tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-3-(benzhydrylcarbamoyl)-5-oxo-7-[(pent-4-ynoylamino)methyl]-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]carbamate | 1151560-24-5

• 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: tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-3-(benzhydrylcarbamoyl)-5-oxo-7-[(pent-4-ynoylamino)methyl]-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]carbamate
• CAS: 1151560-24-5
• 化学式: C₃₈H₄₉N₅O₆
• 分子量: 671.837
• InChiKey: NMKIZRHEYNESDK-NNKOJQEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  49
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  146
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-3-(benzhydrylcarbamoyl)-5-oxo-7-[(pent-4-ynoylamino)methyl]-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]carbamate 在 copper diacetate 作用下， 以 乙腈 为溶剂， 反应 0.5h， 以36%的产率得到tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-7-[[[10-[[(3S,6S,7R,9aS)-3-(benzhydrylcarbamoyl)-6-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoyl]amino]-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-7-yl]methylamino]-10-oxodeca-4,6-diynoyl]amino]methyl]-3-(benzhydrylcarbamoyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Homo- and heterodimeric Smac mimetics/IAP inhibitors as in vivo-active pro-apoptotic agents. Part I: Synthesis

  摘要：

  Novel pro-apoptotic, homo-and heterodimeric Smac mimetics/IAPs inhibitors based on the N-AVPI-like 4-substituted 1-aza-2-oxobicyclo[5.3.0]decane scaffold were prepared from monomeric structures connected through a head-head (8), tail-tail (9) or head-tail (10) linker. The selection of appropriate decorating functions for the scaffolds, and of rigid and flexible linkers connecting them, is described. The synthesis, purification and analytical characterization of each prepared dimer 8-10 is thoroughly described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.020
• 作为产物：
  描述：

  tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-7-(azidomethyl)-3-(benzhydrylcarbamoyl)-5-oxo-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]-N-methylcarbamate 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 、 三甲基膦 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 tert-butyl N-[(2S)-1-[[(3S,6S,7R,9aS)-3-(benzhydrylcarbamoyl)-5-oxo-7-[(pent-4-ynoylamino)methyl]-1,2,3,6,7,8,9,9a-octahydropyrrolo[1,2-a]azepin-6-yl]amino]-1-oxobutan-2-yl]carbamate
  参考文献：
  名称：

  Homo- and heterodimeric Smac mimetics/IAP inhibitors as in vivo-active pro-apoptotic agents. Part I: Synthesis

  摘要：

  Novel pro-apoptotic, homo-and heterodimeric Smac mimetics/IAPs inhibitors based on the N-AVPI-like 4-substituted 1-aza-2-oxobicyclo[5.3.0]decane scaffold were prepared from monomeric structures connected through a head-head (8), tail-tail (9) or head-tail (10) linker. The selection of appropriate decorating functions for the scaffolds, and of rigid and flexible linkers connecting them, is described. The synthesis, purification and analytical characterization of each prepared dimer 8-10 is thoroughly described. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.09.020

文献信息

• SMAC mimetic compounds as apoptosis inducers
  申请人：Universita' degli Studi di Milano

  公开号：EP2058312A1

  公开（公告）日：2009-05-13

  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.

  本发明涉及具有凋亡抑制蛋白（IAPs）抑制剂功能的 Smac 的构象受限模拟物化合物，本发明还涉及这些化合物在治疗中的应用，其中诱导细胞凋亡是有益的，特别是在单独或与其他活性成分联合治疗癌症时。
• 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