Reactions of 3-Phenylglycidic Esters. V. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitroaniline and Synthesis of 1,5-Benzodiazepine Derivatives

スポンサーリンク

概要

• 論文の詳細を見る

• Stereochemical aspects of the oxirane-ring opening of methyl trans-3-(4-methoxyphenyl)-glycidate (1) with 2-nitroaniline (5) were investigated. ZnI_2 showed good catalytic activity in this reaction, giving the cis-opening product (6a) predominantly. On the other hand, the reaction on the surface of silica gel proceeded predominantly by trans-opening. Silica gel had rather little effect on the reaction of 1 with 2-nitrothiophenol or 2-nitrophenol. Some 1,5-benzodiazepine derivatives (18-21), 1-aza analogues of diltiazem, were synthesized from 6a, b for pharmacological evaluation. Some oxidative epimerization of 9a, b was observed during cyclization in boiling xylene in the presence of air. The cerebral vasodilating activity of 21a, the most potent compound in this series, was about 0.5 that of racemic diltiazem. The structure-activity relationships are discussed.

• 1985-06-25

著者

• 井上 博純

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd, .

• 武田 幹男

  Organic Chemistry Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 長尾 拓

  Biological Research Laboratory, Tanabe Seiyaku Co., Ltd.

• 長尾 拓

  Biological Research Laboratory:tanabe Seiyaku Co. Ltd. :(present Adress)department Of Toxicology And

• 村田 栄

  Pharmacological Research Laboratory Tanabe Seiyaku Co. Ltd.

• 橋山 富樹

  Lead Optimization Research Laboratory, Tanabe Seiyaku Co., Ltd.,

• 武田 幹男

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd.

• 井上 博純

  Organic Chemistry Research Laboratory Tanabe Seiyaku Co. Ltd .

• 橋山 富樹

  Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.

• Hashiyama Tomiki

  Lead Optimization Research Laboratory Tanabe Seiyaku Co. Ltd.

