SYNTHESIS OF PYRAZOLO-PYRROLO-THIOPYRANO[2,3-D]THIAZOLE AS A POTENTIAL BIOLOGICAL ACTIVE COMPOUND

The purpose of the present study is the synthesis of 6-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)-8-(4-methoxyphe- nyl)-3-methyl-2-thioxo-3,4a,7a,8-tetrahydropyrrolo[3',4':5,6]thiopyrano[2,3-d]thiazole-5,7(2H,6H)-dione and its biological evaluation as a potential bioactive compound.Materials and methods: organic synthesis, 1H, and 13C NMR spectroscopy, liquid chromatography-mass spectrometry, in vitro antimi- crobial and anticancer screening, drug-like prediction.Results. The title compound was obtained via a one-pot/two-step protocol of 4-aminoantipyrine and maleic anhydride with 5-(4-meth- oxybenzylidene)-3-methylthiazolidine-2,4-dithione. The structure of the synthesized compound (yield 69%) was confirmed by 1H, 13C NMR, and LC-MS spectra. According to US NCI protocols, the compound displayed a moderate level of antimitotic activity against melanoma MDA-MB-435 and breast cancer cell lines HS 578T. The synthesized derivative 4 was evaluated for antimicrobial activity against 17 strains of Gram-positive and Gram-negative bacteria, as well as yeasts, demonstrating moderate efficacy against drug-resistant Klebsiella strains. The drug-like properties of the synthesized compound were assessed using SwissADME, showing favorable drug-like parameters.Conclusions. The one-pot/two-step protocol for synthesizing thiopyrano[2,3-d]thiazole derivative is proposed. The title compound was fully characterized by spectral analysis methods. The tested compound displayed moderate activity against melanoma and breast cancer cell lines and moderate antimicrobial activity against drug-resistant Klebsiella strains. The synthesized thiopyrano[2,3-d]thiazole exhibits favora- ble predicted physicochemical and drug-like properties based on in silico analysis and demonstrates promising antimicrobial activity in vitro.The obtained results indicate the potential of this compound for further investigation against antibiotic-resistant microbial strains and tumors that are unresponsive to conventional anticancer agents.