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 | 1151561-19-1

• 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: 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
• CAS: 1151561-19-1
• 化学式: C₇₆H₉₆N₁₀O₁₂
• 分子量: 1341.66
• InChiKey: BSWCUCIPHHQAMK-RQRUDUKKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  98
• 可旋转键数：
  29
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  292
• 氢给体数：
  8
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  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 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 18.0h， 以100%的产率得到
  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)-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

文献信息

• [EN] SMAC MIMETIC COMPOUNDS AS APOPTOSIS INDUCERS<br/>[FR] NOUVEAUX COMPOSÉS MIMÉTIQUES DE SMAC EN TANT QU'INDUCTEURS DE L'APOPTOSE
  申请人：UNIV DEGLI STUDI MILANO

  公开号：WO2009060292A3

  公开（公告）日：2009-06-25
• 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.
• Homo- and heterodimeric Smac mimetics/IAP inhibitors as in vivo-active pro-apoptotic agents. Part I: Synthesis
  作者：Leonardo Manzoni、Laura Belvisi、Aldo Bianchi、Annalisa Conti、Carmelo Drago、Marilenia de Matteo、Luca Ferrante、Eloise Mastrangelo、Paola Perego、Donatella Potenza、Carlo Scolastico、Federica Servida、Gabriele Timpano、Francesca Vasile、Vincenzo Rizzo、Pierfausto Seneci

  DOI：10.1016/j.bmc.2012.09.020

  日期：2012.11

  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.