ethyl 4-(3,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate | 5675-97-8

• 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 4-(3,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
• 英文别名: 4-(3,4-dichlorophenyl)-5-ethoxycarbonyl-6-methyl-3,4-dihydropyrimidine-2(1H)-thione；ethyl 4-(3,4-dichlorophenyl)-6-methyl-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carboxylate
• CAS: 5675-97-8
• 化学式: C₁₄H₁₄Cl₂N₂O₂S
• 分子量: 345.249
• InChiKey: OXMVMGGZCWEAGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  82.4
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 4-(3,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 在 sodium hydride 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 1,4-二氧六环 为溶剂， 反应 8.0h， 生成 C₂₈H₂₂Cl₄N₄O₄S₂
  参考文献：
  名称：

  用CF3SO2Na进行二杂芳基二硫化物的紫外光辐射三氟甲基化

  摘要：

  用CF 3 SO 2 Na对二杂芳基二硫化物进行三氟甲基化，得到三氟甲基硫醚衍生物。该转化具有良好的官能团相容性，无需外部光催化剂，在温和的条件下以中等至良好的产率生成了相应的产物，并且在构建两个S-CF 3键的同时充分利用了二硫键。

  DOI：

  10.1002/ejoc.201801565
• 作为产物：
  描述：

  乙酰乙酸乙酯 、 硫脲 、 3,4-二氯苯甲醛 在 碘 作用下， 反应 0.33h， 以92%的产率得到ethyl 4-(3,4-dichlorophenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate
  参考文献：
  名称：

  在无溶剂条件下通过 Biginelli 反应微波辅助和碘催化合成二氢嘧啶-2-硫酮

  摘要：

  摘要 在无溶剂条件下，在碘存在下，醛、乙酰乙酸酯和硫脲通过 Biginelli 反应合成 3,4-二氢嘧啶-2-硫酮，以良好的收率和纯度完成，无需色谱分离。图形概要

  DOI：

  10.1080/00397911.2011.593289

文献信息

• Metal- and Oxidant-Free Electrochemical Oxidative Desulfurization C–O Coupling of Thiourea-Type Compounds with Alcohols
  作者：Zheng-Jun Quan、Xi-Cun Wang、Zheng-He Zhu、Ming-Zhe Ren、Bao-Qian Cao

  DOI：10.1055/s-0039-1690837

  日期：2020.6

  An efficient desulfurization C–O coupling reaction of 3,4-dihydropyrimidine-2(1H)-thiones (including thioureas) with alcohols was developed under electrochemical oxidation conditions. Herein, transition­-metal catalysts and additives are not required and the alcohol is both the solvent and the alkoxy donor.

  一种高效的脱硫C-O偶联反应是在电化学氧化条件下开发的，该反应使用3,4-二氢嘧啶-2(1H)-硫酮（包括硫脲）与醇的反应。在这种反应中，不需要过渡金属催化剂和添加剂，醇既是溶剂又是烷氧基供体。
• Use of derivatives of 3-oxo-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine or of 3-oxo-2,3-dihydro-5H-imidazolo[3,2-a]pyrimidine for the preparation of pharmaceutical compositions intended for the treatment of cancer
  申请人：INSTITUT NATIONAL DE LA SANTE ET DE LA RECHERCHE MEDICALE (INSERM)

  公开号：EP2000140A1

  公开（公告）日：2008-12-10

  The present invention is related to the use of a compound of formula (I) for the preparation of a pharmaceutical composition intended for the treatment of cancer and in particular for the treatment of the prostate cancer, hepatocarcinomas, head and neck cancer, oesophagus cancer, thyroid gland cancer or non-hodgkinian lymphomas and some new compounds and pharmaceutical compositions containing them.

  本发明涉及使用式（I）的化合物制备用于治疗癌症的药物组合物，特别是用于治疗前列腺癌、肝癌、头颈癌、食管癌、甲状腺癌或非霍奇金淋巴瘤的药物组合物，以及一些新的化合物和含有它们的药物组合物。
• Synthesis, characterization and in silico designing of diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimidine-5-carboxamido) thiophene-2,4-dicarboxylate derivative as anti-proliferative and anti-microbial agents
  作者：Kalpesh Malani、Sampark S. Thakkar、Mukund Chandra Thakur、Arabinda Ray、Hiren Doshi

  DOI：10.1016/j.bioorg.2016.09.001

  日期：2016.10

  A series of eight compounds diethyl-3-methyl-5-(6-methyl-2-thioxo-4-phenyl-1,2,3,4-tetrahydropyrimi dine-5-carboxamido) thiophene-2,4-dicarboxilate (KM10-17) analogues have been prepared by conventional methods and characterized by IR, Mass, NMR and elemental analysis. In silico docking studies on Human topoisomerase IIbeta (PDB Id: 3QX3) have been performed for all molecules (KM10-17) synthesized. The compounds were tested for in vitro anti-proliferative activity on VERO and 786-O cell lines. Out of all the synthesized compounds, KM11 & KM16 showed moderate activity on both cell lines. In vitro anti-microbial activity was also checked against Bacillus subtilis (BS), Staphylococcus aurous (SA), Pseudomonas aeruginosa (PA), Escherichia coli (EC) and Candida albicans (CA) by well diffusion method. The compound KM11 was found to have highest zone of inhibition against BS, SA, PA and EC. The molecules KM13 and KM16 exhibited good activity against CA. The compounds KM14 and KM16 indicated good zone of inhibition against BS. (C) 2016 Elsevier Inc. All rights reserved.
• Synthesis and pharmacological study of new 3,4-dihydro-2H,6H-pyrimido-[2,1-b][1,3]thiazines
  作者：D Bózsing、P Sohár、G Gigler、G Kovács

  DOI：10.1016/0223-5234(96)85874-0

  日期：1996.1

  A series of racemic pyrimido-thiazine derivatives was synthesized and many of their in vivo activities found to be comparable to acetylsalicylic acid and aminophenazone in an antiinflammatory model and an antipyretic test. Analogues 7a and 7e are the most potent in rat carrageenin and yeast fever assays. These compounds did not inhibit prostaglandin biosynthesis in vitro.
• SYNTHESIS AND RADIATION STABILITY OF NOVEL THIAZOLOPYRIMIDINES WITH EXPECTED ANTIFUNGAL ACTIVITY
  作者：M. M. Ghorab、Y. A. Mohamed、S. A. Mohamed、Y. A. Ammar

  DOI：10.1080/10426509608029657

  日期：1996.1.1

  A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4'-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and me structures are stable.