Chemical and Pharmaceutical Bulletin

Pairing of Monomeric Units of Nucleic Acids. 1. Stoichiometric Interactions of Complementary Nucleosides in Methanol. Detection through Conductance Measurements (Studies on Heterocyclic Compounds.V.)

Teisuke Okano, Takao Iwaguchi, Satoshi Mizuno

1967 Volume 15 Issue 4 Pages 373-379
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.373

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With the object of obtaining informations about stoichiometry and specificity of interactions of unit monomers of nucleic acids in solution, specific conductance of mixed methanol solutions of nucleosides of various molar ratios ws measured. Maximum interactions were indicated by the minimum or the inflection point in the conductance-molar ratio relationships, and equimolar interactions were detected in the two component systems of uridine-adenosine, cytidine-adenosine, cytidine-guanosine, deoxythymidine-deoxyadenosine, and deoxycytidine-deoxyguanosine, and also in the three component systems of uridine-cytidine-gyanosine. No interaction was observed between uridine and guanosine, deoxythymidine and guanosine, or uridine and inosine. The whole experimental results were explainable consistently in terms of co-operative hydrogen bonding. Four types of the sets of two hydrogen bonds were classified, and it was clarified that while the hydrogen bond sets were consisted exclusively of N-H…O bond in the negative cases of interaction, N-H…N bond was common to the hydrogen bond sets of the systems which showed positive results. The cause of negative results was ascribed to the O-H…O bond formed between keto group of a base and surrounding methanol molecules, which might interfere with pairing of base moieties of nucleosides.

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The Structures of Mompain and Deoxyhelicobasidin and the Biosynthesis of Helicobasidin, Quinonoid Metabolites of Helicobasidium mompa TANAKA

Shinsaku Natori, Yuko Inouye, Hidejiro Nishikawa

1967 Volume 15 Issue 4 Pages 380-390
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.380

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The structure of mompain, a metabolite of Helicobasidium mompa, was established as 2, 5, 7, 8-tetrahydroxy-1, 4-naphthoquinone (IIa). Deoxyhelicobasin was isolated and the structure was elucidated as Ib. Biosynthesis of helicobasidin (Ia) was studied and its isoprenoid origin has been clarified.

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Studies on the Racemization of Amino Acids and their Derivatives. I. On the Deuterium-Hydrogen Exchange Reaction of Amino Acids Derivatives in Basic Media

Hisayuki Matsuo, Yutaka Kawazoe, Motomu Sato, Masako Ohnishi, Takashi ...

1967 Volume 15 Issue 4 Pages 391-398
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.391

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Studies on Kallikreins.I.Effects of the Gastro-Intestinal System and the Liver on Pancreatic Kallikrein

Hiroshi Moriya, Chiaki Moriwaki, Setsuko Akimoto, Keiko Yamazaki

1967 Volume 15 Issue 4 Pages 399-402
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.399

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Effects of the gastro-intestinal system and the liver, on the hog pancreatic kallikrein were studied. The esterase and the vasodilator activities as the potency of the kallikrein were both measured. The kallikrein was quite unstable to human mixed gastric juice, however, it was not affected by the incubation with human mixed intestinal juice and the rat liver slices.

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Studies on Kallikreins.II.Passage of ¹³¹I-Labelled Hog Pancreatic Kallikrein across the Rat Intestine

Hiroshi Moriya, Chiaki Moriwaki, Setsuko Akimoto

1967 Volume 15 Issue 4 Pages 403-410
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.403

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The hog pancreatic kallikrein was labelled with radioactive iodine (¹³¹I) and was administered to rats in the tied loop of the jejunum. Relatively high distribution of radioactivity was found in the kidney and the liver and the existence of the ¹³¹I-labelled macromolecules in serum was also observed after the intraintestinal administration of ¹³¹I-kallikrein. The sac of everted jejunum was incubated in the Krebs-Ringer bicarbonate buffer containing ¹³¹-kallikrein and itwas observed that the radioactive macromolecule having the vasodilator activity was transferred to the serosal side from the mucosal side. From these results, the possibility of the intestinal absorption of pancreatic kallikrein was discussed.

