13-[(4-tert-butylphenyl)sulfonyl]-9-(trifluoromethyl)-12,13-dihydro-7H-pyrido[2',3':5,6][1,4]diazepino[2,3-f]quinoline | 1339942-89-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯二氮卓类
• 英文名称: 13-[(4-tert-butylphenyl)sulfonyl]-9-(trifluoromethyl)-12,13-dihydro-7H-pyrido[2',3':5,6][1,4]diazepino[2,3-f]quinoline
• 英文别名: 10-(4-tert-butylphenyl)sulfonyl-5-(trifluoromethyl)-2,4,10,16-tetrazatetracyclo[9.8.0.03,8.012,17]nonadeca-1(11),3(8),4,6,12(17),13,15,18-octaene
• CAS: 1339942-89-0
• 化学式: C₂₆H₂₃F₃N₄O₂S
• 分子量: 512.555
• InChiKey: SMQOEXFVZFKSHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  83.6
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  5-氨基-6-硝基喹啉 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 、 乙二醇单丁醚 为溶剂， 反应 46.0h， 生成 13-[(4-tert-butylphenyl)sulfonyl]-9-(trifluoromethyl)-12,13-dihydro-7H-pyrido[2',3':5,6][1,4]diazepino[2,3-f]quinoline
  参考文献：
  名称：

  Discovery of Benzodiazepine Sulfonamide-Based Bombesin Receptor Subtype 3 Agonists and Their Unusual Chirality

  摘要：

  We report herein the discovery of benzodiazepine sulfonamide-based bombesin receptor subtype 3 (BRS-3) agonists and their unusual chirality. Starting from a high-throughput screening lead, we prepared a series of BRS-3 agonists with improved potency and pharmacokinetic properties, of which compound 8a caused mechanism-based, dose-dependent food intake reduction and body weight loss after oral dosing in diet-induced obese mice. This effort also led to the discovery of a novel family of chiral molecules originated from the conformationally constrained seven-membered diazepine ring.

  DOI：

  10.1021/ml200207w

文献信息

• SUBSTITUTED DIAZEPINE SULFONAMIDES AS BOMBESIN RECEPTOR SUBTYPE-1 MODULATORS
  申请人：Baker Robert K.

  公开号：US20100317645A1

  公开（公告）日：2010-12-16

  Certain novel substituted diazepine sulfonamides are ligands of the human bombesin receptor and, in particular, are selective ligands of the human bombesin receptor subtype-3 (BRS-3). They are therefore useful for the treatment, control, or prevention of diseases and disorders responsive to the modulation of BRS-3, such as obesity, and diabetes.

  某些新型取代二氮杂环磺酰胺是人体炸弹素受体的配体，特别是人体炸弹素受体亚型-3（BRS-3）的选择性配体。因此，它们可用于治疗、控制或预防对BRS-3调节敏感的疾病和障碍，如肥胖和糖尿病。
• SUBSTITUTED DIAZEPINE SULFONAMIDES AS BOMBESIN RECEPTOR SUBTYPE-3 MODULATORS
  申请人：Merck Sharp & Dohme Corp.

  公开号：EP2102201B1

  公开（公告）日：2010-10-13
• US8153626B2
  申请人：——

  公开号：US8153626B2

  公开（公告）日：2012-04-10
• Discovery of Benzodiazepine Sulfonamide-Based Bombesin Receptor Subtype 3 Agonists and Their Unusual Chirality
  作者：Ping Liu、Thomas J. Lanza、Marc Chioda、Carrie Jones、Harry R. Chobanian、Yan Guo、Linda Chang、Theresa M. Kelly、Yanqing Kan、Oksana Palyha、Xiao-Ming Guan、Donald J. Marsh、Joseph M. Metzger、Katie Ramsay、Sheng-Ping Wang、Alison M. Strack、Randy Miller、Jianmei Pang、Kathy Lyons、Jasminka Dragovic、Jian G. Ning、Wes A. Schafer、Christopher J. Welch、Xiaoyi Gong、Ying-Duo Gao、Viktor Hornak、Richard G. Ball、Nancy Tsou、Marc L. Reitman、Matthew J. Wyvratt、Ravi P. Nargund、Linus S. Lin

  DOI：10.1021/ml200207w

  日期：2011.12.8

  We report herein the discovery of benzodiazepine sulfonamide-based bombesin receptor subtype 3 (BRS-3) agonists and their unusual chirality. Starting from a high-throughput screening lead, we prepared a series of BRS-3 agonists with improved potency and pharmacokinetic properties, of which compound 8a caused mechanism-based, dose-dependent food intake reduction and body weight loss after oral dosing in diet-induced obese mice. This effort also led to the discovery of a novel family of chiral molecules originated from the conformationally constrained seven-membered diazepine ring.