6-amino-4-(4-chlorophenyl)-5-(5,6-dimethyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile | 1335195-70-4

• 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: 6-amino-4-(4-chlorophenyl)-5-(5,6-dimethyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile
• CAS: 1335195-70-4
• 化学式: C₂₁H₁₆ClN₅
• 分子量: 373.845
• InChiKey: UKWSZFZBKUECHR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  27
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  91.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4，5-二甲基-1，2-苯二胺 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 6-amino-4-(4-chlorophenyl)-5-(5,6-dimethyl-1H-benzimidazol-2-yl)pyridine-3-carbonitrile
  参考文献：
  名称：

  Synthesis, characterization of some benzazoles bearing pyridine moiety: Search for novel anticancer agents

  摘要：

  Thirteen novel benzazole derivatives were synthesized as possible anticancer agents. The first intermediate 1,3-benzothiazol-2-ylacetonitrile (2) was synthesized via cyclodeamination reaction of o-aminothiophenol (1) with malononitrile. Also, the second intermediate 5,6-dimethyl-1H-benzimidazol-2-ylacetonitrile (10) was afforded via cyclocondensation reaction between 4,5-dimethyl-1,2-phenylenediamine (9) and ethylcyanoacetate. Nucleophilic reaction of benzimidazolyl NH of compound (10) with ethylcyanoacetate afforded benzimidazolyl-3-oxopropanenitrile (11). On the other hand, methylenation of CH2 function of compound (10) with dimethylformamide/dimethylacetal afforded benzimidazolylprop-2-enenitrile 12. The synthesis of benzothiazoylpyridines 5a,b and 8a,b as well as benzimidazolylpyridines, 14a,b and 17a-d was carried out through Michael addition of compounds 2 or 10 with arylidenemalononitriles 3a,b and 4a-d. The combination of pharmacophoric anticancer moieties, pyridine and benzazoles was the base on which target compounds 5a,b, 8a,b, 14a,b and 17a-d were designed. Among the synthesized compounds, four derivatives 10 and 17b-d were selected by National Cancer Institute (NCI), USA to be screened for their anticancer activity at a single high dose (10(-5) M) against a panel of 60 cancer cell lines. Compound 17b 4-[p-chlorophenyl]pyridine and 17d 4-[p-methoxyphenyl] pyridine exhibited a broad and moderate antitumor activity against 41 tumor cell lines belonging to the nine subpanels employed and are selected for further evaluation at five dose level screening. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.05.075

文献信息

• Synthesis, characterization of some benzazoles bearing pyridine moiety: Search for novel anticancer agents
  作者：Heba S.A. Elzahabi

  DOI：10.1016/j.ejmech.2011.05.075

  日期：2011.9

  Thirteen novel benzazole derivatives were synthesized as possible anticancer agents. The first intermediate 1,3-benzothiazol-2-ylacetonitrile (2) was synthesized via cyclodeamination reaction of o-aminothiophenol (1) with malononitrile. Also, the second intermediate 5,6-dimethyl-1H-benzimidazol-2-ylacetonitrile (10) was afforded via cyclocondensation reaction between 4,5-dimethyl-1,2-phenylenediamine (9) and ethylcyanoacetate. Nucleophilic reaction of benzimidazolyl NH of compound (10) with ethylcyanoacetate afforded benzimidazolyl-3-oxopropanenitrile (11). On the other hand, methylenation of CH2 function of compound (10) with dimethylformamide/dimethylacetal afforded benzimidazolylprop-2-enenitrile 12. The synthesis of benzothiazoylpyridines 5a,b and 8a,b as well as benzimidazolylpyridines, 14a,b and 17a-d was carried out through Michael addition of compounds 2 or 10 with arylidenemalononitriles 3a,b and 4a-d. The combination of pharmacophoric anticancer moieties, pyridine and benzazoles was the base on which target compounds 5a,b, 8a,b, 14a,b and 17a-d were designed. Among the synthesized compounds, four derivatives 10 and 17b-d were selected by National Cancer Institute (NCI), USA to be screened for their anticancer activity at a single high dose (10(-5) M) against a panel of 60 cancer cell lines. Compound 17b 4-[p-chlorophenyl]pyridine and 17d 4-[p-methoxyphenyl] pyridine exhibited a broad and moderate antitumor activity against 41 tumor cell lines belonging to the nine subpanels employed and are selected for further evaluation at five dose level screening. (C) 2011 Elsevier Masson SAS. All rights reserved.