Potential Antiinflammatory Agents. IV. Stereoselective Synthesis of 6-Chloro-5-(3'- and 4'-hydroxycyclohexyl) indan-1-carboxylic Acids related to Metabolites of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284)
スポンサーリンク
概要
- 論文の詳細を見る
In the course of synthetic study of metabolites of a new potent antiinflammatory agent, 6-chloro-5-cyclohexylindan-1-carboxylic acid (TAI-284), 5-(cis-and trans-3'-hydroxy-cyclohexyl) indan-1-carboxylic acids (25 and 26) and 5-(cis- and trans-4'-hydroxycyclohexyl) indan-1-carboxylic acids (17 and 16) were stereoselectively prepared by sodium borohydride reduction (equatorial alcohol formation) and catalytic hydrogenation (axial alcohol formation) of the corresponding 3'-oxo and 4'-oxo compounds (24 and 15), respectively. Chlorination of 25,26,17 and 16 with molecular chlorine in acetonitrile gave their 6-chloro derivatives (27,28,21 and 20), which were correlated with metabolites of TAI-284. Of these indans, 3'-hydroxy compounds (25-28) were prepared as a pair of racemic diastereoisomers.
- 社団法人日本薬学会の論文
- 1974-10-25
著者
-
青野 哲也
Resarch & Development Division Takeda Chemical Industries Ltd.
-
岸本 彰二
Pharmaceutical Research Laboratories Iii Takeda Chemical Industries Ltd.
-
岸本 彰二
Central Research Division, Takeda Chemical Industries, Ltd.
-
青野 哲也
Central Research Division, Takeda Chemical Industries, Ltd.
-
野口 俊作
Central Research Division, Takeda Chemical Industries, Ltd.
-
荒木 義昭
Central Research Division, Takeda Chemical Industries, Ltd.
-
田中 邦大
Central Research Division, Takeda Chemical Industries, Ltd.
-
南田 勲
Central Research Division, Takeda Chemical Industries, Ltd.
-
野口 俊作
Central Research Division Takeda Chemical Industries Ltd.
-
岸本 彰二
Pharmaceutical Research Laboratories Iii Pharmaceutical Research Division Takeda Chemical Industries
-
南田 勲
Medicinal Research Laboratories Central Research Division Takeda Chemical Industries Ltd.
-
荒木 義昭
Central Research Division Takeda Chemical Industries Ltd.
-
田中 邦大
Central Research Division Takeda Chemical Industries Ltd.
関連論文
- Chemical Modification of Fumagillin. III. Modification of the Spiro-epoxide
- Synthesis and Antitumor Activity of New Amphiphilic Alkylglycerolipids Substituted with a Polar Head Group, 2-(2-Trimethylammonioethoxy)ethyl or a Congeneric Oligo(ethyleneoxy)ethyl Group
- Chemical Modification of Fumagillin. II. 6-Amino-6-deoxyfumagillol and Its Derivatives
- Chemical Modification of Fumagillin. I. 6-O-Acyl, 6-O-Sulfonyl, 6-O-Alkyl, and 6-O-(N-Substituted-carbamoyl)fumagillols
- Synthesis of Carumonam (AMA-1080) and a Related Compound Starting from (2R, 3R)-Epoxysuccinic Acid
- Chemical Modification of Sulfazecin. Synthesis of 4-Methoxycarbonyl-2-azetidinone-1-sulfonic Acid Derivatives
- 1-Indancarboxylic Acids. V. Syntheses of Phenoxy- and (2-Thienylcarbonyl)-1-indancarboxylic Acids, New Antiinflammatory Agents
- 1-Indancarboxylic Acids. IV. A Convenient Synthesis of Antiinflammatory 4-Aroyl-1-indancarboxylic Acids and Their Absolute Configurations
- 1-Indancarboxylic Acids. I. Electrophilic Substitution Reactions of 1-Indancarboxylic Acid and Synthesis of 6-Substituted 1-Indancarboxylic Acids as Potential Antiinflammatory Agents
- Synthesis and Reaction of 1-(N, N-Disubstituted amino) pyrazoles
- Potential Antiinflammatory Agents. V. Synthesis of Metabolites of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) using Microbiological Hydroxylation
