Paper
Design,synthesis and antifungal activity of 8-fluoro-2,3-dihydroquinoline-4(1H)-one semicarbazone derivatives
Published 2012 · Guo Chun
Chinese Journal of Medicinal Chemistry
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Abstract
In recent years,the incidence of fungal infections has reached alarming proportions,and the latest market outlook from data monitor shows that the rate of invasive fungal infection is increasingly rising specially.So it is of great significance to develop more effective and safer antifungal agents with novel mechanism of action.The target compounds were designed based on the bioisosterism and combination principle in drug design,to substitute the sulphur atom of thiochromanones with nitrogen giving the 2,3-dihydroquinolin-4(1H)-one scaffold and combine this moiety with semicarbazones which is the pharmacophore of cysteine protease inhibitors to give the scaffold of 2,3-dihydroquinolin-4(1H)-one semicarbazone.Totally sixteen 8-fluoro-2,3-dihydroquinoline-4(1H)-one semicarbazone derivatives were synthesized and their structures were confirmed by MS and 1H-NMR.The antifungal assay was carried out in vitro by two-fold dilution method,with fluoconazole and itraconazole as the control drugs.The result showed that all the compounds displayed antifungal activities against the tested fungi,Rh,T.r,As,M.g,T.v,C.n,R.r,and C.a,in different levels,of which Ⅰ1,Ⅰ6,Ⅰ7,Ⅰ11,and Ⅰ14 showed better activity.The preliminary structure activity relationship was summarized.
In Vitro Study8-fluoro-2,3-dihydroquinoline-4(1H)-one semicarbazone derivatives show promising antifungal activity against various fungi, with compounds I1,I6,I7,I11,and I14 showing the best activity.
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