methyl (3S,6S,7S,9aS)-7-(hydroxymethyl)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate | 1151561-27-1

• 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: methyl (3S,6S,7S,9aS)-7-(hydroxymethyl)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
• CAS: 1151561-27-1
• 化学式: C₂₂H₃₇N₃O₇
• 分子量: 455.552
• InChiKey: IFHAIALZYPCQPX-XAJHFOFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  126
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl (3S,6S,7S,9aS)-7-(hydroxymethyl)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate 在 水 、 lithium hydroxide 、 盐酸 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 为溶剂， 以100%的产率得到(3S,6S,7S,9aS)-7-(hydroxymethyl)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylic acid
  参考文献：
  名称：

  Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy

  摘要：

  Novel proapoptotic Smac mimics/IAPs inhibitors have been designed, synthesized and characterized. Computational models and structural studies (crystallography, NMR) have elucidated the SAR of this class of inhibitors, and have permitted further optimization of their properties. In vitro characterization (XIAP BIR3 and linker-BIR2-BIR3 binding, cytotox assays, early ADMET profiling) of the compounds has been performed, identifying one lead for further in vitro and in vivo evaluation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.009
• 作为产物：
  描述：

  methyl (3S,6S,7S,9aS)-6-amino-7-(hydroxymethyl)-5-oxooctahydro-1H-pyrrolo[1,2-a]azepine-3-carboxylate 、 N-Boc-(S)-2-甲氨基丁酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 以82%的产率得到methyl (3S,6S,7S,9aS)-7-(hydroxymethyl)-6-[[(2S)-2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepine-3-carboxylate
  参考文献：
  名称：

  Rational design, synthesis and characterization of potent, non-peptidic Smac mimics/XIAP inhibitors as proapoptotic agents for cancer therapy

  摘要：

  Novel proapoptotic Smac mimics/IAPs inhibitors have been designed, synthesized and characterized. Computational models and structural studies (crystallography, NMR) have elucidated the SAR of this class of inhibitors, and have permitted further optimization of their properties. In vitro characterization (XIAP BIR3 and linker-BIR2-BIR3 binding, cytotox assays, early ADMET profiling) of the compounds has been performed, identifying one lead for further in vitro and in vivo evaluation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.07.009

文献信息

• HOMO- AND HETERODIMERIC SMAC MIMETIC COMPOUNDS AS APOPTOSIS INDUCERS
  申请人：Universita' degli Studi di Milano

  公开号：EP2817322B1

  公开（公告）日：2016-04-20
• SMAC MIMETIC COMPOUNDS AS APOPTOSIS INDUCERS
  申请人：Scolastico Carlo

  公开号：US20100267692A1

  公开（公告）日：2010-10-21

  The present invention relates to compounds conformationally constrained mimetics of Smac with function as inhibitors of Inhibitor of Apoptosis Proteins (IAPs), the invention also relates to the use of these compounds in therapy, wherein the induction of apoptotic cell death is beneficial, especially in the treatment of cancer, alone or in combination with other active ingredients.
• New Homo- and Heterodimeric SMAC Mimetic Compounds as Apoptosis Inducers
  申请人：Seneci Pierfausto

  公开号：US20150119342A1

  公开（公告）日：2015-04-30

  The present invention relates to conformationally constrained homo- and heterodimeric mimetics of Smac with function as inhibitors of Inhibitor of Apoptosis Proteins (IAPs), the invention also relates to the use of these compounds in therapy, wherein the induction of apoptotic cell death is beneficial, especially in the treatment of cancer, alone or in combination with other active ingredients.
• US9321808B2
  申请人：——

  公开号：US9321808B2

  公开（公告）日：2016-04-26
• US9730976B2
  申请人：——

  公开号：US9730976B2

  公开（公告）日：2017-08-15