Chemical and Pharmaceutical Bulletin

Studies on Pyridazines. XVIII. Cyanation of 3, 3'-Bipyridazines and Their N-Oxides via Their Quaternary Salts

HIROSHI IGETA, TAKASHI TSUCHIYA, CHISATO OKUDA, HIDEHARU YOKOGAWA

1971 Volume 19 Issue 7 Pages 1297-1300
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1297

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The reaction of quaternary salts of 3, 3'-bipyridazines and their N-oxides with cyanide ion was carried out. 3, 3'-Bipyridazine 1, 1'-dioxides (I, II) gave the dihydro compounds having cyano groups at α-positions to the N-oxide groups (IV, V). The bipyridazines without N-oxide groups (VII, VIII) afforded the dihydro compounds having cyano groups at γ-positions to the N-CH₃ groups (X, XI). And 6, 6'-dimethoxy-3, 3'-bipyridazine (IX) afforded 1, 1'-dimethyl-3, 3'-bipyridazine-6, 6'(1H, 1'H)-dione (XII). As for the 2, 2'-dioxide (III), the compound composed of both the dihydro type ring and the aromatic ring formed by the elimination of the methoxy group (VI), was obtained.

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Influence of Alkylamides of Glutamic Acid and Related Compounds on the Central Nervous System. II. Syntheses of Amides of Glutamic Acid and Related Compounds, and Their Effects on the Central Nervous System

RYOHEI KIMURA, TOSHIRO MURATA

1971 Volume 19 Issue 7 Pages 1301-1307
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1301

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Eleven kinds of 5-alkylamides of L-and DL-glutamic acid were synthesized and assessed for anticonvulsant effects. Against lethal convulsion induced by caffeine, maximum efficacy was observed with alkylamides possessing C₇ to C₈ alkyl radicals in the position 5 of glutamic acid, and the compounds having C₅ to C₇ alkyl groups were shown to have the highest toxity. Differences in the response between L-compound and DL-compound are not significant. Synthesized ω-alkylamides of L-glutamic acid, L-aspartic acid and DL-2-aminoadipic acid did neither increase nor decrease the oxygen consumption by the rat brain cortex slices.

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The Structure of Viscosin, A Peptide Antibiotic. I. Syntheses of D-and L-3-Hydroxyacyl-L-leucine Hydrazides Related to Viscosin

MINORU HIRAMOTO, KOZO OKADA, SOTOO NAGAI, HIROSHI KAWAMOTO

1971 Volume 19 Issue 7 Pages 1308-1314
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1308

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Sixteen D- and L-3-hydroxyacyl-L-leucine hydrazides related to viscosin have been synthesized. Condensation of DL-3-hydroxy fatty acids with L-leucine methyl ester by the azide method or the active ester method gave DL-3-hydroxyacyl-L-leucine methyl esters, which were then converted to their hydrazides. Each of the racemic hydrazides could readily be resolved into the respective optically active diastereoisomers by means of fractional crystallization using alcohols.
All of the D- and L-3-hydroxyacyl-L-leucine hydrazides prepared showed antimicrobial activity against four kinds of microorganisms only comparable to or less than that of the saturated straight chain fatty acids of corresponding carbon numbers.

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The Structure of Viscosin, A Peptide Antibiotic. II. Syntheses of D-and L-3-Hydroxyacylhexapeptides including the Proposed Structure of Viscosin and Its Optical Isomers

MINORU HIRAMOTO, KOZO OKADA, SOTOO NAGAI

1971 Volume 19 Issue 7 Pages 1315-1320
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1315

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Homologs of D- and L-3-hydroxyacylhexapeptide including compound (I-1c) and its optical isomers (I-1'c, I-2c, I-2'c) were synthesized by condensing the tripeptide subunit with the dipeptide subunit followed by azide coupling of the resulting pentapeptide with D-or L-3-hydroxyacylleucine, and their antibacterial properties were examined. None of the synthetic acylhexapeptides was identical with viscosin in both physical and chemical properties and antituberculous activity.

