4-[3-(4-bromophenyl)-3-oxo-propenyl]benzoic acid

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 直链 1,3-二芳基丙烷
• 英文名称: 4-[3-(4-bromophenyl)-3-oxo-propenyl]benzoic acid
• 英文别名: 4-[3-(4-Bromophenyl)-3-oxoprop-1-enyl]benzoic acid
• 化学式: C₁₆H₁₁BrO₃
• 分子量: 331.166
• InChiKey: BQHZMCMKLCBBRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-[3-(4-bromophenyl)-3-oxo-propenyl]benzoic acid 在 4-二甲氨基吡啶 、 一水合肼 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-(1-acetyl-3-(4-bromophenyl)-4,5-dihydro-1H-pyrazol-5-yl)benzoate
  参考文献：
  名称：

  Design, synthesis and biological evaluation of pyrazolyl-nitroimidazole derivatives as potential EGFR/HER-2 kinase inhibitors

  摘要：

  A series of novel pyrazole-nitroimidazole derivatives had been arranged and evaluated for their EGFR/HER-2 tyrosine kinase inhibitory activity as well as their antiproliferative properties on four kinds of cancer cell lines (MCF-7, Hela, HepG2, B16-F10). The bioassay results showed most of the designed compounds exhibited potential antiproliferation activity, with the IC50 values ranging from 0.13 mu M to 128.06 mu M in four tumor cell lines. Among them, compound 5c exhibited remarkable inhibitory activity against EGFR/HER-2 tyrosine kinase with IC50 value of 0.26 mu M/0.51 mu M, respectively, comparable to the positive control erlotinib (IC50 = 0.41 mu M for HER-2 and IC50 = 0.20 mu M for EGFR) and lapatinib (IC50 = 0.54 mu M for HER-2 and IC50 = 0.28 mu M for EGFR). Molecular modeling simulation studies were performed in order to predict the biological activity of the proposed compounds and activity relationship (SAR) of these pyrazole-nitroimidazole derivatives. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2015.11.040
• 作为产物：
  描述：

  4-溴苯乙酮 、 对醛基苯甲酸 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 以77%的产率得到4-[3-(4-bromophenyl)-3-oxo-propenyl]benzoic acid
  参考文献：
  名称：

  伪天然产品Rhonin 针对 RHOGDI

  摘要：

  据报道，伪天然产物罗宁 (Rhonin) 被鉴定为 RHO GDP 解离抑制剂 (RHOGDI) 的第一个小分子调节剂。 Rhonin 与 RHOGDI 结合，并通过破坏 RHOGDI 和 RHO GTPases 之间的相互作用来干扰其功能。

  DOI：

  10.1002/anie.202115193

文献信息

• The Pseudo‐Natural Product Rhonin Targets RHOGDI
  作者：Mohammad Akbarzadeh、Jana Flegel、Sumersing Patil、Erchang Shang、Rishikesh Narayan、Marcel Buchholzer、Neda S. Kazemein Jasemi、Michael Grigalunas、Adrian Krzyzanowski、Daniel Abegg、Anton Shuster、Marco Potowski、Hacer Karatas、George Karageorgis、Niloufar Mosaddeghzadeh、Mia‐Lisa Zischinsky、Christian Merten、Christopher Golz、Lucas Brieger、Carsten Strohmann、Andrey P. Antonchick、Petra Janning、Alexander Adibekian、Roger S. Goody、Mohammad Reza Ahmadian、Slava Ziegler、Herbert Waldmann

  DOI：10.1002/anie.202115193

  日期：2022.4.25

  The identification of the pseudo-natural product Rhonin as the first small-molecule modulator of RHO GDP dissociation inhibitor (RHOGDI) is reported. Rhonin binds to RHOGDI and interferes with its function by disrupting the interaction between RHOGDI and RHO GTPases.

  据报道，伪天然产物罗宁 (Rhonin) 被鉴定为 RHO GDP 解离抑制剂 (RHOGDI) 的第一个小分子调节剂。 Rhonin 与 RHOGDI 结合，并通过破坏 RHOGDI 和 RHO GTPases 之间的相互作用来干扰其功能。
• Design, synthesis and biological evaluation of pyrazolyl-nitroimidazole derivatives as potential EGFR/HER-2 kinase inhibitors
  作者：Xiang-Xiang Tao、Yong-Tao Duan、Long-Wang Chen、Dan-Jie Tang、Meng-Ru Yang、Peng-Fei Wang、Chen Xu、Hai-Liang Zhu

  DOI：10.1016/j.bmcl.2015.11.040

  日期：2016.1

  A series of novel pyrazole-nitroimidazole derivatives had been arranged and evaluated for their EGFR/HER-2 tyrosine kinase inhibitory activity as well as their antiproliferative properties on four kinds of cancer cell lines (MCF-7, Hela, HepG2, B16-F10). The bioassay results showed most of the designed compounds exhibited potential antiproliferation activity, with the IC50 values ranging from 0.13 mu M to 128.06 mu M in four tumor cell lines. Among them, compound 5c exhibited remarkable inhibitory activity against EGFR/HER-2 tyrosine kinase with IC50 value of 0.26 mu M/0.51 mu M, respectively, comparable to the positive control erlotinib (IC50 = 0.41 mu M for HER-2 and IC50 = 0.20 mu M for EGFR) and lapatinib (IC50 = 0.54 mu M for HER-2 and IC50 = 0.28 mu M for EGFR). Molecular modeling simulation studies were performed in order to predict the biological activity of the proposed compounds and activity relationship (SAR) of these pyrazole-nitroimidazole derivatives. (C) 2015 Elsevier Ltd. All rights reserved.