(E)-4-(2-(4-bromobenzylthio)-3-(4-fluoro-3-nitrophenyl)acryloyl)-N-(2-(diethylamino)ethyl)benzamide | 1035200-43-1

• 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: (E)-4-(2-(4-bromobenzylthio)-3-(4-fluoro-3-nitrophenyl)acryloyl)-N-(2-(diethylamino)ethyl)benzamide
• 英文别名: (E)-1-(4-(2-(N,N-diethylamino)ethylcarbamoyl)phenyl)-2-(4-bromophenylmethylsulfenyl)-3-(4-fluoro-3-nitrophenyl)prop-2-en-1-one；(E)-4-(2-(4-Bromobenzylthio)-3-(4-fluoro-3-nitrophenyl)-acryloyl)-N-(2-(diethylamino)ethyl)benzamide；4-[(E)-2-[(4-bromophenyl)methylsulfanyl]-3-(4-fluoro-3-nitrophenyl)prop-2-enoyl]-N-[2-(diethylamino)ethyl]benzamide
• CAS: 1035200-43-1
• 化学式: C₂₉H₂₉BrFN₃O₄S
• 分子量: 614.535
• InChiKey: PMXPPBGETIGOHR-OVVQPSECSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  39
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (E)-4-(2-(4-bromobenzylthio)-3-(4-fluoro-3-nitrophenyl)acryloyl)benzoic acid 、 N,N-二乙基乙二胺 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到(E)-4-(2-(4-bromobenzylthio)-3-(4-fluoro-3-nitrophenyl)acryloyl)-N-(2-(diethylamino)ethyl)benzamide
  参考文献：
  名称：

  Design, synthesis and evaluation of (E)-α-benzylthio chalcones as novel inhibitors of BCR-ABL kinase

  摘要：

  Novel (E)-alpha-benzylthio chalcones are reported with preliminary in vitro activity data indicating that several of them are potent inhibitors (comparable to imatinib, the reference compound) of BCR-ABL phosphorylation in leukemic K562 cells, known to express high levels of BCR-ABL. The ability of such compounds to significantly inhibit K562 cell proliferation suggests that this scaffold could be a promising lead for the development of anticancer agents that are able to block BCR-ABL phosphorylation in leukemic cells. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.01.051

文献信息

• SULFIDE, SULFOXIDE AND SULFONE CHALCONE ANALOGUES, DERIVATIVES THEREOF AND THERAPEUTIC USES THEREOF
  申请人：Reddy E. Premkumar

  公开号：US20100028368A1

  公开（公告）日：2010-02-04

  Compounds useful as antiproliferative agents according to formula (I): wherein Ar 1 , Ar 2 , Ar 3 , m and n are as defined herein, salts, antibody conjugates, pharmaceutical compositions, methods of treatment, and synthetic methods are provided.

  提供了按照公式（I）定义的有用的抗增殖剂化合物，其中Ar1，Ar2，Ar3，m和n的定义如此，还提供了盐，抗体结合物，药物组合物，治疗方法和合成方法。
• US8808702B2
  申请人：——

  公开号：US8808702B2

  公开（公告）日：2014-08-19
• [EN] SULFIDE, SULFOXIDE AND SULFONE CHALCONE ANALOGUES, DERIVATIVES THEREOF AND THERAPEUTIC USES THEREOF<br/>[FR] ANALOGUES DE SULFURE, SULFOXYDE ET SULFONE DE CHALCONE, LEURS DÉRIVÉS ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：UNIV TEMPLE

  公开号：WO2008076270A2

  公开（公告）日：2008-06-26

  [EN] Compounds useful as antiproliferative agents according to formula (I): wherein Ar¹, Ar², Ar³, m and n are as defined herein, salts, antibody conjugates, pharmaceutical compositions, methods of treatment, and synthetic methods are provided.
  [FR] La présente invention a pour objet des composés utiles en tant qu'agents antiprolifératifs selon la formule (I): dans laquelle Ar¹, Ar², Ar³, m et n sont tels que définis dans la présente description, des sels, des conjugués d'anticorps, des compositions pharmaceutiques, des procédés de traitement et des procédés de synthèse.
• Design, synthesis and evaluation of (E)-α-benzylthio chalcones as novel inhibitors of BCR-ABL kinase
  作者：M.V. Ramana Reddy、Venkat R. Pallela、Stephen C. Cosenza、Muralidhar R. Mallireddigari、Revathi Patti、Marie Bonagura、May Truongcao、Balaiah Akula、Shashidhar S. Jatiani、E. Premkumar Reddy

  DOI：10.1016/j.bmc.2010.01.051

  日期：2010.3

  Novel (E)-alpha-benzylthio chalcones are reported with preliminary in vitro activity data indicating that several of them are potent inhibitors (comparable to imatinib, the reference compound) of BCR-ABL phosphorylation in leukemic K562 cells, known to express high levels of BCR-ABL. The ability of such compounds to significantly inhibit K562 cell proliferation suggests that this scaffold could be a promising lead for the development of anticancer agents that are able to block BCR-ABL phosphorylation in leukemic cells. (C) 2010 Elsevier Ltd. All rights reserved.