N-(4-acetylphenyl)-3-amino-1H-indazole-1-carboxamide | 1119859-57-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: N-(4-acetylphenyl)-3-amino-1H-indazole-1-carboxamide
• 英文别名: N-(4-acetylphenyl)-3-aminoindazole-1-carboxamide
• CAS: 1119859-57-2
• 化学式: C₁₆H₁₄N₄O₂
• 分子量: 294.313
• InChiKey: FDPNIXNGPCVKQK-UHFFFAOYSA-N

物化性质

• 熔点：
  228-230 °C(Solvent: 1,4-Dioxane)
• 密度：
  1.36±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-乙酰苯基异氰酸酯 、 3-氨基吲唑 以 四氢呋喃 为溶剂， 反应 24.0h， 以98%的产率得到N-(4-acetylphenyl)-3-amino-1H-indazole-1-carboxamide
  参考文献：
  名称：

  Synthesis and antiproliferative activity of 3-amino-N-phenyl-1H-indazole-1-carboxamides

  摘要：

  A series of new 3-amino-N-phenyl-1H-indazole-1-carboxamides 10 have been prepared from commercially available phenyl isocyanate precursors 8 and 3-aminoindazole 9. Some of the synthesized compounds were evaluated for their in vitro antineoplastic activity against 60 human cell lines derived from seven clinically isolated cancer types (lung, colon, melanoma, renal, ovarian, brain, and leukemia) according to the NCI standard protocol. The test results indicated that 3-amino-1H-indazole-1-carboxamides 10 were endowed with an interesting antiproliferative activity. The most active compounds of this series, 10d,e, were able to inhibit cell growth of many neoplastic cell lines at concentrations lower than 1 mu M (0.0153 mu M in SR leukemia) causing a block in G0-G1 phase of cell cycle. Analysis of pRb expression showed that these two compounds increased the ratio between underphosphorylated pRb and total pRb. The X-ray structure of 10w, confirmed the 3-amino-N-phenyl-1H-indazole-1-carboxamide structure of compounds 10. (C) 2008 Elsevier Masson SAS. All rights reserved,

  DOI：

  10.1016/j.ejmech.2008.03.023

文献信息

• Synthesis and antiproliferative activity of 3-amino-N-phenyl-1H-indazole-1-carboxamides
  作者：Demetrio Raffa、Benedetta Maggio、Stella Cascioferro、Maria Valeria Raimondi、Domenico Schillaci、Giorgio Gallo、Giuseppe Daidone、Salvatore Plescia、Fiorella Meneghetti、Gabriella Bombieri

  DOI：10.1016/j.ejmech.2008.03.023

  日期：2009.1

  A series of new 3-amino-N-phenyl-1H-indazole-1-carboxamides 10 have been prepared from commercially available phenyl isocyanate precursors 8 and 3-aminoindazole 9. Some of the synthesized compounds were evaluated for their in vitro antineoplastic activity against 60 human cell lines derived from seven clinically isolated cancer types (lung, colon, melanoma, renal, ovarian, brain, and leukemia) according to the NCI standard protocol. The test results indicated that 3-amino-1H-indazole-1-carboxamides 10 were endowed with an interesting antiproliferative activity. The most active compounds of this series, 10d,e, were able to inhibit cell growth of many neoplastic cell lines at concentrations lower than 1 mu M (0.0153 mu M in SR leukemia) causing a block in G0-G1 phase of cell cycle. Analysis of pRb expression showed that these two compounds increased the ratio between underphosphorylated pRb and total pRb. The X-ray structure of 10w, confirmed the 3-amino-N-phenyl-1H-indazole-1-carboxamide structure of compounds 10. (C) 2008 Elsevier Masson SAS. All rights reserved,