New N-substituted-2-amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine derivatives were synthesized employing a convenient one-pot three-component method and their structures were characterized by 1 H-NMR and single crystal X-ray diffraction analysis. All the synthesized compounds were in vitro screened for antimicrobial activity against Gram-positive (Sarcina lutea) and Gram-negative bacteria (Escherichia coli). In this work, we introduced a chiral residue on the tetrahydropyridine nitrogen, the hitherto the less investigated position on this pharmacophore in order to explore the effect. The antibacterial results showed that the synthesized compounds were active only against Gram-positive bacteria and the (R)-enantiomers displayed a greater antimicrobial potency than their (S)-counterparts. The structure–activity relationship here investigated may provide some interesting clues for future development of tetrahydrothienopyridine derivatives with higher antimicrobial activity.
Synthesis and Antimicrobial Evaluation of Novel Chiral 2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Derivatives / A. Rossetti, N. Bono, G. Candiani, F. Meneghetti, G. Roda, A. Sacchetti. - In: CHEMISTRY & BIODIVERSITY. - ISSN 1612-1872. - 16:6(2019 Jun).
|Titolo:||Synthesis and Antimicrobial Evaluation of Novel Chiral 2-Amino-4,5,6,7-tetrahydrothieno[2,3-c]pyridine Derivatives|
SACCHETTI, ALESSANDRO (Corresponding)
|Parole Chiave:||antimicrobial agents; biological activity; chiral amine; Gewald reaction; heterocycles; synthesis design; tetrahydrothieno[2,3-c]pyridine; bioengineering; biochemistry; chemistry (all); molecular medicine; molecular biology|
|Settore Scientifico Disciplinare:||Settore CHIM/08 - Chimica Farmaceutica|
Settore CHIM/06 - Chimica Organica
|Data di pubblicazione:||giu-2019|
|Data ahead of print / Data di stampa:||3-apr-2019|
|Digital Object Identifier (DOI):||http://dx.doi.org/10.1002/cbdv.201900097|
|Appare nelle tipologie:||01 - Articolo su periodico|