Ultrasonication-ionic liquid synergy for the synthesis of new potent anti-tuberculosis 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines |
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| Affiliation: | 1. Department of Chemistry, National Institute of Technology, Warangal 506 004, Telangana, India;2. Department of Pharmacy, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, India;3. Department of Chemistry, Birla Institute of Technology & Science-Pilani, Hyderabad Campus, Jawahar Nagar, Hyderabad 500 078, India;1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia;2. Department of Chemistry, Faculty of Science, Mansura University, Mansura, Egypt;3. Department of organic and medicinal chemistry, Faculty of Pharmacy, University of Sadat City, Menofia, Egypt;4. Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt;5. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria 21321, Egypt;1. Department of Chemistry and Research Centre, New Arts, Commerce and Science College, Ahmednagar 414001, India;2. Department of Chemistry, S. P. Mandali’s Sir Parashurambhau College, Tilak Road, Pune 411 030, India;3. Department of Chemistry, Rayat Shikshan Santhsa’s Radhabai Kale Mahila Mahavidyalya, Ahmednagar 414001, India;4. CombiChemBio Resource Centre, National Chemical Laboratory, Pune 411 008, India;1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia;2. Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Ibrahimia, Alexandria, 21321, Egypt;3. Department of Chemistry, Faculty of Science, Mansura University, Mansura, 35516, Egypt;4. Department of Pharmacognosy, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt;5. Department of Medicinal Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura, 35516, Egypt;1. Department of Medicinal Chemistry, Faculty of Pharmacy, Assuit University, Assuit 71526, Egypt;2. Department of Zoology, Faculty of Science, Ain Shams University, Abbassia 11566, Cairo, Egypt;1. School of Pharmaceutical Sciences and New Drug Research & Development Center, Zhengzhou University, Zhengzhou 450001, PR China;2. School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, PR China |
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| Abstract: | The aim of the study is to design and synthesis of a new series of potent anti-TB 1,2,4-triazol-1-yl-pyrazole based spirooxindolopyrrolizidines with their safety profile. A synergetic effect of ultrasonication and ionic liquid was shown successfully as a green methodology for the synthesis of title compounds 6a–t. These derivatives were obtained in shorter reaction time with good yields and well characterized by various spectroscopic methods, single-crystal X-ray diffraction (6f). The in vitro anti-tuberculosis activity for newly-synthesized derivatives has been screened against Mycobacterium tuberculosis. Among all, six compounds 6e, 6k, 6l, 6n, 6q and 6r exhibited equal potent activity compared to standard drug ethambutol (MIC: 1.56 µg/mL) and another compound 6h exhibited outstanding activity (MIC: 0.78 µg/mL) than the standard drug ethambutol. Cytotoxic nature of the anti-TB active compounds was evaluated against RAW 264.7 cells. The 6h, 6e, 6k, 6l, 6n, 6q and 6r exhibited lower toxicity which could be promising hits for anti-tuberculosis. |
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| Keywords: | Ultrasonication-ionic liquid synergy Green methodology Spirooxindoles Anti-tuberculosis activity Cytotoxicity |
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