5-(2,4-dihydroxy-5-isopropyl-benzoyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid cyclopentylamide | 1584301-71-2

• 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-dihydroxy-5-isopropyl-benzoyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid cyclopentylamide
• 英文别名: N-cyclopentyl-5-(2,4-dihydroxy-5-propan-2-ylbenzoyl)-6,7-dihydro-4H-[1,2]oxazolo[4,5-c]pyridine-3-carboxamide
• CAS: 1584301-71-2
• 化学式: C₂₂H₂₇N₃O₅
• 分子量: 413.473
• InChiKey: AZOFIVJONBGOTQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  116
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 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 、 三氯化硼 、 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， 反应 6.5h， 生成 5-(2,4-dihydroxy-5-isopropyl-benzoyl)-4,5,6,7-tetrahydro-isoxazolo[4,5-c]pyridine-3-carboxylic acid cyclopentylamide
  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

文献信息

• 4,5,6,7-Tetrahydro-isoxazolo-[4,5-c]-pyridines as a new class of cytotoxic Hsp90 inhibitors
  作者：Riccardo Baruchello、Daniele Simoni、Paolo Marchetti、Riccardo Rondanin、Stefania Mangiola、Cristiana Costantini、Maria Meli、Giuseppe Giannini、Loredana Vesci、Valeria Carollo、Tiziana Brunetti、Gianfranco Battistuzzi、Manlio Tolomeo、Walter Cabri

  DOI：10.1016/j.ejmech.2014.01.056

  日期：2014.4

  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.