Synthesis and evaluation of original amidoximes as antileishmanial agents

Synthesis and evaluation of monoamidoxime derivatives: Toward new antileishmanial compounds

“…Solvent evaporation was followed by column chromatography (gradient, from chloroform/petroleum ether (1/1) to chloroform/petroleum ether/diethyl ether (5/3/2)), and the product obtained was recrystallized from the appropriate solvent. (14). White solid, mp 152e153 C (isopropyl alcohol) 1 69 (m, 6H, 6CH).…”

“…In the course of our ongoing work on the preparation of antiparasitic compounds [13], we have previously reported the synthesis of diarylamidoxime derivatives, yielding a 2,3-dihydrofuran instead of the furan scaffold of pafuramidine [14]. Several of these diamidoxime derivatives exhibited good activity against L. donovani.…”

New series of monoamidoxime derivatives displaying versatile antiparasitic activity

“…The reaction of cyano derivatives synthesized from both cyclization mediated by manganese(III) acetate and Suzuki-Miyaura cross-coupling reactions (12)(13)(14)(15)(16)(17)(18)(19)(20)(21)(22)(23)(24)(25)(26)(27)(28)(29)(30)(31), with hydroxylamine hydrochloride and potassium tert-butoxide in DMSO [30] led to conversion of the cyano group into amidoximes 32-51 in moderate to excellent yields (28-100%) as reported in Table 4. almost halves the reaction yield.…”

“…[12][13][14] Recently, it enabled 40 mono-and diamidoximes to be synthesized, showing antileishmaniasis potential with valuable antiparasitic activities. [15][16] Findings highlighted the antileishmanial potential of monoamidoxime derivatives, which was increased by fluorine atom or trifluoromethyl groups on the β-ketosulfone moiety. This yielded 4-(5-benzyl-3-(4-fluorophenylsulfonyl)-5-methyl-4,5-dihydrofuran-2-yl)-N'-hydroxy-benzimidamide ( Figure 1): this molecule presents good in vitro antileishmanial activity on L. donovani promastigotes, with a better selectivity index (SI = 6.37) than conventional antileishmanial drugs (pentamidine, amphotericin B).…”

13C NMR substituent-induced chemical shifts in 4-(substituted phenyl)-3-phenyl-1,2,4-oxadiazol-5(4H)-ones (thiones)

“…Meanwhile, amidoxime derivatives have been shown to have a variety of useful properties. These include antioxidant and lipid peroxidation activities [29], antileishmanial and antimicrobial agents [4,30], chelating resin [31], nitric oxide donors [32] and amidine prodrugs [33]. In addition, the main application of these is building blocks, which is related to the construction of 1,2,4-oxadiazoles, 1,2,4-oxadiazines and 1,2,4,5-oxadiazaboroles rings [34][35][36].…”