9-Cyano-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid | 897920-24-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 9-Cyano-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid
• 英文别名: 8-cyano-15-methyltetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid
• CAS: 897920-24-0
• 化学式: C₁₉H₁₅NO₂
• 分子量: 289.334
• InChiKey: HDDCMVPYVWEWHO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  61.1
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-氨基噻唑 、 9-Cyano-9,10-dihydro-11-methyl-9,10-ethanoanthracene-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 8-cyano-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：

  甲基丙烯酸 、 9-氰基蒽 以 硝基苯 为溶剂， 生成 9-Cyano-9,10-dihydro-11-methyl-9,10-ethanoanthracene-11-carboxylic acid 、 1-Cyano-15-methyltetracyclo[6.6.2.02,7.09,14]hexadeca-2,4,6,9,11,13-hexaene-15-carboxylic acid
  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

• Substituted heteroaryl amide modulators of glucocorticoid receptor, AP-1, and/or NF-kB activity and use thereof
  申请人：Sheppeck James

  公开号：US20060154973A1

  公开（公告）日：2006-07-13

  The present invention relates to new class of non-steroidal compounds which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory- and immune-associated diseases, and have the structure including all stereoisomers thereof, tautomers thereof, or a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein X is selected from N, O, and S; Y is N or CR 6 ; Z is a ring; and where R, R a , R b , R c , R d , R 1 , R 2 , R 3 , R 4 , and R 5 are as defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising said compounds.

  本发明涉及一类新的非甾体化合物，用于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括肥胖、糖尿病、炎症和免疫相关疾病，并具有结构，包括其所有立体异构体、互变异构体或前药，或其药用可接受盐，其中X选自N、O和S；Y为N或CR6；Z为一个环；R、Ra、Rb、Rc、Rd、R1、R2、R3、R4和R5如本文所定义。还提供了包含所述化合物的药物组合物和治疗肥胖、糖尿病以及炎症或免疫相关疾病的方法。
• Substituted heteroaryl amide modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof
  申请人：Bristol-Myers Squibb Co.

  公开号：US07361654B2

  公开（公告）日：2008-04-22

  The present invention relates to new class of non-steroidal compounds which are useful in treating diseases associated with modulation of the glucocorticoid receptor, AP-1, and/or NF-κB activity including obesity, diabetes, inflammatory- and immune-associated diseases, and have the structure including all stereoisomers thereof, tautomers thereof, or a prodrug thereof, or a pharmaceutically acceptable salt thereof, wherein X is selected from N, O, and S; Y is N or CR6; Z is a ring; and where R, Ra, Rb, Rc, Rd, R1, R2, R3, R4, and R5 are as defined herein. Also provided are pharmaceutical compositions and methods of treating obesity, diabetes and inflammatory or immune associated diseases comprising such compounds.

  本发明涉及一类新型非甾体化合物，可用于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括肥胖症、糖尿病、炎症和免疫相关疾病，其结构包括所有立体异构体、互变异构体、前药或其药学上可接受的盐，其中X选择自N、O和S; Y为N或CR6; Z为环; R、Ra、Rb、Rc、Rd、R1、R2、R3、R4和R5的定义如本文所述。还提供了包含这些化合物的药物组合物和治疗肥胖症、糖尿病和炎症或免疫相关疾病的方法。
• COMPOSITIONS AND METHODS INVOLVING NUCLEAR HORMONE RECEPTOR SITE II
  申请人：Bristol-Myers Squibb Company

  公开号：EP1575502B1

  公开（公告）日：2010-01-20
• MODULATORS OF THE GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Bristol-Myers Squibb Company

  公开号：EP1844028B1

  公开（公告）日：2011-02-23
• SUBSTITUTED HETEROARYL AMIDE MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NFkB ACTIVITY AND USE THEREOF
  申请人：Bristol-Myers Squibb Company

  公开号：EP1896434B1

  公开（公告）日：2011-02-23