Synthesis of 1,4-Biphenyl-triazole Derivatives as Possible 17β-HSD1 Inhibitors: An in Silico Study

• Published in: ACS omega Vol. 5; no. 23; pp. 14061 - 14068
• Main Authors: Hernández-López, Hiram, Leyva-Ramos, Socorro, Azael Gómez-Durán, Cesar Fernando, Pedraza-Alvarez, Alberto, Rodríguez-Gutiérrez, Irving Rubén, Leyva-Peralta, Mario Alberto, Razo-Hernández, Rodrigo Said
• Format: Journal Article
• Language: English
• Published: American Chemical Society 16-06-2020
• ISSN: 2470-1343; 2470-1343
• DOI: 10.1021/acsomega.0c01519

Triazoles
occupy an important position in medicinal chemistry because
of their various biological activities. The structural features of
1,2,3-triazoles enable them to act as a bioisostere of different functional
groups such as amide, ester, carboxylic acid, and heterocycle, being
capable of forming hydrogen bonds and π–π interactions
or coordinate metal ions with biological targets. In this work, the
synthesis of 1,2,3-triazole derivatives via copper(I)-catalyzed azide–alkyne
cycloaddition (CuAAC) is reported. Overexpression of 17β-hydroxysteroid
dehydrogenase type 1 (17β-HSD1) is often found in breast cancer
cells. Molecular similarity and docking analysis were used to evaluate
the potential inhibitory activity of 1,2,3-triazoles synthesized over
17β-HSD1 for the treatment of mammary tumors. Our
in
silico
analysis shows that compounds
4c
,
4d
,
4f
,
4g
, and
4j
are
good molecular scaffold candidates as 17β-HSD1 inhibitors.