(E)-methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)ethyl)benzoate | 1160152-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (E)-methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)ethyl)benzoate
• 英文别名: methyl 3-chloro-4,6-dihydroxy-2-[(2E)-2-(6-hydroxy-7-methoxy-3-oxo-4H-1,4-benzoxazin-2-ylidene)ethyl]benzoate
• CAS: 1160152-83-9
• 化学式: C₁₉H₁₆ClNO₈
• 分子量: 421.791
• InChiKey: KDYVDUVVUUNIES-YIXHJXPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  (E)-methyl 2-(2-(6-(benzyloxy)-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)ethyl)-3-chloro-4,6-dihydroxybenzoate 在 aluminum (III) chloride 、 甲醇 作用下， 以 苯甲醚 为溶剂， 以83%的产率得到(E)-methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-ylidene)ethyl)benzoate
  参考文献：
  名称：

  Design, Synthesis, and Biological Evaluation of Conformationally Constrained cis-Amide Hsp90 Inhibitors

  摘要：

  Conformationally constrained cis-amide chimeric inhibitors of Hsp90 have been synthesized and evaluated for their Hsp90 inhibitory activity. These new compounds exhibited Hsp90 ATPase inhibition and induced Hsp90-dependent client protein degradation in a dose-dependent manner. Biological data reported herein suggests that amide bond isomerization of geldanamycin derivatives plays an important role in affinity for the heteroprotein complex present in cancer cells.

  DOI：

  10.1021/ol900783m