Antimicrobial and antiurease activities of newly synthesized morpholine derivatives containing an azole nucleus

Abstract

2-[6-(Morpholin-4-yl)pyridin-3-ylamino]acetohydrazide (<b>4</b>) was obtained starting from 6-morpholin-4-ylpyridin-3-amine (<b>2</b>) via the formation of ester (<b>3</b>) and then converted to the corresponding Schiff bases (<b>5, 6</b>) with the reaction with aromatic aldehydes. The carbothioamide (<b>9</b>), obtained from the reaction of hydrazide with phenylisothiocyanate, was converted to the corresponding 1,2,4-triazole (<b>11</b>) and 1,3,4-thiadiazole (<b>12</b>) derivatives by the treatment with NaOH or H₂SO₄, respectively. The cyclocondenzation of <b>9</b> with 4-chlorophenacyl bromide or ethyl bromoacetate produced the corresponding 1,3-thiazole (<b>10</b>) or 1,3-thiazolidine derivatives (<b>13</b>), respectively. Antimicrobial and antiurease activities of newly synthesized compounds were investigated. Some of them were found to be active on <i>M. smegmatis</i>, and they displayed activity toward <i>C. albicans</i> and <i>S. cerevisiae</i> in high concentration. Compound <b>10</b> proved to be the most potent showing an enzyme inhibition activity with an IC₅₀ = 2.37 ± 0.19 μM.