Trifluoromethanesulfonic acid 9-(4-methylthiazol-2-yl)-8-oxo-5,6,7,8-tetrahydro-2,7a-diazadibenzo[a,c]cyclohepten-11-yl ester | 216012-92-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: Trifluoromethanesulfonic acid 9-(4-methylthiazol-2-yl)-8-oxo-5,6,7,8-tetrahydro-2,7a-diazadibenzo[a,c]cyclohepten-11-yl ester
• 英文别名: [13-(4-methyl-1,3-thiazol-2-yl)-12-oxo-4,11-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,13-pentaen-15-yl] trifluoromethanesulfonate
• CAS: 216012-92-9
• 化学式: C₁₈H₁₄F₃N₃O₄S₂
• 分子量: 457.454
• InChiKey: SSFDZORGJANJGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  126
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Trifluoromethanesulfonic acid 9-(4-methylthiazol-2-yl)-8-oxo-5,6,7,8-tetrahydro-2,7a-diazadibenzo[a,c]cyclohepten-11-yl ester 在 palladium diacetate 、 三乙胺 、 三苯基膦 作用下， 以 甲酸 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到13-(4-Methyl-1,3-thiazol-2-yl)-4,11-diazatricyclo[9.4.0.02,7]pentadeca-1(15),2(7),3,5,13-pentaen-12-one
  参考文献：
  名称：

  Synthesis of tricyclic pyridones by radical cyclization

  摘要：

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00652-8
• 作为产物：
  描述：

  3-bromo-4-[3-hydroxypropyl]pyridine 在 偶氮二异丁腈 、 三正丁基氢锡 、 三溴化硼 、 sodium hydride 、 lithium bromide 作用下， 以 吡啶 、 乙二醇二甲醚 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 丙酮 、 苯 为溶剂， 反应 77.75h， 生成 Trifluoromethanesulfonic acid 9-(4-methylthiazol-2-yl)-8-oxo-5,6,7,8-tetrahydro-2,7a-diazadibenzo[a,c]cyclohepten-11-yl ester
  参考文献：
  名称：

  Synthesis of tricyclic pyridones by radical cyclization

  摘要：

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(99)00652-8

文献信息

• Tricyclic pyridin-2-one analogue as a GABA receptor ligand
  申请人：——

  公开号：US20010053776A1

  公开（公告）日：2001-12-20

  9-(4-Methylthiazol-2-yl)- 11-(pyridin-4-yl)-6,7-dihydro-5H-2, 7a-diazadibenzo[a,c]cyclohepten-8-one, and pharmaceutically acceptable salts thereof, are selective ligands for GABAA receptors, in particular having high affinity for the a2 and/or a3 subunit thereof, and are accordingly of benefit in the treatment and/or prevention of disorders of the central nervous system, including anxiety and convulsions.

  9-(4-甲基噻唑-2-基)-11-(吡啶-4-基)-6,7-二氢-5H-2,7a-二氮杂二苯并[a,c]环庚-8-酮及其药学上可接受的盐是GABA A 受体的选择性配体，特别是对其中的a2和/或a3亚单位具有高亲和力，因此对于治疗和/或预防中枢神经系统疾病，包括焦虑和惊厥，具有益处。
• Tricyclic pyridones as functionally selective human GABAAα2/3 receptor-ion channel ligands
  作者：James Crawforth、John R. Atack、Susan M. Cook、Karl R. Gibson、Alan Nadin、Andrew P. Owens、Andrew Pike、Michael Rowley、Alison J. Smith、Bindi Sohal、Francine Sternfeld、Keith Wafford、Leslie J. Street

  DOI：10.1016/j.bmcl.2004.01.057

  日期：2004.4

  A series of tricyclic pyridones has been evaluated as benzodiazepine site ligands with functional selectivity for the alpha(3) over the alpha(1) containing subtype of the human GABA(A) receptor ion channel. This investigation led to the identification of a high affinity, functionally selective, orally bioavailable benzodiazepine site ligand that demonstrated activity in rodent anxiolysis models and reduced sedation relative to diazepam. (C) 2004 Elsevier Ltd. All rights reserved.
• Synthesis of tricyclic pyridones by radical cyclization
  作者：Alan Nadin、Timothy Harrison

  DOI：10.1016/s0040-4039(99)00652-8

  日期：1999.5

  A general and novel route for the synthesis of tricyclic pyridones by 5-, 6- and 7-exo-trig radical cyclization is described. The use of Pd-catalyzed cross-coupling reactions to introduce functionality at the 5-position of a pyridone is also presented. (C) 1999 Published by Elsevier Science Ltd. All rights reserved.