2-[(2-chloro-4-amino)phenyl]-5-benzoxazoleacetic acid methyl ester | 695186-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-[(2-chloro-4-amino)phenyl]-5-benzoxazoleacetic acid methyl ester
• 英文别名: Methyl 2-[2-(4-amino-2-chlorophenyl)-1,3-benzoxazol-5-yl]acetate
• CAS: 695186-49-3
• 化学式: C₁₆H₁₃ClN₂O₃
• 分子量: 316.744
• InChiKey: BSQLJWRFSNPVCM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  78.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-[(2-chloro-4-amino)phenyl]-5-benzoxazoleacetic acid methyl ester 在 lithium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-[2-chloro-4-[(4-bromo)phenylacryloylamino]phenyl]-5-benzoxazoleacetic 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 、 氢气 、 对甲苯磺酸 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 乙酸乙酯 、 甲苯 为溶剂， 生成 2-[(2-chloro-4-amino)phenyl]-5-benzoxazoleacetic acid methyl ester
  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：WO2004046122A3

  公开（公告）日：2004-07-15