1-(4-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one | 1258952-00-9

• 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: 1-(4-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
• CAS: 1258952-00-9
• 化学式: C₁₅H₁₀BrClO₂
• 分子量: 337.6
• InChiKey: HWRQKFLAGDDJGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1-(4-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one 在 一水合肼 作用下， 反应 8.0h， 生成
  参考文献：
  名称：

  Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors

  摘要：

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.020
• 作为产物：
  描述：

  4-溴苯乙酮 、 5-氯代水杨醛 在 sodium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 生成 1-(4-bromophenyl)-3-(5-chloro-2-hydroxyphenyl)prop-2-en-1-one
  参考文献：
  名称：

  Synthesis, biological evaluation of novel 4,5-dihydro-2H-pyrazole 2-hydroxyphenyl derivatives as BRAF inhibitors

  摘要：

  A series of novel 4,5-dihydropyrazole derivatives (3a-3t) containing hydroxyphenyl moiety as potential V600E mutant BRAF kinase (BRAF(V600E)) inhibitors were designed and synthesized. Docking simulation was performed to insert compounds 3d (1-(5-(5-chloro-2-hydroxyphenyl)-3-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) and 3m (1-(3-(4-chlorophenyl)-5-(3,5-dibromo-2-hydroxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)ethanone) into the crystal structure of BRAF(V600E) to determine the probable binding model, respectively. Based on the preliminary results, compound 3d and 3m with potent inhibitory activity in tumor growth may be a potential anticancer agent. Results of the bioassays against BRAF(V600E), MCF-7 human breast cancer cell line and WM266.4 human melanoma cell line all showed several compounds had potent activities IC50 value in low micromolar range, among them, compound 3d and compound 3m showed strong potent anticancer activity, which were proved by that 3d: IC50 = 1.31 mu M for MCF-7 and IC50 = 0.45 mu M for WM266.5, IC50 = 0.22 mu M for BRAF(V600E), 3m: IC50 = 0.97 mu M for MCF-7 and IC50 = 0.72 mu M for WM266.5, IC50 = 0.46 mu M for BRAF(V600E), which were comparable with the positive control Erlotinib. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.08.020

文献信息

• Efficient Method for the Synthesis of Optically Active 2-Amino-2-chromene Derivatives via One-Pot Tandem Reactions
  作者：Jian-Wu Xie、Xiong Huang、Li-Ping Fan、Dong-Cheng Xu、Xin-Sheng Li、Hong Su、Yi-Hang Wen

  DOI：10.1002/adsc.200900579

  日期：2009.12

  The asymmetric synthesis of functionalized 2-amino-2-chromene derivatives with high enantioselectivities via one-pot tandem reactions of functionalized α,β-unsaturated ketones with malononitrile catalyzed by 9-amino-9-deoxyepiquinine (1a) in combination with (R)-1,1′-binaphth-2,2′-diyl hydrogen phosphate (1c) is reported for the first time.

  具有高对映选择性官能化的2-氨基-2-苯并吡喃衍生物的不对称合成通过官能化的α，β不饱和酮与丙二腈由9-氨基-9- deoxyepiquinine（催化的一锅串联反应1A组合地）与（[R ）首次报道了-1,1'-联萘-2,2'-二氢磷酸氢盐（1c）。
• 一种手性季碳恶唑啉酮化合物的合成方法
  申请人：苏州大学

  公开号：CN104447604B

  公开（公告）日：2016-08-24

  本发明公开了一种手性季碳恶唑啉酮化合物的合成方法，具体为以邻羟基查尔酮与吖内酯为反应物，在手性多功能手性奎宁硫脲催化下，在溶剂中合成得到产物。本发明公开的方法原料简单易得，反应条件温和，后处理简单方便，适用的底物范围广，收率高，对映选择性高；由此合成得到的产物可用以合成药物和杀虫剂的中间体。
• 一种手性3,4-二氢香豆素衍生化合物合成方 法
  申请人：苏州大学

  公开号：CN104860911B

  公开（公告）日：2017-03-22

  本发明公开了一种手性3，4‑二氢香豆素衍生化合物的合成方法，具体为以邻羟基查尔酮与吖内酯为反应物，在手性多功能手性奎宁硫脲催化下，在溶剂中合成得到产物。本发明公开的方法原料简单易得，反应条件温和，后处理简单方便，适用的底物范围广，收率高，对映选择性高；由此合成得到的产物可用以合成药物和杀虫剂的中间体。
• Asymmetric Synthesis of Dihydrocoumarins Containing Contiguous Quaternary and Tertiary Stereogenic Centers Catalyzed by a<i>Cinchona</i>-Alkaloid-Based Bifunctional Thiourea Derivative
  作者：Shao-Yun Zhang、Ming Lv、Shao-Jie Yin、Nai-Kai Li、Jun-Qi Zhang、Xing-Wang Wang

  DOI：10.1002/adsc.201500666

  日期：2016.1.7

  contiguous quaternary and tertiary stereogenic centers has been efficiently constructed via domino asymmetric Michael addition/transesterification reactions of azlactones with o‐hydroxychalcones using a quinine‐derived thiourea as bifunctional organocatalyst. Under mild reaction conditions, the optically active 3,4‐dihydrocoumarins were generally obtained in 63–96% yields with >20:1 dr and 81–96% ee.

  通过奎宁衍生的硫脲作为双功能有机催化剂，通过氮杂内酰胺与邻羟基查尔酮的多米诺不对称迈克尔加成/酯交换反应，已经有效地构建了一系列包含对映体的3,4-二氢香豆素，这些连续的季铵和叔立体构型中心。在温和的反应条件下，通常以63-96％的产率获得旋光的3,4-二氢香豆素，dr > 20：1 ，ee达到81-96％。