Synthesis and Characterization of Proton Transfer Salts of 2-Aminobenzothiazole Derivatives

Abstract

In this study, (E)-4-oxo-4-(3-sulfamoylphenyl)amino)but-2-enoic acid (Habsmal) was first obtained from the reaction of maleic anhydride (mal) with 3-aminobenzenesulfonamide (abs). Then, salts of 2-aminobenzothiazole (abt) (1) and 2-amino-6-ethoxybenzothiazole (EtOabt) (2) were synthesized by Habsmal. In addition, proton transfer salts were obtained from the reactions of 5-sulfosalicylic acid (H3ssa) with 2-amino-6-hydroxybenzothiazole (HOabt) (3) and 2-amino-6-nitrobenzothiazole (NO2abt) (4). The structures of proton transfer salts obtained in amorphous state have been proposed by elemental analysis, NMR (1H and 13C), FT-IR, charge balance and previous studies. According to the results of this analysis, the acid and base association ratios were found to be 1:1

Antimicrobial Activity of Proton Salts of 3-(Sulfamoylphenylcarbamoyl)acrylic Acid Derivatives With Aminopyridine Derivatives

“…Proton transfer salts 9-18, which we synthesized and characterized in our previous studies [32][33][34][35][36]. The structures of free ligands (1-8) and proton transfer salts (9-18) are given in Figure 1.…”

“…The biological activity of acrylic acid derivatives which are the acid compound of this study are known such as anti-inflammatory [27], dielectric properties [28], antimicrobial activity [28,29], virus type 1 (HIV-1) [30] and antiglaucoma [31,32]. In the literature, 2-amino-3/4/5/6-methylpyridines [34], 2-aminopyridine [33], 2-aminobenzothiazole and 2-amino-6-ethoxybenzothiazole [35] proton transfer salts with (E)-3-(3-sulfamoylphenylcarbamoyl)acrylic acid (7) while 1H-benzimidazole, 2aminopyridine [32], 2-amino-3/4/5/6-methylpyridine, 3-aminopyridine [36] proton transfer salts are synthesized with (E)-3-(4-sulfamoylphenylcarbamoyl)acrylic acid (8) have been synthesized. The antimicrobial properties of metal complexes of 8 are investigated [37].…”

“…In this study, salts 9-13 of between 7 and 1-5, and 14-18 of between 8 and 1-6 were synthesized by methods found in the literature [32][33][34][35][36]. The antimicrobial activities of the compounds 1-6 and 8 [37] and 9-18 were tested against C. albicans (yeast) and E. coli, L. monocytogenes, B. subtilis, P. aeruginosa, E. faecalis, and S. aureus bacterial microorganisms.…”