Novel thiophene derivatives with sulfonamide, isoxazole, benzothiazole, quinoline and anthracene moieties as potential anticancer agents

A novel series of thiophenes having biologically active sulfonamide (2-11), 3-methylisoxazole (12), 4-methoxybenzo[d]thiazole (13), quinoline (14, 15), benzoylphenylamino (16) and anthracene-9,10-dione (17) moieties were prepared. Structures of the newly synthesized compounds were established by elemental analysis and spectral data. All newly synthesized compounds were evaluated for their in vitro anticancer activity against human breast cancer cell line (MCF7). Most of the screened compounds showed cytotoxic activities compared to doxorubicin as a positive control. Compounds 6, 7, 9 and 13 (IC50 values 10.25, 9.70, 9.55 and 9.39 µmol L–1 revealed higher cytotoxic activities than that of doxorubicin (IC50 = 32.00 µmol L). Also, compounds 5, 8 and 10 were found nearly as active as doxorubicin (IC50 values 28.85, 23.48 and 27.51 µmol L–1)

Study of reactivity of cyanoacetohydrazonoethyl-<i>N</i>-ethyl-<i>N</i>-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase

<p>This article describes the synthesis of some novel heterocyclic sulfonamides having biologically active thiophene <b>3</b>, <b>4</b>, <b>5</b>, <b>6</b>, coumarin <b>8</b>, benzocoumarin <b>9</b>, thiazole <b>7</b>, piperidine <b>10</b>, pyrrolidine <b>11</b>, pyrazole <b>14</b> and pyridine <b>12</b>, <b>13</b>. Starting with 4-(1-(2-(2-cyanoacetyl)hydrazono)ethyl)-N-ethyl-N-methylbenzenesulfonamide <b>(2)</b>, which was prepared from condensation of acetophenone derivative <b>1</b> with 2-cyanoacetohydrazide. The structures of the newly synthesized compounds were confirmed by elemental analysis, IR, ¹H NMR, ¹³C NMR, ¹⁹F NMR and MS spectral data. All the newly synthesized heterocyclic sulfonamides were evaluated as <i>in-vitro</i> anti-breast cancer cell line (MCF7) and as <i>in-vitro</i> antimicrobial agents. Compounds <b>8</b>, <b>5</b> and <b>11</b> were more active than MTX reference drug and compounds <b>12</b>, <b>7</b>, <b>4</b>, <b>14</b>, <b>5</b> and <b>8</b> were highly potent against <i>Klebsiella pneumonia</i>. Molecular operating environment performed virtual screening using molecular docking studies of the synthesized compounds. The results indicated that some prepared compounds are suitable inhibitor against dihydrofolate reductase (DHFR) enzyme (PDBSD:4DFR) with further modification.</p