3-amino-2-carbomethoxy-4-cyanobenzothiophene | 181283-25-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻吩类
• 英文名称: 3-amino-2-carbomethoxy-4-cyanobenzothiophene
• 英文别名: 3-Amino-2-carbomethoxy-4-cyano-benzthiophene；Methyl 3-amino-4-cyano-1-benzothiophene-2-carboxylate
• CAS: 181283-25-0
• 化学式: C₁₁H₈N₂O₂S
• 分子量: 232.263
• InChiKey: MXNSKVQOUQDTGV-UHFFFAOYSA-N

物化性质

• 沸点：
  440.0±40.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-amino-2-carbomethoxy-4-cyanobenzothiophene 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]-2,4-dioxo-1H-[1]benzothiolo[3,2-d]pyrimidine-9-carbonitrile
  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
• 作为产物：
  描述：

  3-硝基邻苯二腈 、 巯基乙酸甲酯 在 sodium carbonate 作用下， 以 甲醇 为溶剂， 以47%的产率得到3-amino-2-carbomethoxy-4-cyanobenzothiophene
  参考文献：
  名称：

  Tricyclic substituted hexahydrobenz [e]isoindole alpha-1 adrenergic

  摘要：

  本发明涉及一种具有以下结构的化合物##STR1##及其药用可接受的盐，其中W是一个三环杂环环系统；它是一种α-1肾上腺素受体拮抗剂，对治疗BPH有用；还公开了α-1拮抗剂组合物和拮抗α-1受体并治疗BPH的方法。

  公开号：

  US05597823A1

文献信息

• TRICYCLIC SUBSTITUTED HEXAHYDROBENZ[E]ISOINDOLE ALPHA-1 ADRENERGIC ANTAGONISTS
  申请人：Abbott Laboratories

  公开号：EP0808318B1

  公开（公告）日：2000-06-28
• US5597823A
  申请人：——

  公开号：US5597823A

  公开（公告）日：1997-01-28