1-benzyl-6-cyclopropylamino-3-(3,5-dimethylbenzyl)uracil | 1453172-35-4

• 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-benzyl-6-cyclopropylamino-3-(3,5-dimethylbenzyl)uracil
• 英文别名: 1-Benzyl-6-(cyclopropylamino)-3-[(3,5-dimethylphenyl)methyl]pyrimidine-2,4-dione；1-benzyl-6-(cyclopropylamino)-3-[(3,5-dimethylphenyl)methyl]pyrimidine-2,4-dione
• CAS: 1453172-35-4
• 化学式: C₂₃H₂₅N₃O₂
• 分子量: 375.47
• InChiKey: QWONFPBPEBUMSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  52.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1-benzyl-6-chloro-3-(3,5-dimethylbenzyl)uracil 、 环丙胺 在 sodium carbonate 作用下， 以 乙醇 为溶剂， 以94%的产率得到1-benzyl-6-cyclopropylamino-3-(3,5-dimethylbenzyl)uracil
  参考文献：
  名称：

  Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents

  摘要：

  A novel series of uracil derivatives with a 3,5-dimethylbenzyl group at the N-3-position were synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Some of these compounds showed good-to-moderate activity with EC50 values in the submicromolar range. Among them, compound 10c showed significant potency against HIV-1 activity with an EC50 value of 0.03 mu M and a high selectivity index of 2863. Preliminary structure-activity relationships and molecular modeling analyses were used to explore the major interactions between HIV-1 reverse transcriptase and the potent inhibitor 10c, which may serve as an important lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.06.061

文献信息

• Synthesis and evaluation of novel 3-(3,5-dimethylbenzyl)uracil analogs as potential anti-HIV-1 agents
  作者：Norikazu Sakakibara、Takayuki Hamasaki、Masanori Baba、Yosuke Demizu、Masaaki Kurihara、Kohji Irie、Masatoshi Iwai、Eriko Asada、Yoshihisa Kato、Tokumi Maruyama

  DOI：10.1016/j.bmc.2013.06.061

  日期：2013.9

  A novel series of uracil derivatives with a 3,5-dimethylbenzyl group at the N-3-position were synthesized and evaluated as non-nucleoside HIV-1 reverse transcriptase inhibitors. Some of these compounds showed good-to-moderate activity with EC50 values in the submicromolar range. Among them, compound 10c showed significant potency against HIV-1 activity with an EC50 value of 0.03 mu M and a high selectivity index of 2863. Preliminary structure-activity relationships and molecular modeling analyses were used to explore the major interactions between HIV-1 reverse transcriptase and the potent inhibitor 10c, which may serve as an important lead for further optimization. (C) 2013 Elsevier Ltd. All rights reserved.