6-amino-4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile | 1435939-77-7

• 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: 6-amino-4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile
• 英文别名: 6-amino-4-(4-chlorophenyl)-2-sulfanylidene-3,4-dihydro-1H-pyrimidine-5-carbonitrile
• CAS: 1435939-77-7
• 化学式: C₁₁H₉ClN₄S
• 分子量: 264.738
• InChiKey: IYFTZFCLMNHJML-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-amino-4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 在 三乙胺 作用下， 以 乙醇 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 8-amino-10-(4-chlorophenyl)-4-methyl-2-(4-methylpiperidin-1-yl)-5H,10H-dipyrimido[2,1-b:4',5'-d][1,3]thiazine-9-carbonitrile
  参考文献：
  名称：

  新的 5H,10H-dipyrimido[2,1-b:4',5'-d][1,3]thiazine 的区域选择性合成：结合实验和计算研究

  摘要：

  摘要 通过 2,4-二氯-5-() 分子间和分子内杂环化合成了新型三环系统 'dipyrimido[2,1-b:4',5'-d][1,3]thiazine' 的几种衍生物。氯甲基)-6-甲基嘧啶和 6-氨基-4-芳基-2-硫代-1,2,3,4-四氢嘧啶-5-甲腈在温和条件下的短反应时间内。进行了 X 射线分析和计算计算，以深入了解反应的区域选择性。图形概要

  DOI：

  10.1080/17415993.2019.1576685
• 作为产物：
  描述：

  4-氯苄亚基丙二腈 、 硫脲 在 sodium methylate 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以10%的产率得到4-amino-6-(4-chlorophenyl)-2-mercaptopyrimidine-5-carbonitrile
  参考文献：
  名称：

  Tacripyrimidines，第一个他克林-二氢嘧啶杂化物，作为阿尔茨海默氏病的多靶标定向配体

  摘要：

  尽管在多靶点治疗方法中胆碱酯酶（ChE）抑制和钙通道阻滞相结合被认为对对抗阿尔茨海默氏病（AD）具有潜在的益处，但几乎没有研究这种策略。为了探索这一有前途的路线，一系列的5-氨基-4-芳基-3,4,6,7,8,9-六氢嘧啶基[4,5-b]喹啉-2（1 H）-硫酮（tacripyrimidines）（通过并置他克林，一种ChE抑制剂（ChEI）和3,4-二氢嘧啶-2（1 H）-硫酮设计了4a - 1）作为有效的钙通道阻滞剂（CCBs）。根据其设计，所有tacripyrimidines，未取代的母体化合物及其p-甲氧基衍生物，起中等至强效CCB的作用，其活性通常与参考CCB药物尼莫地平相似或更高，并且是中等至良好的ChEI。最有趣的是，3'-甲氧基衍生物（4e）作为第一种平衡良好的ChEI / CCB试剂出现，起低微摩尔hChEI（分别在hAChE和hBuChE上分别为3.05μM和3.19μM）和中等CCB（1μM时为30

  DOI：

  10.1016/j.ejmech.2018.06.044

文献信息

• Synthesis and evaluation of cytotoxicity of 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles
  作者：Hoda Atapour-Mashhad、Mohammad Soukhtanloo、Abdolhossien Massoudi、Ali Shiri、Mehdi Bakavoli

  DOI：10.1134/s1068162016020047

  日期：2016.5

  and human colon carcinoma (HT29) cell lines. Malignant and non-malignant cells were cultivated in RPMI medium and incubated with different concentrations of these pyrimidines. Cell viability was evaluated by MTT assay. Apoptotic cells were determined using DAPI (4'-6-diamidino-2-phenylindole) and propidium iodide staining of DNA fragmentation by flow cytometry (sub-G1 peak). 6-Amino-4-(4-chlorophenyl)-2-thioxo-1

