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Synthesis of 1,2,4‐triazolopyridazines, isoxazolofuropyridazines, and tetrazolopyridazines as antimicrobial agents
Journal of Heterocyclic Chemistry ( IF 2.4 ) Pub Date : 2020-07-30 , DOI: 10.1002/jhet.4065
Ameen A. Abu‐Hashem 1, 2 , Usama Fathy 3 , Moustafa A. Gouda 4, 5
Affiliation  

Through current and previous researches, it was found that the derivatives of pyridazine, isoxazole, tetrazole, quinazoline, hydrazinyl, and 1,2,4‐triazole have many pharmacological activities. Thus, a series of novel furopyridazinones (7), isoxazolopyridazine (8), sub‐benzylidene‐furopyridazinones (9a‐c), isoxazolofuropyridazines (10a‐c), 3‐chloro‐(pyridin‐4‐ylmethylene)‐dihydropyridazines (11), tetrazolopyridazines (12), pyridazinoquinazolinones (13), piperazinyl/morpholino‐pyridazines (14a,b), hydrazinyl‐pyridazines (15), and 1,2,4‐triazolo‐pyridazines (16a,b) in good yields (72%‐90%) were synthesized from substituted ethyl 4‐oxo‐4‐phenylbutanoate (2), 6‐phenyl‐4,5‐dihydropyridazinone (3), and 6‐phenyl‐4‐(pyridin‐4‐ylmethylene)‐4,5‐dihydropyridazinone (4) as beginning materials. All the chemical structures of the new compounds have been demonstrated by different spectroscopy analyses such as infrared, NMR, mass spectrum, and elemental analysis. Also, the activities of the newly prepared compounds were tested against many types of bacteria and fungi in vitro. Hence, 1,2,4‐triazolopyridazines (16a,b), isoxazolofuropyridazines (10a‐c), tetrazolopyridazines (12), Piperazinyl/morpholinyl‐pyridazines (14a,b) displayed the most efficient antimicrobial activities compared with the cefotaxime sodium and nystatin as standard drugs.

中文翻译:

1,2,4-三唑并哒嗪,异恶唑并呋喃哒嗪和四唑并哒嗪作为抗菌剂的合成

通过当前和先前的研究,发现哒嗪,异恶唑,四唑,喹唑啉,肼基和1,2,4-三唑的衍生物具有许多药理活性。因此,一系列新的呋喃并嘧啶酮(7),异恶唑并哒嗪(8),亚苄叉基-呋喃并哒嗪酮(9a-c),异恶唑并呋喃哒嗪(10a-c),3-氯-(吡啶-4-基亚甲基)-二氢哒嗪(11) ,四唑并哒嗪(12),哒嗪并喹唑啉酮(13),哌嗪基/吗啉代-哒嗪(14a,b),肼基-哒嗪(15)和1,2,4-三唑并哒嗪(16a,b)由取代的4-氧代-4-苯基丁酸乙酯(2),6-苯基-4,5-二氢哒嗪酮(3)和6-苯基-4-(吡啶基- )合成高收率(72%-90%)起始原料为4-(亚甲基)-4-,5-二氢哒嗪酮(4)。新化合物的所有化学结构已通过不同的光谱分析进行了证明,例如红外,NMR,质谱和元素分析。同样,在体外测试了新制备的化合物针对多种类型的细菌和真菌的活性。因此,1,2,4-三唑并哒嗪(16a,b),异恶唑并呋喃哒嗪(10a‐c),四唑并哒嗪(12),哌嗪基/吗啉基-哒嗪(与作为标准药物的头孢噻肟钠和制霉菌素相比,图14a,b)显示出最有效的抗菌活性。
更新日期:2020-09-08
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