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Chemistry for Sustainable Development

2021 year, number 4

Biologically Active Norbornene Derivatives: Synthesis of Bicyclo[2.2.1]heptene Mannich Bases

G. E. HAJIYEVA
Institute of Petrochemical Processes named after Academician Yu. G. Mamedaliyev Azerbaijan National Academy of Sciences, Baku, Azerbaijan
Keywords: norbornene-containing derivatives, biological activity, Mannich bases, drugs
Pages: 391-410

Abstract

A review of scientific publications and the results of experiments in the area of synthesis and investigation of the biological activity of functionally substituted norbornene derivatives is presented. The high antibacterial, antifungal and antiseptic activity of different derivatives of bicyclo[2.2.1]-heptene was demonstrated, which is explained by the presence of a pharmacophore conformational rigid framework of the norbornene fragment, as well as its saturated analogue. The synthesis of norbornene-containing Mannich bases was carried out through a one-pot three-component aminomethylation participated by norbornenylmethanol, formaldehyde and secondary amines. It is stressed that norbornenylmethanol, synthesized previously on the basis of a diene synthesis reaction between cyclopentadiene and allyl alcohol, was first used as an alcohol component in the Mannich reaction. The synthesized norbornene-containing Mannich bases were tested for antimicrobial and antifungal activity against various microorganisms. It was established that the synthesized compounds exhibit high antimicrobial activity against gram-positive ( Staphylococcus aureus ), gram-negative ( Escherichia coli , Pseudomonas aeruginosa ) bacteria, and antifungal activity against the fungi of Candida genus. The minimum inhibitory and minimum bactericidal concentrations of these compounds against some of the above-listed microorganisms were determined. Comparative characteristics of the antimicrobial and antifungal properties of the synthesized norbornene-containing Mannich bases with respect to well-known reference drugs widely used in medical practice (carbolic acid, rivanol, furacilin, chloramine) were determined. It was shown that the synthesized compounds possess higher biological activity than the reference preparations.

DOI: 10.15372/CSD2021317