7-{[3-(trifluoromethyl)phenyl]amino}-2H-benzo[b][1,4]thiazin-3(4H)-one | 1611467-38-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并噻嗪类
• 英文名称: 7-{[3-(trifluoromethyl)phenyl]amino}-2H-benzo[b][1,4]thiazin-3(4H)-one
• 英文别名: 7-[3-(trifluoromethyl)anilino]-4H-1,4-benzothiazin-3-one
• CAS: 1611467-38-9
• 化学式: C₁₅H₁₁F₃N₂OS
• 分子量: 324.326
• InChiKey: ZVRAARQTTFEQRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  66.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  间氨基三氟甲苯 、 7-溴-2H-[1,4]-苯并噻嗪-3(4H)-酮 在 tris-(dibenzylideneacetone)dipalladium(0) 、 sodium t-butanolate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲苯 为溶剂， 反应 9.0h， 以65%的产率得到7-{[3-(trifluoromethyl)phenyl]amino}-2H-benzo[b][1,4]thiazin-3(4H)-one
  参考文献：
  名称：

  Optimization of diaryl amine derivatives as kinesin spindle protein inhibitors

  摘要：

  Structure-activity relationship studies of diaryl amine-type KSP inhibitors were carried out. Diaryl amine derivatives with a pyridine ring or urea group were less active when compared with the parent carboline and carbazole derivatives. Optimization studies of a lactam-fused diphenylamine-type KSP inhibitor revealed that the aniline NH group and 3-CF3 phenyl group were indispensable for potent KSP inhibition. Modification with a seven-membered lactam-fused phenyl group and a 4-(trifluoromethyl)pyridin-2-yl group improved aqueous solubility while maintaining potent KSP inhibitory activity. From these studies, we identified novel diaryl amine-type KSP inhibitors with a favorable balance of potency and solubility. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2014.04.008

文献信息

• Optimization of diaryl amine derivatives as kinesin spindle protein inhibitors
  作者：Tomoki Takeuchi、Shinya Oishi、Masato Kaneda、Ryosuke Misu、Hiroaki Ohno、Jun-ichi Sawada、Akira Asai、Shinya Nakamura、Isao Nakanishi、Nobutaka Fujii

  DOI：10.1016/j.bmc.2014.04.008

  日期：2014.6

  Structure-activity relationship studies of diaryl amine-type KSP inhibitors were carried out. Diaryl amine derivatives with a pyridine ring or urea group were less active when compared with the parent carboline and carbazole derivatives. Optimization studies of a lactam-fused diphenylamine-type KSP inhibitor revealed that the aniline NH group and 3-CF3 phenyl group were indispensable for potent KSP inhibition. Modification with a seven-membered lactam-fused phenyl group and a 4-(trifluoromethyl)pyridin-2-yl group improved aqueous solubility while maintaining potent KSP inhibitory activity. From these studies, we identified novel diaryl amine-type KSP inhibitors with a favorable balance of potency and solubility. (C) 2014 Elsevier Ltd. All rights reserved.