Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives.
In this work, we performed the design, synthesis, and the structure-activity relationship studies of 13 new derivatives of thieno[2,3-b]pyridine. These derivatives were prepared in high yields (96-70%) and their structures were elucidated by IR, (1)H, (13)C NMR, and MS. The biological results showed some derivatives as antiparasitic agents against Giardia lamblia. Computational analysis of HOMO and LUMO energy, HOMO orbital coefficient distribution, electrostatic potential map, dipole moment, and density HOMO was performed to gain insight into the SAR aspects. This study pointed the p-methoxy substituted derivative as a leading compound for the development of new microbicidal medicines based on thieno[2,3-b]pyridine analogs.
Bernardino
Alice Maria Rolim
AM
Universidade Federal Fluminense, Instituto de Química, Departamento de Química Orgânica, Programa de Pós-Graduação em Química Orgânica, Campus do Valonguinho, Niterói, RJ, Brazil. alice@rmn.uff.br
da Silva Pinheiro
Luiz Carlos
LC
Rodrigues
Carlos Rangel
CR
Loureiro
Natália Izabel
NI
Castro
Helena Carla
HC
Lanfredi-Rangel
Adriana
A
Sabatini-Lopes
Juliano
J
Borges
Júlio César
JC
Carvalho
Jane Maria
JM
Romeiro
Gilberto Alves
GA
Ferreira
Vitor Francisco
VF
Frugulhetti
Izabel C P P
IC
Vannier-Santos
Marcos André
MA
D000631:Aminopyridines / Q000138:chemical synthesis / Q000494:pharmacology*; D000818:Animals; D000981:Antiprotozoal Agents / Q000138:chemical synthesis / Q000494:pharmacology*; D016829:Giardia lamblia / Q000187:drug effects* / Q000378:metabolism; D015186:Hominidae / Q000469:parasitology; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D013329:Structure-Activity Relationship; D013876:Thiophenes / Q000138:chemical synthesis / Q000494:pharmacology*
D000631:Aminopyridines; D000981:Antiprotozoal Agents; D013876:Thiophenes