3-氨基-4-氯苯并[b]噻吩-2-羧酸乙酯 | 67189-92-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 中文名称: 3-氨基-4-氯苯并[b]噻吩-2-羧酸乙酯
• 英文名称: 4-chloro-3-amino-2-carboethoxybenzothiophene
• 英文别名: Ethyl-4-chlor-3-aminobenzothiophen-2-carboxylat；3-amino-4-chloro-benzo[b]thiophene-2-carboxylic acid ethyl ester；3-amino-4-chloro-benzothiophene-2-carboxylic acid ethyl ester；Ethyl 3-amino-4-chloro-1-benzothiophene-2-carboxylate
• CAS: 67189-92-8
• 化学式: C₁₁H₁₀ClNO₂S
• 分子量: 255.725
• InChiKey: YGLSXTDCHUONFR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  80.6
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险品标志：
  Xi
• 安全说明：
  S26,S37/39
• 危险类别码：
  R36/37/38
• 海关编码：
  2934999090
• 危险性防范说明：
  P264,P280,P337+P313,P305+P351+P338,P302+P352,P332+P313,P362
• 危险性描述：
  H315,H319

反应信息

• 作为反应物：
  描述：

  3-氨基-4-氯苯并[b]噻吩-2-羧酸乙酯 以 甲苯 为溶剂， 反应 6.0h， 生成 3-[2-[(3aR,9bR)-6-methoxy-1,3,3a,4,5,9b-hexahydrobenzo[e]isoindol-2-yl]ethyl]-9-chloro-1H-[1]benzothiolo[3,2-d]pyrimidine-2,4-dione
  参考文献：
  名称：

  Structure−Activity Studies for a Novel Series of Tricyclic Substituted Hexahydrobenz[e]isoindole α_1A Adrenoceptor Antagonists as Potential Agents for the Symptomatic Treatment of Benign Prostatic Hyperplasia (BPH)

  摘要：

  In search of a uroselective agent that exhibits a high level of selectivity for the alpha(1A) receptor, a novel series of tricyclic hexahydrobenz[e]isoindoles was synthesized. A generic pharmacophoric model was developed requiring the presence of a basic amine core and a fused heterocyclic side chain separated by an alkyl chain. It was shown that the 6-OMe substitution with R, R stereochemistry of the ring junction of the benz[e]isoindole and a two-carbon spacer chain were optimal. In contrast to the highly specific requirements for the benz[e]isoindole portion and linker chain, a wide variety of tricyclic fused heterocyclic attachments were tolerated with retention of potency and selectivity. In vitro functional assays for the alpha(1) adrenoceptor subtypes were used to further characterize these compounds, and in vivo models of vascular vs prostatic tone were used to assess uroselectivity.

  DOI：

  10.1021/jm990567u