N-(1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)benzamide | 1314863-20-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: N-(1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)benzamide
• 英文别名: N-[1-(4-nitrophenyl)pyrrolo[3,2-c]pyridin-4-yl]benzamide
• CAS: 1314863-20-1
• 化学式: C₂₀H₁₄N₄O₃
• 分子量: 358.356
• InChiKey: FAMPIZARIJNGTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  92.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)benzamide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 10.0h， 生成 1-(4-(4-benzamido-1H-pyrrolo[3,2-c]pyridin-1-yl)phenyl)-3-(3,4-dichlorophenyl)urea
  参考文献：
  名称：

  Design, synthesis, and antiproliferative activity of new 1H-pyrrolo[3,2-c]pyridine derivatives against melanoma cell lines

  摘要：

  Synthesis of a new series of diarylureas and diarylamides having 1H-pyrrolo[3,2-c]pyridine scaffold is described. Their in vitro antiproliferative activity against A375P human melanoma cell line was tested and the effect of substituents on pyrrolo[3,2-c]pyridine nucleus was investigated. The newly synthesized compounds, except three N-tolyl derivatives (8f, 9f, and 9h), generally showed superior activity against A375P to Sorafenib. Among all of these derivatives, compounds 8b, 8g, and 9a-e showed the highest potency against A375P with IC50 in nanomolar range. In addition, compounds 8d, 8e, 8h, 9g, 9i, and 9j were more potent than Sorafenib but with IC50 in micromolar range. Compounds 8b, 8g, 9b-d, and 9i demonstrated higher selectivity towards A375P compared with NIH3T3 fibroblasts. The most potent diarylurea 8g and diarylamide 9d were further tested and showed high potency over nine melanoma cell lines at the NCI. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.04.031
• 作为产物：
  描述：

  4-氯-7-氮杂吲哚 在 二异丙胺 作用下， 以 乙腈 为溶剂， 反应 8.0h， 生成 N-(1-(4-nitrophenyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)benzamide
  参考文献：
  名称：

  对FMS激酶具有潜在抑制作用的吡咯并[3,2-c]吡啶衍生物：体外生物学研究。

  摘要：

  测试了一系列十八种吡咯并[3,2-c]吡啶衍生物对FMS激酶的抑制作用。在所有其他测试的类似物中，化合物1e和1r最有效（分别为IC50 = 60 nM和30 nM）。它们的效价分别是我们的先导化合物KIST101029（IC50 = 96 nM）的1.6和3.2倍。用包括FMS在内的40种激酶对化合物1r进行了测试，并对FMS激酶发挥了选择性。还针对骨髓衍生的巨噬细胞（BMDM）进行了测试，其IC50为84 nM（效力比KIST101029高2.32倍（IC50 = 195 nM））。还测试了化合物1r对一组六种卵巢，两种前列腺和五种乳腺癌细胞系的抗增殖活性，其IC50值为0.15-1.78 µM。

  DOI：

  10.1080/14756366.2018.1491563

文献信息

• Design and Synthesis of an Anticancer Diarylurea Derivative with Multiple-Kinase Inhibitory Effect
  作者：Mohammed I. El-Gamal、Chang-Hyun Oh

  DOI：10.5012/bkcs.2012.33.5.1571

  日期：2012.5.20

  A diarylurea compound 1 possessing pyrrolo[3,2-$c$]pyridine nucleus was designed and synthesized with structure similarity to Sorafenib. Compound 1 was tested over 60-cancer cell line panel at a single dose concentration of 10 $\mu}M$ and showed high activity. It was further tested in a five-dose mode to determine its $IC_50}$, TGI, and $LC_50}$ values over the 60 cell lines. Compound 1 showed high potency and good efficacy, and was accordingly tested at a single dose concentration of 10 $\mu}M$ over a panel of 40 kinases. At this concentration, it completely inhibited the enzymatic activities of a number of oncogenic kinases, including ABL, ALK, c-RAF, FLT3, KDR, and TrkB. The target compound was subsequently tested over these 6 kinases in 10-dose testing mode in order to determine its $IC_50}$ values.

  设计并合成了一种具有吡咯并[3,2-$c$]吡啶核的二元脲化合物1，其结构与索拉非尼相似。化合物 1 在单剂量浓度为 10 $\mu}M 的 60 种癌症细胞系中进行了测试，显示出很高的活性。化合物1还以五剂量模式进行了测试，以确定其在60种细胞系中的$IC_50}$、TGI和$LC_50}$值。化合物 1 显示出很高的效力和良好的疗效，因此以 10 $mu}M$ 的单剂量浓度对 40 种激酶进行了测试。在此浓度下，它能完全抑制多种致癌激酶的酶活性，包括 ABL、ALK、c-RAF、FLT3、KDR 和 TrkB。随后，在 10 剂量测试模式下，对目标化合物进行了针对这 6 种激酶的测试，以确定其 $IC_50}$ 值。