3-(3-aminobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide | 1344141-65-6

• 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-(3-aminobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide
• 英文别名: 3-[(3-aminophenyl)methylamino]-N-[4-(trifluoromethoxy)phenyl]thiophene-2-carboxamide
• CAS: 1344141-65-6
• 化学式: C₁₉H₁₆F₃N₃O₂S
• 分子量: 407.416
• InChiKey: JKHQXSLSCWFWLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  28
• 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：
  105
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  3-(3-aminobenzylamino)-N-(4-trifluoromethoxyphenyl)thiophene-2-carboxamide 、 溴乙酰溴 在 碳酸氢钠 作用下， 以 四氢呋喃 为溶剂， 反应 0.08h， 以35%的产率得到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
• 作为产物：
  描述：

  3-smino-N-(4-(trifluoromethoxy)phenyl)thiophene-2-carboxamide 在 platinum(IV) oxide 、 sodium tetrahydroborate 、 氢气 、 三氟乙酸 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 20.0 ℃ 、275.8 kPa 条件下， 反应 0.5h， 生成 3-(3-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

文献信息

• Inhibition of c-Kit, VEGFR-2 (KDR), and ABCG2 by analogues of OSI-930
  作者：Jay P. Patel、Ye-Hong Kuang、Zhe-Sheng Chen、Vijaya L. Korlipara

  DOI：10.1016/j.bmcl.2011.08.070

  日期：2011.11

  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.