1-(4-chlorobenzo[b]thiophen-2-yl)-2-(methylsulfinyl)ethanone | 1207537-70-9

• 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: 1-(4-chlorobenzo[b]thiophen-2-yl)-2-(methylsulfinyl)ethanone
• 英文别名: 1-(4-Chlorobenzo[b]thien-2-yl)-2-(methylsulfinyl)ethanone；1-(4-chloro-1-benzothiophen-2-yl)-2-methylsulfinylethanone
• CAS: 1207537-70-9
• 化学式: C₁₁H₉ClO₂S₂
• 分子量: 272.776
• InChiKey: LRHFAAMLYNDUCD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 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：
  81.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  ethyl 4-chlorobenzo[b]thiophene-2-carboxylate 、 二甲基亚砜 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到1-(4-chlorobenzo[b]thiophen-2-yl)-2-(methylsulfinyl)ethanone
  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.
• 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
  作者：Hui-fang Guo、Hua-yi Shao、Zhao-yong Yang、Si-tu Xue、Xue Li、Zong-ying Liu、Xiao-bo He、Jian-dong Jiang、Yue-qin Zhang、Shu-yi Si、Zhuo-rong Li

  DOI：10.1021/jm901685n

  日期：2010.2.25

  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.