4-[2-oxo-1-(3-phenylpropyl)-1,2,5,6-tetrahydropyridin-3-yl]butyric acid methyl ester | 942924-81-4

• 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-[2-oxo-1-(3-phenylpropyl)-1,2,5,6-tetrahydropyridin-3-yl]butyric acid methyl ester
• 英文别名: Methyl 4-[6-oxo-1-(3-phenylpropyl)-2,3-dihydropyridin-5-yl]butanoate
• CAS: 942924-81-4
• 化学式: C₁₉H₂₅NO₃
• 分子量: 315.412
• InChiKey: PCKWZDIWITUJCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 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-[2-oxo-1-(3-phenylpropyl)-1,2,5,6-tetrahydropyridin-3-yl]butyric acid methyl ester 在 羟胺钾盐 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以57%的产率得到N-hydroxy-4-[2-oxo-1-(3-phenyl-propyl)-1,2,5,6-tetrahydro-pyridin-3-yl]-butylamide
  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：

  3-苯基-1-丙胺 在 Grubbs catalyst first generation 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 20.0h， 生成 4-[2-oxo-1-(3-phenylpropyl)-1,2,5,6-tetrahydropyridin-3-yl]butyric 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

• Structure−Activity Relationship Studies of a Series of Novel δ-Lactam-Based Histone Deacetylase Inhibitors
  作者：Hwan Mook Kim、Dong-Kyu Ryu、Yongseok Choi、Bum Woo Park、Kiho Lee、Sang Bae Han、Chang-Woo Lee、Moo-Rim Kang、Jong Soon Kang、Shanthaveerappa K. Boovanahalli、Song-Kyu Park、Jung Whan Han、Tae-Gyu Chun、Hee-Yoon Lee、Ky-Youb Nam、Eun Hyun Choi、Gyoonhee Han

  DOI：10.1021/jm0613828

  日期：2007.5.1

  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.