2-(methylthio)-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile | 97693-21-5

• 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: 2-(methylthio)-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile
• 英文别名: 4-Hydroxy-2-(methylsulfanyl)-6-phenyl-5-pyrimidinecarbonitrile；2-methylsulfanyl-6-oxo-4-phenyl-1H-pyrimidine-5-carbonitrile
• CAS: 97693-21-5
• 化学式: C₁₂H₉N₃OS
• mdl: MFCD00297980
• 分子量: 243.289
• InChiKey: QEMPGPIZKSTYKP-UHFFFAOYSA-N

物化性质

• 溶解度：
  >36.5 [ug/mL]

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  90.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(methylthio)-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile 在 一水合肼 、 三氯氧磷 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 2,4-dihydrazino-6-phenyl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  El-Reedy, A. M.; Hussain, S. M.; Ali, A. S., Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 42, p. 231 - 236

  摘要：

  DOI：
• 作为产物：
  描述：

  Potassium; 5-cyano-4-oxo-6-phenyl-1,4-dihydro-pyrimidine-2-thiolate 在 potassium carbonate 、 溶剂黄146 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-(methylthio)-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Glycosylation of 2-Thiouracil Derivatives. A Synthetic Approach to 3-Glycosyl-2, 4-dioxypyrimidines

  摘要：

  Reaction of 6-aryl-5-cyano-2-thiouracils 2a-d with glycosyl halides 4a,b under alkaline conditions gave the respective bisglycosylated derivatives 5a-h. However, their deacetylation with ammonia in methanol caused a cleavage of the S-glycosyl residue and gave the N-3 glycosylated analogues 6a-h.

  DOI：

  10.1080/07328319708001360

文献信息

• Design, synthesis, and antihypertensive activity of new pyrimidine derivatives endowing new pharmacophores
  作者：Ahmed M. Farghaly、Omaima M. AboulWafa、Yaseen A. M. Elshaier、Waleed A. Badawi、Haridy H. Haridy、Heba A. E. Mubarak

  DOI：10.1007/s00044-019-02289-6

  日期：2019.3

  A new series of achiral pyrimidine derivatives based on nifedipine-like structure was designed and synthesized. These pyrimidyl derivatives contained hydrazine, hydrazones, acetohydrazide, differently substituted benzylidene functionalities, benzosulfohydrazine, various heterocycles such as pyrazole, pyrazolidinedione, thiazoline, and thiazolidinone rings, and fused ring systems such as triazolopyrimidine

  设计合成了一系列新的基于硝苯地平样结构的非手性嘧啶衍生物。这些嘧啶基衍生物包含肼，，乙酰肼，不同取代的亚苄基官能团，苯并磺酰肼，各种杂环如吡唑，吡唑烷二酮，噻唑啉和噻唑烷酮环，以及稠合环系统如三唑并嘧啶和嘧啶三嗪环。与硝苯地平治疗的兔子相比，化合物5a，5b，11b，8b，9b–d和15b的兔子平均动脉血压（MABP）降低了51.4至78.2 mmHg。在这些衍生物中，化合物5a，5b，9b和9c被发现对兔主动脉制剂具有钙通道阻断活性。与硝苯地平（57.6％）相比，它们的舒张范围为89.2％至74.4％，并且心率下降。化合物的组织病理学作用5a，5b中的内皮型一氧化氮合酶（eNOS）的表达也Ë xamined对大鼠主动脉。对于化合物5b，在主动脉内皮中看到了eNOS免疫染色的强烈表达，表明它通过激活主动脉中的eNOS表达降低了血压。
• Synthesis and Anti-HBV Activity of Novel Substituted Pyrimidine Glycosides and Their Acyclic Analogues
  作者：M. A. Hawata、W. A. El-Sayed、Adel A.-H. Abdel-Rahman

  DOI：10.1134/s1070363218080285

  日期：2018.8

  New aryl substituted uracil and thiouracil glycosides are synthesized by glycosylation at N1 in the pyrimidine nucleus using glycopyranosyl halides in basic medium. In addition C-linked hydrazinyl acyclic sugar derivatives exhibiting different sugar moieties, attached at C6, are also prepared. Antiviral activity of the newly synthesized compounds is studied against Hepatitis B virus (HBV). The antiviral

