title: Design, synthesis, SAR, and biological evaluation of new 4-(phenylamino)thieno[2,3-b]pyridine derivatives.
abstract: 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.
authors.affiliation: 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
authors.forename: Alice Maria Rolim
authors.initials: AM
authors.lastname: Bernardino
authors.forename: Luiz Carlos
authors.initials: LC
authors.lastname: da Silva Pinheiro
authors.forename: Carlos Rangel
authors.initials: CR
authors.lastname: Rodrigues
authors.forename: Natália Izabel
authors.initials: NI
authors.lastname: Loureiro
authors.forename: Helena Carla
authors.initials: HC
authors.lastname: Castro
authors.forename: Adriana
authors.initials: A
authors.lastname: Lanfredi-Rangel
authors.forename: Juliano
authors.initials: J
authors.lastname: Sabatini-Lopes
authors.forename: Júlio César
authors.initials: JC
authors.lastname: Borges
authors.forename: Jane Maria
authors.initials: JM
authors.lastname: Carvalho
authors.forename: Gilberto Alves
authors.initials: GA
authors.lastname: Romeiro
authors.forename: Vitor Francisco
authors.initials: VF
authors.lastname: Ferreira
authors.forename: Izabel C P P
authors.initials: IC
authors.lastname: Frugulhetti
authors.forename: Marcos André
authors.initials: MA
authors.lastname: Vannier-Santos
mesh_terms: 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*
chemical_list: D000631:Aminopyridines; D000981:Antiprotozoal Agents; D013876:Thiophenes