2-甲基-4-苯基-5-恶唑羧酸 | 51143-21-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-甲基-4-苯基-5-恶唑羧酸
• 英文名称: 2-methyl-4-phenyloxazole-5-carboxylic acid
• 英文别名: 2-Methyl-4-phenyl-5-oxazolcarbonsaeure；2-Methyl-4-phenyl-5-oxazolcarboxylsaeure；2-Methyl-4-phenyl-1,3-oxazole-5-carboxylic acid
• CAS: 51143-21-6
• 化学式: C₁₁H₉NO₃
• 分子量: 203.197
• InChiKey: GCTADCJWXIPOCS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  63.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-甲基-4-苯基-5-恶唑羧酸 在 盐酸 、 戴斯-马丁氧化剂 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 N-[(2S)-4-amino-1-(4-hydroxyphenyl)-3,4-dioxobutan-2-yl]-2-methyl-4-phenyl-1,3-oxazole-5-carboxamide
  参考文献：
  名称：

  [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF
  [FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES

  摘要：

  公开号：

  WO2018064119A8
• 作为产物：
  描述：

  ethyl 2-methyl-4-phenyloxazole-5-carboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以80%的产率得到2-甲基-4-苯基-5-恶唑羧酸
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Aryloxazole Derivatives as Antimitotic and Vascular-Disrupting Agents for Cancer Therapy

  摘要：

  A series of aryloxazole, thiazole, and isoxazole derivatives was synthesized as vascular-targeting anticancer agents. Antiproliferative activity and tumor vascular-disrupting activity of all of the synthesized compounds were tested in vitro using various human cancer cell lines and HUVECs (human umbilical vein endothelial cells). Several compounds with an arylpiperazinyl oxazole core showed excellent cytotoxicity and metabolic stability in vitro. Among this series, two representative compounds (6-48 and 6-51) were selected and tested for the evaluation of anticancer effects in vivo using tumor-bearing mice. Compound 6-48 effectively reduced tumor growth (42.3% reduction in size) at the dose of 100 mg/kg. We believe that compound 6-48 will serve as a good lead compound for antimitotic and vascular-disrupting agents; further investigation to improve the in vivo efficacy of this series is underway.

  DOI：

  10.1021/jm400840p

文献信息

• Calpain modulators and therapeutic uses thereof
  申请人：Blade Therapeutics, Inc.

  公开号：US10934261B2

  公开（公告）日：2021-03-02

  Disclosed herein are small molecule calpain modulator compositions, pharmaceutical compositions, the use and preparation thereof.

  本文公开了小分子钙蛋白酶调节剂组合物、药物组合物及其用途和制备方法。
• [EN] CALPAIN MODULATORS AND THERAPEUTIC USES THEREOF<br/>[FR] MODULATEURS DE CALPAIN ET LEURS UTILISATIONS THÉRAPEUTIQUES
  申请人：BLADE THERAPEUTICS INC

  公开号：WO2018064119A8

  公开（公告）日：2019-04-25
• Synthesis and Biological Evaluation of Aryloxazole Derivatives as Antimitotic and Vascular-Disrupting Agents for Cancer Therapy
  作者：Min Jeong Choi、Eun Sun No、Dhanaji Achyutrao Thorat、Jae Wan Jang、Hakkyun Yang、Jaeick Lee、Hyunah Choo、Soo Jin Kim、Chang Sik Lee、Soo Young Ko、Jiyoun Lee、GhilSoo Nam、Ae Nim Pae

  DOI：10.1021/jm400840p

  日期：2013.11.27

  A series of aryloxazole, thiazole, and isoxazole derivatives was synthesized as vascular-targeting anticancer agents. Antiproliferative activity and tumor vascular-disrupting activity of all of the synthesized compounds were tested in vitro using various human cancer cell lines and HUVECs (human umbilical vein endothelial cells). Several compounds with an arylpiperazinyl oxazole core showed excellent cytotoxicity and metabolic stability in vitro. Among this series, two representative compounds (6-48 and 6-51) were selected and tested for the evaluation of anticancer effects in vivo using tumor-bearing mice. Compound 6-48 effectively reduced tumor growth (42.3% reduction in size) at the dose of 100 mg/kg. We believe that compound 6-48 will serve as a good lead compound for antimitotic and vascular-disrupting agents; further investigation to improve the in vivo efficacy of this series is underway.