6-(2,6-Difluorophenylmethyl)-3,4-dihydro-2-N,N-dimethylaminopyrimidin-4-(3H)-one

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 6-(2,6-Difluorophenylmethyl)-3,4-dihydro-2-N,N-dimethylaminopyrimidin-4-(3H)-one
• 英文别名: 4-[(2,6-difluorophenyl)methyl]-2-(dimethylamino)-1H-pyrimidin-6-one
• 化学式: C₁₃H₁₃F₂N₃O
• 分子量: 265.263
• InChiKey: ARRLMRHYVRHARM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  44.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  1,1-二甲基硫酸胍 、 ethyl 4-(2,6-difluorophenyl)-3-oxobutanoate 在 乙醇 、 sodium 、 水 、 溶剂黄146 作用下， 反应 8.0h， 以88%的产率得到6-(2,6-Difluorophenylmethyl)-3,4-dihydro-2-N,N-dimethylaminopyrimidin-4-(3H)-one
  参考文献：
  名称：

  Substituted 6-benzyl-4-oxopyrimidines, process for their preparation and pharmaceutical compositions containing them

  摘要：

  该发明涉及新型的取代6-苄基-4-氧基嘧啶及其药用盐。这些化合物抑制人类免疫缺陷病毒（HIV）编码的逆转录酶，可用于预防和治疗HIV感染和获得性免疫缺陷综合征（AIDS）。还设想了含有这些化合物的药物组合物以及用于治疗AIDS和HIV病毒感染的其他药物的方法。

  公开号：

  US06635636B1

文献信息

• Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4-oxopyrimidines
  申请人：——

  公开号：US20030008887A1

  公开（公告）日：2003-01-09

  A method for inhibiting sexual transmission of HIV comprising topically applying to the skin or epithelial tissue of a human a composition comprising a non-nucleoside reverse transcriptase inhibitor (“NNRTI”) that is able to inhibit viral replication for periods exceeding 12, 24, or even 36 days, at concentrations below even 10 &mgr;M. In one embodiment the NNRTI is a dihydro-alkyloxy-benzyl-oxopyrimidine (DABO).

  一种抑制HIV性传播的方法，包括将一种含有非核苷类反转录酶抑制剂（“NNRTI”）的组合物局部涂抹于人体的皮肤或上皮组织上，该NNRTI能够在浓度低于10 &mgr;M的情况下抑制病毒复制，持续时间超过12、24或36天。在一种实施方式中，NNRTI是一种二氢烷氧基苯基嘧啶（DABO）。
• Methods for inhibiting the transmission of HIV using topically applied substituted 6-benzyl-4- oxopyrimidines
  申请人：Idenix Pharmaceuticals, Inc.

  公开号：US20030225114A1

  公开（公告）日：2003-12-04

  A method for inhibiting sexual transmission of HIV comprising topically applying to the skin or epithelial tissue of a human a composition comprising a non-nucleoside reverse transcriptase inhibitor (“NNRTI”) that is able to inhibit viral replication for periods exceeding 12, 24, or even 36 days, at concentrations below even 10 &mgr;M. In one embodiment the NNRTI is a dihydro-alkyloxy-benzyl-oxopyrimidine (DABO).

  一种抑制艾滋病毒性传播的方法，包括在人的皮肤或上皮组织局部施用一种组合物，该组合物包含一种非核苷类逆转录酶抑制剂（"NNRTI"），它能够抑制病毒复制超过 12、24 或甚至 36 天，浓度甚至低于 10 &mgr;M。在一个实施方案中，NNRTI 是一种二氢-烷氧基-苄基-氧代嘧啶（DABO）。
• Synthesis and Biological Properties of Novel 2-Aminopyrimidin-4(3<i>H</i>)-ones Highly Potent against HIV-1 Mutant Strains
  作者：Antonello Mai、Marino Artico、Dante Rotili、Domenico Tarantino、Imma Clotet-Codina、Mercedes Armand-Ugón、Rino Ragno、Silvia Simeoni、Gianluca Sbardella、Maxim B. Nawrozkij、Alberta Samuele、Giovanni Maga、José A. Esté

  DOI：10.1021/jm070811e

  日期：2007.11.1

  Following the disclosure of dihydro-alkoxy-, dihydro-alkylthio-, and dihydro-alkylamino-benzyl-oxopyrimidines (DABOs, S-DABOs, and NH-DABOs) as potent and selective anti-HIV-1 agents belonging to the non-nucleoside reverse transcriptase inhibitor (NNRTI) class, we report here the synthesis and biological evaluation of a novel series of DABOs bearing a NN-disubstituted amino group or a cyclic amine at the pyrimidine-C, position, a hydrogen atom or a small alkyl group at C-5 and/or at the benzylic position, and the favorable 2,6-difluorobenzyl moiety at the C-6 position (F,NN-DABOs). The new compounds were highly active up to the subnanomolar level against both wt HIV-1 and the Y181C mutant and at the submicromolar to nanomolar range against the K103N and Y188L mutant strains. Such derivatives were more potent than S-DABOs, NH-DABOs, and nevirapine and efavirenz were chosen as reference drugs. The higher inhibitor adaptability to the HIV- I RT non-nucleoside binding site (NNBS) may account for the higher inhibitory effect exerted by the new molecules against the mutated RTs.
• US6545007B2
  申请人：——

  公开号：US6545007B2

  公开（公告）日：2003-04-08
• US6635636B1
  申请人：——

  公开号：US6635636B1

  公开（公告）日：2003-10-21