6-Methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone | 132938-38-6

• 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: 6-Methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone
• 英文别名: 6-methyl-5-prop-2-ynyl-2-sulfanylidene-1H-pyrimidin-4-one
• CAS: 132938-38-6
• 化学式: C₈H₈N₂OS
• 分子量: 180.23
• InChiKey: OZGWGBPFBSKPTN-UHFFFAOYSA-N

物化性质

• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  73.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  6-Methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone 在 氯乙酸 、 三氯氧磷 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2,4-Dichloro-6-methyl-5-(2-propynyl)pyrimidine
  参考文献：
  名称：

  2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines

  摘要：

  The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described. Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone. Hydrolysis of the 2-thione and chlorination with POCl3 gives 2,4-dichloro-6-methyl-5(2-propynyl)pyrimidine. Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.

  DOI：

  10.1021/jo00007a026
• 作为产物：
  描述：

  ethyl 2-acetylpent-4-ynoate 在 potassium carbonate 、 三氯氧磷 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.0h， 生成 6-Methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone
  参考文献：
  名称：

  2,4-Dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine: a potential synthon for 5-(1-o-carboranylmethyl)pyrimidines

  摘要：

  The synthesis of 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine is described. Synthetically, this novel o-carboranyl pyrimidine is approached from ethyl 2-acetyl-4-pentynoate through alkylation of ethyl acetoacetate with propargyl bromide and subsequent condensation with thiourea to yield 6-methyl-5-(2-propynyl)-2-thio-4(1H,3H)-pyrimidinone. Hydrolysis of the 2-thione and chlorination with POCl3 gives 2,4-dichloro-6-methyl-5(2-propynyl)pyrimidine. Gentle refluxing of this product with B10H14/CH3CN in toluene yields the target, 2,4-dichloro-5-(1-o-carboranylmethyl)-6-methylpyrimidine, a potential synthon for a variety of 2,4-substituted 5-(1-o-carboranylmethyl)-6-methylpyrimidines and/or the corresponding nido-undecaborates.

  DOI：

  10.1021/jo00007a026

文献信息

• Synthesis of 1,2,3-triazolyl nucleoside analogues and their antiviral activity
  作者：Olga V. Andreeva、Bulat F. Garifullin、Vladimir V. Zarubaev、Alexander V. Slita、Iana L. Yesaulkova、Liliya F. Saifina、Marina M. Shulaeva、Maya G. Belenok、Vyacheslav E. Semenov、Vladimir E. Kataev

  DOI：10.1007/s11030-020-10141-y

  日期：2021.2

  Abstract Based on the fact that a search for influenza antivirals among nucleoside analogues has drawn very little attention of chemists, the present study reports the synthesis of a series of 1,2,3-triazolyl nucleoside analogues in which a pyrimidine fragment is attached to the ribofuranosyl-1,2,3-triazol-4-yl moiety by a polymethylene linker of variable length. Target compounds were prepared by the

  摘要 基于在核苷类似物中寻找流感抗病毒药物很少引起化学家关注的事实，本研究报告了一系列 1,2,3-三唑基核苷类似物的合成，其中嘧啶片段与呋喃核糖基相连。 -1,2,3-triazol-4-yl 部分由可变长度的聚亚甲基接头组成。通过 Cu 炔烃-叠氮化物环加成 (CuAAC) 反应制备目标化合物。尿嘧啶、6-甲基尿嘧啶、3,6-二甲基尿嘧啶、胸腺嘧啶和喹唑啉-2,4-二酮的衍生物，在N 1 (或N 5) 原子上具有 ω-炔烃取代基和叠氮基 2,3,5-三-O-乙酰基-D-β-呋喃核糖苷用作CuAAC反应的组分。评估了所有合成的化合物对流感病毒 A/PR/8/34/(H1N1) 和柯萨奇病毒 B3 的抗病毒活性。IC 50（抑制浓度）和 SI（选择性指数）的最佳值由先导化合物4i证明，其中 1,2,3-三唑基呋喃核糖基片段连接到quinazoline-2,4-dione的N 1 原子通过丁烯接头
• Synthesis and antiviral activity of 1,2,3-triazolyl nucleoside analogues with <i>N</i>-acetyl-<scp>d</scp>-glucosamine residue
  作者：Bulat F. Garifullin、Leysan R. Khabibulina、Maya G. Belenok、Liliya F. Saifina、Vladimir V. Zarubaev、Alexander V. Slita、Alexandrina S. Volobueva、Vyacheslav E. Semenov、Vladimir E. Kataev