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Metabolism of Drugs. L II.Enzymatic Study on Secobarbital Metabolism

Hiroyuki Ide, Hidetoshi Yoshimura, Hisao Tsukamoto

1967 Volume 15 Issue 4 Pages 411-419
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.411

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ω-and (ω-1)-Oxidation of secobarbital was studied with cell free systems of rabbit liver. By gas chromatography, secobarbital was found to be metabolized into (ω-1)-hydroxy-secobarbital, ω-carboxysecobarbital, and (ω-1)-oxosecobarbital by incubation with 9000g supernatant fraction of liver homogenate. When secobarbital was incubated with microsomes with addition of NADPH and oxygen, formation of (ω-1)-hydroxysecobarbital and (ω-1)-hydroxymethylhexabital dehydrogenase were not concerned with metabolism of secobarbital in rabbit liver.

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Studies on the Molecular Compound of Organic Medicinals.III. The Structure of the Molecular Compound of Sulfanilamide and Sulfathiazole

Keiji Ito, Keiji Sekiguchi

1967 Volume 15 Issue 4 Pages 420-426
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.420

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In order to elucidate the nature of bonding in the molecular compound of sulfanilamide and sulfathiazole, infrared absorption measurements were carried out with the compound, its components including the two polymorphic modifications of sulfathiazole and their deuterated products. Also, thermodynamic calcultions were done with the solubility data at various temperatures. On careful comparison of the spectra, it is suggested that in the compound the sulfonamido group of each component combines together by two hydrogen bonds to form a ring structure and that each p-amino group exists freely. The heat and the entropy change of the molecular compound formation in aqueous solution which are calculated at -8.3 kcal./mole and -21.3 cal./mole/deg., respectively, are thought to be too large to expect a linear combination of the components by one hydrogen bond but are adequate for the ring structure containing two hydrogen bonds. Thus, the same conclusion is reached both from the spectral evidences and from the thermodynamic calculations.

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Studies on the Metabolic Products of a Strain of Aspergillus fumigatus (DH 413).III.Biosynthesis of Toluquinones

Yuzuru Yamamoto, Keiichi Nitta, Akiko Jinbo

1967 Volume 15 Issue 4 Pages 427-431
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.427

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The relationship among the metabolites of Aspergillus fumigatus DH 413 was studied by using ¹⁴C-labelled compounds : ¹⁴C-Labelled 2-methyl-5-methoxy-6-hydroxy-2, 3-epoxy-p-benzoquinone (III) was well incorporated into fumigatin and fumigatin quinol, but the reverse reation was not observed, and it is suggested that the epoxydation step should be involved in the biosynthesis of toluquinones.

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Homoplantaginin, a New Flavonoid Glycoside in Leaves of Plantago asiatica LINNAEUS

Masakazu Aritomi

1967 Volume 15 Issue 4 Pages 432-434
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.432

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Besides plantaginin, ¹⁾ a new flavonoid glycoside, homoplantaginin, m.p. 241∼242°(decomp.) or m.p. 219∼220/256∼258°(decomp.), was isolated from the leaves of Plantago asiatica LINNAEUS, and was found to be formulated as hispidulin 7-O-_D-glucoside.

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Reductive Radical Formation of Hetero Aromatic N-Oxides

Michiya Itoh, Toshihiko Okamoto

1967 Volume 15 Issue 4 Pages 435-439
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.435

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Pyridine 1-oxide gave the 4, 4'-dipyridyl anion radical in 1, 2-dimethoxyethane by reduction with the potassium metal in vacuo. The 3, 5-lutidine, pyrazine and 3-nitropyridine anion radicals were also obtained from the parent N-oxides by the reduction, accompanied with the removal of oxygen atoms, while the 4-nitro- and 4-nitroso-pyridine 1-oxide anion radicals were obtained from the parent compounds without the deoxygenation.

