2-amino-4-(4-chlorophenyl)-3,5-dicyano-6-ethoxypyridine | 30464-18-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(4-chlorophenyl)-3,5-dicyano-6-ethoxypyridine
• 英文别名: 2-amino-4-(4-chloro-phenyl)-6-ethoxy-pyridine-3,5-dicarbonitrile；2-Amino-4-(4-chlorophenyl)-6-ethoxypyridine-3,5-dicarbonitrile
• CAS: 30464-18-7
• 化学式: C₁₅H₁₁ClN₄O
• 分子量: 298.732
• InChiKey: DPMHNMIJAZETCQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  95.7
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-amino-4-(4-chlorophenyl)-3,5-dicyano-6-ethoxypyridine 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 56.0h， 生成 4-(4-Acetyl-phenyl)-N'-[4-(4-chloro-phenyl)-3,5-dicyano-6-ethoxy-pyridin-2-yl]-N,N-dimethyl-piperazine-1-carboxamidine
  参考文献：
  名称：

  Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines

  摘要：

  2-Guanadino-3-cyanopyridines 8-33 and pyrido[2,3-d]-pyrimidines 35-52 were synthesized by nucleophilic displacement and cyclization of the chloroamidines 6a-d easily obtained by reaction of 2-aminocyanopyridines 5a-d with phosgene iminium chloride and their action on the release of histamine by mast cells examined under immunological and chemical stimulus, with and without pre-incubation. Several 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines are shown to be inhibitors of the release of histamine when stimulated with ovoalbumin as antigen or with polymer 48/80 as chemical stimulus. Guanadino-3-cyanopyridine 30 and pyrido[2,3-d]-pyrimidine 49 are the more active of all, inhibiting the release of histamine in all the conditions tested (30-60% inhibition). Guanadinocyanopyridines 15, 17, and 19 are very potent stimulators of the release of histamine (150-300%) while pyrido[2,3-d]-pyrimidines are mostly inactive. Compounds 28 and 14 present moderate in vitro cytotoxic activity against P-388, A-549, HT-29, and MEL-28 cell lines. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0968-0896(97)00108-9
• 作为产物：
  描述：

  乙醇 、 4-氯苯甲醛 、 丙二腈 在 potassium carbonate 作用下， 以 水 为溶剂， 反应 8.0h， 以86%的产率得到2-amino-4-(4-chlorophenyl)-3,5-dicyano-6-ethoxypyridine
  参考文献：
  名称：

  Karimi, Ali R.; Khodadadi, Azam, Letters in Organic Chemistry, 2012, vol. 9, # 6, p. 422 - 426

  摘要：

  DOI：

文献信息

• Karimi, Ali R.; Khodadadi, Azam, Letters in Organic Chemistry, 2012, vol. 9, # 6, p. 422 - 426
  作者：Karimi, Ali R.、Khodadadi, Azam

  DOI：——

  日期：——
• Synthesis and antihistaminic activity of 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines
  作者：JoséM. Quintela、Carlos Peinador、Luis Botana、Manuel Estévez、Ricardo Riguera

  DOI：10.1016/s0968-0896(97)00108-9

  日期：1997.8

  2-Guanadino-3-cyanopyridines 8-33 and pyrido[2,3-d]-pyrimidines 35-52 were synthesized by nucleophilic displacement and cyclization of the chloroamidines 6a-d easily obtained by reaction of 2-aminocyanopyridines 5a-d with phosgene iminium chloride and their action on the release of histamine by mast cells examined under immunological and chemical stimulus, with and without pre-incubation. Several 2-guanadino-3-cyanopyridines and pyrido[2,3-d]-pyrimidines are shown to be inhibitors of the release of histamine when stimulated with ovoalbumin as antigen or with polymer 48/80 as chemical stimulus. Guanadino-3-cyanopyridine 30 and pyrido[2,3-d]-pyrimidine 49 are the more active of all, inhibiting the release of histamine in all the conditions tested (30-60% inhibition). Guanadinocyanopyridines 15, 17, and 19 are very potent stimulators of the release of histamine (150-300%) while pyrido[2,3-d]-pyrimidines are mostly inactive. Compounds 28 and 14 present moderate in vitro cytotoxic activity against P-388, A-549, HT-29, and MEL-28 cell lines. (C) 1997 Elsevier Science Ltd.