1-methyl-2-(methylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile | 95534-78-4

• 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: 1-methyl-2-(methylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
• 英文别名: 5-cyano-3-N-methyl-2-methylthio-6-phenyl-3,4-dihydropyrimidin-4-one；6-phenyl-5-cyano-2-methylthio-3-N-methyl-3,4-dihydropyrimidin-4-one；6-phenyl-5-cyano-2-thiomethyl-3-N-methyl-3,4-dihydropyrimidin-4-one；5-cyano-1-methyl-2-methylthio-4-phenyl-6-oxopyrimidine；1-Methyl-2-(methylsulfanyl)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile；1-methyl-2-methylsulfanyl-6-oxo-4-phenylpyrimidine-5-carbonitrile
• CAS: 95534-78-4
• 化学式: C₁₃H₁₁N₃OS
• mdl: MFCD00446616
• 分子量: 257.316
• InChiKey: PFPMIKYWOXSUFN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  81.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-methyl-2-(methylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 11.0h， 生成 6-Cyano-8-methyl-5-phenyl-1,2,4-triazolo<4,3-a>pyrimidin-7-one
  参考文献：
  名称：

  嘧啶酮硫酮衍生物的反应：N-Methyl-2-Hydrizinopyrimidine-4-One、噻唑并[3,4-b] N-甲基嘧啶酮的合成；2-(1-吡唑啉) N-Methylpyrimidine-4-one 和 2-Hydrazino-N-Methyl Pyrimidine-4-One 衍生物

  摘要：

  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。

  DOI：

  10.1002/jccs.200400082
• 作为产物：
  描述：

  苯甲醛 在 sodium hydroxide 、 sodium acetate 作用下， 以 乙醇 为溶剂， 反应 7.0h， 生成 1-methyl-2-(methylthio)-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitrile
  参考文献：
  名称：

  Hussain, S. M.; El-Barbary, A. A.; Mansour, S. A., Journal of Heterocyclic Chemistry, 1985, vol. 22, p. 169 - 171

  摘要：

  DOI：

文献信息

• Synthesis, biological evaluation and molecular docking studies of some pyrimidine derivatives
  作者：Ahmed M. Fargualy、Nargues S. Habib、Khadiga A. Ismail、Ahmed M.M. Hassan、Marwa T.M. Sarg

  DOI：10.1016/j.ejmech.2013.05.028

  日期：2013.8

  Some novel pyrimidine-5-carbonitrile derivatives bearing various substituent have been synthesized. The structures of target compounds were confirmed by elemental analysis and spectral data. Some selected members of the newly synthesized compounds were investigated for their cytotoxic potency against certain human tumor cell lines. Five representative active anticancer compounds 6a, 6c, 6d, 17a and

  已经合成了一些带有各种取代基的新颖的嘧啶-5-腈衍生物。通过元素分析和光谱数据确认了目标化合物的结构。研究了新合成化合物的某些选定成员对某些人类肿瘤细胞系的细胞毒性。使用MOE程序，对两种酶的3D结构，对五个代表性的活性抗癌化合物6a，6c，6d，17a和18a进行对接。胸苷酸合酶和二氢叶酸还原酶。测试了合成化合物对金黄色葡萄球菌，铜绿假单胞菌的抗菌活性。，志贺志贺菌和白色念珠菌。化合物2c，7a和9c显示了广谱抗菌活性。
• 5-Cyano-6-aryluracil and 2-thiouracil derivatives as potential chemotherapeutic agents. IV
  作者：Vishnu J. Ram、D. A. Vanden Berghe、A. J. Vlietinck

  DOI：10.1002/jhet.5570210513

  日期：1984.9

  2-(pyrazol-1-yl)-3-methyl-4-oxo-5-cyano-6-substituted pyrimidines 10, and 11. Some of the compounds were screened for antibacterial-, antifungal- and antiviral activities and a few of them showed significant chemotherapeutical activities.

  已经制备了一系列5-氰基-6-芳基尿嘧啶和2-硫尿嘧啶1a-h ，并且通过用卤代烷进行亲电取代，将其烷基化为1，3-二烷基尿嘧啶2a-d和2-烷基硫尿嘧啶3、4和6。1b与二溴乙烷和1,3-二溴丙烷反应生成相应的双环产物7-芳基-6-氰基-2,3-二氢噻唑[3,2 - a ]嘧啶-5-酮5a，b和8-芳基- 7-氰基-3,4-二氢-2 H-嘧啶基[2,3- b ] [1,3]噻嗪-6-酮5c-g。用肼在6上进行亲核取代导致7将其用甲酸中回流，得到5-芳基-6-氰基-8-甲基小号-三唑并[3,4- b ]嘧啶-7-酮（9），同时用乙酸和丙酸只2- acylhydrazino -3-分离出-甲基-4-氧代-5-氰基-6-芳基嘧啶8a，b。肼7与乙酰丙酮和甲基二甲基巯基丙烯酸酯进行环化，从而提供2-（吡唑-1-基）-3-甲基-4-氧代-5-氰基-6-取代的嘧啶10和11。筛选了一些化合物的抗细菌
• Synthesis of some dihydropyrimidine-based compounds bearing pyrazoline moiety and evaluation of their antiproliferative activity
  作者：Fadi M. Awadallah、Gary A. Piazza、Bernard D. Gary、Adam B. Keeton、Joshua C. Canzoneri

  DOI：10.1016/j.ejmech.2013.10.003

  日期：2013.12

  Two series of 2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-4-phenyl-1,6-dihydropyrimidine-5-carbonitriles 5a-h and 4-(4-chlorophenyl)-2-(3,5-diaryl-4,5-dihydropyrazol-1-yl)-1-methyl-6-oxo-1,6-dihydropyrimidine-5-carbonitriles 6a-h were synthesized via a cydocondensation reaction of the corresponding 2-hydrazinopyrimidines 3a,b with the appropriate 2-propen-1-ones 4a h. The target compounds were screened for their antiproliferative activity against A 549 (lung), HT 29 (colon), MCF 7 and MDA-MB 231 (breast) cell lines. The two most susceptible cell lines were the colon (HT 29) and breast (MDA-MB 231). Generally, the 4-unsubstitutedphenylpyrimidine derivatives 5a h were more active than their 4-chlorophenylpyrimidine analogs 6a h. Compounds 5e and 5g, showed high activity against three of the cell lines. The most active compound 5c possessed IC50 = 1.76 mu M against A 549 cell line. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Basavaraja; Padmashali, Basavaraj; Vijaykumar, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 237 - 240
  作者：Basavaraja、Padmashali, Basavaraj、Vijaykumar、Hussain, Mumtaz M.、Chidananda

  DOI：——

  日期：——
• Basavaraja; Padmashali, Basavaraj; Bhat, K. Ishwar, Indian Journal of Heterocyclic Chemistry, 2011, vol. 20, # 3, p. 241 - 244
  作者：Basavaraja、Padmashali, Basavaraj、Bhat, K. Ishwar、Hussain, Mumtaz M.、Vijaykumar

  DOI：——

  日期：——