4-(4-chloro-N-methylanilino)pyridine | 124705-36-8

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(4-chloro-N-methylanilino)pyridine
• 英文别名: N-(4-chlorophenyl)-N-methylpyridin-4-amine
• CAS: 124705-36-8
• 化学式: C₁₂H₁₁ClN₂
• 分子量: 218.686
• InChiKey: PWQDNSSRMPSKAR-UHFFFAOYSA-N

物化性质

• 沸点：
  355.4±22.0 °C(Predicted)
• 密度：
  1.220±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  16.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3,5-三(溴甲基)苯 、 4-(4-chloro-N-methylanilino)pyridine 以 丁酮 为溶剂， 以78.8%的产率得到
  参考文献：
  名称：

  Choline kinase inhibitory effect and antiproliferative activity of new 1,1′,1″-(benzene-1,3,5-triylmethylene)tris?4-[(disubstituted)amino]pyridinium? tribromides

  摘要：

  Four derivatives of 1,1'-(benzene-1,3-diylmethylene)bis{4-[(disubstituted)amino]-pyridinium} dibromides (2-5) and six derivatives of 1, 1', 1"-(benzene-1,3,5-triylmethylene)-tris{4-[(disubstituted)amino]pyridinium} tribromides (6-11) were synthesised and examined for their inhibition of human choline kinase (ChoK) and antiproliferative activities. The latter are more potent as ChoK inhibitors than the former, but the antiproliferative activities against the HT-29 cell line show the opposite tendency. The higher affinity of the trispyridinium compared with the bispyridinium ones may be due to direct binding of the third pyridinium group to ChoK or may arise from a reduction of the unfavourable entropy of binding via an increase of the 'local concentration' of pyridinium groups. (C) 2003 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)00004-1
• 作为产物：
  描述：

  4-氨基吡啶 在 盐酸 作用下， 以 1,4-二氧六环 、 乙醇 、 二甲基亚砜 为溶剂， 反应 31.17h， 生成 4-(4-chloro-N-methylanilino)pyridine
  参考文献：
  名称：

  吡咯盐对氨基杂环的选择性功能化

  摘要：

  提出了使用四氟硼酸吡啶鎓试剂（Pyry-BF 4）对氨基杂环进行官能化的方法。该试剂可与多种杂环胺有效地缩合，并为亲核芳香族取代反应准备C-N键。本文公开了用于形成CO，CN，CS或CS 2 R键的60多个例子。与通过重氮化和多烷基化进行CN活化相反，该方法的特点是条件温和且对官能团的耐受力强。除小分子衍生化外，Pyry-BF 4还允许以后期方式引入官能团，以提供高度官能化的结构。

  DOI：

  10.1002/anie.201806271

文献信息

• Synthesis, biological evaluation, in silico modeling and crystallization of novel small monocationic molecules with potent antiproliferative activity by dual mechanism
  作者：Lucía Serrán- Aguilera、Elena Mariotto、Gianluca Rubbini、Francisco Fermín Castro Navas、Carmen Marco、María Paz Carrasco-Jiménez、Marco Ballarotto、Antonio Macchiarulo、Ramón Hurtado-Guerrero、Giampietro Viola、Luisa Carlota Lopez-Cara

  DOI：10.1016/j.ejmech.2020.112797

  日期：2020.12

  Seeking for new anticancer drugs with strong antiproliferative activity and simple molecular structure, we designed a novel series of compounds based on our previous reported pharmacophore model composed of five moieties. Antiproliferative assays on four tumoral cell lines and evaluation of Human Choline Kinase CKα1 enzymatic activity was performed for these compounds. Among tested molecules, those

  为了寻找具有强抗增殖活性和简单分子结构的新抗癌药物，我们根据先前报道的由五个部分组成的药效团模型设计了一系列新型化合物。对这些化合物进行了四种肿瘤细胞系的抗增殖测定和人胆碱激酶CKα1酶活性的评估。在测试的分子中，那些具有联苯间隔基的分子表现出更好的酶促和抗增殖活性（nv）。对接和结晶研究验证了该假设并确认了结果。最活跃的化合物（吨）诱导了G0 / G1期细胞周期的明显停滞，最终导致了线粒体途径后的细胞凋亡，正如其他胆碱激酶抑制剂所证明的那样。然而，另外的测定表明，胆碱摄取的抑制也可能与这类化合物的抗增殖结果有关。
• Delta2-1,2,3-triazoline anticonvulsants and their active metabolite analogues, the aminoalkylpyridines, are excitatory amino acid antagonists and antiischemic agents, useful in the treatment of cerebral ischemia resulting from stroke
  申请人：Kadaba K. Pankaja

