11-methyl-N-(1,3-thiazol-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11-carboxamide | 312317-98-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 11-methyl-N-(1,3-thiazol-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11-carboxamide
• 英文别名: 15-methyl-N-(1,3-thiazol-2-yl)tetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxamide
• CAS: 312317-98-9
• 化学式: C₂₁H₁₈N₂OS
• 分子量: 346.453
• InChiKey: QYEYUIJWYCBKBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  70.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  11-methyl-N-(1,3-thiazol-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11-carboxamide 在 chiral HPLC 作用下， 生成 (15R)-15-methyl-N-(1,3-thiazol-2-yl)tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9(14),10,12-hexaene-15-carboxamide 、 (15S)-15-methyl-N-(1,3-thiazol-2-yl)tetracyclo[6.6.2.0^{2,7}.0^{9,14}]hexadeca-2,4,6,9(14),10,12-hexaene-15-carboxamide
  参考文献：
  名称：

  Discovery of novel dihydro-9,10-ethano-anthracene carboxamides as glucocorticoid receptor modulators

  摘要：

  A series of dihydro-9,10-ethano-anthracene-11-carboxamides as novel glucocorticoid receptor modulators is reported. SAR exploration identified compounds from this series displaying a promising dissociation pro. le in discriminating between transrepression and transactivation activities. 17a is a partial agonist of GR-mediated transactivation which elicits potent and efficacious transrepression in reporter gene assays. A hypothetical binding mode is provided which accounts for the induction of functional activity by a bridgehead methyl group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.006
• 作为产物：
  描述：

  2-氨基噻唑 、 9,10-dihydro-9,10-ethano-anthracene-11-methyl-11-carboxylic acid 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 11-methyl-N-(1,3-thiazol-2-yl)-9,10-dihydro-9,10-ethanoanthracene-11-carboxamide
  参考文献：
  名称：

  Discovery of novel dihydro-9,10-ethano-anthracene carboxamides as glucocorticoid receptor modulators

  摘要：

  A series of dihydro-9,10-ethano-anthracene-11-carboxamides as novel glucocorticoid receptor modulators is reported. SAR exploration identified compounds from this series displaying a promising dissociation pro. le in discriminating between transrepression and transactivation activities. 17a is a partial agonist of GR-mediated transactivation which elicits potent and efficacious transrepression in reporter gene assays. A hypothetical binding mode is provided which accounts for the induction of functional activity by a bridgehead methyl group. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.03.006

文献信息

• US7442554B2
  申请人：——

  公开号：US7442554B2

  公开（公告）日：2008-10-28