Abstract
Aiming for the synthesis of new heterocyclic compounds containing a sulfonamido moiety suitable for use as antibacterial agents, the precursor ethyl {[4-N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenylazo}cyanoacetate was reacted with a variety of active methylene compounds producing pyran, pyridine and pyridazine derivatives. Also, the reactivity of the precursor hydrazone towards hydrazine derivatives to give pyrazole and oxazole derivatives was studied. On the other hand, treatment of the same precursor with urea, thiourea and/or guanidine hydrochloride furnished pyrimidine and thiazine derivatives, respectively. The newly synthesized compounds were tested for antibacterial activity, whereby eight compounds were found to have high activities.
Highlights
Simple nitrogen-containing heterocycles attached to sulfonamido moieties have received a large amount of attention in the literature, as a consequence of their exciting biological properties and their role as pharmacophores of considerable historical importance
Molecules 2013, 18 carbonic anhydrase inhibitors [1,2,3], antibacterial agents [4], anticancer, anti-inflammatory and analgesic agents [5], β3-adrenergic receptor agonists [6], PC-1 inhibitors [7], antifungal agents [8] and antiviral agents [9]. For these vast biological activities and in continuation of our work [10,11,12,13,14,15,16,17,18] on the synthesis of novel heterocyclic systems exhibiting biological activity, we undertook the synthesis of a new series of compounds incorporating the abovementioned biologically active moieties in one molecule
Synthesis of the precursor hydrazone 3 was achieved by diazotization of sulfamethazine
Summary
Simple nitrogen-containing heterocycles attached to sulfonamido moieties have received a large amount of attention in the literature, as a consequence of their exciting biological properties and their role as pharmacophores of considerable historical importance. Heterocyclic sulfonamides are used as Molecules 2013, 18 carbonic anhydrase inhibitors [1,2,3], antibacterial agents [4], anticancer, anti-inflammatory and analgesic agents [5], β3-adrenergic receptor agonists [6], PC-1 inhibitors [7], antifungal agents [8] and antiviral agents [9]. For these vast biological activities and in continuation of our work [10,11,12,13,14,15,16,17,18] on the synthesis of novel heterocyclic systems exhibiting biological activity, we undertook the synthesis of a new series of compounds incorporating the abovementioned biologically active moieties in one molecule
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