3-amino-4-trifluoromethyl-6-phenylindazole | 945224-59-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡唑类
• 英文名称: 3-amino-4-trifluoromethyl-6-phenylindazole
• 英文别名: 3-amino-6-phenyl-4-(trifluoromethyl)-1H-indazole-7-carbonitrile
• CAS: 945224-59-9
• 化学式: C₁₅H₉F₃N₄
• 分子量: 302.258
• InChiKey: GJGXVVNOTSCXCG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  78.5
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3-amino-4-trifluoromethyl-6-phenylindazole 在 溶剂黄146 作用下， 反应 0.05h， 生成
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines

  摘要：

  A series of novel pyrimido[1,2-b]indazoles 5, 7 have been prepared from 3-trifluoromethyl-5-phenyl-2,6-dicyano anilines 1 via novel indazole regioisomers 3 and 4 through a facile strategy. Specific examples were evaluated for anticancer activity in vitro and found to exhibit promising activity against A-549 cell lines and are more effective than Etoposide. QSAR models were developed and validated by cross-validation method. The results of the best QSAR model were further compared with the crystal structure of tubulin protein. The binding energies estimated were found to have a good correlation with the experimental inhibitory potencies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.087
• 作为产物：
  描述：

  2,6-二氰基-3-三氟甲基-5-苯基苯胺 在 盐酸 、 一水合肼 、 sodium nitrite 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 2.0h， 生成 3-amino-4-trifluoromethyl-6-phenylindazole
  参考文献：
  名称：

  Synthesis and structure–activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines

  摘要：

  A series of novel pyrimido[1,2-b]indazoles 5, 7 have been prepared from 3-trifluoromethyl-5-phenyl-2,6-dicyano anilines 1 via novel indazole regioisomers 3 and 4 through a facile strategy. Specific examples were evaluated for anticancer activity in vitro and found to exhibit promising activity against A-549 cell lines and are more effective than Etoposide. QSAR models were developed and validated by cross-validation method. The results of the best QSAR model were further compared with the crystal structure of tubulin protein. The binding energies estimated were found to have a good correlation with the experimental inhibitory potencies. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.03.087

文献信息

• GdCl3 catalysed Grieco condensation: A facile approach for the synthesis of novel pyrimidine and annulated pyrimidine fused indazole derivatives in single pot under mild conditions and their anti-microbial activity
  作者：T. Yakaiah、B.P.V. Lingaiah、B. Narsaiah、K. Pranay Kumar、U.S.N. Murthy

  DOI：10.1016/j.ejmech.2007.03.031

  日期：2008.2

  2 were independently reacted with formaldehyde followed by unsymmetrical, symmetrical and cyclic electron rich olefins in presence of GdCl(3) as catalyst and obtained pyrimidine fused indazole derivatives 3 and 4, respectively. The reaction is found to be concerted and an exclusive product is formed. Representative examples of compounds 3 and 4 were screened against Gram-positive, Gram-negative bacteria

  吲唑区域异构体为3-氨基-4-（三氟甲基）-6-苯基-1H-吲唑-7-腈1和3-氨基-6-（三氟甲基）-4-苯基-1H-吲唑-7-腈2在GdCl（3）作为催化剂存在下，与甲醛独立反应，然后与不对称，对称和环状富电子烯烃反应，分别获得嘧啶稠合的吲唑衍生物3和4。发现该反应是一致的，并且形成了排他的产物。在体外针对革兰氏阳性，革兰氏阴性细菌和真菌物种（例如酵母和丝状真菌）筛选了化合物3和4的代表性实例。化合物3f对所有革兰氏阳性和革兰氏阴性细菌均表现出显着的活性，而化合物3h和4a相对于青霉素和链霉素显示的活性最低。
• Synthesis and structure–activity relationships of novel pyrimido[1,2-b]indazoles as potential anticancer agents against A-549 cell lines
  作者：T. Yakaiah、B.P.V. Lingaiah、B. Narsaiah、B. Shireesha、B. Ashok Kumar、S. Gururaj、T. Parthasarathy、B. Sridhar

  DOI：10.1016/j.bmcl.2007.03.087

  日期：2007.6

  A series of novel pyrimido[1,2-b]indazoles 5, 7 have been prepared from 3-trifluoromethyl-5-phenyl-2,6-dicyano anilines 1 via novel indazole regioisomers 3 and 4 through a facile strategy. Specific examples were evaluated for anticancer activity in vitro and found to exhibit promising activity against A-549 cell lines and are more effective than Etoposide. QSAR models were developed and validated by cross-validation method. The results of the best QSAR model were further compared with the crystal structure of tubulin protein. The binding energies estimated were found to have a good correlation with the experimental inhibitory potencies. (c) 2007 Elsevier Ltd. All rights reserved.