Synthesis, Antibacterial and Anti-Corrosive Activity of 2,3-Dihydroimidazo[1,2-a]Pyridinium Bromides

Abstract

The paper describes the synthesis of a set of new 2,3-dihydroimidazo[1,2-a]pyridinium bromides which demonstrate antibacterial properties against sulfatereducing bacteria of Desulfomicrobium and Desulfovibrio strains and inhibit their functioning in the binary culture under the steel microbial corrosion. The compounds demonstrate antibiofilm and anticorrosive properties in the medium with sulfate-reducing bacteria, steel anticorrosion rate is up to 70.6 %.

Features of (Benzo)Imidazo[2,1-b][1,3]thiazine Mezylates Reaction with Nucleophilic Reagents

“…It is usually characterized by a significant degree of conversion and high yields of target products. However, imidazo[2,1-b][1,3]thiazine derivatives were not systematically studied in this kind of transformations, except for the report [19] that described the synthesis of 6bromo-2,3-diphenylimidazo[2,1-b] [1,3]thiazine and 3chlorobenzo [4,5]imidazo[2,1-b] [1,3]thiazine by halogenation of the corresponding 6(3)-hydroxy(benzo) imidazo[2,1-b] [1,3]thiazines. Therefore, we decided to investigate the possibility of using hydroxy-substituted (benzo)imidazo[2,1-b][1,3]thiazines 10,[20][21][22] as basic substrates in nucleophilic substitution reactions with sodium azide, potassium thiocyanate, and sodium cyanide.…”

“…The preferred thiocyanates 3b,c were isolated, and their structure was confirmed by IR spectra with narrow absorption bands of SCN groups at 2155-2162 cm -1 and 13 С NMR spectra with signals of carbon atoms of the thiocyanate group at 110.7-110.8 ppm. However, among the minor products only 3isothiocyanato-3,4-dihydro-2H-benzo [4,5] imidazo[2,1b] [1,3]thiazine 4b could be isolated. Its IR spectrum is characterized by a wide absorption band of the NCS group at 1954 cm -1 , and the 13 С NMR spectrum has the signal of the carbon atom of this group at 156.8 ppm.…”

“…0.12 mL (6.7 mmol) of methanesulfochloride was added to the solution of 6.4 mmol of (benzo) [4,5]imidazo [2,1-b] [1,3]thiazine 1a-c in 20 mL of dry pyridine. The reaction mixture was stirred at room temperature for 48 h, the resulting suspension was poured onto ice, the formed precipitate was filtered and dried in a drying cabinet.…”

“…Recently, the attention of specialists in the field of medical and pharmaceutical chemistry is increasingly focused on the design and synthesis of functional condensed heterocyclic systems, among which azole-azine structures occupy a prominent place. [1][2][3][4][5][6] Among the latter, it is worth highlighting various derivatives of imidazo[2,1b] [1,3]thiazines, which are characterized by a wide spectrum of biological activity. In particular, compounds with antioxidant, 7 antibacterial, 8 antiviral, 9 antituberculosis, 10 and antitrypanocidal 11 effects and cytotoxic effects on non-cancerous F2408 and cancerous 5RP7 cells 12 were found among them.…”

“…Generally, the use of nucleophilic substitution reactions in heterocyclic cores yielded a number of compounds interesting in terms of structure and properties, which can directly be used as objects of bioscreening studies, and act as synthetic blocks for the construction of more complex molecular structures. However, the information is quite scarce regarding the modification of the (benzo) [4,5]imidazo [2,1-b] [1,3] thiazine core by nucleophilic transformations. That is why it seemed advisable to study the possibility of hydroxyl group participation in available hydroxy(benzo) imidazo[2,1-b] [1,3]thiazines in substitution reactions with various types of nucleophilic reagents.…”