2-(4-chlorophenyl)-10-propionyl-5,6-dihydro<1>benzothiepino<5,4-c>pyridazin-3(2H)-one | 149139-07-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并硫平类
• 英文名称: 2-(4-chlorophenyl)-10-propionyl-5,6-dihydro<1>benzothiepino<5,4-c>pyridazin-3(2H)-one
• 英文别名: 2-(4-Chlorophenyl)-10-propanoyl-5,6-dihydro-[1]benzothiepino[5,4-c]pyridazin-3-one
• CAS: 149139-07-1
• 化学式: C₂₁H₁₇ClN₂O₂S
• 分子量: 396.897
• InChiKey: BRZIBOBPCOVJHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  75
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-chlorophenyl)-10-propionyl-5,6-dihydro<1>benzothiepino<5,4-c>pyridazin-3(2H)-one 在 三乙基硅烷 、 双氧水 作用下， 以 溶剂黄146 、 三氟乙酸 为溶剂， 反应 21.0h， 生成 2-(4-chlorophenyl)-10-propyl-5,6-dihydro<1>benzothiepino<5,4-c>pyridazin-3(2H)-one 7-oxide
  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：

  丙酰氯 、 2-(4-chlorophenyl)-5,6-dihydro-[1]benzothiepino[5,4-c]-pyridazin-3(2H)-one 在 三氯化铝 作用下， 生成 2-(4-chlorophenyl)-10-propionyl-5,6-dihydro<1>benzothiepino<5,4-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

• FUSED PYRIDAZINE COMPOUND AND PHARMACEUTICAL USE THEREOF
  申请人：YOSHITOMI PHARMACEUTICAL INDUSTRIES, LTD.

  公开号：EP0601184A1

  公开（公告）日：1994-06-15

  A fused pyridazine compound represented by the general formula (I) and an antianxiety drug containing the same as the active ingredient: wherein R¹ represents carboxyl, formyl, cyano, hydroxy-iminomethyl, acyl, etc.; R² represents hydrogen, C₁ to C₈ alkyl, hydroxyalkyl, alkanoyloxyalkyl, aryl, aralkyl, heteroaryl, etc.; A represents sulfur or -CH=CH-; E represents -CH₂- or -S(O)m-, wherein m represents 0, 1 or 2; n represents 1 or 2; and the bond represented by both solid and broken lines is either a single or a double bond; provided that when A represents sulfur, E represents -CH₂-, while when A represents -CH=CH-, E represents -S(O)m-, wherein m represents 0, 1 or 2, and n represents 2. This compound is reduced in side effects such as muscular relaxation, anesthesia potentiation, sedation, sleep/alcohol potentiation, etc., thus being useful as an antianxiety drug which selectively acts against anxiety.

  一种由通式(I)代表的融合哒嗪化合物和一种以其为有效成分的抗焦虑药物： 其中R¹代表羧基、甲酰基、氰基、羟基亚氨甲基、酰基等；R²代表氢、C₁至C₈烷基、羟基烷基、烷酰氧基烷基、芳基、芳烷基、杂芳基等。A代表硫或-CH＝CH-；E代表-CH₂-或-S(O)m-，其中m代表0、1或2；n代表1或2；实线和断线所代表的键为单键或双键；条件是当A代表硫时，E代表-CH₂-，而当A代表-CH＝CH-时，E代表-S(O)m-，其中m代表0、1或2，n代表2。这种化合物可减少副作用，如肌肉松弛、麻醉增效、镇静、睡眠/酒精增效等，因此可作为抗焦虑药物，选择性地对抗焦虑。
• 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.