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Studies of Nuclesides and Nucleotides.XXXI.Reaction of Nitrous Acid with Mono- and Di-esters of Phosphoramidate

Morio Ikehara, Seiichi Uesugi, Toshikazu Fukui

1967 Volume 15 Issue 4 Pages 440-447
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.440

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Reaction of mono- and di-esterified phosphoramidate with nitrous acid or isoamyl nitrite was investigated. While in the monoesterified phosphoramidate the rection enhanced intensively by both nitrous acid and isoamyl nitrite, in the case of dibenzylphoramidate nitrous acid did not bring about hydrolysis reaction. Order of the rate of the reacton with diesterified phosphoramidate indicates direct attack of NO⁺ on NH₂. Various in termediates of the reaction of thymidine 5'-phosphoramidate with isoamylnitrite were isolated by the DEAE-cellulose chromatography.

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Studies on Vitamin B₁ and Related Compounds.CVII.Synthesis of Hydroxyethylthiamine Homologs

Yoshikazu Oka, Eiko Imamiya, Hiroshi Hirano

1967 Volume 15 Issue 4 Pages 448-453
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.448

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Two types of dihydrothiamine derivatives, IV, VI, VIII, and V, VII, IX, were obtained by the reaction of I, II, and phenylglyoxal derivatives. On treatment with mineral acids both of those underwent hydrolysis in the presence of water, but in non-aqueous solutions thiamine was afforded under room temperature. Treatments of them with weak acids such as phosphoric acid, formic acid and acetic acid effected the conversion to the aryl homologs of hydroxyethylthiamine, XI, XII and XIII.

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Fundamental Studies on Clinical Chemistry.XI.A New Micromethod for the Determination of General Ketosteroids using p-Nitrophenylhydrazine Reagent

Michiya Kimura, Toshihiro Nishina, Takashi Sakamoto

1967 Volume 15 Issue 4 Pages 454-459
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.454

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A highly sensitive spectrophotometric method for the determination of general ketosteroids was investigated. The development of chromophore with p-nitrophenylhydrazine reagent was achieved efficiently in alkaline dimethylformamide. Micro amounts (0∼50 μg. for saturated ketosteroids ; 0∼25 μg. for Δ⁴-3-ones) of steroids were determined by the standard procedure. One of the remarkable advantages is the possibility to estimate micro quantities of the saturated 3-ketosteroids such as cholestan-3-one, that has been almost impossible by the most published methods. A discussion on the reactivities of different kinds of steroidal keto group for the method derived was also presented from the results of the study using forty oxosteroids.

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Synthesis of Exdysone.I.A Novel Synthesis of 2β, 3β-Dihydroxy Steroids

Hiromu Mori, Kenyu Shibata, Kiyoshi Tsuneda, Masanobu Sawai

1967 Volume 15 Issue 4 Pages 460-465
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.460

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A novel synthesis of 2β, 3β-dihydroxy steroids from 3-oxo compounds in 5α-series was developed. Autoxidation of 3-oxo compound afforded an enol mixture of 2, 3-dioxo compound, which on reduction with sodium borohydride yielded 2β, 3β-dihydroxy steroid. It was found that 2β, 3β-dihydroxy steroid was obtained with high stereospecificity by the reduction of 2-hydroxy-1-en-3-oxo steroid.

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Synthesis of ecdysone.II.Synthesis of and Stereochemistry of 2β, 3β-Dihydroxycholestan-6-ones and Their Derivatives

Hiromu Mori, Kiyoshi Tsuneda, Kenyu Shibata, Masanobu Sawai

1967 Volume 15 Issue 4 Pages 466-473
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.466

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2β, 3β-Dihydroxycholestan-6-ones and their derivatives were prepared and their stereo chemistry was studied. In 2β, 3β-dihydroxy-or 2β, 3β-diacetoxycholestan-6-ones, equilibrium mixture consisted of 5α-and 5β-compound at the ratioof 3 : 2. On the other hand, 5α-compound was found to be exclusively stable in 2β, 3β-dihydroxycholestan-6-one acetonides.

