4-Amino-2-benzooxazol-2-yl-6-methyl-phenol | 626218-32-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-Amino-2-benzooxazol-2-yl-6-methyl-phenol
• 英文别名: 4-amino-2-(1,3-benzoxazol-2-yl)-6-methylphenol
• CAS: 626218-32-4
• 化学式: C₁₄H₁₂N₂O₂
• mdl: MFCD03856669
• 分子量: 240.261
• InChiKey: IELACHKGVHRASW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  72.3
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT

反应信息

• 作为反应物：
  描述：

  2-氯-5-硝基苯甲酰氯 、 4-Amino-2-benzooxazol-2-yl-6-methyl-phenol 在 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以84%的产率得到N-[3-(1,3-benzoxazol-2-yl)-4-hydroxy-5-methylphenyl]-2-chloro-5-nitrobenzamide
  参考文献：
  名称：

  Optimization of Chloronitrobenzamides (CNBs) as Therapeutic Leads for Human African Trypanosomiasis (HAT)

  摘要：

  We previously reported the discovery of the activity of chloronitrobenzamides (CNBs) against bloodstream forms of Trypanosoma brucei. Herein we disclose extensive structure activity relationship and structure property relationship studies aimed at identification of tractable early leads for clinical development. These studies revealed a promising lead compound, 17b, that exhibited nanomolar potency against T. brucei (EC50 = 27 nM for T. b. brucei, 7 nM for T. b. rhodesiense, and 2 nM for T. b. gambiense) with excellent selectivity for parasite cells relative to mammalian cell lines (EC50 > 25 mu M). In addition compound 17b displayed suitable physiochemical characteristics and microsomal stability (t(1/2) > 4 h for human and mouse) to justify pursuing in vivo studies.

  DOI：

  10.1021/jm301687p

文献信息

• Optimization of Chloronitrobenzamides (CNBs) as Therapeutic Leads for Human African Trypanosomiasis (HAT)
  作者：Jong Yeon Hwang、David Smithson、Fangyi Zhu、Gloria Holbrook、Michele C. Connelly、Marcel Kaiser、Reto Brun、R. Kiplin Guy

  DOI：10.1021/jm301687p

  日期：2013.4.11

  We previously reported the discovery of the activity of chloronitrobenzamides (CNBs) against bloodstream forms of Trypanosoma brucei. Herein we disclose extensive structure activity relationship and structure property relationship studies aimed at identification of tractable early leads for clinical development. These studies revealed a promising lead compound, 17b, that exhibited nanomolar potency against T. brucei (EC50 = 27 nM for T. b. brucei, 7 nM for T. b. rhodesiense, and 2 nM for T. b. gambiense) with excellent selectivity for parasite cells relative to mammalian cell lines (EC50 > 25 mu M). In addition compound 17b displayed suitable physiochemical characteristics and microsomal stability (t(1/2) > 4 h for human and mouse) to justify pursuing in vivo studies.