trans 2-[3-[4-[(5-methoxycarbonylmethyl)benzoxazol-2-yl]-3-fluorophenyl]]propenoic acid | 695188-23-9

• 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-[3-[4-[(5-methoxycarbonylmethyl)benzoxazol-2-yl]-3-fluorophenyl]]propenoic acid
• 英文别名: (E)-3-[3-fluoro-4-[5-(2-methoxy-2-oxoethyl)-1,3-benzoxazol-2-yl]phenyl]prop-2-enoic acid
• CAS: 695188-23-9
• 化学式: C₁₉H₁₄FNO₅
• 分子量: 355.322
• InChiKey: LGRNJZBVNIZETE-QPJJXVBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  26
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  89.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  trans 2-[3-[4-[(5-methoxycarbonylmethyl)benzoxazol-2-yl]-3-fluorophenyl]]propenoic acid 在 lithium hydroxide 、 草酰氯 、 三乙胺 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 为溶剂， 生成 trans 2-[4-[3-(2,4-dichlorophenylamino)-3-oxo-1-propenyl]-2-fluorophenyl]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
• 作为产物：
  描述：

  4-羟基-3-硝基苯乙酸 在 palladium on activated charcoal 盐酸 、 palladium diacetate 、 氢气 、 三乙胺 、 三(邻甲基苯基)磷 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 trans 2-[3-[4-[(5-methoxycarbonylmethyl)benzoxazol-2-yl]-3-fluorophenyl]]propenoic 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

• 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.