4-oxo-2-propyl-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid | 135279-00-4

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 4-oxo-2-propyl-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid
• 英文别名: 2-(4-oxo-2-propyl-6,7-dihydro-5H-thieno[2,3-b]thiepin-5-yl)acetic acid
• CAS: 135279-00-4
• 化学式: C₁₃H₁₆O₃S₂
• 分子量: 284.4
• InChiKey: GPQSARWDZKHLHF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-oxo-2-propyl-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid 在 氢溴酸 、 sodium acetate 作用下， 以 乙醇 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 18.5h， 生成 2-(4-Chlorophenyl)-9-propyl-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one
  参考文献：
  名称：

  Synthesis and structure-activity analysis of 2-(4-chlorophenyl)-5,6-dihydrothieno[2′,3′:2,3]thiepino[4,5-c]pyridazin-3(2H)-ones as ligands for benzodiazepine receptors

  摘要：

  A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones were synthesized and evaluated in vitro for their affinity tow-ard benzodiazepine receptors (BZRs) in rats and for their intrinsic efficacy in the augmentation of the gamma-aminobutyric acid (GABA)-induced chloride currents in the dissociated frog sensory neurons. Compounds in which the 9-position of the condensed-ring system was substituted with alkyl group or bromine had a high affinity toward BZRs. The substituents at the same position also influenced significantly the GABA-induced chloride currents. As the result, 9-alkyl and 9-bromo substituents would interact with the lipophilic area of BZRs. A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones exhibited partial and full agonistic activities toward BZRs.

  DOI：

  10.1016/0223-5234(96)88305-x
• 作为产物：
  描述：

  2-(4-oxo-2-propyl-6,7-dihydro-5H-thieno[2,3-b]thiepin-5-yl)acetonitrile 在 盐酸 、 溶剂黄146 作用下， 反应 4.0h， 生成 4-oxo-2-propyl-4,5,6,7-tetrahydrothieno[2,3-b]thiepin-5-acetic acid
  参考文献：
  名称：

  Synthesis and structure-activity analysis of 2-(4-chlorophenyl)-5,6-dihydrothieno[2′,3′:2,3]thiepino[4,5-c]pyridazin-3(2H)-ones as ligands for benzodiazepine receptors

  摘要：

  A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones were synthesized and evaluated in vitro for their affinity tow-ard benzodiazepine receptors (BZRs) in rats and for their intrinsic efficacy in the augmentation of the gamma-aminobutyric acid (GABA)-induced chloride currents in the dissociated frog sensory neurons. Compounds in which the 9-position of the condensed-ring system was substituted with alkyl group or bromine had a high affinity toward BZRs. The substituents at the same position also influenced significantly the GABA-induced chloride currents. As the result, 9-alkyl and 9-bromo substituents would interact with the lipophilic area of BZRs. A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones exhibited partial and full agonistic activities toward BZRs.

  DOI：

  10.1016/0223-5234(96)88305-x

文献信息

• Thiophene compounds and their pharmaceutical uses
  申请人：YOSHITIOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0426018A2

  公开（公告）日：1991-05-08

  Thiophene compounds of the formula: wherein R¹ is hydrogen, nitro, amino, halogen or C₁₋₄ alkyl; R² is hydrogen, nitro, amino, halogen, C₁₋₄ alkyl, C₁₋₄ haloalkyl, acyl, C₂₋₅ alkoxycarbonyl, C₁₋₄ alkoxy-C₁₋₄ alkyl, aryloxy-C₁₋₄ alkyl, acyloxy-C₁₋₄ alkyl, hydroxy-C₁₋₄ alkyl, acyloxy-C₂₋₅ alkanoyl, C₁₋₄ alkoxy-C₂₋₅ alkanoyl, hydroxy-­C₂₋₅ alkanoyl, aryloxy-C₂₋₅ alkanoyl or C₂₋₅ haloalkanoyl; R³ is hydrogen, C₁₋₈ alkyl, hydroxy-C₁₋₄ alkyl, C₂₋₅ alkanoyloxy-C₁₋₄ alkyl, aryl, aryl-C₁₋₄ alkyl, heteroaryl, heteroaryl-C₁₋₄ alkyl or aryl, aryl-C₁₋₄ alkyl, heteroaryl or heteroaryl-C₁₋₄ alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C₁₋₄ alkyl, C₁₋₄ alkoxy, C₂₋₅ alkanoylamino, C₁₋₄ haloalkyl, acyloxy, C₂₋₅ alkoxycarbonyl and carboxyl on the aromatic ring; m is 0, 1 or 2; n is 1 or 2; the bond represented by --- is a single bond or a double bond. Thiophene compounds (I) are useful as antianxiety drugs, hypnotics, antiepileptic drugs or nootropics. Thiophene compounds ( II ) are useful as intermediates for said thiophene compounds (I).