  新的芳基取代的尿嘧啶和硫尿嘧啶糖苷是通过在嘧啶核苷中的N 1处在碱性介质中使用吡喃葡萄糖基卤化物进行糖基化合成的。此外，还制备了在C 6处连接的具有不同糖部分的C-连接的肼基无环糖衍生物。研究了新合成化合物对乙型肝炎病毒（HBV）的抗病毒活性。抗病毒测试数据表明化合物6b，6c和12a-12c具有较高的活性，并具有轻微的细胞毒性作用。讨论了除芳基片段上的取代外，与取代的嘧啶系统相连的糖基部分对活性的影响。
• Reaction of Pyrimidinonethione Derivatives: Synthesis of N-Methyl-2-Hydrizinopyrimidine-4-One, Thiazolo[3,4-b] N-Methylpyrimidinone; 2-(1-Pyrazolonyl) N-Methylpyrimidine-4-one and 2-Hydrazino-N-Methyl Pyrimidine-4-One Derivatives
  作者：Abdullah A. Al-Karim Al-Shara'ey

  DOI：10.1002/jccs.200400082

  日期：2004.6

  reacted with hydrazine hydrate to give the sulfur free reaction products 3a-c. These reaction products were taken as the starting materials for the synthesis of several new heterocyclic derivatives. Reaction of 3a-c with acetic anhydride and formic acid gave pyrimido triazines 4a-c and 7a-c, respectively. Their reactions with active methylene containing reagents gave the corresponding 2-(1-pyrazonyl)-N-methyl

  6-Aryl-5-cyano-4-pyrimidinone-2-thion 衍生物 1a-c 与碘甲烷 (1:2) 反应生成相应的 2-S,N-二甲基嘧啶-4-one 衍生物 2a-c。化合物2a-c依次与水合肼反应，得到无硫反应产物3a-c。这些反应产物作为合成几种新型杂环衍生物的原料。3a-c 与乙酸酐和甲酸反应分别得到嘧啶基三嗪 4a-c 和 7a-c。它们与含活性亚甲基的试剂反应分别得到相应的 2-(1-吡唑)-N-甲基嘧啶衍生物 9a-c 和 10a-c。它们与芳香醛反应得到相应的 2-腙基嘧啶衍生物 11a-c。
• Synthesis and antiviral activity of new substituted pyrimidine glycosides
  作者：Mahmoud M. M. Ramiz、Wael A. El-Sayed、Ezzat Hagag、Adel A.-H. Abdel-Rahman

  DOI：10.1002/jhet.686

  日期：2011.9

  A number of N‐substituted pyrimidine glycosides were synthesized by coupling reaction of the pyrimidine base with acetobromosugars followed by deprotection. The synthesized compounds were tested for their antiviral activity against Hepatitis B Virus (HBV). Plaque reduction infectivity assay was used to determine virus count reduction as a result of treatment with tested compounds which showed moderate

  通过使嘧啶碱基与乙酰溴糖偶联反应，然后脱保护，可以合成许多N取代的嘧啶糖苷。测试合成的化合物对乙型肝炎病毒（HBV）的抗病毒活性。噬斑减少感染性测定法被用来确定由于受测试的化合物显示出中等至高的抗病毒活性而减少的病毒计数。J.杂环化​​学。（2011）。
• Reactions With Hydrazonoyl Halides 45: Synthesis of Some New Triazolino[4,3‐<i>a</i>]pyrimidines, Pyrazolo[3,4‐<i>d</i>]pyridazines, Isoxazolo[3,4‐<i>d</i>]pyridazines, and Thieno[2,3‐<i>b</i>]pyridines
  作者：Abdou O. Abdelhamid、Ali A. Al‐Atoom

  DOI：10.1080/00397910500330593

  日期：2006.2

  Abstract Triazolino[4,3‐a]pyrimidines pyrazolo[3,4‐d]pyridazines and isoxazolo[3,4‐d]pyridazines were synthesized from hydrazonoyl halides. Also, 3‐aminothieno[2,3‐b]pyridines and pyrimidino[4′,5′:4,5]thieno[2,3‐b]pyridines were synthesized from cynothioacetamide. Structures of the newly synthesized compounds were established on the basis of elemental analyses and spectral data.

  摘要 三唑并[4,3-a]嘧啶类吡唑并[3,4-d]哒嗪和异恶唑并[3,4-d]哒嗪由腙酰卤化物合成。此外，3-氨基噻吩并[2,3-b]吡啶和嘧啶并[4',5':4,5]噻吩并[2,3-b]吡啶由犬硫代乙酰胺合成。新合成化合物的结构是在元素分析和光谱数据的基础上建立的。