1-(benzyloxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione | 1281859-95-7

• 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: 1-(benzyloxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 1-(Benzyloxymethyl)-3-hydroxy-5-methyl-pyrimidine-2,4-dione；3-hydroxy-5-methyl-1-(phenylmethoxymethyl)pyrimidine-2,4-dione
• CAS: 1281859-95-7
• 化学式: C₁₃H₁₄N₂O₄
• 分子量: 262.265
• InChiKey: VXBAXPUKOLHPHN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-benzyloxymethyl-5-methyl-pyrimidine-2,4-dione 在 sodium hydride 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以37%的产率得到1-(benzyloxymethyl)-3-hydroxy-5-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

  摘要：

  Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (IN Is). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

  DOI：

  10.1021/jm1014378

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.
• 3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase
  作者：Jing Tang、Kasthuraiah Maddali、Mathieu Metifiot、Yuk Y. Sham、Robert Vince、Yves Pommier、Zhengqiang Wang

  DOI：10.1021/jm1014378

  日期：2011.4.14

  Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (IN Is). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.