2-(4-Chlorophenyl)-9-ethyl-4,4a,5,6-tetrahydrothieno-[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one | 135279-22-0

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 2-(4-Chlorophenyl)-9-ethyl-4,4a,5,6-tetrahydrothieno-[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one
• 英文别名: 2-(4-chlorophenyl)-9-ethyl-4,4a,5,6-tetrahydrothieno[2',3':2,3]thiepino[4,5-c]-pyridazin-3(2H)-one；13-(4-Chlorophenyl)-4-ethyl-5,7-dithia-13,14-diazatricyclo[8.4.0.02,6]tetradeca-1(14),2(6),3-trien-12-one
• CAS: 135279-22-0
• 化学式: C₁₈H₁₇ClN₂OS₂
• 分子量: 376.931
• InChiKey: KDPXFTDJGDTNHQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.2
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-Chlorophenyl)-9-ethyl-4,4a,5,6-tetrahydrothieno-[2',3':2,3]thiepino[4,5-c]pyridazin-3(2H)-one 在 氢溴酸 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 溶剂黄146 、 二甲基亚砜 为溶剂， 反应 5.5h， 生成 2-(4-chlorophenyl)-9-ethyl-5,6-dihydrothieno[2',3':2,3]thiepino-[4,5-c]pyridazin-3(2H)-one 7,7-dioxide
  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-(2-ethyl-4-oxo-6,7-dihydro-5H-thieno[2,3-b]thiepin-5-yl)acetonitrile 在 盐酸 、 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 反应 22.0h， 生成 2-(4-Chlorophenyl)-9-ethyl-4,4a,5,6-tetrahydrothieno-[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

文献信息

• Thiophene compounds and their pharmaceutical uses
  申请人：Yoshitiomi Pharmaceutical Industries Ltd.

  公开号：US05175162A1

  公开（公告）日：1992-12-29

  Thiophene compounds of the formula: ##STR1## wherein R.sup.1 is hydrogen, nitro, amino, halogen or C.sub.1-4 alkyl; R.sup.2 is hydrogen, nitro, amino, halogen, C.sub.1-4 alkyl, C.sub.1-4 haloalkyl, acyl, C.sub.2-5 alkoxycarbonyl, C.sub.1-4 alkoxy-C.sub.1-4 alkyl, aryloxy-C.sub.1-4 alkyl, acyloxy-C.sub.1-4 alkyl, hydroxy-C.sub.1-4 alkyl, acyloxy-C.sub.2-5 alkanoyl, C.sub.1-4 alkoxy-C.sub.2-5 alkanoyl, hydroxy-C.sub.2-5 alkanoyl, aryloxy-C.sub.2-5 alkanoyl or C.sub.2-5 haloalkanoyl; R.sup.3 is hydrogen, C.sub.1-8 alkyl, hydroxy-C.sub.1-4 alkyl, C.sub.2-5 alkanoyloxy-C.sub.1-4 alkyl, aryl, aryl-C.sub.1-4 alkyl, heteroaryl, heteroaryl-C.sub.1-4 alkyl or aryl, aryl-C.sub.1-4 alkyl, heteroaryl or heteroaryl-C.sub.1-4 alkyl substituted by at least one substituent selected from the group consisting of halogen, hydroxy, amino, nitro, cyano, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, C.sub.2-5 alkanoylamino, C.sub.1-4 haloalkyl, acyloxy, C.sub.2-5 alkoxycarbonyl and carboxyl on the aromatic ring; m is 0, 1 or 2; n is 1 or 2; the bond represented by.sub.---- 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).

  公式：##STR1## 其中R.sup.1是氢、硝基、氨基、卤素或C.sub.1-4烷基；R.sup.2是氢、硝基、氨基、卤素、C.sub.1-4烷基、C.sub.1-4卤代烷基、酰基、C.sub.2-5烷氧羰基、C.sub.1-4烷氧基-C.sub.1-4烷基、芳氧基-C.sub.1-4烷基、酰氧基-C.sub.1-4烷基、羟基-C.sub.1-4烷基、酰氧-C.sub.2-5脂肪酰基、C.sub.1-4烷氧基-C.sub.2-5脂肪酰基、羟基-C.sub.2-5脂肪酰基、芳氧基-C.sub.2-5脂肪酰基或C.sub.2-5卤代脂肪酰基；R.sup.3是氢、C.sub.1-8烷基、羟基-C.sub.1-4烷基、C.sub.2-5酰氧基-C.sub.1-4烷基、芳基、芳基-C.sub.1-4烷基、杂芳基、杂芳基-C.sub.1-4烷基或被选自卤素、羟基、氨基、硝基、氰基、C.sub.1-4烷基、C.sub.1-4烷氧基、C.sub.2-5烷氧羰基、C.sub.1-4卤代烷基、酰氧基、C.sub.2-5烷氧羰基和羧基的至少一种取代的芳环上的杂芳基、杂芳基-C.sub.1-4烷基、芳基或芳基-C.sub.1-4烷基；m为0、1或2；n为1或2；.sub.---- 表示单键或双键。化合物（I）用作抗焦虑药、催眠药、抗癫痫药或智力药。化合物（II）用作所述化合物（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.