1-(3-chlorobenzyl)-5-(phenylamino)uracil | 1261109-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(3-chlorobenzyl)-5-(phenylamino)uracil
• 英文别名: 5-anilino-1-[(3-chlorophenyl)methyl]pyrimidine-2,4-dione
• CAS: 1261109-58-3
• 化学式: C₁₇H₁₄ClN₃O₂
• 分子量: 327.77
• InChiKey: WHKYEUVMDPSHSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 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：
  61.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  3-氯苄溴 、 2,4-(trimethylsilyloxy)-5-(phenylamino)pyrimidine 以 1,2-二氯乙烷 为溶剂， 反应 14.0h， 以72%的产率得到1-(3-chlorobenzyl)-5-(phenylamino)uracil
  参考文献：
  名称：

  1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents

  摘要：

  Pyrimidine analogs have long found use over a broad chemotherapeutic spectrum. In an effort to further explore the antiviral potential of several uracil derivatives previously synthesized in our laboratories, a series of benzylated pyrimidines were designed and synthesized. Introduction of the benzyl residue onto the 5-phenylaminouracil scaffold was carried out using 2,4-bis(trimethylsilyloxy) pyrimidine with the corresponding benzyl bromides. Similarly, 1-benzyl-5-(benzylamino)- and 1-benzyl-5-(phenethylamino) uracils were obtained via amination of 1-benzyl-5-bromouracils with benzylamine or phenylethylamine. The results of the broad screen antiviral studies revealed that compounds 5 and 11 exhibit promising inhibitory activity against HIV-1 in CEM-SS culture. A 50% protective effect was observed at concentrations of 11.9 and 9.5 mu M, respectively. Moreover, compounds 8 and 3 exhibited good inhibitory effects against EBV in AKATA cell culture with EC50 values of 2.3 and 12 mu M, respectively. The synthesis and biological studies are detailed herein. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.09.070

文献信息

• 1-Benzyl derivatives of 5-(arylamino)uracils as anti-HIV-1 and anti-EBV agents
  作者：Mikhail S. Novikov、Robert W. Buckheit、Kartik Temburnikar、Anastasia L. Khandazhinskaya、Alexander V. Ivanov、Katherine L. Seley-Radtke

  DOI：10.1016/j.bmc.2010.09.070

  日期：2010.12

  Pyrimidine analogs have long found use over a broad chemotherapeutic spectrum. In an effort to further explore the antiviral potential of several uracil derivatives previously synthesized in our laboratories, a series of benzylated pyrimidines were designed and synthesized. Introduction of the benzyl residue onto the 5-phenylaminouracil scaffold was carried out using 2,4-bis(trimethylsilyloxy) pyrimidine with the corresponding benzyl bromides. Similarly, 1-benzyl-5-(benzylamino)- and 1-benzyl-5-(phenethylamino) uracils were obtained via amination of 1-benzyl-5-bromouracils with benzylamine or phenylethylamine. The results of the broad screen antiviral studies revealed that compounds 5 and 11 exhibit promising inhibitory activity against HIV-1 in CEM-SS culture. A 50% protective effect was observed at concentrations of 11.9 and 9.5 mu M, respectively. Moreover, compounds 8 and 3 exhibited good inhibitory effects against EBV in AKATA cell culture with EC50 values of 2.3 and 12 mu M, respectively. The synthesis and biological studies are detailed herein. (C) 2010 Elsevier Ltd. All rights reserved.