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The hetero-Diels–Alder reaction is the main synthetic tool for obtaining pharmacological agents with a thiopyrano[2,3-d]thiazole motif. In the present work, an efficient method for the synthesis of pyrazoline-containing thiopyrano[2,3-d]thiazole is described. The pyrazoline-bearing dienophile was proposed and used as effective building block for the synthesis of the title compound. The structure of the synthesized rel-2-[4-chloro-2-[(5R,6R,7S)-6-[5-(4-methoxyphenyl)-3-(2-naphthyl)-3,4-dihydropyrazole-2-carbonyl]-5-methyl-2-oxo-3,5,6,7-tetrahydrothiopyrano[2,3-d]thiazol-7-yl]phenoxy]acetic acid (3) was confirmed by 1H, 13C, 2D NMR, and LC-MS spectra. Anticancer activity in "60 lines screening" (NCI DTP protocol) was studied in vitro for the title compound. [ABSTRACT FROM AUTHOR]

The pharmacophore hybridization approach is widely used for the design of drug-like small molecules with anticancer properties. In the present work, a "cost-effective" approach to the synthesis of the novel non-condensed pyrazoline-bearing hybrid molecule with 1,3,4-thiadiazole and dichloroacetic acid moieties is proposed. The 5-amino-1,3,4-thiadiazole-2-thiol was used as a starting reagent, and the synthetic strategy includes stepwise alkylation of the sulfur atom and acylation of the nitrogen atom to obtain the target title compound. The structure of the synthesized 2,2-dichloro-N-[5-[2-[3-(4-methoxyphenyl)-5-phenyl-3,4-dihydro-2H-pyrazol-2-yl]-2-oxoethyl]sulfanyl-1,3,4-thiadiazol-2-yl]acetamide (yield 90%) was confirmed by 1H, 13C, 2D NMR and LC-MS spectra. Anticancer activity in "60 lines screening" (NCI DTP protocol) was studied in vitro for the title compound. [ABSTRACT FROM AUTHOR]