2-[3-(4-chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl]-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 2-[3-(4-chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl]-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 2-[5-(4-Chlorophenyl)-3-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-1-methyl-6-oxo-4-phenylpyrimidine-5-carbonitrile；2-[5-(4-chlorophenyl)-3-(4-methoxyphenyl)-3,4-dihydropyrazol-2-yl]-1-methyl-6-oxo-4-phenylpyrimidine-5-carbonitrile
• 化学式: C₂₈H₂₂ClN₅O₂
• 分子量: 495.968
• InChiKey: BLUNEGGTGFULFM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  81.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  1-methyl-2-(methylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile 在 hydrazine hydrate 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 84.0h， 生成 2-[3-(4-chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydropyrazol-1-yl]-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity

  摘要：

  Two series of 2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitriles 5a-h and 4-(4-chlorophenyl)-2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitriles 6a-h were synthesized via a cydocondensation reaction of the corresponding 2-hydrazinopyrimidines 3a,b with the appropriate 2-propen-1-ones 4a h. The target compounds were screened for their antiproliferative activity against A 549 (lung), HT 29 (colon), MCF 7 and MDA-MB 231 (breast) cell lines. The two most susceptible cell lines were the colon (HT 29) and breast (MDA-MB 231). Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a h were more active than their 4-chlorophenylpyrimidine analogs 6a h. Compounds 5e and 5g, showed high activity against three of the cell lines. The most active compound 5c possessed IC50 = 1.76 mu M against A 549 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.10.003

文献信息

• Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity
  作者：Fadi M. Awadallah、Gary A. Piazza、Bernard D. Gary、Adam B. Keeton、Joshua C. Canzoneri

  DOI：10.1016/j.ejmech.2013.10.003

  日期：2013.12

  Two series of 2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitriles 5a-h and 4-(4-chlorophenyl)-2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitriles 6a-h were synthesized via a cydocondensation reaction of the corresponding 2-hydrazinopyrimidines 3a,b with the appropriate 2-propen-1-ones 4a h. The target compounds were screened for their antiproliferative activity against A 549 (lung), HT 29 (colon), MCF 7 and MDA-MB 231 (breast) cell lines. The two most susceptible cell lines were the colon (HT 29) and breast (MDA-MB 231). Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a h were more active than their 4-chlorophenylpyrimidine analogs 6a h. Compounds 5e and 5g, showed high activity against three of the cell lines. The most active compound 5c possessed IC50 = 1.76 mu M against A 549 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.