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Nitrenes. VIII. A Novel Synthesis of 3-Cyano-2-ethoxy-6, 7-disubstitutedquinolines with Triethyl Phosphite (Studies on the Syntheses of Heterocyclic Compounds. CDXVI)

TETSUJI KAMETANI, KIYOSATO NYU, TOHRU YAMANAKA

1971 Volume 19 Issue 7 Pages 1321-1324
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1321

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Treatment of ethyl 3, 4-disubstituted-benzylidenecyanoacetate (V, VI and VII), whose ethoxycarbonyl group was oriented in the trans configuration to the benzene ring, with triethyl phosphite afforded the 3-cyano-2-ethoxy-6, 7-disubstituted-quinolines (XI, XII, and XIII) in good yield.

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Studies on the Syntheses of Heterocyclic Compounds. CDXVII. Syntheses of 1, 2-Benzoxazepine, Oxindole and Furanoquinolone Derivatives by Cyclization of Hydroxamic Acid with Polyphosphoric Acid

TETSUJI KAMETANI, HIDEO NEMOTO

1971 Volume 19 Issue 7 Pages 1325-1328
Published: July 25, 1971
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.19.1325

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Cyclization of 3-(2, 3, 4-trimethoxyphenyl) propionohydroxamic acid (II), 2-(3, 4-dimethoxyphenyl) acetohydroxamic acid (VI) and 3-(α-diethoxybenzyl)-2, 3, 4, 5-tetrahydro-1-hydroxy-2-ketopyrrole (X) with polyphosphoric acid gave 4, 5-dihydro-3-oxo-[2H]-1, 2-benzoxazepine (IV), 5, 6-dimethoxyoxindole (VII) and 2, 3, 4, 9-tetrahydro-4-oxo-furo [2, 3-b] quinoline (XI), respectively.

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Boron Trifluoride-catalyzed D-Homo Rearrangements of 20β-Acetoxy-5α-pregnanes

SADAO AOYAMA, KAZUO KAMATA, TAICHIRO KOMENO

1971 Volume 19 Issue 7 Pages 1329-1336
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1329

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Boron trifluoride in its complex with ether or acetic acid was found to effect ready D-homo rearrangements of the 20β-acetoxy-5α-pregnanes leading to D-homo-17α-methyl-17aβ-ol acetate. The corresponding 20α-compounds, however, under the same conditions gave complex mixtures.

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Studies on Pyrazine Derivatives. I. Synthesis of Pyrazinoylmorpholine and Related Compounds

FUMIHIKO UCHIMARU, SEIZABURO OKADA, AKIRA KOSASAYAMA, TSUNEO KONNO

1971 Volume 19 Issue 7 Pages 1337-1343
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1337

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For the evaluation of biological activities, 4-pyrazinoylmorpholine (II) and many new compounds have been synthesized from the N-oxide of II. The reactions of 2-(4-morpholinocarbonyl) pyrazine 4-oxide (IV) with halogenation reagents were examined, and the main product was proved to be 6-chloro-2-(4-morpholinocarbonyl) pyrazine (VII) by correlating the product to the known 2-amino-6-chloropyrazine (XIV).

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Studies on Pyrazine Derivatives. II. Synthesis, Reactions, and Spectra of Pyrazine N-Oxide Derivatives

SEIZABURO OKADA, AKIRA KOSASAYAMA, TSUNEO KONNO, FUMIHIKO UCHIMARU

1971 Volume 19 Issue 7 Pages 1344-1357
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1344

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Extensive works have been made of the preparation of six sets of 2-substituted pyrazine 4-oxide and its isomeric new 1-oxide by unambiguous route, and of the reaction between substituted pyrazine mono-N-oxides and a series of halogenation reagents and acylating agents and of nuclear magnetic resonance (NMR), infrared, and ultraviolet spectral investigations in comparison with isomeric N-oxides.
An application of NMR spectroscopy for determination of the position of the N-O function in mono-substituted pyrazine N-oxides and the analysis of N-oxidation reaction mixture are described.

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Synthesis of Pyrazolone Derivatives. XVII. Synthesis of a Pyrazolo [3, 4-c]-[1] benzoxepin and Pyrazolo [3, 4-c][1, 5] benzoxazepines

ISOO ITO, NORIICHI ODA, TAISEI UEDA, MINEKO MARUYAMA

1971 Volume 19 Issue 7 Pages 1358-1362
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1358

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The synthesis of two new type compounds which having the three ring systems, 1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-pyrazolo [3, 4-c][1] benzoxepin-3, 4-dione (I), and 1-methyl-2-phenyl-1, 2, 3, 10-tetrahydro-4H-pyrazolo [3, 4-c][1, 5] benzoxazepin-3-one (II), consisting of the polyphosphoric acid cyclization or the Ullmann reaction of the appropriate pyrazolone derivatives, has been reported.

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Studies on Syntheses of Epoxycardenolides and on Their Cleavage. IV. Cleavage of 3β-Hydroxy-14β, 15β-epoxy-5β, 17α-card-20 (22)-enolide with Hydrochloric Acid or Hydrogen Chloride

YUKIO SAITO, YOSHIKO KANEMASA, MASASHI OKADA

1971 Volume 19 Issue 7 Pages 1363-1367
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1363

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Cleavage of 3β-hydroxy-14β, 15β-epoxy-5β, 17α-card-20 (22)-enolide (Ia) or its acetate (Ib) with hydrochloric acid in methanol or hydrogen chloride in chloroform resulted in the formation of 14β, 15β-dihydroxy-17α-cardenolide (III) and 14β-chloro-15β-hydroxy-17α-cardenolide (IIa or IIb), thus demonstrating an unusual cis-opening of the epoxide ring.

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Purines. II. An Alternative Synthesis of 1-Alkoxy-9-alkyladenine Salts

Tozo FUJII, CHIN C. WU, TAISUKE ITAYA

1971 Volume 19 Issue 7 Pages 1368-1373
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1368

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Treatment of 9-alkyladenines (Ia, b, c) with 30% aqueous hydrogen peroxide in acetic acid at 30° produced the corresponding 9-alkyladenine 1-oxides (II a, b, c) in 51-71% yield. The 1-N-oxides were found to undergo alkylation almost exclusively at the oxygen atoms of the N-oxide groups when treated separately with methyl iodide, ethyl iodide, and benzyl bromide in N, N-dimethylacetamide at room temperature, and the corresponding salts (III) of all the nine possible 1-alkoxy-9-alkyladenines were obtained in excellent yields. 1-Ethoxyadenosine hydriodide and 1-benzyloxyadenosine perchlorate were also prepared from adenosine 1-oxide (II d) in a similar way. The ultraviolet and nuclear magnetic resonance spectral data on the 1-alkoxyadenine derivatives obtained in the previous and present studies are collected in Tables II and III.

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[4, 5-Dimethoxy-α-(3, 4-dim6thoxyphenyl)-o-tolyl] acetonitdle

A By-Product from the Reaction of 3, 4-Dimethoxybenzyl Chloride with Sodium Cyanide

Tozo FUJII, YUKIKO UENO, MORIHIRO MITSUKUCHI

1971 Volume 19 Issue 7 Pages 1374-1380
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1374

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The formation of [4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl] acetonitrile (IV) as a by-product in the metathesis of 3, 4-dimethoxybenzyl chloride (II) with sodium cyanide in dimethyl sulfoxide or N, N-dimethylformamide is reported. The structure of IV has been established by analysis, ultraviolet spectrum, infrared spectrum, nuclear magnetic resonance spectrum, and conversion into 4, 5-dimethoxy-2-(3, 4-dimethoxybenzyl)-N, N-dimethylphenethylamine (XI) through [4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl] acetic acid (VII) and 2-[4, 5-dimethoxy-α-(3, 4-dimethoxyphenyl)-o-tolyl]-N, Ndim thylacetamide (VIII). The sample of XI thus obtained was identical with the one produced by catalytic hydrogenolysis of 1-(3, 4-dimethoxypheny1)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2, 2-dimethylisoquinolinium chloride, which was synthesized from 1-(3, 4-dimethoxyphenyl)-1, 2, 3, 4-tetrahydro-6, 7-dimethoxy-2-methylisoquinoline (IX) by quaternization with methyl iodide and treatment of the resulting methiodide (X) with silver chloride. The reaction of benzyl chloride with sodium cyanide in dipolar aprotic solvents was found to give a small amount of 2, 3-diphenylpropionitrile (XIV) besides benzyl cyanide.

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Studies of Nucleosides and Nucleotides. XLIII, Purine Cyclonucleosides.(10). Optical Rotatory Dispersion and Circular Dichroism of Adenine 8-Cyclonucleosides

MORIO IKEHARA, MASAKATSU KANEKO, YUJI NAKAHARA, SHOJI YAMADA, SEIICHI ...

1971 Volume 19 Issue 7 Pages 1381-1388
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1381

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Optical rotatory dispersion and circular dichroism of 8-cyclonucleosides derived from adenosine were measured.
In the β-cyclonucleosides magnitude of rotatory strengths increased in the order 8, 2'-<8, 3'-<8, 5'-cyclonucleoside both in the case of O- and S-cyclonucleosides. All of these cyclonucleosides had positive Cotton curve at absorption maxima.
In α-cyclonucleoside the sign of the Cotton effect inverted to negative and the magnitude is almost same with β-cyclonucleoside.

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Studies on Acetylenic Compounds. LVI. Syntheses of 4-Isoxazolin-3-ones and 1-Phenyl-3-hydroxypyrazoles

NORIO NAKAMURA, YUKICHI KISHIDA, NOBORU ISHIDA

1971 Volume 19 Issue 7 Pages 1389-1394
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1389

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The reactions of α-acetylenic esters with N-substituted hydroxylamines in the presence of strong bases afforded 2-substituted 4-isoxazolin-3-ones, which were also prepared from α-acetylenic acid chlorides and N-substituted hydroxylamines. 1-Phenyl-3-hydroxypyrazoles were obtained by the reaction of α-acetylenic esters with phenylhydrazine in the presence of alkoxides.

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Inhibitory Mechanism of Imipramine on Barbiturate Metabolism in Rat Liver

KIICHIRO KAKEMI, HITOSHI SEZAKI, RYOJI KONISHI, TOSHIKIRO KIMURA

1971 Volume 19 Issue 7 Pages 1395-1401
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1395

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Inhibition of barbiturate metabolisms by imipramine (IP) was studied systematically in the in vitro system and intact rats with an emphasis on the contribution of metabolism of the inhibitor itself. Both IP and its major metabolite, desmethylimipramine (DMI) were found to inhibit the in vitro microsomal metabolisms of various barbiturates. The time courses of the inhibitory activities of IP and DMI were also studied in the intact animals. The maximum inhibition was observed at approximately 3 hours after the administration of both IP and DMI and the significant inhibition was observed for further about 10 hours. Hexobarbital hypnosis as a pharmacological action was similarly affected by IP administration. The possible participation of the metabolite DMI was confirmed by studying the effect of preincubation of IP in the in vitro system and determining directly the levels of IP and DMI in the liver tissue at various times after IP administration. The effect of dose and long-term pretreatment of IP on the microsomal metabolism of barbiturates was examined and the dispositions of IP were found to be of linear nature. Species differences in the in vitro metabolic inhibition by IP were also examined. And furthermore, as a measure of the physiological availabilities of IP and DMI, lipid solubility, ionization constant, and absorption from the rat small intestine were discussed in connection with the inhibitory mechanism of IP.

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Studies on Fungicides. IX. Chemical Structure of Chitin-like Substances of Cell Walls from Cochliobolus miyabeanus.(3)

HIROAKI NANBA, HISATORA KURODA

1971 Volume 19 Issue 7 Pages 1402-1408
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1402

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The chemical structure of the chitin-like substance, one of the main components of the cell wall of Cochliobolus miyabeanus, was studied. The results of X-ray powder pattern of this chitin-like substance suggested that the chitin molecules are connected with some radicals. The chitin fraction was submitted to enzymic digestion, acid hydrolysis, methylation and X-ray analysis. All the experimental results demonstrated that the hexosamine in the present fungal cell wall is composed of branching points conncected with α-N-acetylgalactosamine residue (connected through C-1) to the straight β-1, 4-acetylglucosaminylchain.

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Studies on Acetylenic Compounds. LVII. Reactions of 2-Propynyl Sulfones with Cyclic Ketones

MASAFUMI YOSHIMOTO, NOBORU ISHIDA, YUKICHI KISHIDA

1971 Volume 19 Issue 7 Pages 1409-1415
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1409

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2-Butynyl phenyl sulfone (VI) and cyclic ketones were treated with sodium hydride to give the corresponding 1: 1 addition products, respectively. The structures were assigned to 1-phenylsulfonyl-3-(1-cyclohexenyl) 2-butanone (VII) and 2-phenylsulfonylmethylene-3-methyloxetane-4-spiro-1'-cyclohexane (VIII) in the case of cyclohexanone and assigned to 1-phenylsulfonyL-3-(1-cyclopentenyL) 2-butanone (XIII) in the case of cyclopentanone, respectively. Acid treatment of VIII afforded three degradation products, VII, X and XI, which confirmed the novel structure of VIII. 2-Propynyl p-tolyl sulfone (XIV) and cyclohexanone with sodium hydride treatment gave also an oxetane compound, XV. A plausible mechanism of the reaction and the physical properties of the products were presented in some detail.

