(E)-1-(benzofuran-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one | 1163744-36-2

• 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: (E)-1-(benzofuran-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one
• 英文别名: (E)-1-(1-benzofuran-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one
• CAS: 1163744-36-2
• 化学式: C₁₇H₁₁ClO₂
• 分子量: 282.726
• InChiKey: RPCFWFNIDTXDCX-MDZDMXLPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  30.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-(hydrazinocarbonylmethyl)-6H-indolo[2,3-b]quinoxaline 、 (E)-1-(benzofuran-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one 以 溶剂黄146 为溶剂， 反应 0.47h， 以92%的产率得到1-[5-(1-Benzofuran-2-yl)-3-(2-chlorophenyl)-3,4-dihydropyrazol-2-yl]-2-indolo[3,2-b]quinoxalin-6-ylethanone
  参考文献：
  名称：

  Microwave assisted synthesis of new indophenazine 1,3,5-trisubstruted pyrazoline derivatives of benzofuran and their antimicrobial activity

  摘要：

  2-[1-(5,8-Dihydro quinoxalino[2,3-b]indoloacetyl)-3-(1-benzofuran-2-yl)-4,5-dihydro-1H-pyrazol-5-yl] phenyl derivatives were synthesized from 2-(5,8-dihydro quinoxalino[2,3-b]indol-5-yl) acetohydrazide and (2E)-1-(1-benzofuran-2-yl)-4-phenylbut-2-en-1-ones derivatives using microwave-assisted route. The structures of all the compounds have been established on the basis of analytical and spectral data. Among the 14 compounds IPB-1, IPB-5, IPB-10, IPB-11 and IPB-12 were found good antibacterial activity and MICs were found bellow 10 mu g/mL against Escherichia coli, Pseudomonas aeruginosa and Streptococcus aureus, which can compared with sparfloxacin and norfloxacin. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.161
• 作为产物：
  描述：

  2-乙酰基苯并呋喃 、 2-氯苯甲醛 在 sodium ethanolate 作用下， 以 乙醇 为溶剂， 以61%的产率得到(E)-1-(benzofuran-2-yl)-3-(2-chlorophenyl)prop-2-en-1-one
  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