N-(p-tolyl)-1H-indazole-3-carboxamide

• 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: N-(p-tolyl)-1H-indazole-3-carboxamide
• 英文别名: N-(4-methylphenyl)-1H-indazole-3-carboxamide
• 化学式: C₁₅H₁₃N₃O
• 分子量: 251.288
• InChiKey: SKMFGOZPQGHDGG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.8
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  乙烷,三氯氟- 、 吲唑-3-羧酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以100%的产率得到N-(p-tolyl)-1H-indazole-3-carboxamide
  参考文献：
  名称：

  Synthesis of N-arylindazole-3-carboxamide and N-benzoylindazole derivatives and their evaluation against α-MSH-stimulated melanogenesis

  摘要：

  We have designed and synthesized twenty-six N-arylindazole-3-carboxamide (3a-p) and N-benzoylindazole (6a-j) derivatives to discover with excellent inhibition activities of alpha-MSH-stimulated melanogenesis. In the bio evaluation studies of these compounds, we discovered eighteen compounds, out of twenty-six exhibited more potent inhibition than the positive control arbutin. From the SAR studies, we identified 3k and 6g as lead compounds which displayed almost 5 and 9 times more potent inhibition of alpha-MSH-stimulated melanogenesis respectively than the reference arbutin. It is also evident the presence of electron withdrawing group at para position (R-3) for the compounds (3a-p) and presence of +M group at ortho position (R-5) for the compounds (6a-j) were crucial for their excellent inhibition activities of alpha-MSH-stimulated melanogenesis.

  DOI：

  10.1016/j.bmcl.2019.07.055

文献信息

• Development of a potent and selective FLT3 kinase inhibitor by systematic expansion of a non-selective fragment-screening hit
  作者：Hirofumi Nakano、Tsukasa Hasegawa、Riyo Imamura、Nae Saito、Hirotatsu Kojima、Takayoshi Okabe、Tetsuo Nagano

  DOI：10.1016/j.bmcl.2016.03.006

  日期：2016.5

  A non-selective inhibitor (1) of FMS-like tyrosine kinase-3 (FLT3) was identified by fragment screening and systematically modified to afford a potent and selective inhibitor 26. We confirmed that 26 inhibited the growth of FLT-3-activated human acute myeloid leukemia cell line MV4-11. Our design strategy enabled rapid development of a novel type of FLT3 inhibitor from the hit fragment in the absence of target-structural information. (C) 2016 Elsevier Ltd. All rights reserved.