(3S)-3-amino-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]pyrrolidin-2-one | 553652-22-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (3S)-3-amino-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]pyrrolidin-2-one
• CAS: 553652-22-5
• 化学式: C₁₆H₂₀FN₅O
• 分子量: 317.366
• InChiKey: RKJUPBUUNLUCMX-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  67.4
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]pyrrolidin-2-one 、 2-(5-chloro-thiophen-2-yl)-ethenesulfonyl chloride 在 吡啶 作用下， 以 乙腈 为溶剂， 生成 (E)-2-(5-chlorothiophen-2-yl)-N-[(3R)-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-2-oxopyrrolidin-3-yl]ethenesulfonamide 、 (S)-2-(5-chlorothiophen-2-yl)-N-(1-(4-(2-((dimethylamino)methyl)-1H-imidazol-1-yl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)ethenesulfonamide
  参考文献：
  名称：

  Structure and property based design of factor Xa inhibitors: Biaryl pyrrolidin-2-ones incorporating basic heterocyclic motifs

  摘要：

  Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles.

  DOI：

  10.1016/j.bmcl.2007.11.019
• 作为产物：
  描述：

  tert-butyl N-[(3S)-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]-2-oxopyrrolidin-3-yl]carbamate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3S)-3-amino-1-[4-[2-[(dimethylamino)methyl]imidazol-1-yl]-2-fluorophenyl]pyrrolidin-2-one
  参考文献：
  名称：

  Structure and property based design of factor Xa inhibitors: Biaryl pyrrolidin-2-ones incorporating basic heterocyclic motifs

  摘要：

  Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles.

  DOI：

  10.1016/j.bmcl.2007.11.019

文献信息

• Pyrrolidine-2-ones as factor xa inhibitors
  申请人：Borthwick David Alan

  公开号：US20050059726A1

  公开（公告）日：2005-03-17

  The present invention relates to novel compounds and pharmaceutically acceptable derivatives thereof. The invention also relates to processes for the preparation of the compounds, pharmaceutical compositions containing the compounds, and to the use of compounds in medicine, particularly in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及新型化合物及其药学上可接受的衍生物。本发明还涉及制备该化合物的过程、含有该化合物的药物组合物以及化合物在医学上的使用，尤其是在改善适应于Xa因子抑制剂的临床病症方面的使用。
• Structure and property based design of factor Xa inhibitors: Biaryl pyrrolidin-2-ones incorporating basic heterocyclic motifs
  作者：Robert J. Young、Alan D. Borthwick、David Brown、Cynthia L. Burns-Kurtis、Matthew Campbell、Chuen Chan、Marie Charbaut、Máire A. Convery、Hawa Diallo、Eric Hortense、Wendy R. Irving、Henry A. Kelly、N. Paul King、Savvas Kleanthous、Andrew M. Mason、Anthony J. Pateman、Angela N. Patikis、Ivan L. Pinto、Derek R. Pollard、Stefan Senger、Gita P. Shah、John R. Toomey、Nigel S. Watson、Helen E. Weston、Ping Zhou

  DOI：10.1016/j.bmcl.2007.11.019

  日期：2008.1

  Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating basic biaryl P4 groups, producing highly potent inhibitors with significant anticoagulant activities and encouraging oral pharmacokinetic profiles.