6-(3,5-dimethylbenzoyl)-5-ethyl-1-((4-fluorophenethoxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione | 1304033-89-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-(3,5-dimethylbenzoyl)-5-ethyl-1-((4-fluorophenethoxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
• 英文别名: 6-(3,5-Dimethylbenzoyl)-5-ethyl-1-[2-(4-fluorophenyl)ethoxymethyl]-3-hydroxy-pyrimidine-2,4-dione；6-(3,5-dimethylbenzoyl)-5-ethyl-1-[2-(4-fluorophenyl)ethoxymethyl]-3-hydroxypyrimidine-2,4-dione
• CAS: 1304033-89-3
• 化学式: C₂₄H₂₅FN₂O₅
• 分子量: 440.471
• InChiKey: SZAXCRJMFRDHIU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  32
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  87.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  对氟苯乙醇 在 三甲基氯硅烷 、 N,O-双三甲硅基乙酰胺 、 sodium hydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 0.75h， 生成 6-(3,5-dimethylbenzoyl)-5-ethyl-1-((4-fluorophenethoxy)methyl)-3-hydroxypyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase

  摘要：

  N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.02.069

文献信息

• [EN] N-HYDROXYPYRIMIDINE-2,4-DIONES AS INHIBITORS OF HIV AND HCV<br/>[FR] N-HYDROXYPYRIMIDINE-2,4-DIONES EN TANT QU'INHIBITEURS DU VIH ET VHC
  申请人：UNIV MINNESOTA

  公开号：WO2012047993A2

  公开（公告）日：2012-04-12

  The invention provides antiviral compounds that can be used in therapy against human immunodeficiency virus (HIV) and hepatitis C virus (HCV). Compounds of the invention can be dual targeted inhibitors of HIV, inhibiting both the reverse transcriptase and the integrase enzyme systems, thus increasing the barrier to development of viral resistance in patients. Prodrugs of the inventive antiviral compounds are also provided. Compounds of the invention can be used to treat HCV secondary infections in HIV-afflicted patients, reducing the need for administration of drug cocktails containing multiple, potentially conflicting, medicinal compounds. Methods of synthesis of the compounds and methods of treatment using the compounds are also provided.
• 6-Benzoyl-3-hydroxypyrimidine-2,4-diones as dual inhibitors of HIV reverse transcriptase and integrase
  作者：Jing Tang、Kasthuraiah Maddali、Christine D. Dreis、Yuk Y. Sham、Robert Vince、Yves Pommier、Zhengqiang Wang

  DOI：10.1016/j.bmcl.2011.02.069

  日期：2011.4

  N-3-Hydroxylation of pyrimidine-2,4-diones was recently found to yield inhibitors of both HIV-1 reverse transcriptase (RT) and integrase (IN). An extended series of analogues featuring a benzoyl group at the C-6 position of the pyrimidine ring was synthesized. Through biochemical studies it was found that these new analogues are dually active against both RT and IN in low micromolar range. Antiviral assays confirmed that these new inhibitors are active against HIV-1 in cell culture at nanomolar to low micromolar range, further validating 3-hydroxypyrimidine-2,4-diones as a viable scaffold for antiviral development. (C) 2011 Elsevier Ltd. All rights reserved.