5-[(4-pentylphenyl)ethynyl]pyrimidin-2,4-dione | 1239708-80-5

• 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: 5-[(4-pentylphenyl)ethynyl]pyrimidin-2,4-dione
• 英文别名: 5-(4-n-pentylphenylethynyl)uracil；5-[2-(4-pentylphenyl)ethynyl]-1H-pyrimidine-2,4-dione
• CAS: 1239708-80-5
• 化学式: C₁₇H₁₈N₂O₂
• 分子量: 282.342
• InChiKey: JDDUKWJGFGDBAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-[(4-pentylphenyl)ethynyl]pyrimidin-2,4-dione 、 氯甲基甲基醚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以23%的产率得到5-(4-pentylphenyl)ethynyl-1-(methoxymethyl)pyrimidin-2,4-dione
  参考文献：
  名称：

  Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines

  摘要：

  A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in good to excellent yields. The 5-endo-dig cyclisation of 5-alkynylpyrimidine derivatives promoted by a Pd-catalyst or base gives the corresponding furo[2,3-d]pyrimidines in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.068
• 作为产物：
  描述：

  4-戊基苯乙炔 、 5-碘尿嘧啶 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以64%的产率得到5-[(4-pentylphenyl)ethynyl]pyrimidin-2,4-dione
  参考文献：
  名称：

  Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines

  摘要：

  A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in good to excellent yields. The 5-endo-dig cyclisation of 5-alkynylpyrimidine derivatives promoted by a Pd-catalyst or base gives the corresponding furo[2,3-d]pyrimidines in good yields. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.07.068

文献信息

• Inhibition of Mycobacterial Replication by Pyrimidines Possessing Various C-5 Functionalities and Related 2′-Deoxynucleoside Analogues Using in Vitro and in Vivo Models
  作者：Naveen C. Srivastav、Dinesh Rai、Christopher Tse、B. Agrawal、Dennis Y. Kunimoto、Rakesh Kumar

  DOI：10.1021/jm100568q

  日期：2010.8.26

  Tuberculosis (TB) has become an increasing problem since the emergence of human immunodeficiency virus and increasing appearance of drug-resistant strains. There is an urgent need to advance our knowledge and discover a new class of agents that are distinct than current therapies. Antimycobacterial activities of several 5-alkyl, 5-alkynyl, furanopyrimiclines and related 2'-deoxynucleosides were investigated against Mycobacterium tuberculosis. Compounds with 5-arylalkynyl substituents (23-26,33, 35) displayed potent in vitro antitubercular activity against Mycobacterium bovis and Mycobacterium tuberculosis. The in vivo activity of 5-(2-pyridylethyny1)-uracil (26) and its 2'-deoxycytidine analogue, 5-(2-pyridylethynyI)-2'-deoxycytidine (35), was assessed in BA LB/c mice infected with M. tuberculosis (H 37 Ra). Both compounds 26 and 35 given at a dose of 50 mg/kg for 5 weeks showed promising in vivo efficacy in a mouse model, with the 2'-deoxycytidine derivative being more effective than the uracil analogue and a reference drug o-cycloserine. These data indicated that there is a significant potential in this class of compounds.
• Efficient palladium-mediated or base-induced 5-endo-dig cyclisation of C5-alkynylated pyrimidine derivatives: conventional and microwave-assisted synthesis of novel furo[2,3-d]pyrimidines
  作者：Tatjana Gazivoda Kraljević、Andrea Bistrović、Matea Dedić、Sandra Kraljević Pavelić、Mirela Sedić、Silvana Raić-Malić

  DOI：10.1016/j.tetlet.2012.07.068

  日期：2012.9

  A series of the novel 5-alkynyl- and furo[2,3-d]pyrimidine derivatives in which the sugar moiety is replaced by a methoxymethyl (MOM) group is synthesised using the Sonogashira cross-coupling reaction under both conventional and microwave conditions, in good to excellent yields. The 5-endo-dig cyclisation of 5-alkynylpyrimidine derivatives promoted by a Pd-catalyst or base gives the corresponding furo[2,3-d]pyrimidines in good yields. (C) 2012 Elsevier Ltd. All rights reserved.