Mannich reaction: A versatile and convenient approach to bioactive skeletons

Abstract

This review gives an insight into the recent applications of Mannich reaction and its variants in the construction of bioactive molecules. Emphasis is given to the Mannich reaction that provides bioactive molecules and/or modifies the property of an existing bioactive molecule. The role of Mannich reaction in the construction of antimalarial, antitumour, antimicrobial, antitubercular, antiinflammatory and anticonvulsant molecules and also the significance of aminoalkyl Mannich side chain on the biological property of molecules is discussed here.

Synthesis and bioactivities of halogen bearing phenolic chalcones and their corresponding bis Mannich bases

“…The chemistry of Mannich bases has been the subject of wide and increasing interest, due to their biological activities such as analgesic, antimalarial, anticonvulsant, antipsychotic, cytotoxic, antiinflammatory, and antimicrobial activities [3][4][5]8,9,[17][18][19][20][21][22] . In addition, the Mannich bases of several bioactive molecules such as Taxol (anticancer agent), SCH48461 (anticholesterol agent), Tramadol (analgesic), Osnervan (antiparkinson), and Moban (neuroleptic) were prepared and they showed increased bioactivities comparing to the parent compounds 23 . Doxorubicin causes multidrug resistance in tumor cells but the synthetic Mannich base analog of Doxorubicin showed signiEcant activity against multi drug-resistant tumor cell lines 23 .…”

“…In addition, the Mannich bases of several bioactive molecules such as Taxol (anticancer agent), SCH48461 (anticholesterol agent), Tramadol (analgesic), Osnervan (antiparkinson), and Moban (neuroleptic) were prepared and they showed increased bioactivities comparing to the parent compounds 23 . Doxorubicin causes multidrug resistance in tumor cells but the synthetic Mannich base analog of Doxorubicin showed signiEcant activity against multi drug-resistant tumor cell lines 23 . The introduction of aminoalkyl Mannich side chain into Topotecan increased the water solubility of this anticancer agent 23 .…”

“…Doxorubicin causes multidrug resistance in tumor cells but the synthetic Mannich base analog of Doxorubicin showed signiEcant activity against multi drug-resistant tumor cell lines 23 . The introduction of aminoalkyl Mannich side chain into Topotecan increased the water solubility of this anticancer agent 23 . Conversion of phenolic chalcones into their corresponding Mannich bases is often accompanied by increased bioactivity in in vitro and/or in vivo studies 2,9,14,17,22,24 .…”

Antimicrobial Properties of Benzimidazole and Mannich Bases of Benzimidazole: A Review

“…Lorand et al studied the antimicrobial properties of unsaturated Mannich ketones and he found that the presence of Mannich side chain increase the water solubility of unsaturated Mannich ketones [11][12].…”

Synthesis of some novel heterocylic compounds derived from 2-[3-(4-chlorophenyl)-5-(4-methoxybenzyl)-4H-1,2,4-triazol-4-yl]acetohydrazide and investigation of their lipase andα-glucosidase inhibition

“…Mannich base is a b-amino-carbonyl compound, which is formed in the reaction of an amine (primery or secondary), formaldehyde and a reactive hydrogen atom 29 . Mannich bases have been reported to be useful agent for potential biological activities such as anticancer, antibacterial, antifungal, analgesic, antiinflammatory, antimalarial and antitubercular 30 . Many Mannich bases of 1,2,4-triazoles carrying N-methylpiperazine moiety are reported to possess protozoacidal and bactericidal activities 31 .…”