Α‐Iodonitroalkenes as Potential Antifungal and Antitubercular Agents. Issue 39 (20th October 2020)

• Record Type: Journal Article
• Authors: Pamarthi, Rambabu; Kumar, Ram; Sankara, Chennikkayala Siva; Lowe, Gabrielle J.; Zuegg, Johannes; Singh, Sudheer Kumar; Ganesh, Madhu
• Is Part Of: ChemistrySelect. Volume 5:Issue 39(2020)
• Page Start: 12272
• Page End: 12277
• Publication Date: 2020-10-20
• Subjects: α-iodonitroolefins -- Halogenation -- Antifungal agents -- Drug-resistant Tuberculosis -- Drug-resistant C.auris; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202003251
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: 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. Abstract : α ‐Iodonitroalkenes were isolated in good to high yields that is classically a result of a base(s) promoted Michael triggered iodination reaction. One of the compounds exhibited an activity against surrogate strain of Mycobacterium tuberculosis H37Ra and several of the compounds exhibited significant inhibitory activity against fluconazole resistant candida strains, like C. Auris, C.tropicalis and C. Glabrata with MIC values up to <0.3 μg/mL. This study provides a starting point for the development of potential antifungal and antimycobacterial agents.