N⁵-(2,4-bis-(benzyloxy)-5-isopropylphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide | 1584301-85-8

• 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: N⁵-(2,4-bis-(benzyloxy)-5-isopropylphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide
• CAS: 1584301-85-8
• 化学式: C₃₃H₃₆N₄O₅
• 分子量: 568.673
• InChiKey: IUKXTSQMCJCXQM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.3
• 重原子数：
  42.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  105.93
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  N⁵-(2,4-bis-(benzyloxy)-5-isopropylphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide 在 三氯化硼 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以64%的产率得到N⁵-(2,4-dihydroxy-5-isopropylphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide
  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 、 对甲苯磺酸 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 12.0h， 生成 N⁵-(2,4-bis-(benzyloxy)-5-isopropylphenyl)-N³-ethyl-6,7-dihydroisoxazolo[4,5-c]pyridine-3,5(4H)-dicarboxamide
  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