Chemical and Pharmaceutical Bulletin

Carbon-13 Nuclear Magnetic Resonance Spectroscopy. VI. Studies on Carbon-13 Magnetic Resonance Spectra in Aromatic and Heteroaromatic Systems.(2). On the Chemical Shifts of Substituted Pyridine Derivatives

GOH MIYAJIMA, YOSHIO SASAKI, MIYOKO SUZUKI

1972 Volume 20 Issue 3 Pages 429-437
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.429

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Studies of Oligosaccharides. IX. Synthesis of Gentiooligosaccharides by Block Condensation

KIYOSHI TAKIURA, SUSUMU HONDA, TOSHIHIDE ENDO, KAZUAKI KAKEHI

1972 Volume 20 Issue 3 Pages 438-442
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.438

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Gentio-triose, -tetraose, -pentaose and-hexaose were synthesized by Konigs-Knorr condensation between acetobromo sugars and preformed oligosaccharide blocks bearing unprotected primary hydroxyl groups at non-reducing terminals. Incidental acetyl migration in the latter reactants is also discussed.

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Absorption of Drugs from the Skeletal Muscle of the Rats.(3). Effect of Watersoluble Adjuvants and Vehicles on the Intramuscular Absorption

KIICHIRO KAKEMI, HITOSHI SEZAKI, KATSUHIKO OKUMURA, HIROSHI KOBAYASHI, ...

1972 Volume 20 Issue 3 Pages 443-451
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.443

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The effect of various kinds of adjuvants or vehicles was studied with a view to examine the mechanism of intramuscular drug absorption. From the relationship between in vitro absorption studies and various in vitro diffusion experiments, it was clarified which step was the rate-limiting one in the intramuscular absorption.
1) The absorption mechanism of a drug with water-soluble adjuvants did not differ from that in aqueous solution without any adjuvant.
2) There was a good correlationship between the parenteral absorption rate and the reciprocal of viscosity of an injectable solution, provided that the molecular weight of an adjuvant was comparatively small such as propylene glycol, glycerin, and PEG 400. Effect of these solvents on the drug absorption was general in nature and not specific to drugs. In the case of an adjuvant having higher molecular weight such as PEG 4000 dextran, and methylcellurose, rate of drug absorption was greater than that expected from the viscosity, suggesting that macromolecules could hardly diffuse through the pores of the capillary wall.
3) From in vitro diffusion study using Visking membrane, glass filter, and slice of muscle, it was concluded that the contribution of the diffusion process through the pores of capillary wall was dominant compared with the one through the muscle fiber space.

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Studies on the Reaction between Polynitrobenzene Compounds and Active Methylene Groups. IX. On the Janovsky Complexes derived from Some I-Substituted 2, 4, 6-Trinitrobenzene Derivatives

MICHIYA KIMURA, NOBORU OBI, MASAHIKO KAWAZOI

1972 Volume 20 Issue 3 Pages 452-458
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.452

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Janovsky reaction of picrylchloride (PC) performed in the acetone solution containing sodium methoxide gave the Janovsky complex (Ic) and no evidence of the formation of an alternative one (IIc) was obtainable. 2, 4, 6-Trinitroanisole (TNA) also gave the analogus result. In the case of sodium 2, 4, 6-trinitrobenzene-l-sulfonate, Id was the major complex and the other one (IId) was also formed. The stability of the Janovsky complexes of 1, 3, 5-trinitrobenzene (TNB), PC and TNA were studied and their large stability constants were noticed. The ratios of the formation constants, K_TNB/K_TNA, K_TNB/K_PC and K_PC/K_TNA, were determined as 3.3, 1.6 and 2.1, respectively.

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Study on Synthesis of Antipodal Steroid

AKIRA TAHARA, YOSHIHIRO HARIGAYA, MASAYUKI ONDA

1972 Volume 20 Issue 3 Pages 459-468
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.459

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Conversion of l-abietic acid, the main component of pine rosin, to steroids was planned, and syntheses of the ketone compounds (VI and VII), important intermediates in the synthesis of the skeleton of steroid antipodes, was successfully concluded in the present series of work. Since the conversion of these VI and VII to steroidal skeleton is already known in analogous compounds, availability of these intermediates has opened a way for the synthesis of steroid antipodes from diterpenes.

