3-amino-N-(4-butoxyphenyl)-6-chloro-1H-indazole-1-carboxamide | 1263320-05-3

• 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-amino-N-(4-butoxyphenyl)-6-chloro-1H-indazole-1-carboxamide
• 英文别名: 3-amino-N-(4-butoxyphenyl)-6-chloroindazole-1-carboxamide
• CAS: 1263320-05-3
• 化学式: C₁₈H₁₉ClN₄O₂
• 分子量: 358.827
• InChiKey: YXKFYQIYBZXZFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  82.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-正丁氧基苯酚异氰酸酯 、 3-氨基-6-氯-1H-吲唑 以 四氢呋喃 为溶剂， 反应 24.0h， 以56%的产率得到3-amino-N-(4-butoxyphenyl)-6-chloro-1H-indazole-1-carboxamide
  参考文献：
  名称：

  Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity

  摘要：

  Several new N-phenyl-1H-indazole-1-carboxamides 1c-h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 21 respectively. Chemical transformations of compounds la,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b, and 3,5-diamino-N-phenyl-1H-indazole-1-carboxamide derivatives 4i, j respectively. Finally, 3,5-diacetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 6a,b were prepared by acetylation of 4i, j. Some of synthesized compounds were evaluated for their in vitro anti-proliferative activity against the full NCI tumor cell lines panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). Compound 1c, the most active of the series, was able to inhibit cell growth showing GI(50) values in the 0.041-33.6 mu M range, mean GI(50) 1.90 mu M, being very effective against colon and melanoma cell lines. Cell cycle analysis in K562 cells showed that 1c causes a marked increase of cells in G0-G1 phase. Moreover, it increases the ratio between hypophosphorylated pRb and total pRb. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.10.032

文献信息

• Synthesis of substituted 3-amino-N-phenyl-1H-indazole-1-carboxamides endowed with antiproliferative activity
  作者：Benedetta Maggio、Maria Valeria Raimondi、Demetrio Raffa、Fabiana Plescia、Stella Cascioferro、Salvatore Plescia、Manlio Tolomeo、Antonietta Di Cristina、Rosaria Maria Pipitone、Stefania Grimaudo、Giuseppe Daidone

  DOI：10.1016/j.ejmech.2010.10.032

  日期：2011.1

  Several new N-phenyl-1H-indazole-1-carboxamides 1c-h and 4l,m were prepared by reacting phenyl isocyanate derivatives 3a,b with 3-amino-1H-indazole derivatives 2c,e,g or 1H-indazole 21 respectively. Chemical transformations of compounds la,b and 1g,h gave 3-acetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 5a,b, and 3,5-diamino-N-phenyl-1H-indazole-1-carboxamide derivatives 4i, j respectively. Finally, 3,5-diacetamido-N-phenyl-1H-indazole-1-carboxamide derivatives 6a,b were prepared by acetylation of 4i, j. Some of synthesized compounds were evaluated for their in vitro anti-proliferative activity against the full NCI tumor cell lines panel derived from nine clinically isolated cancer types (leukemia, non-small cell lung, colon, CNS, melanoma, ovarian, renal, prostate and breast). Compound 1c, the most active of the series, was able to inhibit cell growth showing GI(50) values in the 0.041-33.6 mu M range, mean GI(50) 1.90 mu M, being very effective against colon and melanoma cell lines. Cell cycle analysis in K562 cells showed that 1c causes a marked increase of cells in G0-G1 phase. Moreover, it increases the ratio between hypophosphorylated pRb and total pRb. (C) 2010 Elsevier Masson SAS. All rights reserved.