6-(2-chloro-6-fluorobenzyl)-5-iso-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one | 1044749-16-7

• 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: 6-(2-chloro-6-fluorobenzyl)-5-iso-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
• 英文别名: 5-isopropyl-2-thioxo-6-(2-fluoro-6-chlorobenzyl)-2,3-dihydropyrimidin-4(1H)-one；5-Isopropyl-2-thioxo-6-(2-fluoro-6-chloro-benzyl)-2,3-dihydropyrimidin-4(1h)-one；6-[(2-chloro-6-fluorophenyl)methyl]-5-propan-2-yl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 1044749-16-7
• 化学式: C₁₄H₁₄ClFN₂OS
• 分子量: 312.795
• InChiKey: NQWHHFUMRPXVHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-(2-chloro-6-fluorobenzyl)-5-iso-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one 在 methyloxirane 、 sodium hydroxide 作用下， 以 水 为溶剂， 以78%的产率得到6-(6-chloro-2-fluorobenzyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Experimental and quantum chemical study of the reactions of 2-methyloxirane with 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo1,2-dihydropyrimidine-4(3H)-one derivatives

  摘要：

  在碱性介质中，5-烷基-6-(2,6-二卤苄基)-2-硫酮-1,2-二氢嘧啶-4(3H)-酮与 2-甲基环氧乙烷反应生成了尿嘧啶和 2-[(2-羟基丙-1-基)硫]嘧啶-4(3H)-酮衍生物。利用 DFT/B3LYP/311+G** 量子化学方法对这些转化的机理进行了研究，并显示了 Nathan-Baker 效应对反应产物化学性质和组成的影响。

  DOI：

  10.1007/s11172-015-0896-4
• 作为产物：
  描述：

  2-氯-6-氟苯乙睛 在 potassium ethoxide 、 锌 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 生成 6-(2-chloro-6-fluorobenzyl)-5-iso-propyl-2-thioxo-2,3-dihydropyrimidin-4(1H)-one
  参考文献：
  名称：

  Synthesis of new derivatives of 5-alkyl-6-(2,6-dihalobenzyl)-2-(methylsulfanyl)pyrimidin-4(3H)-one and the features of their oxidation

  摘要：

  The synthesis and features of the regioselective S-monomethylation of new 5-alkyl-6-(arylmethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones were investigated, and also the character of the oxidative degradation of these compounds when treated with the system H2O2-AcOH.

  DOI：

  10.1134/s1070428010110151

文献信息

• 5-Alkyl-6-benzyl-2-(2-oxo-2-phenylethylsulfanyl)pyrimidin-4(3<i>H</i>)-ones, a Series of Anti-HIV-1 Agents of the Dihydro-alkoxy-benzyl-oxopyrimidine Family with Peculiar Structure−Activity Relationship Profile
  作者：Maxim B. Nawrozkij、Dante Rotili、Domenico Tarantino、Giorgia Botta、Alexandre S. Eremiychuk、Ira Musmuca、Rino Ragno、Alberta Samuele、Samantha Zanoli、Mercedes Armand-Ugón、Imma Clotet-Codina、Ivan A. Novakov、Boris S. Orlinson、Giovanni Maga、José A. Esté、Marino Artico、Antonello Mai

  DOI：10.1021/jm800340w

  日期：2008.8.1

  A series of dihydro-alkylthio-benzyl-oxopyrimidines (S-DABOs) bearing a 2-aryl-2-oxoethylsulfanyl chain at pyrimidine C2, an alkyl group at C5, and a 2,6-dichloro-, 2-chloro-6-fluoro-, and 2,6-difluoro-benzyl substitution at C6 (oxophenethyl-S-DABOs, 6-8) is here described. The new compounds showed low micromolar to low nanomolar (in one case subnanomolar) inhibitory activity against wt HIV-1. Against clinically relevant HIV-1 mutants (K103N, Y181C, and Y188L) as well as in enzyme (wt and K103N, Y181I, and L1001 mutated RTs) assays, compounds carrying an ethylliso-propyl group at C5 and a 2,6-dichloro-/2-chloro-6-fluoro-benzyl moiety at C6 were the most potent derivatives, also characterized by low fold resistance ratio. Interestingly, the structure-activity relationship (SAR) data drawn from this DABO series are more related to HEPT than to DABO derivatives. These findings were at least in part rationalized by the description of a fair superimposition between the 6-8 and TNK-651 (a HEPT analogue) binding modes in both WT and Y181C RTs.
• The specific character of the reaction of derivatives of 2-thioxo-2,3-dihydropyrimidin-4(1H)-one with iodomethane and alkyl chloromethyl sulfides
  作者：I. A. Novakov、B. S. Orlinson、M. B. Nawrozkij、A. Mai、M. Artico、D. Rotili、A. S. Eremiychuk、E. A. Gordeeva、L. L. Brunilina、J. A. Este

  DOI：10.1007/s10593-010-0492-3

  日期：2010.6

  The alkylation of 5-alkyl-6-(2,6-dihalobenzyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-ones with MeI, AllSCH(2)Cl, and MeSCH(2)Cl in the K(2)CO(3)-DMF, NaOMe-MeOH, and KOH-EtOH systems was investigated. A hypothetical mechanism for the reaction is examined, and an explanation is proposed for the composition of the reaction products. The presence of high anti-HIV-1 activity was established in the obtained derivatives of 2-[(allylsulfanyl)methyl]sulfanyl}pyrimidin-4(3H)-one.