Green synthesis of highly functionalized octahydropyrrolo[3,4-c]pyrrole derivatives using subcritical water, and their anti(myco)bacterial and antifungal activity

Abstract

A series of novel 2-(thiazol-2-yl)-octahydropyrrolo [3,4-c]pyrroles was synthesized by reaction of octahydropyrrolo [3,4-c]pyrrole N-benzoylthiourea derivatives and α-haloketones in subcritical water at 130 °C in 75-91% yield. Both the thiourea intermediates and the end products were synthesized in subcritical water, which proved a suitable green alternative to acetone by delivering the desired compounds in much shorter reaction times and practically the same yields. The antimicrobial activity of the compounds was determined against five bacterial strains and three fungal strains, and MIC values of 15.62-250 g/mL were observed. Moreover, the compounds exhibited antimycobacterial activity against M. tuberculosis H37Rv with MIC values of 7.81-62.5 µg/mL.

Antimicrobial activity of citric acid against Escherichia coli, Staphylococcus aureus and Candida albicans as a sanitizer agent

“…Therefore, surfaces often are disinfected with many active chemicals, but most of the chemicals pose a concern for food safety as they leave residue and pose a threat to health (Akinyemi et al 2006). Therefore, the importance of naturally originated antimicrobials is increasing day by day (Nural et al 2018;Yabalak et al 2020). Besides, microorganisms' gaining resistance against these chemicals over time makes more difficult achieve sufficient and permanent hygiene (Notermans et al 1991).…”

Synthesis of New Thiazole and Pyrazole Clubbed 1,2,3-Triazol Derivatives as Potential Antimycobacterial and Antibacterial Agents

“…5 It is known that thiazole derivatives many compounds have exhibited remarkable antimycobacterial activity. [19][20][21][22][23][24][25][26] Moreover, thiazole derivatives have also exhibited a wide range of other pharmacological activity such as antimicrobial, 27,28 anti-inflammatory, 29 CNS active agents, 30 antimalarial 31 and anticancer 32 activities. Additionally, compounds bearing the pyrazole skeleton have been exhibited to exhibit significant antimycobacterial activity, [33][34][35] as well as antimicrobial, 36 anti-inflammatory 37 anticancer 38 and antimalarial 39 activities.…”

Solvent Free Three-Component Synthesis of 2,4,5-trisubstituted-1H-pyrrol-3-ol-type Compounds from L-tryptophan: DFT-B3LYP Calculations for the Reaction Mechanism and 3H-pyrrol-3-one↔1H-pyrrol-3-ol Tautomeric Equilibrium

“…Such a review ruled that the pyrrole nucleus can be obtained employing cycloaddition, cyclocondensation and carbon-carbon coupling reactions by metalorganic-catalyzed reactions [ 16 ]. All the described synthetic methods are diverse in terms of the employed reactants as well as the variation in the reaction conditions, comprising several representatives, such as Knorr, Hantzsch and Feist methodologies [ 16 , 17 , 18 ]. Some advantages have been achieved, primarily establishing more efficient and greener synthetic protocols [ 19 , 20 , 21 ].…”