3-(4-nitrobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide | 1344141-56-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-(4-nitrobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide
• 英文别名: 3-[(4-nitrophenyl)methylamino]-N-[4-(trifluoromethoxy)phenyl]thiophene-2-carboxamide
• CAS: 1344141-56-5
• 化学式: C₁₉H₁₄F₃N₃O₄S
• 分子量: 437.399
• InChiKey: YNVBBNXJZVZJPN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  30
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(4-nitrobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide 在 platinum(IV) oxide 、 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 0.5h， 以91%的产率得到3-(4-aminobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide
  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
• 作为产物：
  描述：

  3-氨基-2-噻吩甲酸甲酯 在 sodium tetrahydroborate 、 三甲基铝 、 三氟乙酸 作用下， 以 乙酸乙酯 、 甲苯 为溶剂， 反应 40.0h， 生成 3-(4-nitrobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide
  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