2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-thione | 1354958-08-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-thione
• 英文别名: 2-Methylsulfanyl-1,2,4-triazolo[1,5-a]quinazoline-5(4H)-thione；2-methylsulfanyl-1H-[1,2,4]triazolo[1,5-a]quinazoline-5-thione
• CAS: 1354958-08-9
• 化学式: C₁₀H₈N₄S₂
• 分子量: 248.332
• InChiKey: SEJHXXGRAKWEQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  97.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-肼基苯甲酸盐酸盐 在 吡啶 、 盐酸 、 tetraphosphorus decasulfide 、 三乙胺 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-thione
  参考文献：
  名称：

  Synthesis of Novel 2-Methylsulfanyl-4H-[1,2,4]triazolo[1,5-a]quinazolin-5-one and Derivatives

  摘要：

  A novel 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a] quinazolin-5-one was synthesized using dimethyl-n-cyanoimidodithiocarbonate and 2-hydrazinobenzoic acid as building blocks. Chemical transformation of the inherent lactam moiety in the targeted 2-methylsulfanyl-[1,2,4]triazolo[1,5-a] quinazolin-5-one offered access to a variety of derivatives.

  DOI：

  10.1080/00397911.2010.518780

文献信息

• Cytotoxicity and Anti-Inflammatory Activity of Methylsulfanyl-triazoloquinazolines
  作者：Rashad Al-Salahi、Amira Gamal-Eldeen、Amer Alanazi、Mohamed Al-Omar、Mohamed Marzouk、Moustafa Fouda

  DOI：10.3390/molecules18021434

  日期：——

  A series of twenty five 2-methylsulfanyl-[1,2,4]triazolo[1,5-a]quinazoline derivatives 1–25 was previously synthesized. We have now investigated their cytotoxic effects against hepatocellular Hep-G2 and colon HCT-116 carcinoma cells and effect on the macrophage growth, in addition to their influence of the inflammatory mediators [nitric oxide (NO), tumor necrosis factor-α (TNF-α), prostaglandin E-2 (PGE-2) and in bacterial lipopolysachharide (LPS)-stimulated macrophages]. The findings revealed that compounds 13 and 17 showed the highest cytotoxicity and that 3, 6–8 and 25 are promising multi-potent anti-inflammatory agents.

  此前合成了一系列二十五个2-甲硫基-[1,2,4]三唑并[1,5-a]喹唑啉衍生物1至25。我们现已研究了它们对肝细胞Hep-G2和结肠HCT-116癌细咆的毒性作用，以及对巨噬细胞生长的影响，还包括它们对炎症介质[一氧化氮（NO）、肿瘤坏死因子-α（TNF-α）、前列腺素E-2（PGE-2）以及在细菌脂多糖（LPS）刺激的巨噬细胞中]的影响。研究结果显示，化合物13和17显示出最高的细胞毒性，而3、6-8和25是具有良好前景的多效抗炎剂。
• Antimicrobial activity of newly synthesized methylsulfanyl-triazoloquinazoline derivatives
  作者：Rashad Al-Salahi、Mohamed Marzouk、Ghada Awad、Mohamed Al-Omar、Essam Ezzeldin

  DOI：10.1111/jphp.12039

  日期：2013.5.5

  The aim of this research was to study and evaluate the antimicrobial activity of a novel 2-methylsulfanyl-[1,2,4]triazolo[1,5-a]quinazoline and its derivatives. Antibacterial activity of the target compounds was tested against a variety of species of Gram-positive bacteria such as Staphylococcus aureus ATCC 29213, Bacillus subtilis ATCC6633, and Gram-negative bacteria such as Pseudomonas aeruginosa ATCC27953 and Escherichia coli ATCC 25922. In addition some yeast and fungi, Candida albicans NRRL Y-477 and Aspergillus niger, respectively, were screened.

  Antimicrobial tests were carried out by the agar well diffusion method, using 100 μl of suspension containing 1 × 108 CFU/ml of pathological tested bacteria, 1 × 106 CFU/ml of yeast, and 1 × 104 spore/ml of fungi spread on nutrient agar (NA), Sabourand dextrose agar (SDA), and potato dextrose agar (PDA), respectively.

  The minimum inhibitory concentration (MIC) of the tested compounds was determined using the broth double dilution method (serially diluted technique) in proper nutrient. For comparison, ciprofloxacin and ketoconazole were used as antibacterial and antifungal reference drugs, respectively. Compounds 6, 9, 13, 14, and 11 were found to have the highest broad-spectrum antibacterial activity against S. aureus ATCC 29213, B. subtilis ATCC6633 and Gram-negative bacteria such as P. aeruginosa ATCC27953 and E. coli ATCC 25922 with MIC values of 6.25 and 12.50 μg/ml.

  It was clear that many of the synthesized compounds exhibited good antimicrobial activity. This study has revealed that compounds 6, 9, 13, 14, and 11 have been disclosed as moderate antimicrobial agents. These compounds could be useful as templates for further development through modification or derivatization to design more potent antimicrobial agents.

  本研究的目的是研究和评估一种新型2-甲基硫基-[1,2,4]三唑并[1,5-a]喹唑啉及其衍生物的抗菌活性。目标化合物的抗菌活性针对多种革兰氏阳性细菌，如金黄色葡萄球菌ATCC 29213，枯草芽孢杆菌ATCC6633，以及革兰氏阴性细菌，如铜绿假单胞菌ATCC27953和大肠杆菌ATCC 25922进行了测试。此外，还对一些酵母菌和真菌，分别为白念珠菌NRRL Y-477和黑曲霉进行了筛选。

  采用琼脂孔扩散法进行抗菌测试，使用含有1 × 10^8 CFU/ml病原菌、1 × 10^6 CFU/ml酵母菌和1 × 10^4 孢子/ml真菌的悬浮液100 μl分别涂布在营养琼脂（NA）、沙氏葡萄糖琼脂（SDA）和马铃薯葡萄糖琼脂（PDA）上。

  通过在适当营养基中使用双倍稀释法（串联稀释技术）确定了被测试化合物的最小抑制浓度（MIC）。为了比较，分别使用环丙沙星和酮康唑作为抗菌和抗真菌参考药物。发现化合物6、9、13、14和11对金黄色葡萄球菌ATCC 29213、枯草芽孢杆菌ATCC6633以及革兰氏阴性细菌如铜绿假单胞菌ATCC27953和大肠杆菌ATCC 25922具有最高的广谱抗菌活性，MIC值为6.25和12.50 μg/ml。

  许多合成化合物表现出良好的抗菌活性。本研究揭示了化合物6、9、13、14和11作为中等抗菌剂。这些化合物可以作为进一步开发的模板，通过修饰或衍生设计更有效的抗菌剂。

• Synthesis of Novel 2-Methylsulfanyl-4<i>H</i>-[1,2,4]triazolo[1,5-<i>a</i>]quinazolin-5-one and Derivatives
  作者：Rashad Al-Salahi、Detlef Geffken

  DOI：10.1080/00397911.2010.518780

  日期：2011.12.1

  A novel 2-methylsulfanyl-4H-[1,2,4]triazolo[1,5-a] quinazolin-5-one was synthesized using dimethyl-n-cyanoimidodithiocarbonate and 2-hydrazinobenzoic acid as building blocks. Chemical transformation of the inherent lactam moiety in the targeted 2-methylsulfanyl-[1,2,4]triazolo[1,5-a] quinazolin-5-one offered access to a variety of derivatives.