5-嘧啶甲腈,6-(3-氟苯基)-1,2,3,4-四氢-4-羰基-2-硫代- | 128640-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 5-嘧啶甲腈,6-(3-氟苯基)-1,2,3,4-四氢-4-羰基-2-硫代-
• 英文名称: 5-cyano-6-(3-fluorophenyl)-2-thiouracil
• 英文别名: 6-(3-fluorophenyl)-5-cyano-2-thiouracil；6-(3-fluorophenyl)-4-oxo-2-sulfanylidene-1,2,3,4-tetrahydropyrimidine-5-carbonitrile；6-(3-fluorophenyl)-4-oxo-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
• CAS: 128640-95-9
• 化学式: C₁₁H₆FN₃OS
• mdl: MFCD07157491
• 分子量: 247.253
• InChiKey: FLPRABDVIVWYFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  97
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-嘧啶甲腈,6-(3-氟苯基)-1,2,3,4-四氢-4-羰基-2-硫代- 在 sodium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 5-carbonitrile-4-chloro-6-(3-fluorophenyl)-2-(methylthio)pyrimidine
  参考文献：
  名称：

  Suitably functionalised pyrimidines as potential antimycotic agents

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(00)00091-3
• 作为产物：
  描述：

  硫脲 、 丙腈 、 3-氟苯甲醛 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 生成 5-嘧啶甲腈,6-(3-氟苯基)-1,2,3,4-四氢-4-羰基-2-硫代-
  参考文献：
  名称：

  丹皮酚二氢嘧啶酮类衍生物及其制备方法和应用

  摘要：

  本发明公开了一种丹皮酚二氢嘧啶酮类衍生物及其制备方法和应用，制备方法包括如下步骤：将丹皮酚与端基二溴烷烃化合物，在有机溶剂和缚酸剂下进行经亲核取代反应，生成溴代丹皮酚；将芳香醛、氰乙酸乙酯与硫脲，在有机溶剂和催化剂下通过环合反应，合成6‑取代苯基‑5‑氰基‑2‑硫代脲嘧啶；最后将溴代丹皮酚与合成的6‑取代苯基‑5‑氰基‑2‑硫代脲嘧啶，在有机溶剂和缚酸剂下通过亲核取代，合成丹皮酚二氢嘧啶酮类衍生物。本发明提供了一类新的丹皮酚二氢嘧啶酮类衍生物，其制备周期短，操作简单，成本低，且得到的衍生物纯度高，质量稳定；申请人还发现，通过在丹皮酚骨架上引入功能性基团二氢嘧啶酮可以改善化合物的抗肿瘤活性，有进一步的研究意义。

  公开号：

  CN110437156B

文献信息

• Design, Synthesis and Antibacterial Activity of Novel Pyrimidine‐Containing 4 <i>H</i> ‐Chromen‐4‐One Derivatives**
  作者：Shijun Su、Mei Chen、Xuemei Tang、Feng Peng、Tingting Liu、Qing Zhou、Wenliang Zhan、Ming He、Chengwei Xie、Wei Xue

  DOI：10.1002/cbdv.202100186

  日期：2021.8

  6-dihydropyrimidine-5-carbonitrile (4h) showed the best antibacterial activity against R. solanacearum with an EC50 value of 14.7 μg/mL. These results were better than commercial reagents bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL, respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative

  通过结合生物活性亚结构，设计并合成了一系列含嘧啶的 4 H -chromen-4-one 衍生物。初步生物活性结果表明，大多数化合物在体外对轴突黄单胞菌有显着的抑制活性。红蜘蛛（X. axonopodis），白叶枯病。oryzae ( X. oryzae ) 和Ralstonia solanacearum ( R. solanacearum )。特别是，化合物2 - [（3 - [5,7-二甲氧基-4-氧代-2-（3,4,5-三甲氧基苯基）-4- ħ -1-苯并吡喃-3-基]氧基}丙基）硫基]-4-(4-甲基苯基)-6-oxo-1,6-dihydropyrimidine-5-carbonitrile ( 4c) 显示出对X. axonopodis和X. oryzae的良好抑制作用，半数最大有效浓度 (EC 50 ) 值分别为 15.5 和 14.9 μg/mL，化合物 2-[(3-[5
• Chemotherapeutic Agents, XVIII: Synthesis of π-Deficient Pyrimidines and Fused Pyrimidines as Leishmanicidal Agents
  作者：Vishnu J. Ram

