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Synthesis 2019; 51(02): 573-577
DOI: 10.1055/s-0037-1610291
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Antitumor Activity of Novel 1-Substituted 3-(4,5-Substituted 1,2,4-Triazol-3-yl)-β-carboline Derivatives

George Brand
a   Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, Maringá - PR, 87020-900, Brazil   Email: mhsarragiotto@uem.br
,
Carla M. B. Gomes
a   Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, Maringá - PR, 87020-900, Brazil   Email: mhsarragiotto@uem.br
,
Willian F. Costa
a   Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, Maringá - PR, 87020-900, Brazil   Email: mhsarragiotto@uem.br
,
Mary A. Foglio
b   Faculdade de Ciências Farmacêuticas, Universidade Estadual de Campinas, Campinas - SP, 13083-859, Brazil
,
Ana L. T. G. Ruiz
c   Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas, Campinas - SP, 13083-970, Brazil
,
Maria H. Sarragiotto*
a   Departamento de Química, Universidade Estadual de Maringá, Av. Colombo 5790, Maringá - PR, 87020-900, Brazil   Email: mhsarragiotto@uem.br
› Author AffiliationsThis work was supported by Fundação Araucária (Brazil, PR) and Fundação de Amparo à Pesquisa de São Paulo (FAPESP).
Further Information

Publication History

Received: 04 July 2018

Accepted after revision: 30 August 2018

Publication Date:
26 September 2018 (online)

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Abstract

Schiff bases, 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles, and 1,2,4-triazolo[3,4-b][1,3,4]thiadiazoles carrying the β-carboline nucleus were synthesized from 3-(4-amino-5-mercapto-1,2,4-triazol-3-yl)-β-carbolines. The compounds were evaluated for their in vitro antitumor activity against eight human cancer cell lines. The 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazole derivatives showed a broad spectrum of antitumor activity, with GI50 values lower than 13 μM for all cell lines tested. In general, all tested compounds showed potent activity against the breast (MCF-7) cancer cell line, with GI50 values in the range of 2.07 to 4.58 μM.

Key words

β-carbolines - 4,5-substituted 1,2,4-triazoles - Schiff bases - 1,2,4-triazolo[4,3-d][1,2,3,4]thiatriazoles - antitumor activity
 

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