PEG-400 mediated an efficient eco-friendly synthesis of new isoxazolyl pyrido[2,3-d]pyrimidines and their anti-inflammatory and analgesic activity |
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Authors: | Srinivasa Rao Dasari Subbaiah Tondepu Lakshmana Rao Vadali Nareshvarma Seelam |
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Institution: | 1. Department of Chemistry, Koneru Lakshmaiah Education Foundation, Vaddeswaram, Guntur, Andhrapradesh, India;2. API-Chemical Research Division, Mylan Laboratories Ltd, Hyderabad, India dasari80srinivas@gmail.com;4. Department of Chemical Engineering, Vignan’s Foundation for Science, Technology and Research, Guntur, India;5. API-Chemical Research Division, Mylan Laboratories Ltd, Hyderabad, India;6. Department of Chemistry, Koneru Lakshmaiah Education Foundation, Vaddeswaram, Guntur, Andhrapradesh, India |
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Abstract: | Abstract Polyethylene glycol-400 (PEG-400) has been developed as an efficient and eco-friendly reaction medium for the synthesis of new isoxazolyl pyrido2,3-d]pyrimidine derivatives 11 from isoxazolyl cyanoacetamide synthon 7. Compound 7 was employed with various aromatic aldehydes 8 and malononitrile 9 in the presence of triethylamine (Et3N) to afford the corresponding (E)-6-amino-1-(3-methyl-5-styrylisoxazol-4-yl)-2-oxo-4-phenyl-1,2-dihydro- pyridine-3,5-dicarbonitrile 10 at room temperature by using PEG-400 as a solvent medium as well as catalyst. The intermediate 10 on treatment with thiourea in the presence of PEG-400 at 90?°C to give the target compounds isoxazolyl pyrido2,3-d]pyrimidines 11 in good to excellent yields. The newly synthesized compounds 10 and 11 were characterized by IR, 1H NMR, 13C NMR, and HRMS analysis. The target compounds 11a-x was screened for their anti-inflammatory and analgesic activities. Among the tested compounds, the compounds 11s, 11t, 11u, 11v, 11w, and 11x showed significant anti-inflammatory and potent analgesic activities as that of reference drugs. The advantages of this protocol are operational simplicity, catalyst free, environmental safety, wide substrate scope, good yields, and PEG-400 can be recovered and reused. Most significant of all, this protocol is green. |
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Keywords: | Isoxazolyl pyrido[23-d]pyrimidines anti-inflammatory activity analgesic activity green chemistry PEG-400 |
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