Microwave Assisted Synthesis of Some New Fused 1,2,4-Triazines Bearing Thiophene Moieties With Expected Pharmacological Activity

Abstract

Rapid and efficient solvent-free synthesis of 4-amino-3-mercapto-6-[2-(2-thienyl)vinyl]-1,2,4-triazin-5(4H)-one 1 under microwave irradiation is described. Some new fused heterobicyclic nitrogen systems such as 1,2,4-triazino[3,4-b][1,3,4]thiadiazinones, 1,3,4-thiadiazolo[2,3-c][1,2,4]triazinone and pyrazolo[5,1-c]-[1,2,4]triazine-7-carbonitrile, have been synthesized by treatment of 1 with bifunctional oxygen and halogen compounds, CS2/KOH and malononitrile via heterocyclization reactions, in addition to some uncondensed triazines. Structures of the products have been deduced from their elemental analysis and spectral data (IR, 1H-NMR, 13C-NMR). Select new synthesized compounds were screened as anticancer agents, with some showing activity as cytotoxic agents against different cancer cell lines.

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

“…IR spectra were recorded in KBr discs using an IR-470 Shimadzu spectrometer (Shimadzu, Japan). NMR spectra in DMSO-d 6 were recorded on Bruker Ac-500 ultra shield NMR spectrometer (d in ppm, Bruker, Switzerland) at 500 MHz, using TMS as an internal standard. Elemental analyses were performed on a Carlo Erba 1108 Elemental Analyzer (Heraeus, Germany).…”

“…Keywords: thiophenes, sulfonamides, isoxazole, benzothiazole, quinoline, anthracene, anticancer activity Thiophenes have been reported to possess interesting biological and pharmacological activities where several derivatives are used as antibacterial (1-3), anti-inflammatory (4), anticancer (5,6), and antiviral agents (7). Also, sulfonamides constitute an important class of drugs, with several types of pharmacological agents possessing anticancer activity (8)(9)(10)(11)(12), among others.…”

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“…Many attempts were carried out to prepare 1-(4-mtolylthiazol-2-yl)hydrazine (B) where R = CH 3 for derivatives prepared, the first attempt was carried out by the conventional method under reflux for 2hrs., by refluxing thiocarbohydrazide with, 2bromo-1-p-tolylethanone in glacial acetic acid 16,17,18,19 . Where the second method was carried out using microwave free reaction for 1.5-2 min, using the two above compounds without any solvents or liquid media 20 . The formed compound was confirmed by its IR, 1 HNMR, 13 CNMR, and elemental analysis data, the main observation was the presence two broad medium bands one at 600, and the other was at 1400 cm -1 , these bands were proved before as a finger print band as evidence of the presence of thiazole ring 21 .…”

Role of Microwaves in the Synthesis of Fused Five-Membered Heterocycles with Three N-Heteroatoms

“…[35] Among the diseases caused by viruses, hepatitis C is one of the most serious public health problems, affecting about 3% of the World's population, which represents about 170 million infected people. [36] The current treatment against hepatitis C virus (HCV) consists in the use of pegylated interferon-α in combination with ribavirin.…”