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Constituents of Chinese Crude Drug “Wujiapi.” V. On the Structure of Glycoside H₁ of Bei-Wujiapi

SACHIKO KAWANISHI, SEIICHI SAKUMA, JUNZO SHOJI

1972 Volume 20 Issue 3 Pages 469-475
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.469

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The chemical structure of glycoside H₁ (I), C₅₆H₉₀O₂₄, mp 182°, [α]²⁴_D-22. 83°(EtOH), which was isolated from Bei-Wujiapi (cortex of Periploca sepittm BGE.), was established to be Δ5-pregnene-3β, 20α-diol (3)-[2-O-acetyl-β-D-digitalopyranosyl (1_dig→4_cym)-β-D-cymaropyranoside](20)-[β-D-glucopyranosyl (1_glu→6_glu)-β-D-glucopyranosyl (1_glu→2_dig)-β-D-digitalopyranoside].
It should be noted that glycoside H₁ is the first example of the pregnane type glycoside whose sugar moiety links to both C-3 and C-20 hydroxyl groups of the aglycone and that the sugar sequences of Asclepiadaceous glycosides are ruled by certain regularity, such as aglycone-(2, 6-dideoxysugar or its 3-O-methyl derivative) ₀-_l-(6-deoxysugar or its 3-Omethyl derivatives) _o__m-(glucose) _o-_n.

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Synthesis and Pharmacological Activity of gem-Dialky1-9-azabicyclo [3, 3, 1] nonane Derivatives: New Anti-Cholinergic Agent

NAOTO YONEDA, TERUO ISHIHARA, TETSUJI KOBAYASHI, KENTARO OKUMURA, MICH ...

1972 Volume 20 Issue 3 Pages 476-486
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.476

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6, 6-and 7, 7-dialkyl-9-alkyl-9-azabicyclo [3, 3, 1] nonan-3-one (V) and (IX), synthesized from 2, 2- and 3, 3-dialkylglutaraldehyde by the Robinson-Schöpf reaction, were reduced with NaBH₄ and Na-EtOH to afford the A- and B-isomers of the corresponding 6, 6- and 7, 7-dialkyl-9-alkyl-9-azabicyclo [3, 3, 1] nonan-3-ol (VI) and (X), respectively. Hydroxy groups on 3-position of A- and B-isomer of the alcohols were confirmed to be α-and β-configuration by the formation of a tetrahydrooxazine ring, respectively. Various ester and carbamate compounds of the alcohols (VI) and (X) were synthesized and their pharmacological activities were studied. Among their compounds several glycolate derivatives had a potent anti-cholinergic activity and showed high central specificity.

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Lichen Triterpenoids. IV. The Structures of Leucotylic Acid and Methyl Isoleucotylate, an Acid-induced Isomer of Methyl Leucotylate

ITIRO YOSIOKA, TSUTOMU NAKANISHI, MASAE YAMAKI, ISAO KITAGAWA

1972 Volume 20 Issue 3 Pages 487-501
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.487

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The structure of leucotylic acid, isolated together with leucotylin (I) and zeorin (II) from a lichen Parmelia leucotyliza NYL., has been established as 16β, 22-dihydroxy-hopan-23-oic acid (III) on the basis of chemical and physicochemical investigation. Furthermore, methyl isoleucotylate, produced in addition to methyl leucotylidienate (VI) under acidtreatment of methyl leucotylate (IV), has been elucidated as VII isomeric to IV at the C-21 geometry and hence possessing an isohopane carbon framework. The isomerizationprocedure from IV to VII has also been briefly discussed.

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Lichen Triterpenoids. V. On the Neutral Triterpenoids of Pyxine endochrysina N_YL

ITIRO YOSIOKA, HIROSHI YAMAUCHI, ISAO KITAGAWA

1972 Volume 20 Issue 3 Pages 502-513
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.502

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As a continuation of the study on the lichen triterpenoids, the neutral triterpenoids of a lichen Pyxine endochrysina NYL. have been investigated. The structure of diacetylpyxinol, a major component, has been established as 3β, 25-diacetoxy-12β-hydroxy-20 (S), -24 (R)-epoxy-dammarane (II) on the basis of the chemical evidence and the X-ray analysis.In addition, the other minor neutral components have also been elucidated as pyxinol (III), 12-desoxy-diacetylpyxinol (IV), 3-O-acetyl-pyxinol (V), methyl pyxinate (VI), and methyl 3-O-acetyl-pyxinate (VII), among which the latter two compounds possess the hopane skeleton.
Diacetylpyxinol and the analogues are the first examples of the dammarane triterpenoids discovered in the lichen family.

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Studies on Resin Glycosides. III. Complete Structures of Pharbitic Acids C and D

HIKARU OKABE, TOSHIO KAWASAKI

1972 Volume 20 Issue 3 Pages 514-520
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.514

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Pharbitic acids C (II) and D (III), the two major constituents of “pharbitic acid” (I), were shown to have the monosaccharide sequences Ha and Ina among the three IIa-c and IIIa-c, respectively, by characterization of their acetolysis products and examination of mass spectra of their perruethylates (XI and XII).
The modes of linkages and conformations of the component monosaccharides were determined by molecular rotation differences and NMR spectra of II, III, and degradation products (IV, V, XIII, XIV and XV) and their permethylates (VI, VII, VIII, IX, XVI, XVII, XI and XII) to be a-conjugation and 1C conformation for L-rhamnoseand β and C1 for D-glucose and D-quinovose.
Consequently II and III are assigned the structures IIa' and IIIa', respectively.

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Reaction of Biguanides and Related Compounds. II. Reaction of Biguanides with Benzil

MITSURU FURUKAWA, YOKO FUJINO, YOKO KOJIMA, SEIGORO HAYASHI

1972 Volume 20 Issue 3 Pages 521-525
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.521

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Heating of 1-substituted biguanide with benzil in ethanol was found to give 2-substituted guanidilidene-5, 5-diphenylhydantoin, which was easily converted into 1, 1-diphenyl-1-substituted biguanidoacetic acid by hydrolysis with hydrochloric acid. The structureand the formation mechanism of 2-substituted guanidilidene-5, 5-diphenylhydantoin was also discussed.

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Stereochemical Studies. X. Effects of Neighboring Functional Groups on 1, 2-Asymmetric Induction in the Reduction of Propiophenone Derivatives with Sodium Borohydride

KENJI KOGA, SHUN-ICHI YAMADA

1972 Volume 20 Issue 3 Pages 526-538
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.526

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Effects of neighboring functional groups on 1, 2-asymmetric induction in sodium borohydride reduction were examined with eight kinds of ketones (I-VIII) having functional groups, such as -NH₂HCl, -OH, and-OCH₃, at a-and/or β-positions to the carbonylgroup. It was recognized that the stereochemical course of the reduction was highlydependent on the position of these functional groups, i. e. erythro-rich products were obtained in reduction of ketones having a functional group at a-position to the carbonyl group, while threo-rich products were obtained in reduction of ketones having a functional group at β-position to the carbonyl group. A six-membered empirical model (XXXVII) was proposed for predicting the stereochemical course in the reduction of ketones having a functional group at β-position to the carbonyl group.
Determinations of the relative configurations of the diastereomers (X, XI, XII, XIV, XV, and XVI) were also performed.

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Stereochemical Studies. XI. Changes in the Stereochemical Courseof 1, 2-Asymmetric Induction in the Reduction of N-Substituted 2-Aminopropiophenone Derivatives with Sodium Borohydride

KENJI KOGA, SHUN-ICHI YAMADA

1972 Volume 20 Issue 3 Pages 539-542
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.539

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Changes in the stereochemical course of 1, 2-asymmetric induction in the reduction of N-substituted 2-aminopropiophenones with sodium borohydride were examined. It was concluded that substitution for the two hydrogens of the amino group by two bulky groups is important for the synthesis of threo-isomer, while at least one of the two hydrogensof the amino group must be left attached for the synthesis of erythro-isomer. This stereochemical outcome was considered to be attributable to the steric phenomena.

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Stereochemical Studies. XIII. Determination of the Absolute Configuration of Mercaptosuccinic Acid by Chemical Correlation with Glyceraldehyde

YASUOKI MURAKAMI, KENJI KOGA, HISAYUKI MATSUO, SHUN-ICHI YAMADA

1972 Volume 20 Issue 3 Pages 543-549
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.543

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The absolute configuration of mercaptosuccinic acid was unequivocally determined by its chemical correlation with glyceraldehyde via (-) N-acetyl-4-allomercapto-L-proline thiol-lactone ((-) XI), as shown in Chart 2 and Chart 3. It becomes clear that mercaptosuccinic acid, with a positive rotation in water, belongs to the R-series. Our results show that Fredga's proposal, based on the method of quasi-racemate formation, is correct.
This method of configurational correlation is unique since chemical correlation was performed without replacing the C-S bond with the C-O bond.

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Studies of Nucleosides and Nucleotides. LII. Purine Cyclonucleosides.(17). Synthesis and Properties of Cyclonucleosides derived from Inosine and Thioinosine

MORIO IKEHARA, MASAKO MURAOKA

1972 Volume 20 Issue 3 Pages 550-558
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.550

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8, 2'-Anhydro-8-mercapto- 9-β-D-arabinofuranosyladenine (I), 8, 3'-anhydro-8-mercapto-9-β-D-xylofuranosyladenine (II) and 8, 5'-anhydro-8-mercapto-9-β-D-ribofuranosyladenine (III) were deaminated with barium nitrite in acetic acid to give the corresponding S-cycloinosines (IV-VI). These cyclonucleosides had characteristic properties in ultraviolet (UV), nuclear magnetic resonance (NMR), circular dichroism (CD) and mass spectra, which were as expected from those of adenosine cyclonucleosides. Compounds IV-VI were benzoylated on sugar OH groups and subjected to thiolation reaction using phosphorus pentasulfide in pyridine containing water. Deprotection either with sodium methoxide or ammonia in methanol gave 8, 2'-anhydro-6, 8-dimercapto-9-β-D-arabinofuranosylpurine (XVI), 8, 3'-anhydro-6, 8-dimercapto-9-β-D-xylofuranosylpurine (XVII) and 8, 5'-anhydro-6, 8-dimercapto-9-β-D-ribofuranosylpurine (XVIII), respectively. The structure of these cyclonucleosides was confirmed by their characteristic UV, CD, NMR and mass spectra. 6-Mercaptopurine cyclonucleosides were easily oxidized to form disulfides by air oxidation or iodine treatment.

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Untersuchung über die Fettsäuren aus den Früchten und Samen. II.Über eine Neue Fettsäure (Goshuyusäure) aus den Früchten von Evodia rutaecarpa HOOK. fil. et THOMSON

GOICHI KURONO, YOSHIHIRO NISHIKAWA, SUSUMU MIYANO, SETSUKO ABURANO

1972 Volume 20 Issue 3 Pages 559-563
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.559

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Aus den Fettsäure-fraktion, die nach der Verseifung des Ätherextraktes von den Früchten des Evodia rutaecarpa HOOK. fil. et THOMSON (Rutaceae) erhalten wurde, wurde Goshuyusäure isoliert. Diese Säure ist eine Tetradecadiensäure, die bis jetzt niemals in der Natur gefunden worden ist. Der Gehalt dieser Säure beträgt 25% der Gesammtfettsäure in dieser Frucht. Nach dieser Untersuchung wurde eine Struktur cis-5, 8-Tetradecadiensäure (Ia) für Goshuyusäure ermittelt. Wie auf dem Tabelle I gezeigt, wurden auch andere bekannten Fettsäure ermittelt.

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Soil Bacterial Hydrolysis leading to Genuine Aglycone. IV. Four Acylated Derivatives of Barringtogenol C from Jegosaponin

ITIRO YOSIOKA, SHIGEYOSHI SAIJOH, ISAO KITAGAWA

1972 Volume 20 Issue 3 Pages 564-569
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.564

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By virtue of the soil bacterial hydrolysis method applied on jegosaponin (the pericarps saponin of Styrax japonica SIEB. et Zuec.), new four acylated derivatives of barringtogenol C have been isolated in addition to 21-O-tigloyl-barringtogenol C (I) and barringtogenol C (II). The newly isolated sapogenols have been elucidated respectively as 21-O-tigloyl-28-O-acetyl-barringtogenol C (VI), 21-O-tigloyl-22-O-acetyl-barringtogenol C (VIII), 28-O-acetyl-barringtogenol C (IX), and 21 (or 22)-O-2'-cis-hexenoy1-22 (or 21)-O-acetyl-barringtogenol C (X) on the basis of chemical and physicochemical evidences. Consequently, it has become evident that the tigloyl function initially found in I is a genuine form and the anhydro-structure (III or V) is excluded from the partial structure of jegosaponin.

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Transformation and Excretion of Drugs in Biological Systems. VII. Effect of Biotransformation on Renal Excretion of Sulfonamides

TAKAICHI ARITA, RYOHEI HORI, MASAHIKO TAKADA, SHIGETAKA AKUZU, AYAKO M ...

