6-chloro-N-[1-[(2S)-1-morpholin-4-yl-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]-N-(2-oxobutyl)naphthalene-2-sulfonamide

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 6-chloro-N-[1-[(2S)-1-morpholin-4-yl-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]-N-(2-oxobutyl)naphthalene-2-sulfonamide
• 化学式: C₂₅H₃₀ClN₃O₆S
• 分子量: 536.049
• InChiKey: DSPUJUOXCWMCJY-NVHKAFQKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  113
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid 在 palladium on activated charcoal 吡啶 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 三乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 6-chloro-N-[1-[(2S)-1-morpholin-4-yl-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]-N-(2-oxobutyl)naphthalene-2-sulfonamide
  参考文献：
  名称：

  Design and synthesis of orally active pyrrolidin-2-one-based factor Xa inhibitors

  摘要：

  A series of novel, non-basic 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group, was designed and synthesised. Within this series, the N-2-(morpholin-4-yl)-2-oxoethyl derivative 24 was shown to be a potent, selective fXa inhibitor with good anticoagulant activity. Moreover, 24 possessed highly encouraging rat and dog pharmacokinetic profiles with excellent oral bioavailabilities in both species. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.04.053

文献信息

• Design and synthesis of orally active pyrrolidin-2-one-based factor Xa inhibitors
  作者：Nigel S. Watson、David Brown、Matthew Campbell、Chuen Chan、Laiq Chaudry、Máire A. Convery、Rebecca Fenwick、J. Nicole Hamblin、Claudine Haslam、Henry A. Kelly、N. Paul King、Cynthia L. Kurtis、Andrew R. Leach、Gary R. Manchee、Andrew M. Mason、Charlotte Mitchell、Champa Patel、Vipulkumar K. Patel、Stefan Senger、Gita P. Shah、Helen E. Weston、Caroline Whitworth、Robert J. Young

  DOI：10.1016/j.bmcl.2006.04.053

  日期：2006.7

  A series of novel, non-basic 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group, was designed and synthesised. Within this series, the N-2-(morpholin-4-yl)-2-oxoethyl derivative 24 was shown to be a potent, selective fXa inhibitor with good anticoagulant activity. Moreover, 24 possessed highly encouraging rat and dog pharmacokinetic profiles with excellent oral bioavailabilities in both species. (c) 2006 Elsevier Ltd. All rights reserved.