2-bromo-N-(3-((2,5-dioxo-4-(4-(trifluoromethoxy)phenyl)-2,3,4,5-tetrahydro-1H-thieno[3,2-e][1,4]diazepin-1-yl)methyl)phenyl)acetamide | 1344141-88-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻烯杂卓类
• 英文名称: 2-bromo-N-(3-((2,5-dioxo-4-(4-(trifluoromethoxy)phenyl)-2,3,4,5-tetrahydro-1H-thieno[3,2-e][1,4]diazepin-1-yl)methyl)phenyl)acetamide
• 英文别名: 2-bromo-N-[3-[[2,5-dioxo-4-[4-(trifluoromethoxy)phenyl]-3H-thieno[3,2-e][1,4]diazepin-1-yl]methyl]phenyl]acetamide
• CAS: 1344141-88-3
• 化学式: C₂₃H₁₇BrF₃N₃O₄S
• 分子量: 568.371
• InChiKey: CLHRWQVWIOIRLW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-smino-N-(4-(trifluoromethoxy)phenyl)thiophene-2-carboxamide 在 platinum(IV) oxide 、 sodium tetrahydroborate 、 氢气 、 碳酸氢钠 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 0.58h， 生成 2-bromo-N-(3-((2,5-dioxo-4-(4-(trifluoromethoxy)phenyl)-2,3,4,5-tetrahydro-1H-thieno[3,2-e][1,4]diazepin-1-yl)methyl)phenyl)acetamide
  参考文献：
  名称：

  Inhibition of c-Kit, VEGFR-2 (KDR), and ABCG2 by analogues of OSI-930

  摘要：

  The quinoline domain of OSI-930, a dual inhibitor of receptor tyrosine kinases (RTKs) c-Kit and KDR, was modified in an effort to further understand the SAR of OSI-930, and the binding site characteristics of c-Kit and KDR. A series of 16 compounds with heteroatom substituted pyridyl and phenyl ring systems was synthesized and evaluated against a panel of kinases including c-Kit and KDR. Aminopyridyl derivative 6 was found to be the most active member of the series with 91% and 57% inhibition of c-Kit at 10 mu M and 1 mu M, respectively and 88% and 50% inhibition of KDR at 10 mu M and 1 mu M, respectively. The target compounds were also tested for their ability to inhibit efflux of mitoxantrone through inhibition of ATP dependent ABCG2 pump. Nitropyridyl derivative 5 and o-nitrophenyl derivative 7 exhibited complete inhibition of the ABCG2 pump with IC50 values of 13.67 mu M and 16.67 mu M, respectively. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.08.070