4-(benzylbut-3-enylcarbamoyl)pent-4-enoic acid methyl ester | 905970-78-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-(benzylbut-3-enylcarbamoyl)pent-4-enoic acid methyl ester
• 英文别名: Methyl 4-[benzyl(but-3-enyl)carbamoyl]pent-4-enoate
• CAS: 905970-78-7
• 化学式: C₁₈H₂₃NO₃
• 分子量: 301.386
• InChiKey: HQBMKNRMOUIXTM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  22
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(benzylbut-3-enylcarbamoyl)pent-4-enoic acid methyl ester 在 Grubbs catalyst first generation 羟胺钾盐 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 32.0h， 生成 N-hydroxy-3-(1-benzyl-2-oxo-1,2,5,6-tetrahydro-pyridin-3-yl)-propionamide
  参考文献：
  名称：

  Structure−Activity Relationship Studies of a Series of Novel δ-Lactam-Based Histone Deacetylase Inhibitors

  摘要：

  We synthesized a series of delta-lactam-based HDAC inhibitors that were identified with various degrees of anti-inflammatory and cell growth inhibitory activities. Compounds possessing significant HDAC inhibitory activity exhibited both anti-inflammatory and cell growth inhibitory activities as well as significant tumor growth inhibition in the in vivo tumor xenograft experiments. Besides, these compounds demonstrated anti-inflammatory properties in vitro via suppression of the production of the proinflammatory cytokine TNF-alpha and nitric oxide by LPS-stimulated RAW264.7 cells.

  DOI：

  10.1021/jm0613828
• 作为产物：
  描述：

  苄胺 在 4-二甲氨基吡啶 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成 4-(benzylbut-3-enylcarbamoyl)pent-4-enoic acid methyl ester
  参考文献：
  名称：

  Structure−Activity Relationship Studies of a Series of Novel δ-Lactam-Based Histone Deacetylase Inhibitors

  摘要：

  We synthesized a series of delta-lactam-based HDAC inhibitors that were identified with various degrees of anti-inflammatory and cell growth inhibitory activities. Compounds possessing significant HDAC inhibitory activity exhibited both anti-inflammatory and cell growth inhibitory activities as well as significant tumor growth inhibition in the in vivo tumor xenograft experiments. Besides, these compounds demonstrated anti-inflammatory properties in vitro via suppression of the production of the proinflammatory cytokine TNF-alpha and nitric oxide by LPS-stimulated RAW264.7 cells.

  DOI：

  10.1021/jm0613828

文献信息

• Synthesis, enzymatic inhibition, and cancer cell growth inhibition of novel δ-lactam-based histone deacetylase (HDAC) inhibitors
  作者：Hwan Mook Kim、Kiho Lee、Bum Woo Park、Dong Kyu Ryu、Kangjeon Kim、Chang Woo Lee、Song-Kyu Park、Jung Whan Han、Hee Yoon Lee、Hyun Yong Lee、Gyoonhee Han

  DOI：10.1016/j.bmcl.2006.04.091

  日期：2006.8

  delta-Lactam-based hydroxamic acids, inhibitors of histone deacetylase (HDAC), have been synthesized via ring closure metathesis of key diene intermediates followed by conversion to hydroxamic acid analogues. The hydroxamic acids 12a, 12b, and 17c showed potent inhibitory activity in HDAC enzyme assay. The hydroxamic acid 12b exhibited growth inhibitory activity on five human tumor cell lines, showing good sensitivity on the MDA-MB-231 breast tumor cell. (c) 2006 Elsevier Ltd. All rights reserved.