5-allyl-6-chloro-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione | 1466431-40-2

• 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: 5-allyl-6-chloro-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-Chloro-1-(methoxymethyl)-5-prop-2-enylpyrimidine-2,4-dione；6-chloro-1-(methoxymethyl)-5-prop-2-enylpyrimidine-2,4-dione
• CAS: 1466431-40-2
• 化学式: C₉H₁₁ClN₂O₃
• 分子量: 230.651
• InChiKey: JFXRODCTFSWLOY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-allyl-6-chloro-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione 在 三乙胺 作用下， 以 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 5-allyl-3-benzoyl-6-(cyclohexylamino)-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Rapid Access to 10-(Cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione Derivatives for HIV-1 Reverse Transcriptase Inhibition via Ruthenium-Catalyzed Ring-Closing Metathesis

  摘要：

  HIV-1 reverse transcriptase, a multifunctional enzyme critical in the viral replication process, is an important target for suppression of virus spread. To date, there has been considerable effort to develop drugs against this enzyme with high activity and specificity, notably TNK-651 and its derivatives. In order to further improve the efficacy and to explore the structure-activity relationship, we have introduced the diazaspiro[4.5]decane-6,8-dione scaffold, with both a pyrimidine and an alicyclic ring, and have synthesized several new compounds in this class. Appreciable overall yield was achieved with minimized purification of the intermediates. Several compounds were tested against HIV-1 reverse transcriptase in vitro using nevirapine as a reference. One compound showed potent inhibitory activity, with an IC50 value (ca. 1.65 M) comparable to that of nevirapine. Our synthetic method provides a rapid access to compounds in this class. Thus, many other similar compounds can be further studied in a timely and cost-effective manner.

  DOI：

  10.1055/s-0033-1339179
• 作为产物：
  描述：

  5-烯丙基-2,4,6-三氯嘧啶 在 N,O-双三甲硅基乙酰胺 、 sodium hydroxide 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 5-allyl-6-chloro-1-(methoxymethyl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Rapid Access to 10-(Cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione Derivatives for HIV-1 Reverse Transcriptase Inhibition via Ruthenium-Catalyzed Ring-Closing Metathesis

  摘要：

  HIV-1 reverse transcriptase, a multifunctional enzyme critical in the viral replication process, is an important target for suppression of virus spread. To date, there has been considerable effort to develop drugs against this enzyme with high activity and specificity, notably TNK-651 and its derivatives. In order to further improve the efficacy and to explore the structure-activity relationship, we have introduced the diazaspiro[4.5]decane-6,8-dione scaffold, with both a pyrimidine and an alicyclic ring, and have synthesized several new compounds in this class. Appreciable overall yield was achieved with minimized purification of the intermediates. Several compounds were tested against HIV-1 reverse transcriptase in vitro using nevirapine as a reference. One compound showed potent inhibitory activity, with an IC50 value (ca. 1.65 M) comparable to that of nevirapine. Our synthetic method provides a rapid access to compounds in this class. Thus, many other similar compounds can be further studied in a timely and cost-effective manner.

  DOI：

  10.1055/s-0033-1339179

文献信息

• Rapid Access to 10-(Cyclohexylimino)-7,9-diazaspiro[4.5]decane-6,8-dione Derivatives for HIV-1 Reverse Transcriptase Inhibition via Ruthenium-Catalyzed Ring-Closing Metathesis
  作者：Xiaowei Wang、Junyi Liu、Tongbo Zhang、Shaotong Wu、Yuanyuan Cao、Yuhong Fu、Ying Guo、Liang Zhang、Li Li、Han Zhou、Xiangyi Liu、Chao Li、Xiaowan Tang、Zhili Zhang、Chao Tian

  DOI：10.1055/s-0033-1339179

  日期：——

  HIV-1 reverse transcriptase, a multifunctional enzyme critical in the viral replication process, is an important target for suppression of virus spread. To date, there has been considerable effort to develop drugs against this enzyme with high activity and specificity, notably TNK-651 and its derivatives. In order to further improve the efficacy and to explore the structure-activity relationship, we have introduced the diazaspiro[4.5]decane-6,8-dione scaffold, with both a pyrimidine and an alicyclic ring, and have synthesized several new compounds in this class. Appreciable overall yield was achieved with minimized purification of the intermediates. Several compounds were tested against HIV-1 reverse transcriptase in vitro using nevirapine as a reference. One compound showed potent inhibitory activity, with an IC50 value (ca. 1.65 M) comparable to that of nevirapine. Our synthetic method provides a rapid access to compounds in this class. Thus, many other similar compounds can be further studied in a timely and cost-effective manner.