1972 Volume 20 Issue 3 Pages 570-580
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.570

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Sulfanilamide, sulfathiazole, sulfisomezole and their five biotransformed products were applied to renal clearance experiments in dogs and protein binding experiments to dog plasma protein in order to elucidate their renal excretion behaviors.
Clearance ratio of sulfisomezole is considerably low compared with that of other two sulfonamides.
Biotransformation of sulfisomezole to sulfisomezole-N4-acetate and sulfisomezole-N¹-glucuronide led to remarkable rise of clearance ratio.
N⁴-acetylation of sulfathiazole rather reduced clearance ratio compared with the original sulfonamide. On the contrary, N⁴-acetylation of sulfanilamide lead to rise of clearance ratio, in spite of high clearance ratio of sulfanilamide.
N⁴-acetylated products of the three sulfonamides are considerably secreted through proximal tubule. Proximal tubular secretion of sulfisomezole-N¹-glucuronide is insufficient.
N⁴-acetylation of the three sulfonamides increased affinity for dog plasma protein. On the other hand, reduced affinity of sulfisomezole-N¹-glucuronide for dog plasma protein was observed.
Furthermore, correlation between renal excretion and biotransformation of several sulfonamides was extensively discussed.

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The Structure of Iodine [¹³¹I] Labeled 3, 3'-(TetrabromophthalidyHdene)-bis [6-hydroxybenzenesulfonic Acid]

SADATAKE KATO, KUNIO KURATA, TAKAO WAKEBAYASHI, NOBORU SATOH, YUKIKO K ...

1972 Volume 20 Issue 3 Pages 581-583
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.581

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Studies on Heterocyclic Compounds. XVI. Synthesis of Furo [2, 3-d] pyridazine Derivatives.(5). Synthesis of 4, 7-Dichlorofuro [2, 3-d] pyridazine-2-carboxaldehyde and some of Its Derivatives

SHIGETAKA YOSHINA, ISAMU MAEBA, VALLAPHA LAOHATHAI

1972 Volume 20 Issue 3 Pages 584-588
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.584

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Determination of Dexamethasone and Related Compounds with Isoniazid Dihydrochloride and Its Application to Pharmaceutical Analysis

TSUNETOSHI KAITO, KOJI KASUYA, MIYAKO YOKOTA

1972 Volume 20 Issue 3 Pages 589-592
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.589

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Benzodiazepines. VI. A Rearrangement of 2-Aminoacetanilides to Anilinoacetamides

KIKUO ISHIZUMI, SHIGEHO INABA, HISAO YAMAMOTO

1972 Volume 20 Issue 3 Pages 592-596
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.592

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Studies on Chromophore Groups of Streptothricin Group Antibiotics by Optical Rotatory Dispersion and Circular Dichroism

HYOZO TANIYAMA, YOSUKE SAWADA

1972 Volume 20 Issue 3 Pages 596-600
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.596

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Studies on the β-Lysine Peptide. III. Synthesis of βA-(L-β-Lysyl)-L-β-lysine

HYOZO TANIYAMA, YOSUKE SAWADA, KUNIHIRO MIYAZEKI, FUMIHIKO MIYOSHI

1972 Volume 20 Issue 3 Pages 601-604
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.601

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The Reaction of 5-Phenylazo-6-aminopyrimidines with Lead Tetraacetate. A Convenient Synthesis of 2-Pheny1-7-amino-v-triazolo [4, 5-d]-pyrimidines

YOSHIFUMI MAKI, EDWARD C. TAYLOR

1972 Volume 20 Issue 3 Pages 605-606
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.605

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The Double Smiles Rearrangement

YOSHIFUMI MAKI, MIKIO SUZUKI

1972 Volume 20 Issue 3 Pages 607-609
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.607

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Synthesis of β-(Pyrazolyl-N)-DL-alanine

ISAMU MURAKOSHI, SHIGERU OHMIYA, JOJU HAGINIWA

1972 Volume 20 Issue 3 Pages 609-611
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.609

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Reaction of Biguanides and Related Compounds. III. Reaction of Biguanide and Amidinoisourea with Oxamate

MITSURU FURUKAWA, YOKO FUJINO, SHIGEKI YOSHIMATSU, YOKO KOJIMA, SEIGOR ...