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Reactions of Aromatic N-Oxides with Enamines of Cyclohexanone in the Presence of Acylating Agents (3).Reactions of Chloro- and Hydroxy-pyridine and -quinoline N-Oxides

Masatomo Hamana, Hiroshi Noda

1967 Volume 15 Issue 4 Pages 474-480
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.474

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The reactions of 2- and 4-chloro or -hydroxy derivatives of pyridine and quinoline N-oxides with morpholine enamine of cyclohexanone in the presence of an acylating agent were examined. From N-oxides of 4-chloroe derivatives (I, II), 2-(4-chloro-2-pyridyl and -quinolyl) cyclohexanone (III, IV) were obtained in good yields. 2-Chloropyridine 1-oxide gave 2-(2-chloro-4-pyridyl cyclohexanone (X) as the main product accompanied by a few percent of the 6-pyridyl compound (IX)). Similarly 2-chloroquinoline 1-oxide (XII) yielded 2-(2-chloro-4-quinolyl) cyclohexanone (XIII) as a sole product, no dispalcement of 2-chloro atom being detectable. The reaction of 4-quinolinol 1-oxide (XV) led to the formation of 2-(4-hydroxy-3-quinolyl) cyclohexanone (XVI), accompanied by small amounts of by-products.

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Syntheses of 1-Dimethoxy-phenyl-3-alkylaminobutanols.I.

Yutaka Kasuya, Minoru Watanabe, Yoshio Kanai, Hiroaki Hamano

1967 Volume 15 Issue 4 Pages 481-484
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.481

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The 1-derivatives of 1-(2, 5-dimethoxyphenyl)-3-alkylaminobutanols (III) were synthesized in order to investigate their pharmacological action. 2', 5'-Dimethoxycrotonophenone (I) which was prepared from hydroquinone dimethylether and crotonyl chloride by the Friedel-Crafts reaction, was reacted with various aliphatic amines to form 2-alkylamino-2', 5'-dimethoxy-propiophenone (II). Compounds (III) were obtained by the reaction of II with various Grignard's reagents.

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Structure and Absolute Configuration of β-Kessyl Ketone and β-Kessyl Alcohol

Hiroshi Hikino, Yasuyoshi Takeshita, Yasuko Hikino, Tsunematsu Takemot ...

1967 Volume 15 Issue 4 Pages 485-489
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.485

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β-Kessyl ketone obtained by acid-catalyzed isomerization of α-kessyl ketone (II) has been converted into the known β-kessyl alcohol which has been dehydrogenated to give Sguaiazulene (V). From chemical and physical evidence on a number of their derivatives, structures III and IV (R=H) are proposed for β-kessyl ketone and β-kessyl alcohol, respectively.

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Studies on Optical Rotatory Dispersion and Circular Dichroism.I.Absolute Configuration of Cyclic α-Amino-ketones and Octant Rule

Shun-ichi Yamada, Takehisa Kunieda

1967 Volume 15 Issue 4 Pages 490-498
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.490

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The absolute configurations of cyclic amino-ketones, hexahydro-1(5H)-indolizinone (III), hexahydro-2H-quinolizin-1(6H)-one(IV), 3, 4, 11, 11a-tetrahydro-2H-benzo [b] quinolizin-1(6H)-one (V) and 3, 4, 11, 11a-tetrahydro-1H-benzo [b] quinolizin-2(6H)-one (XIX) were determined by the chemical correlation with indolizidine (IX), 1-methylenequinolizidine (X), 1, 3, 4, 6, 11, 11a-hexahydro-2H-benzo [b] quinolizine (XII) and phenylalanine, respectively. A good agreement of the octant rule predictions with the experimental results was observed in the cases of hexahydro-1H-pyrrolizin-1-one (II), III and XIX, while the reverse rtesult to the predictions was obtained in IV and V.

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Studies on Indole Series.I.Studies on the Synthesis of Optically Active Indole Derivatives

Shun-ichi Yamada, Takehisa Kunieda

1967 Volume 15 Issue 4 Pages 499-503
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.499

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R(+)- and S(-)-1, 2, 3, 4, 6, 7, 12, 12b-Octahydroindolo [2, 3-α] quinolizine (IIIa, b), and R(+)- and S(-)-5, 7, 8, 13, 13b, 14-hexahydrobenz [b] indolo [2, 3-α] quinolizine (IVa, b) were synthesized by the application of the Fischer indole synthesis on optically active hexahydro-2H-quinolizin-1(6H)-one (Ia, b) and 3, 4, 11, 11a-tetrahydro-2H-benzo [b] quinolizin-1(6H)-one (IIa, b) of known absolute configuration.