  通过 Biginelli 型反应合成了 6-amino-4-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles 的几种衍生物，并测试了它们对人乳腺癌 (MCF-7) 的抗增殖活性) 和人结肠癌 (HT29) 细胞系。恶性和非恶性细胞在 RPMI 培养基中培养，并与不同浓度的这些嘧啶一起培养。通过MTT测定评估细胞活力。使用 DAPI（4'-6-二脒基-2-苯基吲哚）和通过流式细胞术（亚 G1 峰）对 DNA 片段化的碘化丙啶染色确定凋亡细胞。6-氨基-4-(4-氯苯基)-2-硫代-1,2,3,4-四氢嘧啶-5-甲腈和6-氨基-4-[4-二甲氨基)苯基]-2-硫代-1，与 L929 细胞相比，2,3,4-四氢嘧啶-5-腈降低 MCF-7 和 HT29 细胞的活力。
• An Efficient One-Pot Synthesis of New 2- Thioxo and 2-oxo-pyrimidine-5-carbonitriles in Ball-Milling Under Solvent-Free and Catalyst-Free Conditions
  作者：Mohamed Ould M’hamed、Omar K. Alduaij

  DOI：10.1080/10426507.2013.818995

  日期：2014.1.1

  Various 2-thioxo and 2-oxo-1,2,3,4-tetrahydro-pyrimidine-5-carbonitriles were synthesized in very high yields in 40min through a direct condensation of an equimolar amount of an aldehyde, malononitrile, and thiourea/urea under ball mill solvent-free and catalyst-free conditions.
• Synthesis and antimicrobial evaluation of novel substituted pyrimidine scaffold
  作者：Hardik B. Ghodasara、Amit R. Trivedi、Vipul B. Kataria、Bharat G. Patel、Viresh H. Shah

  DOI：10.1007/s00044-013-0596-2

  日期：2013.12

  Synthesis and biological evaluation of substituted pyrimidine derivatives containing 4-amino and 5-cyano substituted derivatives are described. Biginelli typed three component reactions between an aldehyde, malononitrile, and a urea constituent give a rapid facile pyrimidine ring. The constitution of the products has been delineated by elemental analysis and spectral analysis. The products were assayed for their in vitro biological assay antibacterial activity against S. pyogenes MTCC-442, S. aureus MTCC-96, E. coli MTCC-443, and B. subtilis MTCC-441 bacterial strain and antifungal activity against Aspergillus niger MTCC-282 and Candida albicans MTCC-227 at different concentrations, which compared with Ampicillin, Chloramphenicol, Ciprofloxacin, Norfloxacin, and Griseofulvin as standard drug which are presented.
• Synthesis and Antitumor Evaluation of Novel Dihydropyrimidine, Thiazolo[3,2-a]Pyrimidine and Pyrano[2,3-d]Pyrimidine Derivatives
  作者：Nadia Y. Megally Abdo

  DOI：10.17344/acsi.2014.867

  日期：2015.3.15

  A simple and efficient method has been developed for the synthesis of 4,5-dihydro-2-mercapto-4-oxo-6-substituted arylpyrimidine derivatives (2a-e) and their fused rings (3b, 4b, 5b & 6b) and also 1,4-dihydro-2-mercaptopyrimidine derivatives (7a-e) & (9a-e) using triethylamine as a catalyst. The structure of the newly synthesized compounds was confirmed on the basis of their spectral data and elemental analysis. All the synthesized compounds were evaluated for their in vitro anticancer activity against six human cancer cell lines and normal fibroblasts. Thirteen of the tested compounds: 2a-e, 3b, 4b, 5b, 7d, 8, 9a, 9c and 9d exhibited significant cytotoxicity against most cell lines. Among these derivatives compounds 2a, 3b and 9c are the most potent, they exhibited cytotoxic effect against the six cancer cell lines with IC(50) values < 330 nM compared to the standard CHS 828. Normal fibroblast cells (WI38) were affected to a much lesser extent (IC(50) >10,000 nM).