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Synthesis and cytotoxic activity of some new heterocycles incorporating cyclohepta[b]thiophene‐3‐carboxamide derivatives
Author(s) -
Gouda Moustafa A.,
AlGhorbani Mohammed,
AlZaqri Nabil
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.4085
Subject(s) - chemistry , thiophene , cyanoacetamide , knoevenagel condensation , carboxamide , combinatorial chemistry , aryl , cytotoxic t cell , derivative (finance) , reagent , stereochemistry , moiety , isothiocyanate , in vitro , medicinal chemistry , organic chemistry , catalysis , biochemistry , alkyl , economics , financial economics
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).