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Studies on Peptides.XIII.Contribution of the Arginine Residue in L-Histidyl-L-phenylalanyl-L-arginyl-L-tryptophyl-glycine to Its Melanotripic Activity

Haruaki Yajima, Kazuo Kubo, Yasuhiko Kinomura

1967 Volume 15 Issue 4 Pages 504-510
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.504

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Synthesis and melanotropic activity (expressed as MSH U/g.) of three pentapeptides, L-histidyl-L-phenylalanyl-L-ornithyl-L-tryptophylglycine (practically inactive), L-histidyl-L-phenylalanyl-L-lysyl-L-tryptophylglycine (1×10⁴) and L-histidyl-L-phenylalanyl-D-arginyl-L-tryptophylglycine (practically inactive) were reported and the physiological role of the arginine residue in L-histidyl-L-phenylalanyl-L-arginyl-L-tryptophylglycine(I), an active fragment of α-melanocyte-stimulating hormone (α-MSH) was discussed. In addition, MSH activity of D-histidyl-L-phenylalanyl-D-arginyl-L-tryptophylglycine (practically inactive) and L-histidyl-D-phenylalanyl-L-arginyl-D-tryptophylglycine (1×10⁶) was recorded and stereochemical nature of I was discussed in relation to the in vitro MSH activity.

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C-Alkylation of Active Methylene Compounds by Means of Alcohols.III.A New Synthesis of 1, 2-Dipyridylethylene and Related Compounds

Seiji Miyano, Nobuhiro Abe

1967 Volume 15 Issue 4 Pages 511-514
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.511

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A new method for the syntheses of 1, 2-dipyridylethylene and its derivatives is described. The method involves condensation between N-oxides of picoline, lutidine, and quinaldine and pyridinemethanol in the presence of potassium hydroxide. Some stilbazole syntheses were also described.

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Syntheses of N-Pyridylmethylanilines and Its Reaction Mechanism

Seiji Miyano, Akiko Uno, Nobuhiro Abe

1967 Volume 15 Issue 4 Pages 515-517
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.515

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Investigations on Steroids.VII.Derivatives of 17β-Hydroxyandrostano [2, 3-c] furazan substituted at Position 16

Katsujiro Ueno, Genkichi Ohta

1967 Volume 15 Issue 4 Pages 518-522
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.518

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Investigations on Steroids.VIII.Synthesis of Steroidal [2, 3-c] furazans of Pregnane Series

Katsujiro Ueno, Kazunaga Obata, Masao Shimizu

1967 Volume 15 Issue 4 Pages 523-527
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.523

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Method for Obtaining the Rate Constant of a Reversible Reaction

Masaichiro Masui, Hidenobu Ohmori

1967 Volume 15 Issue 4 Pages 527-531
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.527

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The Fischer Indole Synthesis with Formic Acid.I.A Convenient Synthesis of 4a-Ethyl-9-formyl-1, 2, 3, 4, 4a, 9a-hexahydro-9H-carbazole

Yoshio Ban, Takeshi Oishi, Yoshiko Kishio, Ikuo Iijima

1967 Volume 15 Issue 4 Pages 531-533
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.531

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Borate Complex of Hydroxamic Acids

Junichi Hase, Kyoichi Kobashi, Kenji Kumaki

1967 Volume 15 Issue 4 Pages 534-536
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.534

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Synthesis of 3-L-Lysine-bradykinin and Its O-Acetyl Compound

Kenji Suzuki, Takashi Abiko

1967 Volume 15 Issue 4 Pages 536-539
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.536

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Synthesis of 2'-Deoxy-2'-thio-3'-deoxy-3'-aminouridine

Takao Sekiya, Tyunosin Ukita

1967 Volume 15 Issue 4 Pages 542-545
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.542

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Tricyclic Amines from Azabicyclic Compounds through Carbenes

Sadao Oida, Eiji Ohki

1967 Volume 15 Issue 4 Pages 545-547
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.545

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The Sapogenin Constituent of the Seeds of Camellia sasanqua THUNB

Itiro Yosioka, Akiko Matsuda, Isao Kitagawa

1967 Volume 15 Issue 4 Pages 547-548
Published: April 25, 1967
Released on J-STAGE: March 31, 2008

DOIhttps://doi.org/10.1248/cpb.15.547

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