKI HIROHASHI, HISAO YAMAMOTO1976 Volume 24 Issue 5 Pages 1076-1082
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSOxidation of 3-methyl-or benzyl-substituted or unsubstituted 2-aminomethylindole was described. 1, 4-Benzodiazepin-2-one derivatives (VIIa-c) were synthesized by oxidative ring enlargement of corresponding 2-aminomethylindole derivatives (VIa-c). Also, oxidation of VIa and VIc with O3 gave 1, 4-benzodiazepin-2, 5-dione derivatives VIIIa and VIIIc, respectively, oxidation of VIa with CrO3 gave isatin derivative IX and oxidation of VIc with H2O2 afforded 2-oxindole derivative X as unexpected product.View full abstractDownload PDF (899K) -
KIYOSHI IMAI, YUICHI KAWAZOE, TANEZO TAGUCHI1976 Volume 24 Issue 5 Pages 1083-1089
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFor the purpose of expanding our former finding that cyclohexylmagnesium chloride acted as reductive reagent to convert a ketoxime to an aziridine, following ten ketoximes were treated with cyclohexylmagnesium chloride or isobutylmagnesium bromide : Oximes (4-13) of dibenzyl ketone, phenyl benzyl ketone, 2-benzhydrylcyclohexanone, 2-benzoylcyclohexanone, 2-(1-phenyl) cyclohexylcyclohexanone, propiophenone, 4-phenyl-4-methyl-pentan-2-one, cyclohexanone, benzophenone and camphor. By this treatment, ketoximes (4-10) suffered reduction to be converted to aziridines. Among those, the cases of 9 and 10 were accompanied with Hoch-Campbell reaction. 12 and 13 were converted to ketimines by the same treatment.View full abstractDownload PDF (750K) -
YASUHIRO MORISAWA, MITSURU KATAOKA, TAIICHIRO WATANABE1976 Volume 24 Issue 5 Pages 1089-1093
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe Diels-Alder reaction of 5-ethoxy-4-methyloxazole with unsymmetrical dienophiles was investigated and it was found that steric interaction during the course of the Diels-Alder reaction of an unsymmetrical dienophile with oxazole affected the structural isomeric distribution of the resulting products. On the basis of the above result, α4-norpyridoxol has been synthesized by the Dields-Alder reaction of 5-ethoxy-4 methyloxazole with allyl alcohol or its derivatives. With the latter, acid hydrolysis of the adduct was necessary to obtain the title compound.View full abstractDownload PDF (715K) -
MASAKO MAEDA, MOTOKO IKEDA, AKIO TSUJI1976 Volume 24 Issue 5 Pages 1094-1097
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSPyridoxal (PL) or pyridoxal phosphate (PLP) reacts with glycine in the presence of zinc (II) ion in pyridine-methanol and gives a highly fluorescence with excitation maximum at 390nm and emission maximum at 475nm. The fluorogen of this reaction is N-pyridoxylidene zinc (II) chelate. Nanomoles of PL or PLP can be estimated spectrofluorophotometrically by using this reaction which is also very specific. Other amino acids, sugars and related substances caused no influence on the determination of PL or PLP. Application of the method to biological samples, such as blood and tissue, is suggested.View full abstractDownload PDF (586K) -
HISASHI YOSHIOKA, FUKUJI HIGASHIDE1976 Volume 24 Issue 5 Pages 1097-1099
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe SO4-radicals was formed in γ-irradiated H2SO4-SiO2 system at -196°. The formation of the SO3-radicals are accompanied when γ-irradiation is carried out after heat-treatment at 500°, indicating that H2SO4 on SiO2 is stable even at 500°.View full abstractDownload PDF (431K) -
MASUKO SUZUKI, TATSUJI MATSUMOTO, TAKESHI MIKAMI, SHIGEO SUZUKI1976 Volume 24 Issue 5 Pages 1100-1103
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe mannan from baker's yeast was modified by stearoylation and phosphorylation, and the water-soluble part of the resultant product, stearoyl mannan phosphate (SMP), was resolved by gel-filtration with Sephadex G-75 into two fractions, SMP-Fr. I and -Fr. II. The former fraction was found to contain three components, fatty acid, carbohydrate, and phosphate. The SMP-Fr. I was then fractionated by DEAE-Sephadex chromatography to give four subfractions, SMP-Fr. I-a, -b, -c, and -d. Each fraction except Fr. I-a was found to contain fatty acid, carbohydrate, and phosphate, and to be homogeneous in ultracentrifugal analyses.View full abstractDownload PDF (610K) -
