Synthesis of novel triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-<i>b</i>]pyridine derivatives and their antimicrobial activity
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A series of novel triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-<i>b</i>]pyridine derivatives <b>9a–l</b>, respectively, were prepared starting from 2 (1<i>H</i>) pyridone <b>3</b> through selective O/S-alkylation followed by Thorpe–Ziegler cyclization to form furo/thieno[2,3-<i>b</i>]pyridine derivatives <b>6</b>. Compounds <b>6</b> on reaction with hydrazine hydrate resulted carbohydrazide derivatives <b>7</b> and further reacted with diverse substituted phenyl isothiocyanates to form phenyl hydrazine carbothiamide derivatives <b>8</b>. Each compound <b>8</b> is independently reacted in presence of NaOH, H<sub>2</sub>SO<sub>4</sub>, and N<sub>2</sub>H<sub>4</sub>.H<sub>2</sub>O to form triazolothione, thiadiazole, triazole-functionalized furo/thieno[2,3-<i>b</i>]pyridine derivatives <b>9a–l,</b> respectively. All the products <b>9a–l</b> were screened against Gram +ve, Gram –ve bacteria and fungal strains. Compounds <b>9c–h</b> showed high activity against <i>Bacillus subtilis</i> microbial-type culture collection (MTCC) 121 at <8.0 micromolar concentration. Promising compounds further screened for minimum bactericidal concentration against <i>B. subtilis</i> MTCC 121 using ciprofloxacin as standard and found to show very good activity. These compounds also screened for biofilm inhibition activity against <i>B. subtilis</i> MTCC 121 using erythromycin as standard and confirmed the high activity.
