Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester | 267661-37-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester
• CAS: 267661-37-0
• 化学式: C₃₅H₃₈N₄O₇
• 分子量: 626.709
• InChiKey: GCPOUIPITZHWSN-DWNBPJMTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.67
• 重原子数：
  46.0
• 可旋转键数：
  10.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  149.62
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-5-oxo-octahydro-indolizin-6-yl ester 在 palladium on activated charcoal 盐酸 、 氢气 、 sodium methylate 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 生成 (3S,6S,8S,8aS)-6-Benzyl-6-hydroxy-8-methoxy-5-oxo-octahydro-indolizine-3-carboxylic acid 4-carbamimidoyl-benzylamide; hydrochloride
  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 、 N-甲基吡咯烷酮 、 4-二甲氨基吡啶 、 sodium dihydrogenphosphate 、 四丙基高钌酸铵 、 Davis achiral oxaziridine 、 sodium perchlorate 、 四丁基氟化铵 、 叔丁基锂 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 silver(l) oxide 、 叔丁醇 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 Acetic acid (3S,6S,8S,8aS)-3-(4-{amino-[(Z)-benzyloxycarbonylimino]-methyl}-benzylcarbamoyl)-6-benzyl-8-methoxy-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