[3-(Aminomethyl)pyrrolidin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone | 849632-77-5

• 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: [3-(Aminomethyl)pyrrolidin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone
• CAS: 849632-77-5
• 化学式: C₁₆H₂₄N₄O
• 分子量: 288.393
• InChiKey: YLPMNTSEBAXWMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  504.9±40.0 °C(Predicted)
• 密度：
  1.168±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  62.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [3-(Aminomethyl)pyrrolidin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone 、 6-chloro-1-benzothiophene-2-sulfonyl chloride 在 碳酸氢钠 作用下， 以 乙酸乙酯 为溶剂， 生成 C₂₄H₂₇ClN₄O₃S₂
  参考文献：
  名称：

  Amino(methyl) pyrrolidines as novel scaffolds for factor Xa inhibitors

  摘要：

  The design and synthesis of a novel class of amino(methyl) pyrrolidine-based sulforiamides as potent and selective FXa inhibitors is reported. The amino(methyl) pyrrolidine scaffolds were designed based on the proposed bioisosterism to the piperazine core in known FXa inhibitors. The SAR study led to compound 15 as the most potent FXa inhibitor in this series, with an IC50 Of 5.5 nM and PT EC2x. of 1.7 mu M. The proposed binding models show that the pyrrolidine cores are in van der Waals contact with the enzyme surface, and the flexibility of amino(methyl) pyrrolidines allows the two nitrogen atoms to anchor both the PI and P4 groups to fit similarly in the S I and S4 pockets. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.063
• 作为产物：
  描述：

  tert-butyl ((1-(1-(pyridin-4-yl)piperidine-4-carbonyl)pyrrolidin-3-yl)methyl)carbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 [3-(Aminomethyl)pyrrolidin-1-yl]-(1-pyridin-4-ylpiperidin-4-yl)methanone
  参考文献：
  名称：

  Amino(methyl) pyrrolidines as novel scaffolds for factor Xa inhibitors

  摘要：

  The design and synthesis of a novel class of amino(methyl) pyrrolidine-based sulforiamides as potent and selective FXa inhibitors is reported. The amino(methyl) pyrrolidine scaffolds were designed based on the proposed bioisosterism to the piperazine core in known FXa inhibitors. The SAR study led to compound 15 as the most potent FXa inhibitor in this series, with an IC50 Of 5.5 nM and PT EC2x. of 1.7 mu M. The proposed binding models show that the pyrrolidine cores are in van der Waals contact with the enzyme surface, and the flexibility of amino(methyl) pyrrolidines allows the two nitrogen atoms to anchor both the PI and P4 groups to fit similarly in the S I and S4 pockets. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.063

文献信息

• Pyrrolidine and piperidine derivatives as factor Xa inhibitors
  申请人：Shi Yan

  公开号：US20050119266A1

  公开（公告）日：2005-06-02

  The present application describes pyrrolidine and piperidine derivatives or pharmaceutically acceptable salt forms thereof. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.

  本申请描述了吡咯烷和哌嗪衍生物或其药学上可接受的盐形式。本发明的化合物可用作胰蛋白酶样丝氨酸蛋白酶的抑制剂，特别是因子Xa的抑制剂。
• PYRROLIDINE AND PIPERIDINE DERIVATIVES AS FACTOR XA INHIBITORS
  申请人：Bristol-Myers Squibb Company

  公开号：EP1684744A2

  公开（公告）日：2006-08-02
• EP1684744A4
  申请人：——

  公开号：EP1684744A4

  公开（公告）日：2008-12-17
• [EN] PYRROLIDINE AND PIPERIDINE DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DERIVES DE PYRROLIDINE ET DE PIPERIDINE UTILISES EN TANT QU'INHIBITEURS DU FACTEUR XA
  申请人：BRISTOL MYERS SQUIBB CO

  公开号：WO2005032472A2

  公开（公告）日：2005-04-14

  The present application describes pyrrolidine and piperidine derivatives or pharmaceutically acceptable salt forms thereof. Compounds of the present invention are useful as inhibitors of trypsin-like serine proteases, specifically factor Xa.