Department of Chemistry, University of Lucknow, Lucknow 226007, India.
Eur J Med Chem. 2010 Jun;45(6):2418-26. doi: 10.1016/j.ejmech.2010.02.023. Epub 2010 Feb 13.
2-chloro-3-(4-methylpiperazin-1-yl)naphthalene-1,4-dione (3a), 2-chloro-3-(pyrrolidin-1-yl)naphthalene-1,4-dione (3b), 2-chloro-3-(piperidin-1-yl)naphthalene-1,4-dione (3c), 2-chloro-3-morpholinonaphthalene-1,4-dione (3d), 2-chloro-3-(2-phenylhydrazinyl)naphthalene-1,4-dione (3e), 2-(allylamino)-3-chloronaphthalene-1,4-dione (3f), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetic acid (3g), 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)succinic acid (3h), methyl 2-(3-chloro-1,4-dioxo-1,4-dihydronaphthalen-2-ylthio)acetate (3i), 2-chloro-3-(2-mercaptoethylthio)naphthalene-1,4-dione (3j), 3-hydroxy-4-methyl-4H-naphtho[2,3-b][1,4]thiazine-5,10-dione (3k) and compounds 3l-q have been synthesized by a green methodology approach using water as solvent and evaluated for their antifungal and antibacterial activity. The antifungal profile of 3a-n indicated that compounds 3a-d, 3j, 3e and 3k have potent antifungal activity. Amongst the most promising antifungal compounds, 3a-g, 3j, 3k showed better antifungal activity than clinically prevalent antifungal drugs Fluconazole and Amphotericin-B against Trichophyton mentagraphytes and compounds 3j and 3k have been found to be lead antifungal bicyclic and tricyclic 1,4-naphthoquinones. Compound 3k also exhibited pronounced antibacterial activity.
2-氯-3-(4-甲基哌嗪-1-基)萘-1,4-二酮(3a)、2-氯-3-(吡咯烷-1-基)萘-1,4-二酮(3b)、2-氯-3-(哌啶-1-基)萘-1,4-二酮(3c)、2-氯-3-(吗啉-4-基)萘-1,4-二酮(3d)、2-氯-3-(2-苯肼基)萘-1,4-二酮(3e)、2-(烯丙氨基)-3-氯萘-1,4-二酮(3f)、2-(3-氯-1,4-二氧代-1,4-二氢萘-2-基硫代)乙酸(3g)、2-(3-氯-1,4-二氧代-1,4-二氢萘-2-基硫代)琥珀酸(3h)、2-(3-氯-1,4-二氧代-1,4-二氢萘-2-基硫代)乙酸甲酯(3i)、2-氯-3-(2-巯基乙硫基)萘-1,4-二酮(3j)、3-羟基-4-甲基-4H-萘并[2,3-b][1,4]噻嗪-5,10-二酮(3k)以及化合物 3l-q 已通过使用水作为溶剂的绿色方法学方法合成，并对其抗真菌和抗菌活性进行了评估。3a-n 的抗真菌谱表明，化合物 3a-d、3j、3e 和 3k 具有很强的抗真菌活性。在最有前途的抗真菌化合物中，3a-g、3j 和 3k 对 Trichophyton mentagraphytes 的抗真菌活性优于临床常用的抗真菌药物氟康唑和两性霉素 B，而化合物 3j 和 3k 被发现是具有抗真菌作用的双环和三环 1,4-萘醌。化合物 3k 还表现出明显的抗菌活性。
