5-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)-N-(2-chloroethyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxamide | 1584301-96-1

• 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: 5-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)-N-(2-chloroethyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxamide
• CAS: 1584301-96-1
• 化学式: C₃₃H₃₄ClN₃O₅
• 分子量: 588.103
• InChiKey: LWJHOZUXIKRFRW-UHFFFAOYSA-N

物化性质

• 沸点：
  807.1±65.0 °C(Predicted)
• 密度：
  1.256±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.12
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  93.9
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)-N-(2-chloroethyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxamide 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以65%的产率得到5-(2,4-dihydroxy-5-isopropyl-benzoyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid (2-chloro-ethyl)-amide
  参考文献：
  名称：

  4,5,6,7-Tetrahydro-isoxazolo-[4,5-c]-pyridines as a new class of cytotoxic Hsp90 inhibitors

  摘要：

  Hsp90 is considered an interesting therapeutic target for anticancer drug development. Here we describe a new class of 4,5,6,7-tetrahydro-isoxazolo-[4,5-c]pyridine compounds. A small library of derivatives has been synthesized and investigated. Some reported compounds show interesting properties combining both notable binding to Hsp90 and potent cell growth inhibitory activity. N-5 substitution with a 2,4 resorcinol carboxamide appears crucial for activity. Moreover, a derivative bearing a hydroxamic acid residue bound to C-3 amide portion was found to inhibit both Hsp90 and HDAC6. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.056
• 作为产物：
  描述：

  N-乙酰基-4-哌啶酮 在 盐酸 、 lithium hydroxide monohydrate 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 1-羟基苯并三唑 、 对甲苯磺酸 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 生成 5-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)-N-(2-chloroethyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxamide
  参考文献：
  名称：

  4,5,6,7-Tetrahydro-isoxazolo-[4,5-c]-pyridines as a new class of cytotoxic Hsp90 inhibitors

  摘要：

  Hsp90 is considered an interesting therapeutic target for anticancer drug development. Here we describe a new class of 4,5,6,7-tetrahydro-isoxazolo-[4,5-c]pyridine compounds. A small library of derivatives has been synthesized and investigated. Some reported compounds show interesting properties combining both notable binding to Hsp90 and potent cell growth inhibitory activity. N-5 substitution with a 2,4 resorcinol carboxamide appears crucial for activity. Moreover, a derivative bearing a hydroxamic acid residue bound to C-3 amide portion was found to inhibit both Hsp90 and HDAC6. (C) 2014 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2014.01.056