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Studies on the Sulfur-containing Chelating Agents. XXXI. Catalytic Effect of Copper (II) Ion to Formation of Mixed Disulfide

HIROMU SAKURAI, AKIRA YOKOYAMA, HISASHI TANAKA

1971 Volume 19 Issue 7 Pages 1416-1423
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1416

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In order to discuss the possibility of the contribution of the chelating ability to the radioprotective activity in cysteamine, effects of copper (II) ion to the formation of the mixed disulfide was investigated in the systems of cysteamine and cysteine, glutathione and albumin respectively as the reactions between two kinds of thiol compound and in the system of cystamine and cysteine as the reaction between disulfide and thiol compound by the use of ³⁵S-cysteamine or ¹⁴C-cysteine. Separations of the mixed disulfides were achieved by electrophoresis and amounts of the mixed disulfides were estimated by the measurement of radioactivity. Remarkable catalytic effects were observed depending upon the reaction conditions. Whereas inhibitive effects were observed in some cases. Relationship between the effect of copper (II) ion and the reaction condition was discussed and an intermediate copper chelate was presumed for the reaction mechanism.

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Total Svntheses of (±)-N-Nordasycarpidone and (±)-Dasycarpidone (Studies on the Syntheses of Heterocyclic Compounds. CDXVIII)

TETSUJI KAMETANI, TOSHIO SUZUKI

1971 Volume 19 Issue 7 Pages 1424-1425
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1424

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The stereoselective total syntheses of (±)-N-nordasycarpidone (I) and (±)-dasycarpidone (II) are herein described. The key step in the approach to these syntheses involved cis addition with catalytic reduction of a hydrochloride (VIII).

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Pyrido [2, 3-d] pyrimidine Antibacterial Agents. II. Piromidic Acid and Related Compounds

SHINSAKU MINAMI, TOSHIHIRO SHONO, JUN-ICHI MATSUMOTO

1971 Volume 19 Issue 7 Pages 1426-1432
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1426

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A series of 8-alkyl-2-amino (or substituted-amino)-5, 8-dihydro-5-oxopyrido [2, 3-d]-pyrimidine-6-carboxylic acids and related compounds were synthesized and evaluated as antibacterial agents. The most active compounds in vitro against Escherichia coli and Staphylococcus aureus were 8-ethyl-5, 8-dihydro-2-dimethylamino-5-oxopyrido [2, 3-d]-pyrimidine-6-carboxylic acid (VII a) and 8-ethyl-5, 8-dihydro-5-oxo-2-pyrrolidinopyrido-[2, 3-d] pyrimidine-6-carboxylic acid, piromidic acid, (VIIb). Structure-activity relationships are discussed.

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Studies on L-Ascorbic Acid Derivatives. VI. Phosphorylation of L-Ascorbic Acid and Its Isopropylidene Derivative

HIROAKI NOMURA, MASAFUMI SHIMOMURA, SHIRO MORIMOTO

1971 Volume 19 Issue 7 Pages 1433-1437
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1433

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Phosphorylation of L-ascorbic acid and its 5, 6-isopropylidene acetal with phosphoryl chloride under conditions using water as solvent and pyridine as base yielded almost quantitatively and selectively L-ascorbic acid 3-phosphate which has been a useful compound in cosmetic field. The reaction is suitable for manufacturing of the phosphate in a good yield. The effects of changes in solvent and base upon the phosphorylation reaction are also discussed by comparison of the yield and the composition of the products.

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Studies on Monoterpene Glucosides and Related Natural Products. XV. Confirmation of the Absolute Configuration of Catalpol

HIROYUKI INOUE, TAKASHI YOSHIDA

1971 Volume 19 Issue 7 Pages 1438-1443
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1438

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The absolute configuration at C-6 of catalpol (1) was established by the chemical conversion of the glucoside to tetrahydroaucubin-B hexaacetate (16). Information was also obtained on the configuration at C-8.

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Esterification of Model Peptides in Aqueous Solution

TATSUO HAMADA, OSAMU YONEMITSU

1971 Volume 19 Issue 7 Pages 1444-1449
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1444

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Acyl amino acids and peptides were esterified with triethyloxonium fluoroborate in neutral or slightly basic aqueous solution at room temperature, and this simple and convenient method may provide a potential new method in the area of peptide and protein chemistry.