  DOI：10.1002/ardp.19903231103

  日期：——

  1a–d from the condensation‐cyclization of an aromatic aldehyde, thiourea and ethyl cyanoacetate has been described. Alkylation of 1a–d under different reaction conditions with mono‐and dihalo‐alkanes yielded 2, 3, and 6. Interaction of 1 with POCl3 provided halopyrimidines 8a, b. Nucleophilic substitution on 8 and 3 with aromatic amines gave 9a–d and 7a–d respectively. 6‐Chloro‐5‐nitro‐3‐methyluracil

  6-芳基-5-氰基-2-硫尿嘧啶1a-d的合成已经描述了从芳香醛、硫脲和氰基乙酸乙酯的缩合-环化。1a-d 在不同反应条件下与单卤代烷烃和二卤代烷烃烷基化产生 2、3 和 6。1 与 POCl3 的相互作用提供卤代嘧啶 8a、b。用芳香胺对 8 和 3 进行亲核取代分别得到 9a-d 和 7a-d。6 - 氯 - 5 - 硝基 - 3 - 甲基尿嘧啶 (11) 通过硝化 10 与胺进行亲核取代，提供 12。一些被筛选为利什曼原虫的化合物没有表现出任何显着的活性。
• Efficient synthesis and evaluation of antiviral and antitumor activity of novel 3-phosphonylated thiazolo[3,2-a]oxopyrimidines
  作者：Anastasia A. Babushkina、Albina V. Dogadina、Dmitrij M. Egorov、Julia L. Piterskaia、Anna A. Shtro、Yulia V. Nikolaeva、Anastasia V. Galochkina、Anton A. Kornev、Vitali M. Boitsov

  DOI：10.1007/s00044-021-02801-x

  日期：2021.12

  A series of 3-phosphonylated thiazolo[3,2-a]oxopyrimidines 3a-k was synthesized for the first time by the reactions of chloroethynylphosphonates with 5,6-disubstituted 2-thiouracils. In vitro antiviral activities have shown that the compounds 1i, 1j, 3b and 3e were shown activity against influenza A virus. In vitro antitumor activity was conducted for all compounds against human erythroleukemia (K562)

  通过氯乙炔基膦酸酯与5,6-二取代2-硫尿嘧啶的反应，首次合成了一系列3-膦酰化噻唑并[3,2- a ]氧代嘧啶3a-k。体外抗病毒活性表明化合物1i、1j、3b和3e显示出抗甲型流感病毒的活性。通过 MTS 测定对所有化合物对人红白血病 (K562) 和宫颈癌 (HeLa) 细胞系进行体外抗肿瘤活性。在靶向化合物3c 中，3h和3j对人红白血病 (K562) 细胞系具有活性，而3c和3j对宫颈癌 (HeLa) 细胞系有活性。发现用化合物3c和3j处理后的 HeLa 细胞显着减少了具有应力纤维和丝状伪足样膜突起的细胞数量。得出的结论是，靶向化合物具有抑制细胞生长的作用，这可能导致肌动蛋白丝的形成减少以及丝状伪足样膜突起的数量减少。
• 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.
• Upadhyay; Agarwal, Nidhi; Goel, Atul, Journal of Chemical Research - Part S, 2003, # 6, p. 380 - 382
  作者：Upadhyay、Agarwal, Nidhi、Goel, Atul、Ram, Vishnu Ji.

  DOI：——

  日期：——