5-(2,4-bis-(benzyloxy)-5-isopropylbenzoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid | 1584301-67-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-(2,4-bis-(benzyloxy)-5-isopropylbenzoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid
• CAS: 1584301-67-6
• 化学式: C₃₁H₃₀N₂O₆
• 分子量: 526.589
• InChiKey: AYSDEKNSUMIZDF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.85
• 重原子数：
  39.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  102.1
• 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)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三氯化硼 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 4.5h， 生成 methyl 7-(5-(2,4-dihydroxy-5-isopropyl-benzoyl)-6,7-dihydro-4H-isoxazolo[4,5-c]pyridine-3-carboxamido)-heptanoate
  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：

  ethyl 5-(2,4-bis(benzyloxy)-5-isopropylbenzoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylate 在 lithium hydroxide monohydrate 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 5-(2,4-bis-(benzyloxy)-5-isopropylbenzoyl)-4,5,6,7-tetrahydroisoxazolo[4,5-c]pyridine-3-carboxylic acid
  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