TOSHIHIKO MAEDA, HIDEYO SHINDO1976 Volume 24 Issue 5 Pages 1104-1106
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSMetabolic pathway of L-3-methoxy, 4-hydroxyphenylalanine (3-O-methylDOPA) in rat liver was investigated in vitro. 3-O-MethylDOPA was proved to be first transaminated to 3-methoxy, 4-hydroxyphenylpyruvate by tyrosine aminotransferase, which was then reduced to 3-methoxy, 4-hydroxyphenyllactate by lactate dehydrogenase. No evidence was obtained for the O-demethylation of 3-O-methylDOPA.View full abstractDownload PDF (473K) -
TAKUSHI KURIHARA, TOSHIKO SAKAGUCHI, HIROSHI HIRANO1976 Volume 24 Issue 5 Pages 1106-1107
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESS4-(o-Nitrobenzylidene)-3, 5-dimethylisopyrazole (1) was converted to 1-acyl-4-(α-hydroxy-o-nitrobenzyl)-3, 5-dimethylpyrazoles (2, 3) or 3-(1'-acyl-3', 5'-dimethylpyrazolo)-5-chloroanthranils (6, 7) by treatment with acyl chlorides with or without pyridine.View full abstractDownload PDF (339K) -
AKIRA KAMEI, HIDEO YOSHIZUMI, SHUZO AKASHI, KOSHIRO KAGABE1976 Volume 24 Issue 5 Pages 1108-1110
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSSimultaneous determination of a reducing-end hexose and the molar ratios of component hexoses of an oligosaccharide (containing mannose, glucose and/or galactose) can be achieved by mass fragmentography with gas chromatography-mass spectroscopy equipped with multiple ion detector.View full abstractDownload PDF (456K) -
HARUAKI YAJIMA, YOSHIRO MORI, YOSHIAKI KISO, KANAME KOYAMA, TAKAYOSHI ...1976 Volume 24 Issue 5 Pages 1110-1113
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSIn a conventional manner, the tritriacontapeptide amide corresponding to the entire amino acid sequence of the desulfated form of porcine cholecystokinin-pancreozymin (CCKPZ) was synthesized by applying protecting groups removable by hydrogen fluoride. Synthetic peptide, though it is not too biological active, was smoothly and efficiently converted to the labeled compound with 126I (specific activity 200-250 μci/μg).View full abstractDownload PDF (555K) -
HITOSHI ITO, MAMORU SUGIURA1976 Volume 24 Issue 5 Pages 1114-1115
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSNone dialyzable polysaccharide fraction (F-1) and dialyzable one (F-2) were isolated by separation through a Dia filter and precipitation with ethanol from Sargassum thunbergii. F-1 was highly effective against Ehrlich ascites carcinoma, transplanted intraperitoneally into mice, but F-2 was almost ineffective. The antitumor active substances were suggested to be acid polysaccharides.View full abstractDownload PDF (334K) -
EIICHI FUJITA, YOSHIMITSU NAGAO, KIMIYOSHI KANEKO1976 Volume 24 Issue 5 Pages 1115-1118
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThioacetals (1-6) have been dethioacetalized by the treatment with thallium (III) nitrate under mild conditions for a short time to recover the parent carbonyl compounds in good yields. The reaction mechanisms are also discussed.View full abstractDownload PDF (449K) -
KAZUTAKE SHIMADA, YUKO SATO, YOUICHI FUJII, TOSHIO NAMBARA1976 Volume 24 Issue 5 Pages 1118-1120
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSThe isolation and characterization of nine new bufotoxins from the skin of Japanese toad was described. They were efficiently separated and purified by high-speed liquid chromatography. The structures were elucidated to be bufalitoxin homologs (Ia-c), cinobufotoxin homologs (IIa-d), arenobufotoxin (III), and cinobufotalitoxin (IV) by degradative means.View full abstractDownload PDF (459K) -
TSUTOMU FURUYA, MANABU HIKICHI, YOICHI IITAKA1976 Volume 24 Issue 5 Pages 1120-1122
Published: May 25, 1976
Released on J-STAGE: March 31, 2008
JOURNAL FREE ACCESSFukinotoxin (I), a novel pyrrolizidine alkaloid, was isolated from young scape of Petasites japonicus and its structure has been shown to be (12R, 13R, 15R, 3'R)-12-hydroxy-4, 12, 13-trimethyl-4, 8-secosenec-1-enine-15-spiro-2'-(3'-methyl) oxiran with the aid of chemical and X-ray crystallographic analyses.View full abstractDownload PDF (353K)
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