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Rapid, Greener and Ultrasound Irradiated One‐Pot Synthesis of 4‐(Substituted‐1 H ‐Pyrazol‐4‐yl)Methylene)‐3‐Isopropylisoxazol‐5(4 H )‐ones and Their In Vitro Anticancer Activity
Author(s) -
Bhatt Tejal D.,
Gojiya Dinesh G.,
Kalavadiya Prakash L.,
Joshi Hitendra S.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201902164
Subject(s) - chemistry , methylene , aldehyde , isoxazole , proton nmr , in vitro , nuclear chemistry , solvent , ethanol , pyridine , stereochemistry , organic chemistry , biochemistry , catalysis
In the current research framework, an efficient and greener synthesis has been developed for novel isoxazole scaffolds one‐pot three‐component reaction. We have developed a new method for convenient and rapid synthesis of 4‐(substituted‐1 H ‐pyrazol‐4‐yl)methylene)‐3‐isopropylisoxazol‐5(4 H )‐ones via one‐pot three‐component reaction between methyl 4‐methyl‐3‐oxovalerate, hydroxylamine hydrochloride and various pyrazole aldehyde in the presence of pyridine as a base, water:EtOH (1:1) act as greener solvent under conventional and ultrasonic irradiation methods. From the comparisition between conventional and ultrasound‐assisted synthesis, it was observed that the ultrasound‐assisted method gave 82–96% yields in 30–45 min against 70–90 min required to get 66–79% yields by a conventional method. All the final compounds were characterized by FT‐IR, 1 H NMR, 13 C NMR and Mass spectroscopic analysis. Some selected compounds were evaluated for their in‐vitro anticancer activity against a panel of 60 different human tumor cell lines. All the selected compounds were highly active against the leukemia cancer cell line.