1972 Volume 20 Issue 3 Pages 611-613
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.611

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Platelet Aggregation Inhibitors. I. Hydroxylamine: A Potent Inhibitor of Platelet Aggregation

KAZUHIRO IIZUKA, KIYOMI KIKUGAWA

1972 Volume 20 Issue 3 Pages 614-616
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.614

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Platelets have been known to function in the formation of thrombi and plug, and thekey role of adenosine diphosphate (ADP) as an important initiator of platelet aggregation hasbeen well docum. ented. A wide variety of compounds that inhibit platelet aggregationhave been extensively investigated. Among them inhibitors of several enzymes such asmonoiodoacetate, p-chloromercuribenzoate, N-ethyl maleimide and methyl mercuric nitrate, have been shown to inhibit ADP-induced platelet reaction. This paper describes strongalteration in the ability of platelets to agglutinate with ADP, collagen and thrombin, whenrabbit platelets were treated with hydroxylamine, a kind of enzyme inhibitors.

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Stereochemical Studies. XII. Effects of Neighboring Functional Groups on 1, 2-Asymmetric Induction in the Reduction of Propiophenone Derivatives by Catalytic Hydrogenation

KENJI KOGA, YOSHIMITSU YAMAMOTO, SHUN-ICHI YAMADA

1972 Volume 20 Issue 3 Pages 616-618
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.616

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Decomposition of Dithiocarbamates in weakly Acidic Solutions

FUMITAKA TAKAMI, SHIGERU WAKAHARA, TAKASHI MAEDA

1972 Volume 20 Issue 3 Pages 619-620
Published: March 25, 1972
Released on J-STAGE: January 31, 2011

DOIhttps://doi.org/10.1248/cpb.20.619

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Investigation of Rhubarbs. II. Isolation of Sennoside E, a New Purgative Compound

HARUJI OSHIO, SHUNJI IMAI, SHOJI FUJIOKA, TOHRU SUGAWARA, MASUO MIYAMO ...

1972 Volume 20 Issue 3 Pages 621-622
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.621

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A One-step Synthesis of Purine Ring from Formamide

HIROSHI YAMADA, TOSHIHIKO OKAMOTO

1972 Volume 20 Issue 3 Pages 623-624
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.623

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Biogenetic-Type Transformation of α-[α-(Hydroxymethyl)-3, 4-dimethoxystyryl]-3, 4-methylenedioxycinnamic Acid γ-Lactone into Diphyllin

ZEN-ICHI HORII, KAZUO OHKAWA, CHUZO IWATA

1972 Volume 20 Issue 3 Pages 624-625
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.624

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The Structure of Caudatin

TAKASHI YAMAGISHI, HIROSHI MITSUHASHI

1972 Volume 20 Issue 3 Pages 625-626
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.625

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Cupric Ion Catalyzed Guanidide Hydrolysis

TADAKAZU TSUJI

1972 Volume 20 Issue 3 Pages 627-628
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.627

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On the Structure of Kidjolanin and the Position of the Esterlinkage of Penupogenin

TAMIHIKO SASAKI, KOJI HAYASHI, HIROSHI MITSUHASHI

1972 Volume 20 Issue 3 Pages 628-629
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.628

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Protobassic Acid, a Genuine Sapogenol of Seed Kernels of Madhuca longifolia L.

ISAO KITAGAWA, AKIRA INADA, ITIRO YOSIOKA, R. SOMANATHAN, M.U.S. SULTA ...

1972 Volume 20 Issue 3 Pages 630-632
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.630

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Thermal Hydrogen-Deuterium Exchange Reaction between Aromatic Ring Deuterium and Active Hydrogen of Substituent Group

YOSHIO SASAKI, MIYOKO SUZUKI, SETSUO MORI, MAKIKO SUGIURA

1972 Volume 20 Issue 3 Pages 632-633
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.632

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On the Retention Index

TOYOZO UNO, HIDEKI OKUDA, YOSHIO SASAKI, MIYOKO SUZUKI

1972 Volume 20 Issue 3 Pages 634-635
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.634

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Synthesis and Properties of 8, 2'-Cyclothioguanosine and Related Compounds

MASAKATSU KANEKO, MISAKO KIMURA, BUNJI SHIMIZU

1972 Volume 20 Issue 3 Pages 635-637
Published: March 25, 1972
Released on J-STAGE: February 08, 2011

DOIhttps://doi.org/10.1248/cpb.20.635

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