  公开号：US20060058357A1

  公开（公告）日：2006-03-16

  Pharmaceutical compositions comprise as the active ingredient, nonneurotixic antiischemic compounds that are highly effective by the intraperitoneal route, and that are excitatory amino acid and NMDA/sigma receptor antagonists and are selected from the group consisting of those of the formulae, wherein R 2 is 4-pyridyl, 3-pyridyl, or 2-oxo-1-pyrrolidino and R 2 is 3,4- or 3,5-dichloro, p- or m-chloro, p- or m-bromo, p- or m-fluoro, p- or m-trifluoromethyl, p-methyl, p-methoxy, or hydrogen, and those of the formulae, wherein R 2 is 4-pyridyl or 3-pyridyl, R 3 is hydrogen, methyl or ethyl and R 1 is 3,4- or 3,5-dichloro, p- or m-chloro, p- or m-bromo, p- or m-fluoro, p- or m-trifluoromethyl, p-methyl, p-methoxy or hydrogen.

  药物组成包含作为活性成分的非神经毒性抗缺血化合物，通过腹腔注射途径非常有效，是兴奋性氨基酸和NMDA / sigma受体拮抗剂，从以下化合物组合中选择：其中R2为4-吡啶基，3-吡啶基或2-氧代-1-吡咯烷基，R2为3,4-或3,5-二氯，对氯，对溴，对氟，对三氟甲基，对甲基，对甲氧基或氢，以及其中R2为4-吡啶基或3-吡啶基，R3为氢，甲基或乙基，R1为3,4-或3,5-二氯，对氯，对溴，对氟，对三氟甲基，对甲基，对甲氧基或氢的化合物。
• Derivatives of pyridine and quinoline
  申请人：Lacal Sanjuan Juan Carlos

  公开号：US20070185170A1

  公开（公告）日：2007-08-09

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了I式化合物，通过选择性阻断肿瘤细胞或受寄生虫感染的细胞中的胆碱激酶酶的方式，阻断磷酸胆碱生物合成，因此可应用于治疗动物，包括人类中的肿瘤和寄生虫病或由病毒和真菌引起的疾病;以及一种制备本发明化合物和该方法的某些中间体的方法。
• PYRIDINIUM AND QUINOLINIUM DERIVATIVES
  申请人：Lacal Sanjuán Juan Carlos

  公开号：US20110178124A1

  公开（公告）日：2011-07-21

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了一种公式I的化合物，通过选择性阻断肿瘤细胞或受寄生虫感染的细胞中的胆碱激酶酶的方式阻断磷酸胆碱生物合成，因此可应用于治疗动物（包括人类）中的肿瘤和寄生虫病或由病毒和真菌引起的疾病；以及用于制备本发明化合物和该方法的某些中间体。
• Pyridinium and quinolinium derivatives as Choline kinase inhibitors
  申请人：Consejo Superior De Investigaciones Científicas

  公开号：EP2085386A2

  公开（公告）日：2009-08-05

  The invention provides compounds of formula I blocking phosphorylcholine biosynthesis by means of the selective blocking of the choline kinase enzyme in tumor cells or in cells affected by parasitic infection and therefore being applicable in the treatment of tumors and parasitic diseases or diseases produced by viruses and fungi in animals, including human beings; as well as to a method for preparing the compounds of the invention and certain intermediates of said method.

  本发明提供了通过选择性阻断肿瘤细胞或受寄生虫感染细胞中的胆碱激酶，从而阻断磷酸胆碱生物合成的式 I 化合物，因此适用于治疗肿瘤和寄生虫病或由病毒和真菌引起的动物（包括人类）疾病；以及制备本发明化合物的方法和所述方法的某些中间体。