  式中的噻吩化合物： 其中 R¹ 是氢、硝基、氨基、卤素或 C₁₋₄ 烷基；R² 是氢、硝基、氨基、卤素、C₁₋₄ 烷基、C₁₋₄ 卤代烷基、酰基、C₂₋₅ 烷氧基羰基、C₁₋₄ 烷氧基-C₁₋₄ 烷基、芳氧基-C₁₋₄ 烷基、酰氧基-C₁₋₄ 烷基、羟基-C₁₋₄烷基、酰氧基-C₂₋₅ 烷酰基、C₁₋₄烷氧基-C₂₋₅ 烷酰基、羟基-C₂₋₅ 烷酰基、芳氧基-C₂₋₅ 烷酰基或 C₂₋₅ 卤代烷酰基；R³ 是氢、C₁₋₈烷基、羟基-C₁₋₄ 烷基、C₂₋₅烷酰氧基-C₁₋₄ 烷基、芳基、芳基-C₁₋₄ 烷基、杂芳基、杂芳基-C₁₋₄ 烷基或芳基、芳基-C₁₋₄ 烷基、杂芳基或杂芳基-C₁₋₄烷基被至少一个选自卤素、羟基、氨基、硝基、氰基组成的取代基取代、C₁₋₄ 烷基、C₁₋₄ 烷氧基、C₂₋₅烷酰氨基、C₁₋₄ 卤代烷基、酰氧基、C₂₋₅烷氧羰基和芳香环上的羧基；m 是 0、1 或 2；n 是 1 或 2；由----表示的键是单键或双键。 噻吩化合物（I）可用作抗焦虑药、催眠药、抗癫痫药或促智药。噻吩化合物（II）可用作上述噻吩化合物（I）的中间体。
• Thiophene compounds and their use as intermediates in the preparation of antianxiety drugs, hypnotics, antiepileptic drugs and nuotropics
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0729960A1

  公开（公告）日：1996-09-04

  Thiophene compounds of the formula: wherein R1 is hydrogen, nitro, amino, halogen or C1-4 alkyl; R2 is hydrogen, nitro, amino, halogen, C1-4 alkyl, C1-4 haloalkyl, acyl, C2-5 alkoxycarbonyl, C1-4 alkoxy-C1-4 alkyl, aryloxy-C1-4 alkyl, acyloxy-C1-4 alkyl, hydroxy-C1-4 alkyl, acyloxy-C2-5 alkanoyl, C1-4 alkoxy-C2-5 alkanoyl, hydroxy-C2-5 alkanoyl, aryloxy-C2-5 alkanoyl or C2-5 haloalkanoyl; R3 is hydrogen, C1-8 alkyl, hydroxy-C1-4 alkyl, C2-5 alkanoyloxy-C1-4 alkyl, aryl, aryl-C1-4 alkyl, heteroaryl, heteroaryl-C1-4 alkyl or aryl, aryl-C1-4 alkyl, heteroaryl or heteroaryl-C1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C1-4 alkyl, C1-4 alkoxy, C2-5 alkanoylamino, C1-4 haloalkyl, acyloxy, C2-5 alkoxycarbonyl and carboxyl on the aromatic ring; m is 0, 1 or 2; n is 1 or 2; the bond represented by ---- is a single bond or a double bond. Thiophene compounds () are useful as antianxiety drugs, hypnotics, antiepileptic drugs or nootropics. Thiophene compounds () are useful as intermediates for said thiophene compounds ().

  式中的噻吩化合物： 其中R1是氢、硝基、氨基、卤素或C1-4烷基；R2是氢、硝基、氨基、卤素、C1-4烷基、C1-4卤代烷基、酰基、C2-5烷氧基羰基、C1-4烷氧基-C1-4烷基、芳氧基-C1-4烷基、酰氧基-C1-4烷基、羟基-C1-4烷基、酰氧基-C2-5烷酰基、C1-4烷氧基-C2-5烷酰基、羟基-C2-5烷酰基、芳氧基-C2-5烷酰基或C2-5卤代烷酰基；R3 是氢、C1-8 烷基、羟基-C1-4 烷基、C2-5 烷酰氧基-C1-4 烷基、芳基、芳基-C1-4 烷基、杂芳基、杂芳基-C1-4 烷基或芳基、芳基-C1-4 烷基、在芳香环上被至少一个取代基取代的杂芳基或杂芳基-C1-4 烷基，该取代基选 自卤素、羟基、氨基、硝基、氰基、C1-4 烷基、C1-4 烷氧基、C2-5 烷酰氨基、C1-4 卤代烷基、酰氧基、C2-5 烷氧羰基和羧基组成的组；m 是 0、1 或 2；n 是 1 或 2；---- 所代表的键是单键或双键。 噻吩化合物（）可用作抗焦虑药、催眠药、抗癫痫药或健脑药。噻吩化合物（）可用作上述噻吩化合物（）的中间体。
• US5175162A
  申请人：——

  公开号：US5175162A

  公开（公告）日：1992-12-29
• US5329016A
  申请人：——

  公开号：US5329016A

  公开（公告）日：1994-07-12
• Synthesis and structure-activity analysis of 2-(4-chlorophenyl)-5,6-dihydrothieno[2′,3′:2,3]thiepino[4,5-c]pyridazin-3(2H)-ones as ligands for benzodiazepine receptors
  作者：H Tanaka、S Kirihara、H Yasumatsu、T Yakushiji、T Nakao

  DOI：10.1016/0223-5234(96)88305-x

  日期：1995.1

  A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones were synthesized and evaluated in vitro for their affinity tow-ard benzodiazepine receptors (BZRs) in rats and for their intrinsic efficacy in the augmentation of the gamma-aminobutyric acid (GABA)-induced chloride currents in the dissociated frog sensory neurons. Compounds in which the 9-position of the condensed-ring system was substituted with alkyl group or bromine had a high affinity toward BZRs. The substituents at the same position also influenced significantly the GABA-induced chloride currents. As the result, 9-alkyl and 9-bromo substituents would interact with the lipophilic area of BZRs. A series of 2-(4-chlorophenyl)-5,6-dihydrothieno[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-ones exhibited partial and full agonistic activities toward BZRs.