(2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid | 478645-34-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid
• 英文别名: (2S)-2-[(3S)-3-[(6-chloronaphthalen-2-yl)sulfonylamino]-2-oxopyrrolidin-1-yl]propanoic acid
• CAS: 478645-34-0
• 化学式: C₁₇H₁₇ClN₂O₅S
• 分子量: 396.851
• InChiKey: NOAVDWOUDADYBW-BONVTDFDSA-N

物化性质

• 沸点：
  678.7±65.0 °C(predicted)
• 密度：
  1.54±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  112
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid 在 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 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-N-(2-Amino-ethyl)-2-[(S)-3-(6-chloro-naphthalene-2-sulfonylamino)-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 、 三氟乙酸 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 (2S)-2-((3S)-3-{[(6-chloro-2-naphthyl)sulfonyl]amino}-2-oxopyrrolidin-1-yl)propanoic acid
  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

• [EN] PYRROLIDIN-2-ONE DERIVATIVES AS INHIBITORS OF FACTOR XA<br/>[FR] DERIVES PYRROLIDINE-2-UN COMME INHIBITEURS DE FACTEUR XA
  申请人：GLAXO GROUP LTD

  公开号：WO2002100886A1

  公开（公告）日：2002-12-19

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及式(Ic)化合物、其制备过程、含有它们的药物组合物以及它们在医学上的应用，特别是在改善适用于因子Xa抑制剂的临床状况方面的应用。
• [EN] PYRROLIDINE DERIVATIVES AS FACTOR XA INHIBITORS<br/>[FR] DERIVES DE PYRROLIDINE SERVANT D'INHIBITEURS DU FACTEUR XA
  申请人：GLAXO GROUP LTD

  公开号：WO2002100830A1

  公开（公告）日：2002-12-19

  The invention relates to compounds of formula (I) which processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及式（I）的化合物，以及制备它们的方法，包含它们的制药组合物以及它们在医学上的使用，特别是在改善需要使用Factor Xa抑制剂的临床状况方面的使用。
• Pyrrolidine derivatives as factor xa inhibitors
  申请人：Chan Chuen

  公开号：US20050107379A1

  公开（公告）日：2005-05-19

  The invention relates to compounds of formula (I) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及公式（I）的化合物、其制备方法、包含它们的药物组合物以及它们在医学中的使用，特别是在改善需要使用Xa因子抑制剂的临床病情方面的使用。
• 2-(3-Sulfonylamino-2-oxopyrrolidin-1-yl)propanamides as factor xa inhibitors
  申请人：Borthwick David Alan

  公开号：US20050004119A1

  公开（公告）日：2005-01-06

  The invention relates to compounds of formula (I) pharmaceutical compositions containing the same as well as methods of treating patients suffering from a condition susceptible to amelioration by a Factor Xa inhibitor using the same.

  本发明涉及化合物(I)的配方、包含该化合物的药物组合物，以及使用该组合物治疗患有易于通过因子Xa抑制剂改善的疾病的患者的方法。
• Chemical compounds
  申请人：Chan Chuen

  公开号：US20060160886A1

  公开（公告）日：2006-07-20

  The invention relates to compounds of formula (Ic) processes for their preparation, pharmaceutical compositions containing them and to their use in medicine, particularly use in the amelioration of a clinical condition for which a Factor Xa inhibitor is indicated.

  本发明涉及式(Ic)化合物，其制备方法，含有它们的药物组合物以及它们在医学上的应用，特别是在改善适应于Xa因子抑制剂的临床状况方面的应用。