2-(4-nitrobenzylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile | 890195-17-2

• 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-(4-nitrobenzylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 2-[(4-Nitrobenzyl)sulfanyl]-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile；2-[(4-nitrophenyl)methylsulfanyl]-6-oxo-4-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 890195-17-2
• 化学式: C₁₈H₁₂N₄O₃S
• 分子量: 364.384
• InChiKey: UULFOUCELPTWQU-UHFFFAOYSA-N

物化性质

• 熔点：
  247-248 °C
• 沸点：
  567.3±60.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)
• 溶解度：
  52 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  136
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  苯甲醛 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-(4-nitrobenzylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis of novel 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles as potential antimicrobial agents

  摘要：

  New series of 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles namely, 2-substitued thio-6-phenyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles (5a-d, 6, 7a-d, 8), 2-(4-chlorobenzylthio)-4-chloro-6-phenylpyrimidine-5-carbonitrile (9), 2-(4-chlorobenzylthio)-4-arylthio-6-phenylpyrimidine-5-carbonitriles (10a-d) and 2-(4-chlorobenzylthio)-4-arylamino-6-phenylpyrimidine-5-carbonitriles (11a-d) was synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 5b, 5c, 6, 7a, 7b, 7c, 9 and 11a displayed marked antibacterial activity particularly against the tested Gram-positive bacteria, while compounds 6, 7c, 7d and 9 were moderately or weakly active against C. albicans. (C) 2011 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2011.08.003

文献信息

• Synthesis and Anti-HIV-1 Integrase Activitiy of Cyano Pyrimidinones
  作者：R. Ramajayam、Nilesh B. Mahera、Nouri Neamati、Mange Ram Yadav、Rajani Giridhar

  DOI：10.1002/ardp.200900066

  日期：2009.12

  6‐dihydropyrimidine‐5‐carbonitrile were synthesized and tested against recombinant HIV‐1 integrase in an enzyme assay. 2‐(Phenethylthio)‐4‐(4‐chlorophenyl)‐6‐oxo‐1,6‐dihydropyrimidine‐5‐carbonitrile 4m and 2‐(phenethylthio)‐4‐(3‐chlorophenyl)‐6‐oxo‐1,6‐dihydropyrimidine‐5‐carbonitrile 4o showed significant inhibition against integrase in the assay (strand transfer: IC50 values of 16 and 17 μM, respectively).

  合成了一系列 2-苯乙基/苄硫基-6-氧代-4-苯基-1,6-二氢嘧啶-5-甲腈，并在酶测定中针对重组 HIV-1 整合酶进行了测试。2-(苯乙硫基)-4-(4-氯苯基)-6-氧代-1,6-二氢嘧啶-5-甲腈4m和2-(苯乙硫基)-4-(3-氯苯基)-6-氧代-1,6 -dihydropyrimidine-5-carbonitrile 4o 在测定中显示出对整合酶的显着抑制（链转移：IC50 值分别为 16 和 17 μM）。
• Synthesis, docking studies, and evaluation of pyrimidines as inhibitors of SARS-CoV 3CL protease
  作者：R. Ramajayam、Kian-Pin Tan、Hun-Ge Liu、Po-Huang Liang

  DOI：10.1016/j.bmcl.2010.04.118

  日期：2010.6

  A series of 2-(benzylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine as SARS-CoV 3CL protease inhibitors were developed and their potency was evaluated by in vitro protease inhibitory assays. Two candidates had encouraging results for the development of new anti-SARS compounds. (C) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of novel 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles as potential antimicrobial agents
  作者：Ebtehal S. Al-Abdullah、Abdul-Rahman M. Al-Obaid、Omar A. Al-Deeb、Elsayed E. Habib、Ali A. El-Emam

  DOI：10.1016/j.ejmech.2011.08.003

  日期：2011.9

  New series of 6-phenyl-2,4-disubstituted pyrimidine-5-carbonitriles namely, 2-substitued thio-6-phenyl-3,4-dihydro-4-oxopyrimidine-5-carbonitriles (5a-d, 6, 7a-d, 8), 2-(4-chlorobenzylthio)-4-chloro-6-phenylpyrimidine-5-carbonitrile (9), 2-(4-chlorobenzylthio)-4-arylthio-6-phenylpyrimidine-5-carbonitriles (10a-d) and 2-(4-chlorobenzylthio)-4-arylamino-6-phenylpyrimidine-5-carbonitriles (11a-d) was synthesized and tested for in vitro activities against a panel of Gram-positive and Gram-negative bacteria and the yeast-like pathogenic fungus Candida albicans. Compounds 5b, 5c, 6, 7a, 7b, 7c, 9 and 11a displayed marked antibacterial activity particularly against the tested Gram-positive bacteria, while compounds 6, 7c, 7d and 9 were moderately or weakly active against C. albicans. (C) 2011 Elsevier Masson SAS. All rights reserved.