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Studies on Fungal Polysaccharides. VIII. Extracellular Heteroglycans of Rhizopus nigricans

TOSHIO MIYAZAKI, TSUTOMU IRINO

1971 Volume 19 Issue 7 Pages 1450-1454
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1450

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Main extracellular polysaccharide of R. nigricans, [α] D+68.1°, is a highly heterogenous glycan composed of fucose, mannose, glucose, galactose, N-acctylglucosamine, and Nacetylgalactosamine in a relative ratio of 1: 22: 4: 5: 3.8: 3.8. The results of periodate oxidation, Smith degradation, and partial acid hydrolysis indicate that the polysaccharide contains (1→2) and (1→4)-linked hexopyranose residues as the main linkages.
The minor polysaccharide, [α] D-45.6°, is an acidic heteroglycan consistillg of fucose, galactose, and glucuronic acid, and its chemical structure is discussed.

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Water-Soluble Constituents of Rehmanniae Radix. I. Carbohydrates and Acids of Rehmannia glutinosa f. hueichingensis

MASASHI TOMODA, SHOKO KATO, MIE ONUMA

1971 Volume 19 Issue 7 Pages 1455-1460
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1455

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The water extract of the roots of Rehmannia glutinosa LIBOS. forma hueichingensis HSIAO was fractionated by the chromatographies on two types of ion-exchange resin. Fifteen amino acids and D-glucosamine were found and determined in the basic fraction. Phosphoric acid was detected and estimated as a component of the acidic fraction. Neutral fraction, the main fraction of the water extract, was mostly constituted with carbohydrates. D-Glucose, D-galactose, D-fructose, sucrose, raffinose, manninotriose, stachyose, verbascose and D-mannitol were identified and determined. It was found that stachyose is the main component of the water extract and the yield of the substance was 48.3% from the dried material.

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Studies on Syntheses of Epoxycardenolides and on Their Cleavage. V. Hydrolytic Cleavage of 3β-Hydroxy-14α, 15α-epoxy-5β-card-20 (22)-enolide and 3β-Acetoxy-14β, 15β-epoxy-5β-card-20 (22)-enolide with Hydrochloric Acid

YUKIO SAITO, YOSHIKO KANEMASA, MASASHI OKADA

1971 Volume 19 Issue 7 Pages 1461-1465
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1461

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Studies on Heterocyclic Compounds. XV. Synthesis of Furo [2, 3-d] pyridazine Derivatives.(4). Synthesis of 2-[2-(5-Nitro-2-furyl) vinyl]-4, 7-dichlorofuro-[2, 3-d] pyridazine and Related Compounds by the Wittig Reaction

SHIGETAKA YOSHINA, ISAMU MAEBA

1971 Volume 19 Issue 7 Pages 1465-1469
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1465

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Studies on the Constituents of Asclepiadaceae Plants. XXIX. Mass Spectra of C/D cis Pregnane Derivatives

MASAMICHI FUKUOKA, KOJI HAYASHI, HIROSHI MITSUHASHI

1971 Volume 19 Issue 7 Pages 1469-1476
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1469

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Reaction of Aminotropones with Diketene. IV. Effects of the pK_a Values of Aminotropones and Basic Catalysts on the Reaction of Aminotropones with Diketene

HIROKO TODA, SHUICHI SETO

1971 Volume 19 Issue 7 Pages 1477-1482
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1477

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Pyrido [2, 3-d] pyrimidine Antibacterial Agents. I. 8-Alkyl-5, 8-dihydro-5-oxopyrido [2, 3-d]-pyrimidine-6-carboxylic Acids and Related Compounds

SHINSAKU MINAMI, TOSHIHIRO SHONO, JUN-ICHI MATSUMOTO

1971 Volume 19 Issue 7 Pages 1482-1486
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1482

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Studies on the Gastrointestinal Hormones. V. Distribution of Gastric Secretory Inhibiting Substance in Whale Gastrointestinal Mucosa

HISATOSHI KABENO, TETURO HONDA, YASUAKI KOBAYASHI, TOSHIRO MURATA

1971 Volume 19 Issue 7 Pages 1487-1490
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1487

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Gastrone, enterogastrone, and secretin have been known as the substances contained in mammalian digestive tract and having inhibitory action on the secretion of gastric juice.
A glycoprotein fraction, designated as E fraction, has been isolated from the gastric mucosal layer of finback whale and found to have a marked inhibitory action on the gastric juice secretion by the authors.
In order to clarify the mechanism of the inhibitory action on the gastric juice secretion, the distribution of the substance in the mucosal layer of gastrointestinal tissues from the 3rd stomach to small intestine of sperm whale was studied in this paper.

