3-nitro-N-(2-(piperidin-1-yl)ethyl)benzamide | 1170370-33-8

• 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-nitro-N-(2-(piperidin-1-yl)ethyl)benzamide
• 英文别名: 3-nitro-N-(2-piperidin-1-ylethyl)benzamide
• CAS: 1170370-33-8
• 化学式: C₁₄H₁₉N₃O₃
• 分子量: 277.323
• InChiKey: SVZSGEDYCJRKFP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  78.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-nitro-N-(2-(piperidin-1-yl)ethyl)benzamide 在 tris-(dibenzylideneacetone)dipalladium(0) 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 、 2-二环己基磷-2,4,6-三异丙基联苯 作用下， 以 甲醇 、 叔丁醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 20.0h， 生成 N-(2-(piperidin-1-yl)ethyl)-3-((4-(3-(pyridin-3-ylmethoxy)phenyl)-7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)amino)benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 2-anilino-7H-pyrrolopyrimidines as PDK1 inhibitors

  摘要：

  An efficient and scalable route for a series of novel substituted 2-anilino-7H-pyrrolopyrimidine compounds as potential inhibitors of PDK1, an important regulator of the PI3K/Akt pathway that is dysregulated in many cancers, was developed and is described. The synthetic strategy was designed around Suzuki and Buchwald-Hartwig cross-couplings of a boronate fragment and various customised anilines sequentially with 2,4-dichloro-7-tosyl-7H-pyrrolopyrimidine. All fragments were constructed separately and cross-coupled to provide access to a range of novel compounds. Biological evaluation of these was undertaken, with modest inhibition observed. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.033
• 作为产物：
  描述：

  1-(2-氨乙基)哌啶 、 间硝基苯甲酸 在 三乙胺 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以80%的产率得到3-nitro-N-(2-(piperidin-1-yl)ethyl)benzamide
  参考文献：
  名称：

  Synthesis and biological evaluation of substituted 2-anilino-7H-pyrrolopyrimidines as PDK1 inhibitors

  摘要：

  An efficient and scalable route for a series of novel substituted 2-anilino-7H-pyrrolopyrimidine compounds as potential inhibitors of PDK1, an important regulator of the PI3K/Akt pathway that is dysregulated in many cancers, was developed and is described. The synthetic strategy was designed around Suzuki and Buchwald-Hartwig cross-couplings of a boronate fragment and various customised anilines sequentially with 2,4-dichloro-7-tosyl-7H-pyrrolopyrimidine. All fragments were constructed separately and cross-coupled to provide access to a range of novel compounds. Biological evaluation of these was undertaken, with modest inhibition observed. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.05.033

文献信息

• Design, synthesis, and biological evaluation of novel water-soluble N-mustards as potential anticancer agents
  作者：Naval Kapuriya、Rajesh Kakadiya、Huajin Dong、Amit Kumar、Pei-Chih Lee、Xiuguo Zhang、Ting-Chao Chou、Te-Chang Lee、Ching-Huang Chen、King Lam、Bhavin Marvania、Anamik Shah、Tsann-Long Su

  DOI：10.1016/j.bmc.2010.11.005

  日期：2011.1

  ether linkage. The preliminary antitumor studies revealed that these agents exhibited potent cytotoxicity in vitro and therapeutic efficacy against human tumor xenografts in vivo. Remarkably, complete tumor remission in nude mice bearing human breast carcinoma MX-1 xenograft and significant suppression against prostate adenocarcinoma PC3 xenograft were achieved by treating with compound 9aa′ at the maximum

  合成了一系列带有脲连接基的新型水溶性N-芥子气-苯共轭物。苯部分含有各种亲水性侧链，它们通过羧酰胺或醚键与尿素连接基的间位或对位连接。初步的抗肿瘤研究表明，这些药物在体外表现出有效的细胞毒性，并且在体内对人肿瘤异种移植物具有治疗功效。值得注意的是，通过用化合物9aa处理，可在携带人乳腺癌MX-1异种移植物的裸鼠中完全缓解肿瘤，并显着抑制前列腺癌PC3异种移植物。在最大可耐受剂量下具有相对较低的毒性。我们还证明了新合成的化合物能够通过碱性琼脂糖凝胶位移试验诱导DNA交联。还研究了代表性9aa ′在大鼠中的药代动力学特征。目前的研究表明，这种药物是临床前研究的有希望的候选者。
• Synthesis and biological evaluation of substituted 2-anilino-7H-pyrrolopyrimidines as PDK1 inhibitors
  作者：Nathan J. O'Brien、Martin Brzozowski、David J.D. Wilson、Leslie W. Deady、Belinda M. Abbott

  DOI：10.1016/j.tet.2014.05.033

  日期：2014.8

  An efficient and scalable route for a series of novel substituted 2-anilino-7H-pyrrolopyrimidine compounds as potential inhibitors of PDK1, an important regulator of the PI3K/Akt pathway that is dysregulated in many cancers, was developed and is described. The synthetic strategy was designed around Suzuki and Buchwald-Hartwig cross-couplings of a boronate fragment and various customised anilines sequentially with 2,4-dichloro-7-tosyl-7H-pyrrolopyrimidine. All fragments were constructed separately and cross-coupled to provide access to a range of novel compounds. Biological evaluation of these was undertaken, with modest inhibition observed. Crown Copyright (C) 2014 Published by Elsevier Ltd. All rights reserved.