benzyl (3S,6S,10aR)-6-(tert-butoxycarbonylamino)-5,8-dioxodecahydropyrrolo[1,2-a]azocine-3-carboxylate | 957134-94-0

• 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: benzyl (3S,6S,10aR)-6-(tert-butoxycarbonylamino)-5,8-dioxodecahydropyrrolo[1,2-a]azocine-3-carboxylate
• 英文别名: benzyl (3S,6S,10aR)-6-[(2-methylpropan-2-yl)oxycarbonylamino]-5,8-dioxo-1,2,3,6,7,9,10,10a-octahydropyrrolo[1,2-a]azocine-3-carboxylate
• CAS: 957134-94-0
• 化学式: C₂₃H₃₀N₂O₆
• 分子量: 430.501
• InChiKey: WDRKPHGHOOAMNK-WDSOQIARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl (3S,6S,10aR)-6-(tert-butoxycarbonylamino)-5,8-dioxodecahydropyrrolo[1,2-a]azocine-3-carboxylate 、 benzyl (3S,6S,10aR)-6-(tert-butoxycarbonylamino)-5,9-dioxodecahydropyrrolo[1,2-a]azocine-3-carboxylate 在 硫酸 sodium cyanoborohydride 作用下， 以 甲醇 为溶剂， 以94%的产率得到benzyl (3S,6S,SR,10aR)-6-(tert-butoxycarbonylamino)-9-hydroxy-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxylate
  参考文献：
  名称：

  WO2007/130626

  摘要：

  公开号：
• 作为产物：
  描述：

  benzyl (3S,6S,9R,10aR)-6-(tert-butoxycarbonylamino)-9-hydroxy-5-oxodecahydropyrrolo[1,2-a]azocine-3-carboxylate 在 戴斯-马丁氧化剂 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以28%的产率得到benzyl (3S,6S,10aR)-6-(tert-butoxycarbonylamino)-5,9-dioxodecahydropyrrolo[1,2-a]azocine-3-carboxylate
  参考文献：
  名称：

  WO2007/130626

  摘要：

  公开号：

文献信息

• Nonpeptidic and Potent Small-Molecule Inhibitors of cIAP-1/2 and XIAP Proteins
  作者：Haiying Sun、Jianfeng Lu、Liu Liu、Han Yi、Su Qiu、Chao-Yie Yang、Jeffrey R. Deschamps、Shaomeng Wang

  DOI：10.1021/jm100487z

  日期：2010.9.9

  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.
• 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
• US8202902B2
  申请人：——

  公开号：US8202902B2

  公开（公告）日：2012-06-19