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Synthesis of novel 4,5-dihydropyrrolo[1,2-a]quinoxalines,pyrrolo[1,2-a]quinoxalin]-2-ones and their antituberculosis and anticancer activity |
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| Authors: | Vitthal B Makane Eruva Vamshi Krishna Uattam B Karale Dattatraya A Babar Saradhi Kalari Estharla M Rekha Manjulika Shukla Grace Kaul Dharmarajan Sriram Sidharth Chopra Sunil Misra Haridas B Rode |
| Institution: | 1. Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India
Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India;2. Department of Applied Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India;3. Department of Pharmacy, Birla Institute of Technology and Science-Pilani, Hyderabad, Telangana, India;4. Department of Microbiology, CSIR-Central Drug Research Institute, Lucknow, Uttar Pradesh, India;5. Academy of Scientific and Innovative Research, Ghaziabad, Uttar Pradesh, India Department of Applied Biology, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India;6. Department of Organic Synthesis and Process Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad, Telangana, India |
| Abstract: | A facile strategy was developed for the synthesis of biologically important 4,5-dihydropyrrolo1,2-a]quinoxalines and pyrrolo1,2-a]quinoxalin]-2-ones by treating 2-(1H-pyrrol-1-yl)anilines with imidazo1,2-a]pyridine-3-carbaldehyde or isatin, using amidosulfonic acid (NH3SO3) as a solid catalyst in water at room temperature. The protocol has been extended to electrophile ninhydrin. The catalyst could be recycled for six times without the loss of activity. The compounds were evaluated for their antituberculosis, antibacterial, and anticancer activities. It is worth noting that compounds 3d and 3e demonstrated a minimum inhibitory concentration value of 6.25 µM against Mycobacterium tuberculosis H37Rv, whereas compounds 3d , 3g , 5d , 5e , and 5i showed a remarkable inhibition of A549, DU145, HeLa, HepG2, MCF-7, and B16-F10 cell lines, respectively. Staphylococcus aureus was inhibited by compounds 5b , 5e , 5d , 5g , and 5l at 32 µg/ml. |
| Keywords: | 4 5-dihydropyrrolo[1 2-a]quinoxalines antituberculosis agents pyrrolo[1 2-a]quinoxalin-2-ones reusable catalyst |