Synthesis, Single Crystal X-Ray, and Anticancer Activity of Some New Thiophene and 1,3-Thiazolidine Derivatives

Resumo

New series of thiophenes 6a–6e and 1,3-thiazolidines 13a–13f and 15a–15e were synthesized starting from 2-(4-methoxybenzoyl)-3-(phenylamino)-3-thioxopropanoate 3. The reaction of 3 with 1-aryl-2-bromoethanones 4a–4e yielded thiophenes 6a–6e. The X-ray single crystal analysis data accumulated for 6c and its structural features can be extended to the analogues 6a, 6b and 6d, 6e. Treatment of 3 with ethyl 2-bromoacetate afforded 1,3-thiazolidinone 11 which upon treatment with aldehydes 12a-f or isatins 14a–4e gave 5-arylidene derivatives 13a–13f and 4-oxo-5(-2-oxoindolin)-3-ylidenes 15a–15e, respectively. The newly synthesized compounds were tested in vitro for their anti-cancer activity against two cell lines (HepG-2 and MCF-7) using MTT assay. Most of these compounds demonstrated a significant anticancer activity compared with that of doxorubicin. Isatin derivative 15a was the most potent compound against HepG-2 cancer cells whereas p-MeO substituted benzylidine 13b showed the highest anticancer activity against MCF-7 cancer cells. The fluoro substituted isatin 15d showed anticancer activity more potent than doxorubicin against both HepG-2 and MCF-7 cancer cells, respectively.