1-p-aminophenylindazole | 169781-26-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-p-aminophenylindazole
• 英文别名: 4-(1H-indazol-1-yl)aniline；4-indazol-1-ylaniline
• CAS: 169781-26-4
• 化学式: C₁₃H₁₁N₃
• mdl: MFCD16716773
• 分子量: 209.25
• InChiKey: AQQPNMUWIKGWGI-UHFFFAOYSA-N

物化性质

• 沸点：
  339.4±34.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  43.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-氯-3-三氟甲基异氰酸苯酯 、 1-p-aminophenylindazole 以 甲醇 、 二氯甲烷 为溶剂， 以49%的产率得到1-[4-Chloro-3-(trifluoromethyl)phenyl]-3-(4-indazol-1-ylphenyl)urea
  参考文献：
  名称：

  Synthesis of indazole based diarylurea derivatives and their antiproliferative activity against tumor cell lines

  摘要：

  New series of indazole based diarylureas were synthesized and their anticancer activity against cancer cells H460, A549, OS-RC-2, HT-29, Lovo, HepG2, Bel-7402, SGC-7901 and MDA-MB-231 were examined. These derivatives of diarylureas, except azaindazole based diarylureas 5f, 51 and 5m, showed superior or similar activity against most of these selected cancer cell lines to the reference compound sorafenib. The effect of substituents on the indazole ring was also investigated. Derivatives with trifluoromenthy or halogen substituents on the indazole ring showed higher activity against the selected cancer cell lines than sorafenib. The acute toxicity assay showed that compounds 5a, 5b and 5i possessed lower toxicity than sorafenib. Compound 5i with 4-(trifluoromenthy)-1H-indazole and 4-(trifluoromenthy) benzene moieties exhibited the most potent anticancer activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.034
• 作为产物：
  描述：

  吲唑 在 盐酸 、 碳酸氢钠 、 magnesium sulfate 、 caesium carbonate 、 tin(ll) chloride 作用下， 以 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-p-aminophenylindazole
  参考文献：
  名称：

  Synthesis of indazole based diarylurea derivatives and their antiproliferative activity against tumor cell lines

  摘要：

  New series of indazole based diarylureas were synthesized and their anticancer activity against cancer cells H460, A549, OS-RC-2, HT-29, Lovo, HepG2, Bel-7402, SGC-7901 and MDA-MB-231 were examined. These derivatives of diarylureas, except azaindazole based diarylureas 5f, 51 and 5m, showed superior or similar activity against most of these selected cancer cell lines to the reference compound sorafenib. The effect of substituents on the indazole ring was also investigated. Derivatives with trifluoromenthy or halogen substituents on the indazole ring showed higher activity against the selected cancer cell lines than sorafenib. The acute toxicity assay showed that compounds 5a, 5b and 5i possessed lower toxicity than sorafenib. Compound 5i with 4-(trifluoromenthy)-1H-indazole and 4-(trifluoromenthy) benzene moieties exhibited the most potent anticancer activity. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.02.034

文献信息

• FT-IR and ¹³C-NMR Correlations for Some <i>N</i>-Substituted Azoles and Benzazoles
  作者：José Elguero、Manuel Gil、Nerea Iza、Carmen Pardo、Mar Ramos

  DOI：10.1366/0003702953965029

  日期：1995.8

  13C-NMR spectral parameters and Hammett constants σp (or σp-) were correlated, and statistic analysis of the results permitted an estimation of σp values of the nine (azol-1-yl) substituents. An empirical equation to calculate the Hammett constants of new azoles and benzazoles is proposed.

  记录了作为参考化合物的六种对取代苯胺衍生物和九种 1-对氨基苯基唑和苯并唑的 FT-IR（在四氯化碳中）和 13C-NMR（在氘氯仿中）光谱。FT-IR 测得的光谱参数是对称的 vs(NH2) 和反对称的 vas(NH2) 拉伸基本原理及其带强度比 A(vas)/A(vs)，而相应的 13C-NMR 参数为1-对氨基苯基碳的 C-1 到 C-4 化学位移。不同的 IR 和 13C-NMR 光谱参数与哈米特常数 σp（或 σp-）相关联，结果的统计分析允许估计九个（唑-1-基）取代基的 σp 值。提出了计算新型唑类和苯并唑类的哈米特常数的经验方程。
• UREA COMPOUND, PREPARATION METHOD THEREFOR AND MEDICAL USE THEREOF
  申请人：Ancureall Pharmaceutical (Shanghai) Co., Ltd.

  公开号：EP3424924A1

  公开（公告）日：2019-01-09

  Provided are a urea compound represented by general formula (I), a pharmaceutically acceptable salt thereof, a preparation method therefor, and use thereof as an FLT3 tyrosine protein kinase inhibitor, particularly in the prevention and/or treating of cancer.

  本发明提供了通式（I）代表的脲化合物、其药学上可接受的盐、其制备方法，以及其作为FLT3酪氨酸蛋白激酶抑制剂的用途，特别是在预防和/或治疗癌症中的用途。
• Urea compound, preparation method therefor and medical use thereof
  申请人：Ancureall Pharmaceutical (Shanghai) Co., Ltd.

  公开号：US10647680B2

  公开（公告）日：2020-05-12

  Provided are a urea compound represented by general formula (I), a pharmaceutically acceptable salt thereof, a preparation method therefor, and use thereof as an FLT3 tyrosine protein kinase inhibitor, particularly in the prevention and/or treating of cancer.

  本发明提供了通式（I）代表的脲化合物、其药学上可接受的盐、其制备方法，以及其作为FLT3酪氨酸蛋白激酶抑制剂的用途，特别是在预防和/或治疗癌症中的用途。