Synthesis and Antimicrobial Activity of Sulfenimines Based on Pinane Hydroxythiols
Nikita O. Ilchenko,
Denis V. Sudarikov,
Roman V. Rumyantcev,
Diana R. Baidamshina,
Nargiza D. Zakarova,
Monyr Nait Yahia,
Airat R. Kayumov,
Aleksandr V. Kutchin,
Svetlana A. Rubtsova
Affiliations
Nikita O. Ilchenko
Institute of Chemistry, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, Pervomayskaya St. 48, 167000 Syktyvkar, Komi Republic, Russia
Denis V. Sudarikov
Institute of Chemistry, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, Pervomayskaya St. 48, 167000 Syktyvkar, Komi Republic, Russia
Roman V. Rumyantcev
G.A. Razuvaev Institute of Organometallic Chemistry of Russian Academy of Sciences, 49 Tropinina St., 603950 Nizhny Novgorod, Russia
Diana R. Baidamshina
Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Nargiza D. Zakarova
Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Monyr Nait Yahia
Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Airat R. Kayumov
Institute of Fundamental Medicine and Biology, Kazan Federal University, 18 Kremlevskaya Street, 420008 Kazan, Russia
Aleksandr V. Kutchin
Institute of Chemistry, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, Pervomayskaya St. 48, 167000 Syktyvkar, Komi Republic, Russia
Svetlana A. Rubtsova
Institute of Chemistry, Federal Research Centre “Komi Scientific Centre”, Ural Branch of the Russian Academy of Sciences, Pervomayskaya St. 48, 167000 Syktyvkar, Komi Republic, Russia
The widespread presence of multidrug-resistant pathogenic microorganisms challenges the development of novel chemotype antimicrobials, insensitive to microbial tools of resistance. To date, various monoterpenoids have been shown as potential antimicrobials. Among many classes of molecules with antimicrobial activity, terpenes and terpenoids are an attractive basis for the design of antimicrobials because of their low toxicity and availability for various modifications. In this work, we report on the synthesis of sulfenimines from chiral trifluoromethylated and non-fluorinated pinane-type thiols. Final compounds were obtained with yields of up to 81%. Among the 13 sulfenimines obtained, 3 compounds were able to repress the growth of both bacteria (S. aureus, both MSSA and MRSA; P. aeruginosa) and fungi (C. albicans) with an MIC of 8–32 µg/mL. Although compounds exhibited relatively high cytotoxicity (the therapeutic index of 3), their chemotype can be used as a starter point for the development of disinfectants and antiseptics for targeting multidrug-resistant pathogens.
