[1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester | 267661-45-0

• 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: [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester
• CAS: 267661-45-0
• 化学式: C₂₆H₃₀N₄O₅
• 分子量: 478.548
• InChiKey: IBRDWXMHHWKDAK-WOVHNISZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  35.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  134.32
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-5-oxo-octahydro-indolizine-3-carbonyl)-amino]-methyl}-phenyl)-meth-(Z)-ylidene]-carbamic acid benzyl ester 在 palladium on activated charcoal 盐酸 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 以100%的产率得到(3S,6S,8aS)-6-Hydroxy-6-methyl-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：

  (5S,2'S,5'S)-5-[1'-(tert-butoxycarbonyl)-5'-(tert-butyldiphenylsilyloxymethyl)pyrrolidin-2'-yl]-2(5H)-furanone 在 palladium on activated charcoal 吡啶 、 二硫化碳 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 swern reagent 、 B-溴代邻苯二氧硼烷 、 四丁基氟化铵 、 氢气 、 双氧水 、 叔丁基锂 、 氧气 、 sodium methylate 、 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 、 三甲氧基磷 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 反应 0.5h， 生成 [1-Amino-1-(4-{[((3S,6S,8aS)-6-hydroxy-6-methyl-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