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A ChCl: Gly (DESs) promoted environmentally benign method was developed for the first time using the reaction of aryl aldehydes and dimedone to give excellent yields of xanthene analogues. The major application of this present protocol is the use of green solvent, a wide range of substrate, short reaction times, ease of recovery, the recyclability of the catalyst, high reaction yield, and ChCl: Gly as an alternative catalyst and solvent. In addition to this, all the synthesized compounds were evaluated for their in vitro antimycobacterial activity against <i>M. tuberculosis H37Ra (MTB)</i> and <i>M. bovis BCG</i> strains. The compounds <b>3d</b>, <b>3e</b>, <b>3f</b>, and <b>3j</b> showed significant antitubercular activity against <i>MTB</i> and <i>M. bovis</i> strains with minimum inhibitory concentration (MIC) values of 2.5−15.10 µg/mL and 0.26–14.92 µg/mL, respectively. The compounds <b>3e</b>, <b>3f</b>, and <b>3j</b> were found to be nontoxic against MCF-7, A549, HCT 116, and THP-1 cell lines. All the prepared compounds were confirmed by ¹H NMR and ¹³C NMR analysis.