Synthesis, Reactivity and Antimicrobial Activity of a Series of 2-Arylamino-1,3-selenazoles

Abstract

A series of 2-arylamino-1,3-selenazoles was synthesized and their reactivity was studied. The 2-arylamino-1,3-selenazoles and their reaction products were characterized by various spectroscopic methods and X-ray diffraction. In addition, the antimicrobial activity of the 2-arylamino-1,3-selenazoles in a panel of seven bacteria and fungi was examined.

One-Pot Syntheses of Substituted 2-Aminothiazoles and 2-Aminoselenazoles via Meerwein Arylation of Alkyl Vinyl Ketones

“…3 4 , 15 16 17 18 The selenium analogs of 2-aminothiazoles have also attracted much attention as biologically active compounds. 19 Antibiotic and neuroprotective, 20 anticancer, 18 21 antifungal, 22 antimicrobial as well as anticonvulsant 23 24 activities have been reported, and high-affinity inhibitors of kinase CK2 and efficient phosphorescence biomarkers have also been described. 17…”

“…Most 2-aminothiazole and 2-aminoselenazole derivatives are prepared by reactions of α-halocarbonyl compounds I with thioureas or selenoureas, 5 17 24 25 respectively (Scheme 1 ). A few approaches start from α-thiocyanato­ketones II , 26 isoselenocyanatoalkenes III , 27 or enamines IV .…”

“…19 Antibiotic and neuroprotective, 20 anticancer, 18,21 antifungal, 22 antimicrobial as well as anticonvulsant 23,24 activities have been reported, and high-affinity inhibitors of kinase CK2 and efficient phosphorescence biomarkers have also been described. 17 Most 2-aminothiazole and 2-aminoselenazole derivatives are prepared by reactions of -halocarbonyl compounds I with thioureas or selenoureas, 5,17,24,25 respectively (Scheme 1). A few approaches start from -thiocyanatoketones II, 26 isoselenocyanatoalkenes III, 27 or enamines IV.…”

“…3,4,[15][16][17][18] The selenium analogs of 2-aminothiazoles have also attracted much attention as biologically active compounds. 19 Antibiotic and neuroprotective, 20 anticancer, 18,21 antifungal, 22 antimicrobial as well as anticonvulsant 23,24 activities have been reported, and high-affinity inhibitors of kinase CK2 and efficient phosphorescence biomarkers have also been described. 17 Most 2-aminothiazole and 2-aminoselenazole derivatives are prepared by reactions of -halocarbonyl compounds I with thioureas or selenoureas, 5,17,24,25 respectively (Scheme 1).…”

Construction of the 2-Amino-1,3-selenazole Skeleton via PhICl2/KSeCN-Mediated Selenocyanation/Cyclization

“…A complete NH 2 proton signal appeared in the downfield region (δ 8.10). Furthermore, the carbon signals in 13 C NMR are dramatically shifted to the downfield region from 75.0 ppm (C 2 ) to 160.0 ppm (C 1 ), which was ascribed to the aromaticity of the 1,3-selenazole ring; the 77 Se NMR spectrum of the product displayed a downfield signal at δ 586.5, which is the character region for selenium of 1,3-selenazole . Finally, the reactive selenocyanating source was investigated and identified.…”