ethyl (E)-2-(3-(3,4-dimethoxyphenyl)acryloyl)benzo[b]thiophene-5-carboxylate | 1207537-64-1

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: ethyl (E)-2-(3-(3,4-dimethoxyphenyl)acryloyl)benzo[b]thiophene-5-carboxylate
• 英文别名: ethyl 2-[(E)-3-(3,4-dimethoxyphenyl)prop-2-enoyl]-1-benzothiophene-5-carboxylate
• CAS: 1207537-64-1
• 化学式: C₂₂H₂₀O₅S
• 分子量: 396.464
• InChiKey: VINKPGMVFBXBOF-VMPITWQZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  90.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-乙酰基苯并[b]噻吩-5-羧酸甲酯 、 sodium ethanolate 、 3,4-二甲氧基苯甲醛 以 乙醇 为溶剂， 以10%的产率得到ethyl (E)-2-(3-(3,4-dimethoxyphenyl)acryloyl)benzo[b]thiophene-5-carboxylate
  参考文献：
  名称：

  Substituted Benzothiophene or Benzofuran Derivatives as a Novel Class of Bone Morphogenetic Protein-2 Up-Regulators: Synthesis, Structure−Activity Relationships, and Preventive Bone Loss Efficacies in Senescence Accelerated Mice (SAMP6) and Ovariectomized Rats

  摘要：

  In this work, substituted benzothiophene and benzofuran compounds were found to be a new class of potential anabolic agents by enhancing BMP-2 expression. A series of benzothiophene and benzofuran derivatives have been synthesized, and their activities of up-regulating BMP-2 and bone loss prevention efficacies in SAMP6 mice and OVX rats have been studied. Benzothiophenes 1, 3, 14, 4a, 7a, 8a, and benzofuran analogue 2 showed higher BMP-2 up-regulation rates in vitro. Compound 8111 was found to significantly affect the bone formation rate of tested SAMP6 mice. Compound I showed an improved bone quality in SAMP6 mice and also showed activity in OVX rats. We have demonstrated that Substituted benzothiophene and benzofuran derivatives, especially compounds I and 8a, enhance BMP-2 expression in vitro and in vivo and stimulate bone formation and trabecular connectivity restoration ill vivo. The compounds represent potential leads in the development of a new class of anabolic agents.

  DOI：

  10.1021/jm901685n

文献信息

• [EN] BENZO 5-MEMBERED UNSATURATED HETEROCYCLIC COMPOUNDS AND PREPARATION METHODS THEREOF<br/>[FR] COMPOSÉS DE BENZO HÉTÉROCYCLIQUES INSATURÉS À 5 ÉLÉMENTS ET PROCÉDÉS POUR LES PRÉPARER
  申请人：INST MED BIOTECHNOLOGY CAMS

  公开号：WO2012068702A1

  公开（公告）日：2012-05-31

  Disclosed are benzo 5-membered unsaturated heterocyclic compounds represented by formula I and their pharmaceutically acceptable salts, preparation methods and uses thereof in the preparation of the drugs for treating osteoporosis, wherein each substituent of formula (I) is defined as the description.