4-(3-chlorophenylamino)-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine-6-carbonitrile | 1446090-63-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 4-(3-chlorophenylamino)-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine-6-carbonitrile
• 英文别名: 4-(3-Chloroanilino)-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine-6-carbonitrile；4-(3-chloroanilino)-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine-6-carbonitrile
• CAS: 1446090-63-6
• 化学式: C₁₉H₁₀Cl₂N₄S
• 分子量: 397.287
• InChiKey: RXDXLRGHPWHKEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  26
• 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：
  89.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-(4-chlorophenyl)-3,4-dihydro-4-oxothieno[2,3-d]pyrimidine-6-carboxamide 在 五氯化磷 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 4.5h， 生成 4-(3-chlorophenylamino)-5-(4-chlorophenyl)thieno[2,3-d]pyrimidine-6-carbonitrile
  参考文献：
  名称：

  Synthetic tactics of new class of 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives acting as antimicrobial agents

  摘要：

  Thermal selective reactions were studied on oxothieno[2,3-d]pyrimidine-6-carboxamide 3 with POCI3 and PCI5. At 25-50 degrees C, the C-7-amide rearranges to nitrile furnished compound 4 in 85-90% yield, while at 80-110 degrees C furnished mixture of products 4 and 5 in 28-68% yields. The chloro displacement with amines in compound 5 yielded 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives 8(a h) and 9(a e). Antimicrobial activity of new compounds was studied against several bacteria such as Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, Pseudomonas aeruginosa MTCC-4 41, Streptococcus pyogenes MTCC-442 and fungi Aspergillus niger MTCC-282, Aspergillus clavatus MTCC-1323, Candida albicans MTCC-227 using broth microdilution method. Compounds 4, 8b, 8d, 8e, 8h and 9a showed promising antibacterial activity compared to ampicillin and compounds 8b, 8h showed better antifungal activity compared to greseofulvin. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.039

文献信息

• Synthetic tactics of new class of 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives acting as antimicrobial agents
  作者：Shrikant B. Kanawade、Raghunath B. Toche、Dhanji P. Rajani

  DOI：10.1016/j.ejmech.2013.03.039

  日期：2013.6

  Thermal selective reactions were studied on oxothieno[2,3-d]pyrimidine-6-carboxamide 3 with POCI3 and PCI5. At 25-50 degrees C, the C-7-amide rearranges to nitrile furnished compound 4 in 85-90% yield, while at 80-110 degrees C furnished mixture of products 4 and 5 in 28-68% yields. The chloro displacement with amines in compound 5 yielded 4-aminothieno[2,3-d]pyrimidine-6-carbonitrile derivatives 8(a h) and 9(a e). Antimicrobial activity of new compounds was studied against several bacteria such as Staphylococcus aureus MTCC-96, Escherichia coli MTCC-443, Pseudomonas aeruginosa MTCC-4 41, Streptococcus pyogenes MTCC-442 and fungi Aspergillus niger MTCC-282, Aspergillus clavatus MTCC-1323, Candida albicans MTCC-227 using broth microdilution method. Compounds 4, 8b, 8d, 8e, 8h and 9a showed promising antibacterial activity compared to ampicillin and compounds 8b, 8h showed better antifungal activity compared to greseofulvin. (C) 2013 Elsevier Masson SAS. All rights reserved.