6-chloro-N-((3S)-1-(4-(1-(ethyl(methyl)amino)ethyl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide | 1208258-70-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-N-((3S)-1-(4-(1-(ethyl(methyl)amino)ethyl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide
• 英文别名: 6-chloro-N-[(3S)-1-[4-[1-[ethyl(methyl)amino]ethyl]-2-fluorophenyl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide
• CAS: 1208258-70-1
• 化学式: C₂₅H₂₇ClFN₃O₃S
• 分子量: 504.025
• InChiKey: GZEWCAHSAJHYKK-KESSSICBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  78.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  tert-butyl ((3S)-1-(4-(1-(ethyl(methyl)amino)ethyl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)carbamate 、 6-氯-2-萘磺酰氯 在 盐酸 、 吡啶 作用下， 以 甲醇 、 乙腈 为溶剂， 生成 6-chloro-N-((3S)-1-(4-(1-(ethyl(methyl)amino)ethyl)-2-fluorophenyl)-2-oxopyrrolidin-3-yl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  Structure and property based design of factor Xa inhibitors: pyrrolidin-2-ones with monoaryl P4 motifs

  摘要：

  Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa inhibitors, incorporating neutral and basic monoaryl P4 groups, ultimately producing potent inhibitors with effective levels of anticoagulant activity and extended oral pharmacokinetic profiles. However, time dependant inhibition of Cytochrome P450 3A4 was a particular issue with this series.

  DOI：

  10.1016/j.bmcl.2009.11.077

文献信息

• Structure and property based design of factor Xa inhibitors: pyrrolidin-2-ones with monoaryl P4 motifs
  作者：Savvas Kleanthous、Alan D. Borthwick、David Brown、Cynthia L. Burns-Kurtis、Matthew Campbell、Laiq Chaudry、Chuen Chan、Marie-Olive Clarte、Máire A. Convery、John D. Harling、Eric Hortense、Wendy R. Irving、Stephanie Irvine、Anthony J. Pateman、Angela N. Patikis、Ivan L. Pinto、Derek R. Pollard、Theresa J. Roethka、Stefan Senger、Gita P. Shah、Gary J. Stelman、John R. Toomey、Nigel S. Watson、Robert I. West、Caroline Whittaker、Ping Zhou、Robert J. Young

  DOI：10.1016/j.bmcl.2009.11.077

  日期：2010.1

  Structure and property based drug design was exploited in the synthesis of sulfonamidopyrrolidin-2-one-based factor Xa inhibitors, incorporating neutral and basic monoaryl P4 groups, ultimately producing potent inhibitors with effective levels of anticoagulant activity and extended oral pharmacokinetic profiles. However, time dependant inhibition of Cytochrome P450 3A4 was a particular issue with this series.