2-[2-[(2-chloropyridine-3-carbonyl)-amino]-3-methoxyphenyl]-benzoxazole-4-carboxylic acid methyl ester | 1086562-20-0

• 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: 2-[2-[(2-chloropyridine-3-carbonyl)-amino]-3-methoxyphenyl]-benzoxazole-4-carboxylic acid methyl ester
• 英文别名: Methyl 2-[2-[(2-chloropyridine-3-carbonyl)amino]-3-methoxyphenyl]-1,3-benzoxazole-4-carboxylate
• CAS: 1086562-20-0
• 化学式: C₂₂H₁₆ClN₃O₅
• 分子量: 437.839
• InChiKey: TYOFMRBZIKEMCC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-[2-[(2-chloropyridine-3-carbonyl)-amino]-3-methoxyphenyl]-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 16.0h， 以90%的产率得到2-[2-[(2-chloropyridine-3-carbonyl)-amino]-3-methoxyphenyl]-benzoxazole-4-carboxylic acid
  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
• 作为产物：
  描述：

  2-羟基烟酸 、 Microechmycin G 在 草酰氯 、 N,N-二甲基甲酰胺 、 吡啶 作用下， 以 二氯甲烷 为溶剂， 以75%的产率得到2-[2-[(2-chloropyridine-3-carbonyl)-amino]-3-methoxyphenyl]-benzoxazole-4-carboxylic acid methyl ester
  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