Acetic acid (3S,6R,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-5-oxo-octahydro-indolizin-6-yl ester | 267661-33-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Acetic acid (3S,6R,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-5-oxo-octahydro-indolizin-6-yl ester
• CAS: 267661-33-6
• 化学式: C₃₄H₃₆N₄O₆
• 分子量: 596.683
• InChiKey: WGOXMVCPTMGDMD-HJRZCVLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.04
• 重原子数：
  44.0
• 可旋转键数：
  9.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  140.39
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,6R,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-5-oxo-octahydro-indolizin-6-yl ester 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到[1-Amino-1-(4-{[((3S,6R,8aS)-6-benzyl-6-hydroxy-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester
  参考文献：
  名称：

  Exploring the chiral space within the active site of α-thrombin with a constrained mimic of d -Phe-Pro-Arg — design, synthesis, inhibitory activity, and X-ray structure of an enzyme–inhibitor complex

  摘要：

  An indolizidinone motif with strategically placed substitutents was designed and synthesized as a constrained mimic of D-Phe-Pro-Arg. Low nanomolar inhibition of a-thrombin validates the design elements in this inhibitor which also exhibits a 20-fold selectivity for thrombin versus trypsin. An X-ray crystal structure of the inhibitor with alpha-thrombin shows the expected interactions with key amino acids within the active site and some notable changes in positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00669-1
• 作为产物：
  描述：

  (3S,8S,9R)-3-(tert-butyldiphenylsilanyloxymethyl)-8-hydroxyhexahydroindolizin-5-one 在 吡啶 、 二硫化碳 、 4-二甲氨基吡啶 、 sodium chlorite 、 sodium dihydrogenphosphate 、 N-甲基吲哚酮 、 四丙基高钌酸铵 、 Davis' achiral oxaziridine 、 四丁基氟化铵 、 叔丁基锂 、 四丁基碘化铵 、 sodium hydride 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 叔丁醇 、 碘甲烷 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 Acetic acid (3S,6R,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-5-oxo-octahydro-indolizin-6-yl ester
  参考文献：
  名称：

  Exploring the chiral space within the active site of α-thrombin with a constrained mimic of d -Phe-Pro-Arg — design, synthesis, inhibitory activity, and X-ray structure of an enzyme–inhibitor complex

  摘要：

  An indolizidinone motif with strategically placed substitutents was designed and synthesized as a constrained mimic of D-Phe-Pro-Arg. Low nanomolar inhibition of a-thrombin validates the design elements in this inhibitor which also exhibits a 20-fold selectivity for thrombin versus trypsin. An X-ray crystal structure of the inhibitor with alpha-thrombin shows the expected interactions with key amino acids within the active site and some notable changes in positions. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00669-1