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Synthesis and Antimicrobial Activity of Novel 1, 2, 4-Triazolopyrimidofuroquinazolinones from Natural Furochromones (Visnagenone and Khellinone)
Medicinal Chemistry ( IF 1.9 ) Pub Date : 2021-07-31 , DOI: 10.2174/1573406416666200406130047
Ameen A Abu-Hashem 1 , Hoda A R Hussein 1 , Ahmed S Aly 1
Affiliation  

Background: Previous and recent scientific research has shown that triazolopyrimidine and furochromones have a wide range of pharmacological activities for the treatment of numerous diseases, including anticancer, antiviral, anti-depressant, anti-microbial, anti-inflammatory, and analgesic activities.

Objective: Preparation of new drugs derived from a natural furochromones as (1-hydrazinyl or methylthio),-furopyrimidoquinazolinone, 1, 2, 4-triazolopyrimidofuroquinazolin-5-one, and quinazoline- pyrimidofuro- quinazoline-8, 10-dione and the study of their biological activity as antimicrobial agents.

Methods: A series of novel N’-furopyrimidoquinazoline-hydrazide; 1, 2, 4-triazolopyrimidofuroquinazolin- 5-one; furopyrimidoquinazolin-3-one and quinazoline-pyrimidofuroquinazoline-8, 10- dione derivatives were synthesized from substituted (methylthio)-furopyrimidoquinazolinone (3ab) and 1-hydrazinyl-furopyrimido- quinazolinone (4a-b) as the starting material.

Results: All compounds were synthesized in good yields (71-95%) in a gradually efficient system under mild condition and some of the procedures were used such as microwave oven. The new compounds have been confirmed by means of different spectroscopic methods such as IR, 1D and 2D -NMR techniques and mass spectrum. The in vitro antimicrobial activities were evaluated for the prepared compounds using many types of bacteria (Gram-positive and Gram-negative) and fungi.

Conclusion: 1, 2, 4-triazolopyrimidofuroquinazolin-5-one derivatives (10a-f, 8a-b, 7a-b and 6a-d) showed the most efficient antimicrobial activities compared with the cefotaxime sodium and nystatin as standard drugs.



中文翻译:


天然呋喃色酮(Visnagenone 和 Khellinone)中新型 1,2,4-三唑并嘧啶呋喃喹唑啉酮的合成和抗菌活性



背景:以往和最近的科学研究表明,三唑并嘧啶和呋喃色酮具有广泛的药理活性,可治疗多种疾病,包括抗癌、抗病毒、抗抑郁、抗微生物、抗炎和镇痛活性。


目的:天然呋喃色酮类(1-肼基或甲硫基),-呋喃并嘧啶并喹唑啉酮,1,2,4-三唑并嘧啶呋喃喹唑啉-5-酮,喹唑啉-嘧啶呋喃-喹唑啉-8, 10-二酮等新药的制备及研究其作为抗菌剂的生物活性。


方法:一系列新型N'-呋喃并嘧啶并喹唑啉酰肼; 1, 2, 4-三唑并嘧啶呋喃喹唑啉-5-一;以取代(甲硫基)-呋喃并嘧啶并喹唑啉酮(3ab)和1-肼基-呋喃并嘧啶并喹唑啉酮(4a-b)为起始原料,合成了呋喃并嘧啶并喹唑啉-3-酮和喹唑啉-嘧啶并呋喃并喹唑啉-8, 10-二酮衍生物。


结果:所有化合物均在温和条件下,在逐步高效的体系中合成,收率良好(71-95%),并使用了微波炉等部分程序。这些新化合物已通过不同的光谱方法(例如红外、一维和二维核磁共振技术以及质谱)得到证实。使用多种类型的细菌(革兰氏阳性和革兰氏阴性)和真菌评估了所制备的化合物的体外抗菌活性。


结论:与标准药物头孢噻肟钠和制霉菌素相比,1,2,4-三唑并嘧啶呋喃喹唑啉-5-酮衍生物(10a-f、8a-b、7a-b和6a-d)显示出最有效的抗菌活性。

更新日期:2021-08-10
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