MMV676162 | 1086562-60-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: MMV676162
• 英文别名: 2-(2-Benzamidophenyl)-1,3-benzoxazole-4-carboxylic acid
• CAS: 1086562-60-8
• 化学式: C₂₁H₁₄N₂O₄
• 分子量: 358.353
• InChiKey: FIEWOUZYTHWIGD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.4
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-(2-benzoylaminophenyl)-benzoxazole-4-carboxylic acid methyl ester 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 12.0h， 以84%的产率得到MMV676162
  参考文献：
  名称：

  In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of N-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes

  摘要：

  The first synthesis and biological evaluation of antibiotic 31 (A-33853) and its analogues are reported. Initial screening for inhibition of L. donovani, T. b. rhodesiense, T cruzi, and P. falciparum cultures followed by determination of IC50 in L. donovani and cytotoxicity on L6 cells revealed 31 to be 3-fold more active than miltefosine, a known antileishmanial drug, Compounds 14, 15, and 25 selectively inhibited L. donovani at nanomolar concentrations and showed much lower cytotoxicity.

  DOI：

  10.1021/jm801241n

文献信息

• In Pursuit of Natural Product Leads: Synthesis and Biological Evaluation of 2-[3-hydroxy-2-[(3-hydroxypyridine-2-carbonyl)amino]phenyl]benzoxazole-4-carboxylic acid (A-33853) and Its Analogues: Discovery of <i>N</i>-(2-Benzoxazol-2-ylphenyl)benzamides as Novel Antileishmanial Chemotypes
  作者：Suresh K. Tipparaju、Sipak Joyasawal、Marco Pieroni、Marcel Kaiser、Reto Brun、Alan P. Kozikowski

  DOI：10.1021/jm801241n

  日期：2008.12.11

  The first synthesis and biological evaluation of antibiotic 31 (A-33853) and its analogues are reported. Initial screening for inhibition of L. donovani, T. b. rhodesiense, T cruzi, and P. falciparum cultures followed by determination of IC50 in L. donovani and cytotoxicity on L6 cells revealed 31 to be 3-fold more active than miltefosine, a known antileishmanial drug, Compounds 14, 15, and 25 selectively inhibited L. donovani at nanomolar concentrations and showed much lower cytotoxicity.