3,4-dihydro-2,6-dimethylmercapto-4-oxopyrimidine-5-carbonitrile | 150807-99-1

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: 3,4-dihydro-2,6-dimethylmercapto-4-oxopyrimidine-5-carbonitrile
• 英文别名: 2,4-dimethylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile；2,4-bis(methylsulfanyl)-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 150807-99-1
• 化学式: C₇H₇N₃OS₂
• 分子量: 213.284
• InChiKey: VABZIQBBIOAIOS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  13
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  116
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-dihydro-2,6-dimethylmercapto-4-oxopyrimidine-5-carbonitrile 在 三氟乙酸 硫酸 、 水 、 间氯过氧苯甲酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 3.5h， 生成 2,4-bis(4-(4-acetylpierazin-1-yl)phenylamino)-6-oxo-1,6-dihydropyrimidine-5-carboxamide
  参考文献：
  名称：

  [EN] OXYPYRIMIDINES AS SYK MODULATORS
  [FR] OXYPYRIMIDINES EN TANT QUE MODULATEURS DE SYK

  摘要：

  本发明涉及式(I)的化合物及其互变异构体或药用可接受的盐、酯和前药，其为Syk激酶的抑制剂。本发明还涉及用于制备这种化合物的中间体，该化合物的制备，含有该化合物的药物组合物，抑制Syk激酶活性的方法，抑制血小板聚集的方法，以及预防或治疗至少部分由Syk激酶活性介导的多种疾病的方法，如不良血栓形成和非霍奇金淋巴瘤。

  公开号：

  WO2012061415A1
• 作为产物：
  描述：

  3,3-双(甲硫基)-2-氰基丙烯酸乙酯 、 S-甲基异硫脲硫酸盐 在 三乙胺 作用下， 以 乙醇 为溶剂， 以80%的产率得到3,4-dihydro-2,6-dimethylmercapto-4-oxopyrimidine-5-carbonitrile
  参考文献：
  名称：

  新型杂环系统的合成：6,8-二甲基-2-(甲基硫烷基)-4-氨基取代嘧啶[4',5':3,4]吡唑并[1,5- a ]嘧啶和9,11-二甲基-5-(甲硫基)嘧啶[2',1':5,1]吡唑并[4,3- e ][1,2,4]三唑并[4,3- c ]嘧啶

  摘要：

  通过4-肼基-2,6-双(甲硫基)嘧啶-5-甲腈与乙酰丙酮的高收率环化反应合成了新型杂环嘧啶并吡唑并嘧啶体系。此外，通过 4-肼基-6,8-二甲基-2-(甲基硫烷基)嘧啶[4',5':3,4]吡唑并[1,5-a]嘧啶与原甲酸三乙酯的环化，合成了另外两个四环体系和亚硝酸钠分别得到嘧啶并吡唑并三唑并嘧啶和嘧啶并吡唑并四唑并嘧啶。

  DOI：

  10.3184/174751914x14117992793459

文献信息

• Ram, Vishnu J; Haque, Navedul; Nath, Mahendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1993, vol. 32, # 7, p. 754 - 759
  作者：Ram, Vishnu J、Haque, Navedul、Nath, Mahendra

  DOI：——

  日期：——
• Suitably functionalised pyrimidines as potential antimycotic agents
  作者：Nidhi Agarwal、Sandeep K. Raghuwanshi、D.N. Upadhyay、P.K. Shukla、Vishnu J. Ram

  DOI：10.1016/s0960-894x(00)00091-3

  日期：2000.4

  Various suitably functionalised pyrimidine derivatives have been synthesized to explore their potential as antimycotic agents. Some of the synthesized compounds 4c, 4d, 8a-e have shown highly significant in vitro antifungal activity against five human pathogenic fungi. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chloropyrimidines as a new class of antimicrobial agents
  作者：Nidhi Agarwal、Pratibha Srivastava、Sandeep K Raghuwanshi、D.N Upadhyay、Sudhir Sinha、P.K Shukla、Vishnu Ji Ram

  DOI：10.1016/s0968-0896(01)00374-1

  日期：2002.4

  In the course of our investigations of pyrimidines as antimycotic agents, we have identified a sub-class, with significant in vitro activity against mycobacteria. The salient feature of these pyrimidine derivatives (3a-o and 7a,b) is their appended aryl, heteroaryl and alkylthio substituent at position 6 and also alkylthio substituent at position 2. The rational design, synthesis, and evaluation of the in vitro antibacterial activity against six pathogenic bacteria including virulent and non-virulent strains of Mycobacterium tuberculosis is described. Some of the synthesized compounds (3c, 3h, 3i, 3o) have displayed only potent in vitro antimycobacterial activity with MIC of 0.75 mug/mL except 3i which also demonstrated activity against Escherichia coli at 12.5 mug/ mL concentration. Only two compounds, 3a and 3b, demonstrated antibacterial activity against Pseudomonas aeruginosa and E. coli with MIC 12.5 mug/mL. All the synthesized compounds were also evaluated for their antimycotic activity against five pathogenic fungi but only some of them 3j-n and 7a,b were found most potent against Aspergillus fumigatus and Trichophyton mentagrophytes. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Ram Vishnu J., Haque Navedul, Nath Mahendra, Indian J. Chem. B, 32 (1993) N 7, S 754-759
  作者：Ram Vishnu J., Haque Navedul, Nath Mahendra

  DOI：——

  日期：——
• Synthesis of Novel Heterocycle Systems: 6,8-Dimethyl-2-(Methylsulfanyl)-4-Amino-Substituted Pyrimido[4′,5′:3,4]Pyrazolo[1,5-<i>a</i>]Pyrimidine and 9,11-Dimethyl-5-(Methylsulfanyl)Pyrimido[2′,1′:5,1]Pyrazolo[4,3-<i>e</i>][1,2,4] Triazolo[4,3-<i>c</i>]Pyrimidine
  作者：Maede Hasanpour、Hossein Eshghi、Mehdi Bakavoli、Mozhdeh Yusefi

  DOI：10.3184/174751914x14117992793459

  日期：2014.11

  The novel heterocyclic pyrimidopyrazolopyrimidine system was synthesised through cyclisation of 4-hydrazinyl-2,6-bis(methylthio)pyrimidine-5-carbonitrile with acetylacetone in high yield. Also, two other tetracyclic systems were synthesised through cyclisation of 4-hydrazinyl-6,8-dimethyl-2-(methylsulfanyl)pyrimido[4′,5′:3,4]pyrazolo[1,5-a]pyrimidine with triethyl orthoformate and sodium nitrite to

  通过4-肼基-2,6-双(甲硫基)嘧啶-5-甲腈与乙酰丙酮的高收率环化反应合成了新型杂环嘧啶并吡唑并嘧啶体系。此外，通过 4-肼基-6,8-二甲基-2-(甲基硫烷基)嘧啶[4',5':3,4]吡唑并[1,5-a]嘧啶与原甲酸三乙酯的环化，合成了另外两个四环体系和亚硝酸钠分别得到嘧啶并吡唑并三唑并嘧啶和嘧啶并吡唑并四唑并嘧啶。