Antifungal Activity of Some Mono, Bis and Quaternary Mannich Bases Derived from Acetophenone

Abstract

The development of resistance to current antifungal therapeutics drives search for new effective agents. Some Mannich bases have antifungal activity, but no information is available regarding the antifungal activity of acetophenone derived Mannich bases. Mono Mannich bases of acetophenone 1-3 were synthesized and converted into their corresponding bis derivatives, 5-7. Representative quaternary derivatives 4 and 8 were also synthesized. Antifungal activities of the compounds were evaluated using some yeasts and dermatophytes in vitro. Mono Mannich base 3 and quaternary compounds 4 and 8 were found to be 2-16 times more potent than the reference compound amphotericin B against dermatophytes: Trichophyton rubrum, Trichophyton mentagrophytes, and Microsporum canis. Compounds 4 and 8 were also found to be 2 times more effective compared with amphotericin B against the yeast Saccharomyces cerevisiae. Quaternization procedure improved the biological activity dramatically, whereas conversion of mono Mannich bases to corresponding bis derivatives generally did not affect antifungal activity. Our results suggest that acetophenone derived mono Mannich base 3 and quaternary derivatives 4 and 8 may serve as leading compounds for further studies to develop new antifungal agents with their highly potent antifungal activity.

Structural characterisation of some vanillic Mannich bases: Experimental and theoretical study

“…Many alkaloids, nucleotides, steroids, peptides, antibiotics and vitamins [6e10] comprise Mannich base fragments. Bioactivity, such as antioxidative [11], antifungal [12], antiinflammatory [13], antimalarial [14], vasorelaxing [15], antitubercular [16], analgesic [17], anticancer [18e21], etc., is a common feature of this class of compounds. Recently, the details on the synthesis and biological activity of some Mannich bases were reported [22].…”

Coumarin derivatives: Synthesis and cation binding properties

“…Mannich bases can display varied biological activities such as antimicrobial [1][2][3][4][5] , cytotoxic [6][7][8][9][10][11][12][13] , anticancer 14,15 , anti-inflammatory 16,17 and anticonvulsant 18,19 and DNA topoisomerase properties 20,21 . In this work, novel aminomethylcoumarin derivatives have been synthesized.…”

Synthesis, hematological, biochemical, and neurotoxicity screening of some Mannich base hydrochlorides

“…Mannich bases are an important class of compounds in medicinal chemistry with a wide range of biological properties including antimicrobial,[3456] anticancer,[78910] anti-inflammatory,[11121314] analgesic,[15] and anticonvulsant[161718] activities. Some of these compounds are also known for their applications as anti-verus of human imminidéficience (VIH) and antituberculosis,[192021222324] antimalaria,[25262728] antifungal,[2930] antiflaviviridae,[31] and spermicidal[32] agents.…”