2-(4-tert-butylbenzenesulfonyl)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one | 861630-83-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 2-(4-tert-butylbenzenesulfonyl)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one
• 英文别名: 2-(4-t-Butylbenzenesulfonyl)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]-1,3,4,7,8,8a-hexahydro-2h-isoquinolin-6-one；2-(4-tert-butylphenyl)sulfonyl-8a-[[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]methyl]-3,4,7,8-tetrahydro-1H-isoquinolin-6-one
• CAS: 861630-83-3
• 化学式: C₃₂H₄₂BNO₅S
• 分子量: 563.566
• InChiKey: IEVPJTLVCWIUDY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  40
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  吗啉 、 2-(4-tert-butylbenzenesulfonyl)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one 生成 2-(4-tert-butylbenzenesulfonyl)-8a-[4-morpholin-4-ylbenzyl]-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one
  参考文献：
  名称：

  2-Benzenesulfonyl-8a-benzyl-hexahydro-2H-isoquinolin-6-ones as selective glucocorticoid receptor antagonists

  摘要：

  The 2-azadecalin ring system was evaluated as a scaffold for the preparation of glucocorticoid receptor (GR) antagonists. High affinity, selective GR antagonists were discovered based on a hypothetical binding mode related to the steroidal GR antagonist RU-43044. 2-Benzenesulfonyl substituted 8a-benzyl-hexahydro-2H-isoquinolin-6-ones exemplified by (R)-37 had low nanomolar affinity for GR with moderate functional activity (200 nM) in a reporter gene assay. These compounds were devoid of affinity for other steroidal receptors (ER, AR, MR, and PR). Analogues based on an alternative putative binding mode (CP-like) were found to be inactive. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.07.055
• 作为产物：
  描述：

  8a-(4-bromobenzyl)-2-(4-t-butylbenzenesulfonyl)-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one 、 联硼酸频那醇酯 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride sodium acetate 作用下， 以 DMF (N,N-dimethyl-formamide) 为溶剂， 反应 0.17h， 生成 2-(4-tert-butylbenzenesulfonyl)-8a-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzyl]-1,3,4,7,8,8a-hexahydro-2H-isoquinolin-6-one
  参考文献：
  名称：

  [EN] AZADECALIN GLUCOCORTICOID RECEPTOR MODULATORS
  [FR] COMPOSES D'AZADECALINE UTILISES EN TANT QUE MODULATEURS DU RECEPTEUR GLUCOCORTICOIDE

  摘要：

  公开号：

  WO2005070893A3

文献信息

• Azadecalin Glucocorticoid Receptor Modulators
  申请人：Clark D. Robin

  公开号：US20070203179A1

  公开（公告）日：2007-08-30

  The present invention provides a novel class of azadecalin compounds and methods of using the compounds as glucocorticoid receptor modulators.

  本发明提供了一种新型的氮杂癸烷化合物，以及使用这些化合物作为糖皮质激素受体调节剂的方法。
• AZADECALIN GLUCOCORTICOID RECEPTOR MODULATORS
  申请人：CLARK Robin D.

  公开号：US20100120759A1

  公开（公告）日：2010-05-13

  The present invention provides a novel class of azadecalin compounds and methods of using the compounds as glucocorticoid receptor modulators.

  本发明提供了一种新型的氮杂萜化合物类别，并提供了使用这些化合物作为糖皮质激素受体调节剂的方法。
• Azadecalin glucocorticoid receptor modulators
  申请人：Corcept Therapeutics, Inc.

  公开号：US08324203B2

  公开（公告）日：2012-12-04

  The present invention provides a novel class of azadecalin compounds and methods of using the compounds as glucocorticoid receptor modulators.

  本发明提供了一种新型的氮杂萜类化合物，以及使用这些化合物作为糖皮质激素受体调节剂的方法。
• Azadecalin Glucocorticoid receptor modulators
  申请人：Corcept Therapeutics, Inc.

  公开号：US07678813B2

  公开（公告）日：2010-03-16

  The present invention provides a novel class of azadecalin compounds and methods of using the compounds as glucocorticoid receptor modulators.

  本发明提供了一种新型的氮杂萜化合物类别以及使用这些化合物作为糖皮质激素受体调节剂的方法。
• 2-Benzenesulfonyl-8a-benzyl-hexahydro-2H-isoquinolin-6-ones as selective glucocorticoid receptor antagonists
  作者：Robin D. Clark、Nicholas C. Ray、Paul Blaney、Peter H. Crackett、Christopher Hurley、Karen Williams、Hazel J. Dyke、David E. Clark、Peter M. Lockey、Rene Devos、Melanie Wong、Anne White、Joseph K. Belanoff

  DOI：10.1016/j.bmcl.2007.07.055

  日期：2007.10

  The 2-azadecalin ring system was evaluated as a scaffold for the preparation of glucocorticoid receptor (GR) antagonists. High affinity, selective GR antagonists were discovered based on a hypothetical binding mode related to the steroidal GR antagonist RU-43044. 2-Benzenesulfonyl substituted 8a-benzyl-hexahydro-2H-isoquinolin-6-ones exemplified by (R)-37 had low nanomolar affinity for GR with moderate functional activity (200 nM) in a reporter gene assay. These compounds were devoid of affinity for other steroidal receptors (ER, AR, MR, and PR). Analogues based on an alternative putative binding mode (CP-like) were found to be inactive. (c) 2007 Elsevier Ltd. All rights reserved.