ethyl 3-(4'-chlorophenyl)imidazo<2,1-b>thiazole-6-carboxylate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并噻唑类
• 英文名称: ethyl 3-(4'-chlorophenyl)imidazo<2,1-b>thiazole-6-carboxylate
• 英文别名: 3-(4-Chlorophenyl)imidazo[2,1-b]thiazole-6-carboxylic acid ethyl ester；ethyl 3-(4-chlorophenyl)imidazo[2,1-b][1,3]thiazole-6-carboxylate
• 化学式: C₁₄H₁₁ClN₂O₂S
• 分子量: 306.773
• InChiKey: UIFRACWFWQZEMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-(4'-chlorophenyl)imidazo<2,1-b>thiazole-6-carboxylate 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以79.2%的产率得到3-(4'-chlorophenyl)imidazo<2,1-b>thiazole-6-carboxylic acid
  参考文献：
  名称：

  Research on heterocyclic compounds. XXXIV. Synthesis and SAR study of some imidazo[2,1-b]thiazole carboxylic and acetic acids with antiinflammatory and analgesic activities

  摘要：

  DOI：

  10.1016/0223-5234(96)88309-7
• 作为产物：
  描述：

  2-氨基-4-(4-氯苯基)噻唑 、 3-溴丙酮酸乙酯 生成 ethyl 3-(4'-chlorophenyl)imidazo<2,1-b>thiazole-6-carboxylate
  参考文献：
  名称：

  Synthesis and benzodiazepine receptor binding of some imidazoand pyrimido[2,1-b]benzothiazoles

  摘要：

  A series of substituted imidazo[2,1-b]benzothiazoles 2a-u was synthesized and the compounds evaluated for their affinity at the central benzodiazepine receptors. Substitution at the 7-position generally resulted in a decreased ligand affinity whereas a significant increase was observed for 5-substituted compounds. The intrinsic efficacy of selected high-affinity ligands 2j,k,q, as well as some previously reported pyrimido[2,1-b]benzothiazoles 1, was measured in vitro through the determination of the GABA ratio and [S-35]TBPS displacement. Consistent with a partial inverse agonist profile, the benzothiazole derivatives 2j,k,q increased [S-35]TBPS binding. For compounds 1c and 1d, a discrepancy between GABA ratio and [S-35]TBPS binding data was observed. Only the latter assay was in full agreement with the pharmacological data, which indicated an inverse agonist and a partial agonist profile for 2k,q and 1c,d respectively. The affinity and intrinsic activity data of compounds 1c,d and 2j,k,q are discussed in the light of the recently proposed pharmacophore model by Skolnick/Cook; in particular, the agonistic activity of 1c,d is interpreted on the basis of a possible interaction of substitutents in position 6 with the receptors lipophilic area L3 of Skolnick/Cook, whereas the observed inverse agonist profile of 2j,k,q is explained taking into account their structural analogy with the well known proconvulsant beta-CCE.

  DOI：

  10.1016/0223-5234(96)89553-5

文献信息

• Research on heterocyclic compounds. XXXIV. Synthesis and SAR study of some imidazo[2,1-b]thiazole carboxylic and acetic acids with antiinflammatory and analgesic activities
  作者：F Palagiano、L Arenare、E Luraschi、P de Caprariis、E Abignente、M D'Amico、W Filippelli、F Rossi

  DOI：10.1016/0223-5234(96)88309-7

  日期：1995.1
• Synthesis and benzodiazepine receptor binding of some imidazoand pyrimido[2,1-b]benzothiazoles
  作者：G Trapani、M Franco、A Latrofa、A Carotti、G Gerichi、M Serra、G Biggio、G Liso

  DOI：10.1016/0223-5234(96)89553-5

  日期：1996.1

  A series of substituted imidazo[2,1-b]benzothiazoles 2a-u was synthesized and the compounds evaluated for their affinity at the central benzodiazepine receptors. Substitution at the 7-position generally resulted in a decreased ligand affinity whereas a significant increase was observed for 5-substituted compounds. The intrinsic efficacy of selected high-affinity ligands 2j,k,q, as well as some previously reported pyrimido[2,1-b]benzothiazoles 1, was measured in vitro through the determination of the GABA ratio and [S-35]TBPS displacement. Consistent with a partial inverse agonist profile, the benzothiazole derivatives 2j,k,q increased [S-35]TBPS binding. For compounds 1c and 1d, a discrepancy between GABA ratio and [S-35]TBPS binding data was observed. Only the latter assay was in full agreement with the pharmacological data, which indicated an inverse agonist and a partial agonist profile for 2k,q and 1c,d respectively. The affinity and intrinsic activity data of compounds 1c,d and 2j,k,q are discussed in the light of the recently proposed pharmacophore model by Skolnick/Cook; in particular, the agonistic activity of 1c,d is interpreted on the basis of a possible interaction of substitutents in position 6 with the receptors lipophilic area L3 of Skolnick/Cook, whereas the observed inverse agonist profile of 2j,k,q is explained taking into account their structural analogy with the well known proconvulsant beta-CCE.