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New thiourea and 1,3‐thiazolidin‐4‐one derivatives effective on the HIV ‐1 virus
Author(s) -
Bielenica Anna,
Sanna Giuseppina,
Madeddu Silvia,
Struga Marta,
Jóźwiak Michał,
Kozioł Anna E.,
Sawczenko Aleksandra,
Materek Ilona B.,
Serra Alessandra,
Giliberti Gabriele
Publication year - 2017
Publication title -
chemical biology and drug design
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.59
H-Index - 77
eISSN - 1747-0285
pISSN - 1747-0277
DOI - 10.1111/cbdd.13009
Subject(s) - thiourea , benzothiazole , moiety , chemistry , cytotoxicity , nucleoside , reverse transcriptase , biological activity , stereochemistry , mode of action , combinatorial chemistry , rna , biochemistry , in vitro , organic chemistry , gene
Thiourea derivatives have been reported to possess many biological activities, among them antiviral and antitumoral properties. As part of our continuing effort to develop new active compounds, we report the synthesis and the evaluation of new fifteen thiourea derivatives with 1,3‐benzothiazole‐2‐yl moiety, among them a group of biologically active ( 1–7 ) also underwent cyclization to 1,3‐thiazolidin‐4‐ones. Molecular structure of four compounds ( 4 , 13 , 15 and 3a ) was determined by an X‐ray crystallography. We here report the evaluation of their cytotoxicity against human leukaemia/lymphoma‐ and solid tumour‐derived cell lines and of their antiviral activity against HIV ‐1 and representatives of ss RNA and ds DNA viruses. Derivative 5 showed an interesting activity against HIV ‐1 wild type and against variants carrying clinically relevant mutations. A colorimetric enzyme immunoassay clarified its mode of action as a non‐nucleoside inhibitor of the reverse transcriptase.