ethyl [(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thio]acetate | 126277-92-7

• 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: ethyl [(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thio]acetate
• 英文别名: ethyl 2-[(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thio]acetate；Ethyl [(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)sulfanyl]acetate；ethyl 2-[(5-cyano-6-oxo-4-phenyl-1H-pyrimidin-2-yl)sulfanyl]acetate
• CAS: 126277-92-7
• 化学式: C₁₅H₁₃N₃O₃S
• mdl: MFCD01239305
• 分子量: 315.353
• InChiKey: XXDPYJIHUCJSEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  117
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl [(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thio]acetate 在 氨 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以70%的产率得到2-(5-Cyano-6-oxo-4-phenyl-1,6-dihydro-pyrimidin-2-ylsulfanyl)-acetamide
  参考文献：
  名称：

  Khalil, Zarif Hallem; Hafez, Ali Ahmed Abdel; Ahmed, Ahmed Abdo, Phosphorus, Sulfur and Silicon and the Related Elements, 1989, vol. 45, p. 81 - 94

  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 ethyl [(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thio]acetate
  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

• Synthesis of Some New Pyrimidine and Pyrimido[4,5-d]pyrimidine Derivatives
  作者：Ahmed A. Fadda、Ehab Abd El-Latif、Samir Bondock、Ahmed Samir

  DOI：10.1080/00397910802326596

  日期：2008.11.13

  Abstract A convenient synthesis of a series of pyrimidine carbonitrile, thiopyrimidine, and pyrimidopyrimidine derivatives, via the reactions of the versatile, readily accessible 6-aryl-4-oxo-2-thioxo-hexahydro-pyrimidine-5-carbonitrile with the appropriate reagents, is described.

  摘要 通过通用的、易于获得的 6-aryl-4-oxo-2-thioxo-hexahydro-pyrimidine-5-carbonitrile 与适当的试剂反应，方便地合成一系列嘧啶腈、硫代嘧啶和嘧啶并嘧啶衍生物，被描述。
• Facile synthesis of novel carbothioylbis[1,2,4]triazolo [4,3-<i>a</i>]pyrimidine and carbothioylbispyrimido[2,1-<i>c</i>] [1,2,4]triazine derivatives
  作者：Kamelia M. El-Mahdy

  DOI：10.1080/17415993.2013.765431

  日期：2013.10.1

  6-dihydropyrimidin-2-yl)thio]acetate with thiocarbohydrazide. Condensation of pyrimidinyl thiocarbohydrazide with carbon disulfide gave carbothioylbis[1,2,4]triazolo[4,3-a]pyrimidine. Several new heterocycles namely carbothioylbispyrimido[2,1-c][1,2,4]triazine derivatives have been synthesized by the reactions of pyrimidinyl thiocarbohydrazide with 1,2-dibromoethane, chloroacetyl chloride and diethyl oxalate.

  迄今为止尚未报道的多功能多功能 N',N"-bis(5-cyano-6-oxo-4-phenyl-1,6-dihydropyrimidin-2-yl)thiocarbohydrazide 是通过乙基 [(5-cyano -6-oxo-4-phenyl-1, 6-dihydropyrimidin-2-yl)thio]acetate 与硫代碳酰肼。嘧啶基硫代碳酰肼与二硫化碳缩合得到硫代碳酰双[1,2,4]三唑并[4,3-a]嘧啶。通过嘧啶基硫代碳酰肼与 1,2-二溴乙烷、氯乙酰氯和草酸二乙酯的反应合成了几种新的杂环，即硫代双嘧啶并 [2,1-c][1,2,4] 三嗪衍生物。讨论了形成新合成化合物的机制方面。
• Discovery of Thiopyrimidinone Derivatives as a New Class of Human Aldose Reductase Inhibitors
  作者：Ilária Lins、Larissa Maciel、Janaína dos Anjos

  DOI：10.21577/0103-5053.20220027

  日期：——

  aldose reductase (AR) inhibitors. In this work, we synthesized and tested new candidates for human AR inhibition containing a 2-thiopyrimidin-4-one heterocycle as a central ring. The fifteen derivatives were tested in vitro and their binding modes were evaluated via molecular docking simulations. AR inhibition assays showed that all synthesized compounds were able to inhibit the AR enzyme at 50 μM

  糖尿病是一种慢性代谢性疾病，其特点是胰岛素产生不足、细胞无法利用胰岛素或两者的组合，从而导致糖尿病神经病变和视网膜病变等继发并发症。预防或控制这些并发症的一种方法是使用醛固酮还原酶（AR）抑制剂。在这项工作中，我们合成并测试了新的人类AR抑制剂候选物，其中包含2-硫代嘧啶-4-酮杂环作为中心环。这十五个衍生物在体外进行了测试，通过分子对接模拟评估了它们的结合模式。AR抑制试验表明，所有合成的化合物均能在50μM时抑制AR酶。从这些结果中，有七个化合物值得注意，它们的半最大抑制浓度（IC50）值被估计为2.0至14.5μM。分子对接模拟显示这些化合物特异地结合于催化亚口袋，结果表明体外和体内研究之间存在良好的关联。
• Design, synthesis and biological evaluation of nitric oxide-releasing 5-cyano-6-phenyl-2, 4-disubstituted pyrimidine derivatives
  作者：Lingling Chi、Hao Wang、Fuqiang Yu、Chao Gao、Honglin Dai、Xiaojie Si、Yuze Dong、Hongmin Liu、Qiurong Zhang

  DOI：10.1016/j.bmcl.2023.129389

  日期：2023.8

  In this study, a series of nitric oxide (NO) -releasing 5-cyano-6-phenyl-2, 4-disubstituted pyrimidine derivatives were designed and synthesized. In the in vitro biological evaluation, compound 24l exhibited optimal antiproliferative activity against MGC-803 cells with the IC50 value of 0.95 µM, significantly better than that of the positive control 5-FU. In addition, preliminary mechanistic studies

  本研究设计并合成了一系列释放一氧化氮（NO）的5-氰基-6-苯基-2,4-二取代嘧啶衍生物。体外生物学评价中，化合物24l对MGC-803细胞表现出最佳的抗增殖活性，IC 50值为0.95 μM，明显优于阳性对照5-FU。此外，初步机制研究表明24l抑制集落形成并阻断MGC-803细胞处于G0/G1期。DAPI染色、活性氧和细胞凋亡测定表明24l诱导MGC-803细胞凋亡。特别是，最有效的化合物24l产生最高水平的NO，并且与NO清除剂预孵育后，抗增殖活性显着降低。总之，化合物24l可被认为是潜在的候选抗肿瘤剂。
• KHALII, ZARIF HALLEM;HAFEZ, ALI AHMED ABDEL;AHMED, AHMED ABDO, PHOSPH. SULFUR AND SILICON AND RELAT. ELEM., 45,(1989) N-2, C. 81-93
  作者：KHALII, ZARIF HALLEM、HAFEZ, ALI AHMED ABDEL、AHMED, AHMED ABDO

  DOI：——

  日期：——