trans 2-[4-[3-(4-bromophenyl)-2-propenamido]phenyl]benzoxazol-5-ylacetic acid

• 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: trans 2-[4-[3-(4-bromophenyl)-2-propenamido]phenyl]benzoxazol-5-ylacetic acid
• 英文别名: 2-(2-(4-(3-(4-Bromophenyl)acrylamido)phenyl)benzo[d]oxazol-5-yl)acetic acid；2-[2-[4-[[(E)-3-(4-bromophenyl)prop-2-enoyl]amino]phenyl]-1,3-benzoxazol-5-yl]acetic acid
• 化学式: C₂₄H₁₇BrN₂O₄
• 分子量: 477.314
• InChiKey: AAEYZBWTBCAWLV-UUILKARUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 palladium on activated charcoal 盐酸 、 lithium hydroxide 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 生成 trans 2-[4-[3-(4-bromophenyl)-2-propenamido]phenyl]benzoxazol-5-ylacetic acid
  参考文献：
  名称：

  Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: novel classes of heparanase inhibitor

  摘要：

  Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of similar to 200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1-propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.03.014

文献信息

• [EN] BENZOXAZOLE, BENZTHIAZOLE AND BENZIMIDAZOLE ACID DERIVATIVES AND THEIR USE AS HEPARANASE INHIBITORS<br/>[FR] DERIVES D'ACIDES DE BENZOXAZOLE, DE BENZOTHIAZOLE, ET DE BENZIMIDAZOLE PHARMACEUTIQUEMENT ACTIFS
  申请人：OXFORD GLYCOSCIENCES UK LTD

  公开号：WO2004046122A2

  公开（公告）日：2004-06-03

  Compounds of formula (I): wherein R1, R2 and R3 are independently, hydrogen, halogen, CF3, OR6, NR7R8, NR8COR10, NR8SO2R10 or C1-6 alkyl optionally substituted by hydroxy, C1-6 alkoxy or NR7R8; R4 is NR8CONR8R9, NR8COR9, NR8SO2R9, or W-CONR8R9, where W is a bond, C1-6 alkylene, C2-6 alkenylene or C2-6 alkynylene; and R5 is Formula (A) methods for their synthesis, pharmaceutical compositions comprising them and their use in medicine, in particular for the treatment of cancer.
• Furanyl-1,3-thiazol-2-yl and benzoxazol-5-yl acetic acid derivatives: novel classes of heparanase inhibitor
  作者：Stephen M. Courtney、Philip A. Hay、Richard T. Buck、Claire S. Colville、David J. Phillips、David I.C. Scopes、Faye C. Pollard、Martin J. Page、James M. Bennett、Margaret L. Hircock、Edward A. McKenzie、Maina Bhaman、Robert Felix、Colin R. Stubberfield、Paul R. Turner

  DOI：10.1016/j.bmcl.2005.03.014

  日期：2005.5

  Using a furanylthiazole acetic acid as a starting point, a novel series of benzoxazol-5-yl acetic acid derivatives have been identified as heparanase inhibitors. Several compounds possess an IC50 of similar to 200 nM against heparanase, for example, trans 2-[4-[3-(3,4-dichlorophenylamino)-3-oxo-1-propenyl]-2-fluorophenyl]benzoxazol-5-yl acetic acid (16e). Several of the compounds show anti-angiogenic properties. Improvement to the DMPK profile of compounds has provided compounds of potential use in in vivo models. (c) 2005 Elsevier Ltd. All rights reserved.