2-(1-acetylpiperidin-4-ylidene)-N-{(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}acetamide | 671205-35-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-(1-acetylpiperidin-4-ylidene)-N-{(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}acetamide
• 英文别名: 2-(1-acetylpiperidin-4-ylidene)-N-[(3R)-1-[(6-fluoronaphthalen-2-yl)methyl]pyrrolidin-3-yl]acetamide
• CAS: 671205-35-9
• 化学式: C₂₄H₂₈FN₃O₂
• 分子量: 409.504
• InChiKey: VSVSVIPQECPZMU-HSZRJFAPSA-N

物化性质

• 沸点：
  650.9±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-((3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl)-2-piperidin-4-ylideneacetamide 、 乙酰氯 以 二氯甲烷 为溶剂， 反应 5.5h， 以17%的产率得到2-(1-acetylpiperidin-4-ylidene)-N-{(3R)-1-[(6-fluoro-2-naphthyl)methyl]pyrrolidin-3-yl}acetamide
  参考文献：
  名称：

  Synthesis, biological evaluation, and metabolic stability of acrylamide derivatives as novel CCR3 antagonists

  摘要：

  Our laboratory has identified several acrylamide derivatives with potent CCR3 inhibitory activity. In the present study, we evaluated the in vitro metabolic stability (CL(int); mL/min/kg) of these compounds in human liver microsomes (HLMs), and assessed the relationship between their structures and CLint values. Among the compounds identified, N-{(3R)-1-[(6-fluoro-2-naphthyl) methyl] pyrrolidin-3-yl}-2-[ 1-(2-hydroxybenzoyl) piperidin-4-ylidene] acetamide (30j) was found to be a potent inhibitor (IC(50) = 8.4 nM) with a high metabolic stability against HLMs. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.06.066

文献信息

• Synthesis, biological evaluation, and metabolic stability of acrylamide derivatives as novel CCR3 antagonists
  作者：Ippei Sato、Koichiro Morihira、Hiroshi Inami、Hirokazu Kubota、Tatsuaki Morokata、Keiko Suzuki、Kazuki Ohno、Yosuke Iura、Aiko Nitta、Takayuki Imaoka、Toshiya Takahashi、Makoto Takeuchi、Mitsuaki Ohta、Shin-ichi Tsukamoto

  DOI：10.1016/j.bmc.2009.06.066

  日期：2009.8

  Our laboratory has identified several acrylamide derivatives with potent CCR3 inhibitory activity. In the present study, we evaluated the in vitro metabolic stability (CL(int); mL/min/kg) of these compounds in human liver microsomes (HLMs), and assessed the relationship between their structures and CLint values. Among the compounds identified, N-(3R)-1-[(6-fluoro-2-naphthyl) methyl] pyrrolidin-3-yl}-2-[ 1-(2-hydroxybenzoyl) piperidin-4-ylidene] acetamide (30j) was found to be a potent inhibitor (IC(50) = 8.4 nM) with a high metabolic stability against HLMs. (C) 2009 Elsevier Ltd. All rights reserved.