  DOI：10.1080/15257770.2023.2189914

  日期：——

  virus A H1N1 (IC50=70.7 µM) as the antiviral drug Rimantadine in control (IC50=77 µM) and good activity against Coxsackievirus B3 (IC50=13.9 µM) which was one and a half times higher than the activity of the antiviral drug Pleconaril in control (IC50=21.6 µM). According to molecular docking simulations, the antiviral activity of the lead compound 3f against Coxsackie B3 virus can be explained by its binding

  摘要 通过尿嘧啶、6-甲基尿嘧啶的N 1-ω-炔基衍生物的铜催化炔烃叠氮环加成(CuAAC)反应合成了一系列带有N-乙酰基-D-葡萄糖胺残基的1,2,3-三唑核苷类似物，胸腺嘧啶和3,4,6-三-O-乙酰基-2-脱氧-2-乙酰氨基-β-D-吡喃葡萄糖基叠氮化物。抗病毒测定显示，先导化合物3f与对照抗病毒药物金刚乙胺(IC 50 = 77 µM)具有相同的抗甲型 H1N1 流感病毒活性(IC 50 = 70.7 µM)，并且具有良好的抗柯萨奇病毒 B3 活性 (IC 50 = 13.9 µM），比对照抗病毒药物 Pleconaril 的活性高一倍半（IC 50 = 21.6 µM）。根据分子对接模拟，先导化合物3f对柯萨奇B3病毒的抗病毒活性可以通过其与该病毒衣壳表面关键片段的结合来解释。
• Wilson, J. Gerald, Inorganic Chemistry, 1994, vol. 33, # 13, p. 2758 - 2760
  作者：Wilson, J. Gerald

  DOI：——

  日期：——
• [EN] CYTIDINE LIBRARIES AND COMPOUNDS SYNTHESIZED BY SOLID-PHASE COMBINATORIAL STRATEGIES<br/>[FR] BIBLIOTHEQUES A CYTIDINE ET COMPOSES DE CES BIBLIOTHEQUES DONT LA SYNTHESE REPOSE SUR DES STRATEGIES COMBINATOIRES EN PHASE SOLIDE
  申请人：RIBAPHARM INC

  公开号：WO2003051896A1

  公开（公告）日：2003-06-26

  Substituted cytidine nucleoside analog libraries and compounds in such libraries are prepared in a combinatorial library approach. Particularly preferred heterocyclic bases in such compounds and libraries include amino acid substituted cytidine nucleosides, 2'-O-substituted cytidine nucleosides, and N-substituted cytidine nucleosides, all of which may be useful in the treatment of various conditions, particularly viral infections and neoplastic diseases.
• [EN] DEAZAPURINE NUCLEOSIDE ANALOGS AND THEIR USE AS THERAPEUTIC AGENTS<br/>[FR] ANALOGUES DE NUCLEOSIDES DE DEAZAPURINE ET UTILISATION DE CEUX-CI EN TANT QU'AGENTS THERAPEUTIQUES
  申请人：RIBAPHARM INC

  公开号：WO2003061576A2

  公开（公告）日：2003-07-31

  Methods, compositions, and uses for various deazapurine nucleoside libraries and library compounds are provided. Particularly preferred deazapurine nucleosides include 7-deazapurine nucleosides, 7-deaza-8-azapurine nucleosides, toyocamycin nucleoside analogs, 3-deazapurine nucleosides, and 9-deazapurine nucleosides, while preferred uses especially inlcude use of such compounds as pharmacological, and particularly antiviral agents.