Abstract
New camphor and fenchon anils, promising materials for the needs of medicine and industry, as well as some of their reduced forms, were synthesized and characterized. In a number of cases, the reduction by the NaBH4—NiCl2 • 6H2O reagent system in EtOH containing water was accompanied by the formation of side products of the aromatic ring hydrogenation in up to 10–18% yields. Aniline derivatives containing a cage monoterpenoid fragment at the nitrogen atom were studied for antibiotic activity in vitro against gram-positive and gram-negative bacteria, yeasts, and imperfect fungi. The results obtained in the Halobacterium salinarum test system allowed us to identify the most active compounds and draw a conclusion about good prospects for the further structural modification in this chemotype series of compounds.
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Funding
This work was financially supported by the Russian Science Foundation (Project No. 22-13-20062, https://rscf.ru/project/22-13-20062/) and grant from the Administration of the Volgograd Region (Agreement No. 2 dated June 10, 2022) and carried out using a fleet of analytical instruments of the Center for Collective Use at the N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences. Biological studies were carried out on the basis of the FSBSI G. F. Gause Research Institute for the Discovery of New Antibiotics.
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Dedicated to Academician of the Russian Academy of Sciences M. P. Egorov on the occasion of his 70th birthday.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 73, No. 1, pp. 168–178, January, 2024.
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Vernigora, A.A., Davidenko, A.V., Salykin, N.A. et al. Aniline derivatives containing a cage monoterpenoid fragment at the nitrogen atom: synthesis and study of antibacterial properties. Russ Chem Bull 73, 168–178 (2024). https://doi.org/10.1007/s11172-024-4129-6
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DOI: https://doi.org/10.1007/s11172-024-4129-6