Synthesis and Biological Activities of Optical Isomers of 2-(4-Chlorophenyl)-5,6-dihydro-(1)benzothiepino[5,4-c]pyridazin-3(2H)-one 7-Oxide
スポンサーリンク
概要
- 論文の詳細を見る
Two enantiomers of 2-(4-chlorophenyl)-5,6-dihydro-(1)benzothiepino[5,4-c]pyridazin-3(2H)-one 7-oxide ((±)-1 : Y-23684) were synthesized in high yields by asymmetric oxidation of the synthetic precursor (2) using modified Sharpless reagent. Among the oxidants tested, cumene hydroperoxide (CHP) gave the highest optical and chemical yields, while tert-butyl, tert-amyl, and 1,1,3,3-tetramethylbutyl hydroperoxides did not show such high enantio-selectivities. The absolute configuration of (+)-1 enantiomer synthesized form 2,Ti(O-iso-Pr)_4,(-)-diethyl tartarate, and CHP was determined to be S by X-ray crystallographic analysis. Both enantiomers, S-(+)-1 and R-(-)-1,and (±)-1 had approximately equivalent in vivo activities to antibicuculline test in mice and anticonflict test in rats, although S-(+)-1 showed about three times higher affinity to benzodiazepine receptor than R-(-)-1 in [^3H]diazepam binding assay.
- 公益社団法人日本薬学会の論文
- 1992-01-25
著者
-
丸林 信洋
Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd.,
-
山口 裕子
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
-
小畑 実
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
-
中尾 達
Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd.,
-
池田 国樹
Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd.,
-
森本 保人
Research Laboratories, Yoshitomi Pharmaceutical Industries, Ltd.,
-
中尾 達
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
-
丸林 信洋
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
-
森本 保人
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
-
池田 国樹
Research Laboratories Yoshitomi Pharmaceutical Industries Ltd.
関連論文
- Atropisomerism in 4-(2-Thienyl)-4H-1,2,4-triazole Derivatives
- Utilization of Protopine and Related Alkaloids. XVI. Nuclear Magnetic Resonance Spectroscopy on the Cycloadducts of Anhydromethylberberines with Dienophiles
- Physagulin C, a New Withanolide from Physalis angulata L.
- TWO NEW ERGOSTANE DERIVATIVES FROM TUBOCAPSICUM ANOMALUM(SOLANA CEAE)
- Potential Neuroleptic Agents, N-[(2-Pyrrolidinyl)methyl]-2,3-dihydrobenzofuran-7-carboxamide Derivatives
- Synthesis and Biological Activities of Optical Isomers of 2-(4-Chlorophenyl)-5,6-dihydro-(1)benzothiepino[5,4-c]pyridazin-3(2H)-one 7-Oxide
- SYNTHESIS OF 2-ARYL-5,6-DIHYDRO-(1)BENZOTHIEPINO[5,4-C]PYRIDAZIN-3(2H)-ONE BY A NOVEL DEHYDROGENATION REACTION
- Dienone-Phenol Rearrangement of (+)-2'-Demethoxydehydrogriseofulvin into a 4-Methylxanthone Derivative
- Utilization of Protopine and Related Alkaloids. XV. Photolysis of 4-Methyl-1-oxoanhydroberberine
- Utilization of Protopine and Related Alkaloids. XIV. Oxidation of the Photoadduct of 1-Oxoanhydromethylberberine with Nitrosobenzene, and Synthesis of Ring C-Substituted Benzo [c] phenanthridines
- Heterocycles. XIII. Syntheses and Absolute Configurations of Chiral Benzo [c] phenanthridines
- Utilization of Protopine and Related Alkaloids. XIII. Attempts to obtain Useful Intermediates for the Syntheses of Chelidonine and Homochelidonine
- Heterocycles. XI. Syntheses of Analogs of 10b-Hydroxychelidonine and 4b-Epichelidonine
- Heterocycles. X. Syntheses and Absolute Configurations of a Chiral Naphthoquinone Epoxide and Chiral Naphtho [1,2-c] isocoumarins
- Heterocycles. VIII. Syntheses of 12-Acetoxybenzo [c] phenanthridines
- Utilization of Protopine and Related Alkaloids. XII. An Improved Route to an Analog of the Alkaloid Corynoline
- Utilization of Protopine and Related Alkaloids. XI. Photolysis of 7,8-Dimethoxy-2-methyl-3-(4', 5'-methylenedioxy-2'-vinyl-phenyl) isocarbostyril and Its Application to the Preparation of Oxychelerythrines
- Parsonsianine, a Macrocyclic Pyrrolizidine Alkaloid from the Leaves of Parsonsia laevigata (Studies on Parsonsia, III)
- CHARACTERIZATION OF A MINOR COMPOUND, WHICH ACCOMPANIES THE USUAL 22α (R)-0,25β (S)-SPIROSTANOL GLYCOSIDE, AS A NOVEL TYPE OF 22β (S)-0,25α (S) ANALOG
- Syntheses and Biological Activities of Optical Isomers of 3-Chloro-5-[3-(2-oxo-1,2,3,5,6,7,8,8a-octahydroimidazo[1,2-a]pyridine-3-spiro-4'-piperidino)propyl]-10,11-dihydro-5H-dibenz[b, f]azepine (Mosapramine) Dihydrochloride
- Studies of the Synthesis of Condensed Pyridazine Derivatives. IV. Synthesis and Anxiolytic Activity of 2-Aryl-5,6-dihydro-(1)benzothiepino[5,4-c]pyridazin-3(2H)-ones and Related Compound
- 縮合Pyridazine誘導体の合成研究(第3報)縮合Triazolopyridazine誘導体の合成とBenzodiazepine受容体親和性
- 縮合Pyridazine誘導体の合成研究(第2報)2-Aryl-4,4a, 5,6-tetrahydropyridazino-[4,3-c]quinolin-3(2H)-one, 2-Aryl-4a, 5-dihydro-2H-(1)benzothiopyrano[4,3-c]-pyridazin-3(4H)-one誘導体, 及び関連化合物の合成と抗不安作用
- 縮合Pyridazine誘導体の合成研究(第1報)2-Substituted-4,4a, 5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one誘導体, 及び関連化合物の合成とBenzodiazepine受容体親和性
- Alschomine and Isoalschomine, New Alkaloids from the Leaves of Alstonia scholaris
- VERSATILE ROUTES TO CHIRAL 4-SUBSTITUTED 2-OXAZOLIDINONES AND α-AMINO ACIDS. USE OF CHIRON, [4+2] CYCLOADDUCTS OF DIALKYL AZODICARBOXYLATES AND 2-OXAZOLONES
- STEREOSELECTIVE OXIDATION OF 2-(4-CHILOROPHENYL)-4a, 5-DIHYDRO-2H-(1)BENZOTHIOPYRANO[4,3-c]PYRIDAZIN-3(4H)-ONE TO SULFOXIDE
- Studies of Peptide Antibiotics. XXVI. Syntheses of Cyclodipeptides containing N^δ-p-Aminobenzenesulfonyl Ornithine Residue