Synthesis and antiviral activity of new 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-4-carboxylic acids derivatives.

Autor: Bernardino, Alice, Azevedo, Alexandre, Pinheiro, Luiz, Borges, Júlio, Carvalho, Vinícius, Miranda, Milene, Meneses, Marcelo, Nascimento, Marcelo, Ferreira, Davis, Rebello, Moacyr, Silva, Viveca, Frugulhetti, Izabel
Zdroj: Medicinal Chemistry Research; Dec2007, Vol. 16 Issue 7-9, p352-369, 18p
Abstrakt: The synthesis of new 4-(phenylamino)-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-4-carboxylic acid (3a-l) derivatives and the new 4-[(methylpyridin-2-yl)amino]-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-4-carboxylic acid (5a–c) derivatives was achieved with an efficient synthetic route. Ethyl 4-chloro-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-5-carboxylate (1) on fusion with appropriate substituted anilines or aminopicolines gave the required new ethyl 4-(phenylamino)-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-5-carboxylates (2a–l) (52–82%) or new ethyl 4-[(methylpyridin-2-yl)amino]-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-5-carboxylates (4a–c) (50–60%), respectively. Subsequent hydrolysis of the esters afforded the corresponding carboxylic acids (3a–l) (86–93%) and (5a–c) in high yield (80–93%). Inhibitory effects of 4-(phenylamino)/4-[(methylpyridin-2-yl)amino]-1-phenyl-1 H-pyrazolo[3,4- b]pyridine-4-carboxylic acids. Derivatives on Herpes simplex virus type 1 (HSV-1), Mayaro virus (MAY) and vesicular stomatitis virus (VSV) were investigated. Compounds 2d, 3f, 3a, and 3c exhibited antiviral activity against HSV-1, MAY, and VSV virus with EC50 values of 6.8, 2.2, 4.8, 0.52, 2.5, and 1.0. None of these compounds showed toxicity for Vero cells. [ABSTRACT FROM AUTHOR]
Databáze: Complementary Index
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