{2-[((S)-2-{(S)-3-[Carbamoylmethyl-(6-chloro-naphthalene-2-sulfonyl)-amino]-2-oxo-pyrrolidin-1-yl}-propionyl)-isopropyl-amino]-ethyl}-carbamic acid tert-butyl ester | 532406-12-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: {2-[((S)-2-{(S)-3-[Carbamoylmethyl-(6-chloro-naphthalene-2-sulfonyl)-amino]-2-oxo-pyrrolidin-1-yl}-propionyl)-isopropyl-amino]-ethyl}-carbamic acid tert-butyl ester
• 英文别名: tert-butyl N-[2-[[(2S)-2-[(3S)-3-[(2-amino-2-oxoethyl)-(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]propanoyl]-propan-2-ylamino]ethyl]carbamate
• CAS: 532406-12-5
• 化学式: C₂₉H₄₀ClN₅O₇S
• 分子量: 638.185
• InChiKey: QTCJWVYQFLMRDT-CYFREDJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  43
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  168
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  {2-[((S)-2-{(S)-3-[Carbamoylmethyl-(6-chloro-naphthalene-2-sulfonyl)-amino]-2-oxo-pyrrolidin-1-yl}-propionyl)-isopropyl-amino]-ethyl}-carbamic acid tert-butyl ester 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (S)-N-(2-Amino-ethyl)-2-{(S)-3-[carbamoylmethyl-(6-chloro-naphthalene-2-sulfonyl)-amino]-2-oxo-pyrrolidin-1-yl}-N-isopropyl-propionamide
  参考文献：
  名称：

  Structure- and property-based design of factor Xa inhibitors: Pyrrolidin-2-ones with acyclic alanyl amides as P4 motifs

  摘要：

  Structure-based drug design was exploited in the synthesis of 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group with acyclic tertiary amide termini. Optimized hydrophobic contacts of one amide substituent in P4 were complemented by hydrophobicity-modulating features in the second, producing potent fXa inhibitors including examples with excellent anticoagulant properties.

  DOI：

  10.1016/j.bmcl.2006.09.001
• 作为产物：
  描述：

  tert-butyl (2S)-2-((3S)-3-{[(benzyloxy)carbonyl]amino}-2-oxopyrrolidin-1-yl)propanoate 在 palladium on activated charcoal 吡啶 、 氢气 、 potassium carbonate 、 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 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 {2-[((S)-2-{(S)-3-[Carbamoylmethyl-(6-chloro-naphthalene-2-sulfonyl)-amino]-2-oxo-pyrrolidin-1-yl}-propionyl)-isopropyl-amino]-ethyl}-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Structure- and property-based design of factor Xa inhibitors: Pyrrolidin-2-ones with acyclic alanyl amides as P4 motifs

  摘要：

  Structure-based drug design was exploited in the synthesis of 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group with acyclic tertiary amide termini. Optimized hydrophobic contacts of one amide substituent in P4 were complemented by hydrophobicity-modulating features in the second, producing potent fXa inhibitors including examples with excellent anticoagulant properties.

  DOI：

  10.1016/j.bmcl.2006.09.001

文献信息

• Structure- and property-based design of factor Xa inhibitors: Pyrrolidin-2-ones with acyclic alanyl amides as P4 motifs
  作者：Robert J. Young、Matthew Campbell、Alan D. Borthwick、David Brown、Cynthia L. Burns-Kurtis、Chuen Chan、Máire A. Convery、Miriam C. Crowe、Satish Dayal、Hawa Diallo、Henry A. Kelly、N. Paul King、Savvas Kleanthous、Andrew M. Mason、Jackie E. Mordaunt、Champa Patel、Anthony J. Pateman、Stefan Senger、Gita P. Shah、Paul W. Smith、Nigel S. Watson、Helen E. Weston、Ping Zhou

  DOI：10.1016/j.bmcl.2006.09.001

  日期：2006.12

  Structure-based drug design was exploited in the synthesis of 3-(6-chloronaphth-2-ylsulfonyl)aminopyrrolidin-2-one-based factor Xa (fXa) inhibitors, incorporating an alanylamide P4 group with acyclic tertiary amide termini. Optimized hydrophobic contacts of one amide substituent in P4 were complemented by hydrophobicity-modulating features in the second, producing potent fXa inhibitors including examples with excellent anticoagulant properties.