- Potential Antiinflammatory Agents. IV. Stereoselective Synthesis of 6-Chloro-5-(3'- and 4'-hydroxycyclohexyl) indan-1-carboxylic Acids related to Metabolites of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284)
- Potential Antiinflammatory Agents. III. Syntheses of 1-Substituted 6-Chloro-5-cyclohexylindans as Related Compounds of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284)
- Potential Antiinflammatory Agents. II. Synthesis and Structure-Activity Relationships of 6-Chloro-5-cyclohexylindan-1-carboxylic Acid (TAI-284) and Related 5-Substituted Indan-1-carboxylic Acids
- 6-Chloro-5-cyclohexylindan-l-carboxylic Acid (TAI-284), a New Antiinflammatory Agent
- Studies on Vitamin B_1 and Related Compounds. CX. Rearrangements of α-Hydroxybenzylthiamin and Its Homologues
- Studies on Vitamin B_1 and Related Compounds. CIX. A Novel Cleavage of Thiamin and Its Homologues by the Reaction with Aromatic Aldehydes
- 1-Indancarboxylic Acids. III. Chemical Modifications of Antiinflammatory 4-Aroyl-1-indancarboxylic Acids
- 1-Indancarboxylic Acids. II. Synthesis of 4- and 6-Aroyl-1-indan-carboxylic Acids as Potential Antiinflammatory Agents
- Synthesis of New Cephalosporins with Potent Antibacterial Activities
- Spirocyclopropane Compounds. V. One-Step Synthesis of 5-Acetylspiro [benzofuran-2 (3H), 1'-cyclopropan]-3-one
- Spirocyclopropane Compounds. II. Synthesis and Biological Activities of Spiro [cyclopropane-1,2'-[2H] indol]-3'(1'H)-ones
- Photochemical Reaction of 21-Methyl-20,21-diketosteroids : The Formation of New 3´, 4´, 16α, 17α-Tetrahydrocyclobut [16,17] androstanes
- Synthesis and Anti-inflammatory Activity of Steroidal 17-Yl-α-Oxothiocarboxamides and Related Compounds
- Steroid [16,17-c]isoxazoline
- Synthesis of 20α-Hydroxy-16-oxosteroids and the C-20 Configuration of Δ^-16-Ocosteroids
- Aldol Condensation of Corticoids with Formaldehyde. II. 21-Hydroxymethylation of Reichstein's Substance S, Dexamethasone and Deoxycorticosterone
- 4.制癌性抗生物貭Chromomycin A_3の化学構造
- Aldol-Condensation of Corticoids with Formaldehyde. Syntheses of 21-Hydroxy-methyl-corticoids and 21-Methyl-11β, 17α-dihydroxy-pregna-1,4-diene-3,20,21-trione 17-Acetate.
- Syntheses of 19-Nor-3-ketosteroids
- Fusarium solaniによるProgesteroneの微生物酸化
- p-Aminomethylphenyl Isopentyl Ketoneのポーラログラフィー
- Studies on Chemotherapeutics for Acid-fast Bacilli. VII. : Further Studies on p-Aminophenyl- and p-Aminomethylphenyl Alkyl Sulfones and Related Compounds.
- Synthesis and Human Immunodeficiency Virus (HIV)-1 Protease Inhibitory Activity of Tripeptide Analogues Containing a Dioxoethylene Moiety
- Synthesis and Biological Activity of (S)-2-Amino-3-(2,5-dihydro-5-oxo-4-isoxazolyl)propanoic Acid (TAN-950 A) Derivatives
- 含窒素複素環式化合物の合成研究-29-Furo〔2,3-d〕pyridazine誘導体の合成
- Synthesis of Polyhydroxysteroids. I. A Modified Degradation of the Diosgenin Side Chain.
- Synthesis of Polyhydroxysteroids. V. Preparation and Infrared Spectra of 16β, 20α-Isopropylidenedioxysteroids.
- Synthesis of Polyhydroxy-steroids. II. Syntheses of Isomeric 5α-Pregnane-3,5,6,16,20-pentols and Related Compounds.
- Enzymatic Hydrolysis of Steroidal Esters and its Application to Syntheses of Steroids
- Studies in Steroids. XIII. Formylation of Steroid Alcohols with Dimethylformamide-Phosgene Complex
- 77.チオール型ビタミンB_1誘導体について(VII) : Thiamine alkyl disulfide類の酸化成績体(第8回大会研究発表要旨)