methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)ethyl)benzoate | 1160152-97-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)ethyl)benzoate
• 英文别名: methyl 3-chloro-4,6-dihydroxy-2-[2-(6-hydroxy-7-methoxy-3-oxo-4H-1,4-benzoxazin-2-yl)ethyl]benzoate
• CAS: 1160152-97-5
• 化学式: C₁₉H₁₈ClNO₈
• 分子量: 423.807
• InChiKey: QWJGBYXOKCLKLW-UHFFFAOYSA-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：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 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：

  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 palladium 10% on activated carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 以85%的产率得到methyl 3-chloro-4,6-dihydroxy-2-(2-(6-hydroxy-7-methoxy-3-oxo-3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)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

文献信息

• GRP94 INHIBITORS
  申请人：Blagg Brian S.J.

  公开号：US20130109684A1

  公开（公告）日：2013-05-02

  The present disclosure provides a series of compounds which exhibit isoform selective inhibition of GRP94, a homologue of Hsp90 that is localized to the endoplasmic recticulum. Through GRP94 inhibition, these compounds are likely to manifest anti-cancer, anti-inflammatory, anti-metastasis, and immunosuppressive activities, as well as utility in the treatment of neurodegenerative diseases, and diabetes.