Semi-synthesis of beta-keto-1,2,3-triazole derivatives from ethinylestradiol and evaluation of the cytotoxic activity

Author(s)

Queiroz, Thayane M. ^[1] ; Orozco, Erika V. M. ^[1] ; Silva, Valdenizia R. ^[2] ; Santos, Luciano S. ^[2] ; Soares, Milena B. P. ^[2] ; Bezerra, Daniel P. ^[2] ; Porto, Andre L. M. ^[1]

Affiliation

^[1] Univ Sao Paulo, Inst Quim Sao Carlos, Lab Quim Organ & Biocatalise, Av Joao Dagnone 1100, Ed Quim Ambiental, BR-13563120 Sao Carlos, SP - Brazil

^[2] Fundacao Oswaldo Cruz, Ctr Pesquisa Goncalo Moniz, R Waldemar Falcao 121, BR-40296710 Salvador, BA - Brazil

• Document type: Journal article
• Source: HELIYON; v. 5, n. 9 SEP 2019.
• Web of Science Citations: 0

Abstract

In this study, we report our contribution to the application of the copper-catalyzed azide-alkyne cycloaddition (CuAAC) reaction for the synthesis of beta-keto-1,2,3-triazole derivatives 3a-f from ethinylestradiol and their application in the inhibition of two human cancer cells lines: human breast adenocarcinoma (MCF-7) and human hepatocellular carcinoma (HepG2). The beta-keto-1,2,3-triazole derivates 3a-f exhibited moderate cytotoxic activity for the HepG2 cells with IC50 values of 29.7 mu M (3a), 16.4 mu M (3b), 17.8 mu M (3c), 20.4 mu M (3d), 28.1 mu M (3e) and 28.2 mu M (3f). The semi-synthetic beta-keto-1,2,3-triazoles derivatives 3a-f were all characterized by FT-IR, NMR, HRMS and {[}alpha](D). (AU)

• FAPESP's process: 14/18257-0 - New approaches in biocatalytic reactions
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants
• FAPESP's process: 16/20155-7 - Biocatalytic reactions of aminolysis and kinetic resolution by lipases and biodegradation of agrochemicals by microorganisms
• Grantee: Andre Luiz Meleiro Porto
• Support Opportunities: Regular Research Grants