関連論文

• Enantioselective Reduction of meso-Cyclic-1,2-dicarboxylic Anhydrides and 1,2-Dicarboximides : Asymmetric Synthesis of Bicyclic Lactones and Hydroxylactams
• Synthesis of C-Nor Emetine Pyman
• Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. IV. Modification of the Phenylpiperazino Moiety of 2-(Phenylpiperazino-alkoxyphenyl)thiazolidine-3-carbothloamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
• Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. II. 2-(Phenylpiperazinoalkoxyphenyl)thiazolidine-3-thioearboxamides and the Corresponding Carboxamides(Medicinal Chemistry,Chemical)
• A New Enantioselective Synthesis of (2R, 3S)-3-(4-Methoxyphenyl)glycidic Ester via the Enzymatic Hydrolysis of erythro-N-Acetyl-β-(4-methoxyphenyl)serine
• A New Synthetic Route to 1,5-Benzothiazepines. Synthesis of Derivatives of Diltiazem
• Asymmetric Reduction of Aromatic Ketones. I. Enantioselective Synthesis of Denopamine
• Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents; III Optically Active Isomers of Ar-Methyl-2-(2-(2-(4-phenylpiperazino)-ethoxy)phenyl)thiazolidine-3-carboxamides(Medicinal Chemistry,Chemical)
• Synthesis of 2-Phenylthiazolidine Derivatives as Cardiotonic Agents. I. 2-Phenylthiazolidine-3-thiocarboxamides(Medicinal Chemistry,Chemical)
• Synthesis of Novel Pyridotriazepinones as Antisecretory Agents(Organic,Chemical)
• Antiulcer Activity of Dehydroabietic Acid Derivatives
• Studies on 1,2,3,4-Tetrahydroisoquinolines. IV. β-Adrenoceptor Activity and Absolute Stereochemistry of (-)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline
• Studies on 1,2,3,4-Tetrahydroisoquinolines. III. Syntheses and β-Adrenoceptor Activities of Methyl Derivatives of Trimetoquinol
• Studies on Antiallergic Agents. I. Phenyl-substituted Heterocycles with a 5-Tetrazolyl or N-(5-Tetrazolyl) carbamoyl Group
• Studies on 1,2,3,4-Tetrahydroisoquinolines. VI. Reutilization of the Unwanted (R)-Isomer of (S)-(-)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (TA-073)
• Studies on 1,2,3,4-Tetrahydroisoquinolines. V. A Convenient Synthesis of (±)-5,7-Dihydroxy-1-(3,4,5-trimethoxybenzyl)-1,2,3,4-tetrahydroisoquinoline (Racemic TA-073)
• Synthesis of the Metabolites of Clentiazem
• Asymmetric Reduction of Aromatic Ketones. II. An Enantioselective Synthesis of Methyl (2R, 3S)-3-(4-Methoxyphenyl)glycidate
• Synthesis of the Optically Active trans-Isomers of Diltiazem and Their Cardiovascular Effects and Ca-Antagonistic Activity
• Synthesis of N-Substituted C-Normorphinans and Their Pharmacological Properties
• Reactions of 3-Phenylglycidic Esters. V. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitroaniline and Synthesis of 1,5-Benzodiazepine Derivatives
• Reaction of 3-Phenylglycidic Esters. III. Reaction of cis-3-Arylglycidic Esters with Various Thiophenols
• Reaction of 3-Phenylglycidic Esters. IV. Reaction of Methyl 3-(4-Methoxyphenyl) glycidate with 2-Nitrophenol and Synthesis of 1,5-Benzoxazepine Derivatives
• A New Class of Nitrosoureas. IX. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-6-yl or methyl 2-acetamido-2-deoxy-α-D-glucopyranosid-6-yl)-1-nitrosoureas
• A New Class of Nitrosoureas. VIII. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(trans-2-hydroxy-cyclohexyl)-1-nitrosoureas
• Azabicycloalkanes as Analgetics. I. Synthesis of 1-Phenyl-6-azabicyclo [3,2,1] octane Derivatives
• Azabicycloalkanes as Analgetics. VII. 1-Phenyl-3-azabicyclo [3. 3. 1] nonanes
• Azabicycloalkanes as Analgetics. VI. 5-Phenyl-2-azabicyclo [3,2,1] octanes
• Azabicycloalkanes as Analgetics. V. 4-Phenyl-2-azabicyclo [2,2,2] octanes
• Azabicycloalkanes as Analgetics. IV. 4-Phenyl-2-azabicyclo [2,2,1] heptanes
• Water-Soluble Antitumor Agents. I. Synthesis and Biological Activity of 6-S-Aminoacyloxymethyl Mercaptopurine Derivatives
• Synthesis of 1,5-Benzothiazepine Derivatives. III
• Synthesis of 1,5-Benzothiazepine Derivatives. II
• Synthesis of 1,5-Benzothiazepine Derivatives. I
• Azabicycloalkanes as Analgetics. II. An Improved Synthesis of 1-Phenyl-6-azabicyclo [3,2,1] octane Derivatives
• 4-Acylaminophenol Derivatives as Novel Lipoxygenase Inhibitors : Synthesis and Inhibitory Effect on 5-Lipoxygenase and Leukotriene B_4 Production
• Studies on Trimetoquinol. II. The Metabolic Fate of Trimetoquinol
• 1,5-Benzothiazepine誘導体の合成(第4報)dl-cis-3-Acetoxy-5-[2-(dimethylamino)ethyl]-2,3-dihydro-2-(p-methoxyphenyl)-1,5-benzothiazepin-4(5H)-one Hydrochlorideの光学分割
• Selective β_1-Adrenoceptor Agonist Activity of Denopamine and Its Derivatives in Dogs
• Synthesis and Pharmacological Properties of Azido Derivatives of 1,5-Benzothiazepine Ca Antagonist
• A New Class of Nitrosoureas. VII. Synthesis and Antitumor Activity of 3-Substituted 1-(2-Chloroethyl)-3-(methyl α-D-glucopyranosid-3-yl)-1-nitrosoureas
• 塩酸ジルチアゼムの開発研究
• 環状イミン類の新しい不斉還元剤 : 不斉水素化トリアシルオキシホウ素ナトリウム
• A New Class of Nitrosoureas. VI. Synthesis and Antitumor Activity of 3-Substituted-1-(2-chloroethyl)-3-(methyl-α-D-glucopyranosid-2-yl)-1-nitrosoureas
• A New Class of Nitrosoureas. V. Structure of Isomeric L-Arabinosylureas and Isomerization Thereof
• Synthesis and Antitumor Activity of 9-Acyloxyellipticines
• Synthesis and Antitumor Activity of Quaternary Salts of 2-(2'-Oxoalkoxy)-9-hydroxyellipticines
• Synthesis and Biological Activity of O-Alkyl-3-N-aminoacyloxymethyl-5-fluoro-2'-deoxyuridine Derivatives
• Synthesis of Bridged 2-Phenylcyclohexylamines as Potential Analgetics
• Synthesis of B/C trans-Fused Morphine Structures. VI. Mass Spectrum, Optical Rotatory Dispersion and Circular Dichroism of B/C trans-Morphine Derivatives
• Synthesis of B/C trans-Fused Morphine Structures. IV. Synthesis of B/C trans-Isomorphine
• 抗うつ剤としてのDidenzo[b, e][1,4]diazepine誘導体の合成
• Synthesis of a B/C trans-fused Morphine Structure
• 14.B/Cトランス・モルフィン環化合物の合成
• Syntheses of Morphine-like Structures. IV. Further Studies on Addition of Borane to 9-Methylenebenzomorphan
• Syntheses of Morphin-like Structures. III. Stereochemical Control of Addition of Borane to 9-Methylenebenzomorphan
• Syntheses of Morphine-like Structures. II. 2'-Methoxy-9-hydroxymethyl-2,5-dimethyl-6,7-benzomorphan
• Syntheses of Morphine-like Structures. I. 9-Hydroxymethyl-2,5-dimethyl-6,7-benzomorphan.
• Studies on Benzoisogranatanine Derivatives. II. Synthesis of 1-Phenethyl-2,4-propano-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolines.
• Alkylsulfonyltoluene Derivatives (Diuretics. II.).
• Alkylsulfonyltoluene Derivatives (Diuretics. I.).
• Ca2+ 拮抗薬 Diltiazem の気管支拡張作用
• 麻酔犬の血行動態ならびに His 束心電図に及ぼす Diltiazem の影響

もっと見る 閉じる

スポンサーリンク