Diastereoselective [3 + 2]-cycloadditions of oxindoles with α,β-disubstituted nitroethylenes: regioreversed spiropyrrolidines show potent MRSA activity.

β-Nitrostyrenes undergo one pot sequential addition-elimination reaction when reacted with finely powdered iodine in presence of sodium bicarbonate as base in water and tetrahydrofuran as solvents to afford seventeen α-iodonitroalkenes in moderate to good yields (40-88 %). These compounds were tested for activity against Mycobacterium tuberculosis H37Ra and MIC was determined using Rifampicin as positive control. One of the iodo compound 14 b, exhibited promising antimycobacterial activity with MIC values of up to 3.125 μM. Further, twelve α-Iodonitroalkenes exhibited significant antifungal activity against Candida albicans, Cryptococcus neoformans and drug-reistant Candida auris. with MIC values up to � 0.25 μM. This opens up the new space in the development of novel pharmacophores for antifungal and antimycobacterial studies.