tert-butyl ((3S,6S,9R,10aR)-9-azido-5-oxo-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)decahydropyrrolo[1,2-a]azocin-6-yl)carbamate | 957134-97-3

• 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 ((3S,6S,9R,10aR)-9-azido-5-oxo-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)decahydropyrrolo[1,2-a]azocin-6-yl)carbamate
• 英文别名: tert-butyl N-[(3S,6S,9R,10aR)-9-azido-5-oxo-3-[[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]carbamoyl]-2,3,6,7,8,9,10,10a-octahydro-1H-pyrrolo[1,2-a]azocin-6-yl]carbamate
• CAS: 957134-97-3
• 化学式: C₂₆H₃₆N₆O₄
• 分子量: 496.61
• InChiKey: UGERUYYDPMTHFL-MPCSADPFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl ((3S,6S,9R,10aR)-9-azido-5-oxo-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)decahydropyrrolo[1,2-a]azocin-6-yl)carbamate 在 盐酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 为溶剂， 生成
  参考文献：
  名称：

  Nonpeptidic and Potent Small-Molecule Inhibitors of cIAP-1/2 and XIAP Proteins

  摘要：

  A series of compounds were designed and synthesized as antagonists of cIAP-1/2 and XIAP based upon our previously identified lead compound SM-122 (1). The most potent of these (7) binds to XIAP, cIAP-1, and cIAP-2 proteins with K(i) values of 36, <1, and <1.9 nM, respectively. Consistent with its potent binding affinities to IAPs, 7 effectively antagonizes XIAP in a cell-free caspase-9 functional assay, efficiently induces cIAP-1 degradation in cells at concentrations as low as 10 nM, and triggers activation of caspases and PARP cleavage in the MDA-MB-231 breast cancer cell line. Compound 7 potently inhibits cell growth in the MDA-MB-231 cancer cell line with an IC(50) value of 200 nM and is 9 times more potent than compound 1.

  DOI：

  10.1021/jm100487z
• 作为产物：
  描述：

  在 叠氮磷酸二苯酯 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 以79%的产率得到tert-butyl ((3S,6S,9R,10aR)-9-azido-5-oxo-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)decahydropyrrolo[1,2-a]azocin-6-yl)carbamate
  参考文献：
  名称：

  Nonpeptidic and Potent Small-Molecule Inhibitors of cIAP-1/2 and XIAP Proteins

  摘要：

  A series of compounds were designed and synthesized as antagonists of cIAP-1/2 and XIAP based upon our previously identified lead compound SM-122 (1). The most potent of these (7) binds to XIAP, cIAP-1, and cIAP-2 proteins with K(i) values of 36, <1, and <1.9 nM, respectively. Consistent with its potent binding affinities to IAPs, 7 effectively antagonizes XIAP in a cell-free caspase-9 functional assay, efficiently induces cIAP-1 degradation in cells at concentrations as low as 10 nM, and triggers activation of caspases and PARP cleavage in the MDA-MB-231 breast cancer cell line. Compound 7 potently inhibits cell growth in the MDA-MB-231 cancer cell line with an IC(50) value of 200 nM and is 9 times more potent than compound 1.

  DOI：

  10.1021/jm100487z

文献信息

• WO2007/130626
  申请人：——

  公开号：——

  公开（公告）日：——
• INTERMEDIATES FOR THE PREPARATION OF BIVALENT SMAC MIMETICS
  申请人：THE REGENTS OF THE UNIVERSITY OF MICHIGAN

  公开号：EP2019671B1

  公开（公告）日：2014-09-24
• Bivalent SMAC mimetics and the uses thereof
  申请人：Wang Shaomeng

  公开号：US20080089896A1

  公开（公告）日：2008-04-17

  The invention relates to bivalent mimetics of Smac which function as inhibitors of Inhibitor of Apoptosis Proteins. The invention also relates to the use of these mimetics for inducing apoptotic cell death and for sensitizing cells to inducers of apoptosis.
• BIVALENT SMAC MIMETICS AND THE USES THEREOF
  申请人：Wang Shaomeng

  公开号：US20090123480A1

  公开（公告）日：2009-05-14

  The invention relates to bivalent mimetics of Smac which function as inhibitors of Inhibitor of Apoptosis Proteins. The invention also relates to the use of these mimetics for inducing apoptotic cell death and for sensitizing cells to inducers of apoptosis.
• US7960372B2
  申请人：——

  公开号：US7960372B2

  公开（公告）日：2011-06-14