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1-Indanone Derivatives from Bracken, Pteridium aquilinum var. latiusculum

KUNITOSHI YOSHIHIRA, MASAMICHI FUKUOKA, MASANORI KUROYANAGI, SHINSAKU ...

1971 Volume 19 Issue 7 Pages 1491-1495
Published: July 25, 1971
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.19.1491

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Structures of Creticosides A and B, Two New Diterpenoid Glucosides from Pleris cretica L

CHIU-MING CHEN, TAKAO MURAKAMI

1971 Volume 19 Issue 7 Pages 1495-1498
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1495

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Recherches Toxicologiques des Substances Métaboliques du Fusarium nivale. VIII. La Quatriéme Substance Métabolique de F. nivale

TAKASHI TATSUNO, MOTOMU SATO, YUKIO KUBOTA, YASUKO KUBOTA, HIROSHI TSU ...

1971 Volume 19 Issue 7 Pages 1498-1500
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1498

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Two New Biflavonyls from Araucaria cunninghamii

NIZAM U. KHAN, W. H. ANSARI, W. RAHMAN, MASAYOSHI OKIGAWA, NOBUSUKE KA ...

1971 Volume 19 Issue 7 Pages 1500-1501
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1500

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The Absolute Configuration of Ushinsunine and the Synthesis of dl-Michelalbine

JUN-ICHI KUNITOMO, MAYUMI MIYOSHI, ETSUKO YUGE, TSANG-HSIUNG YANG, CHI ...

1971 Volume 19 Issue 7 Pages 1502-1503
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1502

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The Synthesis of Secamine and Presecamine Skeletons and the Isolation of Tetrahydrosecamine from Amsonia elliptica ROEM et SCHULT

SHIN-ICHIRO SAKAI, NORIO AIMI, KENJIRO KATO, HISAO IDO, JOUJU HAGINIWA

1971 Volume 19 Issue 7 Pages 1503-1505
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1503

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A Simple Method for Evaluating Analgesic Efficacy of Non-Steroidal Anti-Inflammatory Drugs

EIICHI FUJIHIRA, TOMIZO MORI, MASAO NAKAZAWA, HIKARU OZAWA

1971 Volume 19 Issue 7 Pages 1506-1508
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1506

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C-C Bond Fission in Carboxamide. Intermediacy of Phenylcarbamate Ion in the Alkaline Hydrolysis of Trichloroacetanilide

MASAICHIRO MASUI, HIDENOBU OHMORI, HIROTERU SAYO, TSUNEJI UMEDA

1971 Volume 19 Issue 7 Pages 1508-1509
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1508

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Structure of Erybidine, a New Alkaloid from Erythrina xbidwilli LINDL

KAZUO ITO, HIROSHI FURUKAWA, HITOSHI TANAKA

1971 Volume 19 Issue 7 Pages 1509-1511
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1509

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Metabolism of Benzydamine Hydrochloride

SEIGO KATAOKA, KAZUHIKO TAIRA, EIGO TAKABATAKE

1971 Volume 19 Issue 7 Pages 1511-1513
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1511

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Total Synthesis of Flavinantine and Bracteoline by a Photo-Pschorr Reaction

TETSUJI KAMETANI, HIDEO SUGI, SHIROSHI SHIBUYA, KEIICHIRO FUKUMOTO

1971 Volume 19 Issue 7 Pages 1513-1514
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1513

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Absolute Configuration of Lythrancine-I, -II, -III, -IV, Lythrancepine-I, -II, and-III

EIICHI FUJITA, YUKIKAZU SAEKI

1971 Volume 19 Issue 7 Pages 1515-1516
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1515

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Mechanism of Utilization of Pantetheine-S-Sulfonic Acid by Bifidobacterium bifidum

HIROSHI NAKAMURA, ZENZO TAMURA

1971 Volume 19 Issue 7 Pages 1516-1518
Published: July 25, 1971
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.19.1516

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