N¹-benzyl-4-[3-(phenoxymethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: N¹-benzyl-4-[3-(phenoxymethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
• 英文别名: N-benzyl-4-[3-(phenoxymethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
• 化学式: C₂₂H₂₄N₄O₃
• 分子量: 392.458
• InChiKey: IIIMEFRKOKZZAP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  80.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-苯氧基乙腈 在 盐酸羟胺 、 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.17h， 生成 N¹-benzyl-4-[3-(phenoxymethyl)-1,2,4-oxadiazol-5-yl]piperidine-1-carboxamide
  参考文献：
  名称：

  Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype

  摘要：

  We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biological activity profile studies (COMPARE analysis) demonstrated that 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides act as tubulin inhibitors, and this conclusion was confirmed via biochemical assays with pure tubulin and demonstration of increased numbers of mitotic cells following treatment of a leukemia cell line. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.07.089

文献信息

• Antiproliferative 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides, a new tubulin inhibitor chemotype
  作者：Mikhail Krasavin、Andrey V. Sosnov、Ruben Karapetian、Igor Konstantinov、Olga Soldatkina、Elena Godovykh、Fedor Zubkov、Ruoli Bai、Ernest Hamel、Andrei A. Gakh

  DOI：10.1016/j.bmcl.2014.07.089

  日期：2014.9

  We discovered a new chemical class of antiproliferative agents, 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides. SAR-guided optimization of the two distinct terminal fragments yielded a compound with 120 nM potency in an antiproliferative assay. Biological activity profile studies (COMPARE analysis) demonstrated that 4-(1,2,4-oxadiazol-5-yl)piperidine-1-carboxamides act as tubulin inhibitors, and this conclusion was confirmed via biochemical assays with pure tubulin and demonstration of increased numbers of mitotic cells following treatment of a leukemia cell line. (C) 2014 Elsevier Ltd. All rights reserved.