cyclohexylmethyl 4-(4-cyanophenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 1224682-09-0

• 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: cyclohexylmethyl 4-(4-cyanophenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: cyclohexylmethyl 4-(4-cyanophenyl)-6-ethyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 1224682-09-0；1224682-10-3；1224682-11-4
• 化学式: C₂₁H₂₅N₃O₃
• 分子量: 367.448
• InChiKey: NWGJTLJGUOVTLN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  91.2
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  cyclohexylmethyl 3-oxopentanoate 、 4-氰基苯甲醛 、 尿素 在 ytterbium(III) triflate 作用下， 以 四氢呋喃 为溶剂， 生成 cyclohexylmethyl 4-(4-cyanophenyl)-6-ethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication

  摘要：

  3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) were selected and derivatized through a HIV-1 replication assay based on GFP reporter cells. Compounds 14, 25, 31, and 36 exhibited significant inhibition of HIV-1 replication with a good safety profile. Chiral separation of each enantiomer by fractional crystallization showed that only the S enantiomer retained anti-HIV activity. Compound (S)-40, a novel and potent DHPM analog, could serve as an advanced lead for further development and the determination of the mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.12.090

文献信息

• [EN] ANTI VIRAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIVIRAUX
  申请人：PASTEUR INSTITUT KOREA

  公开号：WO2010046780A2

  公开（公告）日：2010-04-29

  There is provided small molecule anti-human immunodeficiency virus (anti-HIV) compounds as well as a phenotypic cell-based high throughput screening (HTS) assay for their identification.
• Discovery of 3,4-dihydropyrimidin-2(1H)-ones with inhibitory activity against HIV-1 replication
  作者：Junwon Kim、Changmin Park、Taedong Ok、Wonyoung So、Mina Jo、Minjung Seo、Youngmi Kim、Jeong-Hun Sohn、Youngsam Park、Moon Kyeong Ju、Junghwan Kim、Sung-Jun Han、Tae-Hee Kim、Jonathan Cechetto、Jiyoun Nam、Peter Sommer、Zaesung No

  DOI：10.1016/j.bmcl.2011.12.090

  日期：2012.3

  3,4-Dihydropyrimidin-2(1H)-ones (DHPMs) were selected and derivatized through a HIV-1 replication assay based on GFP reporter cells. Compounds 14, 25, 31, and 36 exhibited significant inhibition of HIV-1 replication with a good safety profile. Chiral separation of each enantiomer by fractional crystallization showed that only the S enantiomer retained anti-HIV activity. Compound (S)-40, a novel and potent DHPM analog, could serve as an advanced lead for further development and the determination of the mechanism of action. (C) 2012 Elsevier Ltd. All rights reserved.