2-(5-chloro-2-thienyl)-1,3-thiazole-5-sulfonyl chloride

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(5-chloro-2-thienyl)-1,3-thiazole-5-sulfonyl chloride
• 英文别名: 2-(5-Chlorothiophen-2-yl)-1,3-thiazole-5-sulfonyl chloride
• 化学式: C₇H₃Cl₂NO₂S₃
• 分子量: 300.21
• InChiKey: BFKXBEUUKREYFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S)-3-amino-1-[(1S)-1-methyl-2-(morpholin-4-yl)-2-oxoethyl]pyrrolidin-2-one 、 2-(5-chloro-2-thienyl)-1,3-thiazole-5-sulfonyl chloride 以66%的产率得到2-(5-chlorothiophen-2-yl)-N-[(3S)-1-[(2S)-1-(morpholin-4-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]-1,3-thiazole-5-sulfonamide
  参考文献：
  名称：

  Factor Xa Inhibitors:  S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides

  摘要：

  Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.

  DOI：

  10.1021/jm060870c
• 作为产物：
  描述：

  2-(5-chloro-2-thienyl)-1,3-thiazole 在 正丁基锂 、 二氧化硫 、 N-氯代丁二酰亚胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 0.33h， 生成 2-(5-chloro-2-thienyl)-1,3-thiazole-5-sulfonyl chloride
  参考文献：
  名称：

  Factor Xa Inhibitors:  S1 Binding Interactions of a Series of N-{(3S)-1-[(1S)-1-Methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides

  摘要：

  Factor Xa inhibitory activities for a series of N-{(3S)-1-[(1S)-1-methyl-2-morpholin-4-yl-2-oxoethyl]-2-oxopyrrolidin-3-yl}sulfonamides with different P1 groups are described. These data provide insight into binding interactions within the S1 primary specificity pocket; rationales are presented for the derived SAR on the basis of electronic interactions through crystal structures of fXa-ligand complexes and molecular modeling studies. A good correlation between in vitro anticoagulant activities with lipophilicity and the extent of human serum albumin binding is observed within this series of potent fXa inhibitors. Pharmacokinetic profiles in rat and dog, together with selectivity over other trypsin-like serine proteases, identified 1f as a candidate for further evaluation.

  DOI：

  10.1021/jm060870c

文献信息

• [EN] PYRROLIDINE-2-ONES AS FACTOR XA INHIBITORS<br/>[FR] PYRROLIDINE-2-ONES UTILISEES COMME INHIBITEURS DU FACTEUR XA
  申请人：GLAXO GROUP LTD

  公开号：WO2003053925A1

  公开（公告）日：2003-07-03

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

  该发明涉及式（I）的化合物，以及其药学上可接受的衍生物。该发明还涉及制备式（I）化合物的方法，含有式（I）化合物的药物组合物以及在医学上使用式（I）化合物，特别是在改善需要使用FXa抑制剂的临床病情方面的用途。
• 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。
• PYRROLIDINE-2-ONES AS FACTOR XA INHIBITORS
  申请人：GLAXO GROUP LIMITED

  公开号：EP1456172A1

  公开（公告）日：2004-09-15