methyl 2-(4-nitrophenyl)benzoxazole-5-acetate | 695187-48-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: methyl 2-(4-nitrophenyl)benzoxazole-5-acetate
• 英文别名: 2-(4-nitrophenyl)benzoxazol-5-ylacetic acid methyl ester；Methyl 2-[2-(4-nitrophenyl)-1,3-benzoxazol-5-yl]acetate
• CAS: 695187-48-5
• 化学式: C₁₆H₁₂N₂O₅
• 分子量: 312.282
• InChiKey: HKMYJLZATLYVCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  23
• 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：
  98.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl 2-(4-nitrophenyl)benzoxazole-5-acetate 在 溶剂黄146 、 锌 作用下， 以 乙醇 为溶剂， 生成 methyl 2-(2-(4-aminophenyl)benzo[d]oxazol-5-yl)acetate
  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 作用下， 以 四氢呋喃 、 乙酸乙酯 、 甲苯 为溶剂， 生成 methyl 2-(4-nitrophenyl)benzoxazole-5-acetate
  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

• SYNTHESIS, CHARACTERIZATION AND BIOLOGICAL EVALUATION OF SOME 2-ARYLBENZOXAZOLE ACETIC ACID DERIVATIVES AS PROMISING ANTICANCER AGENTS
  作者：Qais Abualassal、Jamal Jilani、Areej Assaf、Reham Abu shmies

  DOI：10.32383/appdr/127998

  日期：2020.12.10
• [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.