Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene‐3‐carboxamide derivatives

A series of 2‐amino‐5,6,7,8‐tetrahydro‐4H‐cyclohepta[b]thiophene‐3‐carboxamide‐heterocyclic hybrids were synthesized, characterized and their cytotoxic potencies were assessed on four human cell lines. Cyanoacetamide derivative (5) was used as the key synthetic intermediate for the synthesis many de...

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Veröffentlicht in:Journal of heterocyclic chemistry 2020-10, Vol.57 (10), p.3664-3672
Hauptverfasser: Gouda, Moustafa A., Al‐Ghorbani, Mohammed, Al‐Zaqri, Nabil
Format: Artikel
Sprache:eng
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Zusammenfassung:A series of 2‐amino‐5,6,7,8‐tetrahydro‐4H‐cyclohepta[b]thiophene‐3‐carboxamide‐heterocyclic hybrids were synthesized, characterized and their cytotoxic potencies were assessed on four human cell lines. Cyanoacetamide derivative (5) was used as the key synthetic intermediate for the synthesis many derivatives in this study, derivatives 9, 11, 12 were formed by coupled compound 5 with different aryl/heteryl diazonium chlorides, Gewald reaction and Knoevenagel condensation were used for synthesis derivatives 13, 14, 16 by treated cyanoacetamide (5) with different reagents. In another route, compound 5 treated with phenyl isothiocyanate give thiocarbamoyl derivative (7) which used as intermediate underwent oxidative cyclization with different moieties to offer the corresponding thiazoles and thiophene 18, 19, 20, 21, respectively. in vitro cytotoxic activity of prepared compounds were tested against four human tumor cell lines. The result revealed that compound 11a displayed promising cytotoxic activity against HepG2, HCT‐116, MCF‐7, and PC3 cancer cell lines comparing to the positive control (Doxorubicin).
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.4085