In conclusion, we reported the synthesis of fused and isolated triazoles based on thieno[2,3-d]pyrimidines. The synthesized 1,2,4-triazolo compounds were screened for their anticancer activity at a concentration of 10 μΜ against a panel of 60 cell lines derived from nine different types of cancers, and also screened for their PDE 5 inhibitory activity. The possibility of combining 1,2,4-triazolo moiety to thieno[2,3-d]pyrimidines should open new opportunities for the rational design of medicinal agents. Encouragingly, most of the synthesized derivatives possess potent PDE 5 inhibitory activity compared to sildenafil as a reference drug.
Experimental section
General
Melting points were determined on a Boetius melting point apparatus and …show more content…
Then, p-nitrobenzeneazide (0.16 g, 1.0 mmol) was added. The mixture was stirred at room temperature until complete consumption of the starting materials, monitored by TLC. The reaction mixture was diluted with 25 mL of water, cooled in ice, and extracted with CH2Cl2 (3x15 mL). The combined organic extracts were washed with brine, and dried (MgSO4). After removal of the solvent under reduced pressure, the residue was purified on silica gel with n-hexane–ethylacetate (8:2) yielding the target compound 8 as colorless powder (0.42 g, 79%); mp: 182-183 …show more content…
9.76 (s, 1H, NH), 10.35 (s, 1H, NH), 12.34 (s, 1H, NH); 13C-NMR (100 MHz, DMSO-d6): δ 13.8 (CH3), 14.4 (CH3), 14.5 (CH3), 25.8 (C-4), ¬41.0 (C-5), 42.1 (C-7), 60.5 (CH2, ester), 60.8 (CH2, carbamate), 61.2 (CH2, carbamate), 111.5 (C-3), 122.5 (C-3a), 128.9 (C-7a), 149.5 (C-2), 154.5 (C=O), 155.6 (C=O, carbamate), 165.1 (C=O, carbamate), 176.7 (C=S). (EI-MS): m/z calcd.. C17H24N4O6S2 [M]+: 444,11 found:
Experimental section
General
Melting points were determined on a Boetius melting point apparatus and …show more content…
Then, p-nitrobenzeneazide (0.16 g, 1.0 mmol) was added. The mixture was stirred at room temperature until complete consumption of the starting materials, monitored by TLC. The reaction mixture was diluted with 25 mL of water, cooled in ice, and extracted with CH2Cl2 (3x15 mL). The combined organic extracts were washed with brine, and dried (MgSO4). After removal of the solvent under reduced pressure, the residue was purified on silica gel with n-hexane–ethylacetate (8:2) yielding the target compound 8 as colorless powder (0.42 g, 79%); mp: 182-183 …show more content…
9.76 (s, 1H, NH), 10.35 (s, 1H, NH), 12.34 (s, 1H, NH); 13C-NMR (100 MHz, DMSO-d6): δ 13.8 (CH3), 14.4 (CH3), 14.5 (CH3), 25.8 (C-4), ¬41.0 (C-5), 42.1 (C-7), 60.5 (CH2, ester), 60.8 (CH2, carbamate), 61.2 (CH2, carbamate), 111.5 (C-3), 122.5 (C-3a), 128.9 (C-7a), 149.5 (C-2), 154.5 (C=O), 155.6 (C=O, carbamate), 165.1 (C=O, carbamate), 176.7 (C=S). (EI-MS): m/z calcd.. C17H24N4O6S2 [M]+: 444,11 found: