6-chloro-1-methoxymethyl-3-(3,5-dimethylbenzyl)uracil | 1453172-27-4

• 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: 6-chloro-1-methoxymethyl-3-(3,5-dimethylbenzyl)uracil
• CAS: 1453172-27-4
• 化学式: C₁₅H₁₇ClN₂O₃
• 分子量: 308.765
• InChiKey: NIGAWRCYQNPQDR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.93
• 重原子数：
  21.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  53.23
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  6-chloro-1-methoxymethyl-3-(3,5-dimethylbenzyl)uracil 在 B-溴代邻苯二氧硼烷 、 水 、 三苯基膦 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 12.5h， 生成 6-amino-1-cyanomethyl-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
• 作为产物：
  描述：

  3,5-二甲基苯甲醇 、 1-methoxymethyl-6-chlorouracil 在 偶氮二甲酰胺 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 以93%的产率得到6-chloro-1-methoxymethyl-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