Seleno- and Telluro-Functionalization of Quinones: Molecules with Relevant Biological Application

Quinones and organochalcogens are classes of compounds with great biological applicability, such as antioxidant, anticancer, anti-Alzheimer, and antidepressant activities, among others. Thus, the combination of these two classes of compounds is important to obtain new hits with biological activities that are additive or synergistic. Several methodologies for the preparation of this class of hybrid compound have been widely described. Many of the prepared hybrid molecules have shown increased biological activities and, in some cases, to act as two distinct pharmacophores. In this review, methods for the preparation of selenium-quinones, tellurium-quinones and their biological applications are highlighted.

Keywords:
selenides; tellurides; naphthoquinones; organochalcogens; biological activity

Authorship

Pâmella S. Cordeiro

Laboratório SupraSelen, Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, 24020-141 Niterói-RJ, BrazilUniversidade Federal FluminenseBrazilNiterói, RJ, BrazilLaboratório SupraSelen, Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, 24020-141 Niterói-RJ, Brazil

https://orcid.org/0000-0002-3644-1786

Ingrid C. Chipoline

https://orcid.org/0000-0001-7705-2480

Ruan C. B. Ribeiro

Laboratório de Síntese Orgânica Aplicada (LabSOA), Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, 24020-141 Niterói-RJ, BrazilUniversidade Federal FluminenseBrazilNiterói, RJ, BrazilLaboratório de Síntese Orgânica Aplicada (LabSOA), Departamento de Química Orgânica, Instituto de Química, Universidade Federal Fluminense, Campus do Valonguinho, 24020-141 Niterói-RJ, Brazil

https://orcid.org/0000-0001-6847-9300

David R. Pinho

Vitor F. Ferreira

Faculdade de Farmácia, Departamento de Tecnologia Farmacêutica, Universidade Federal Fluminense, 24241-000 Niterói-RJ, BrazilUniversidade Federal FluminenseBrazilNiterói, RJ, BrazilFaculdade de Farmácia, Departamento de Tecnologia Farmacêutica, Universidade Federal Fluminense, 24241-000 Niterói-RJ, Brazil

https://orcid.org/0000-0002-2166-766X

Fernando C. da Silva ^**e-mail: fcsilva@id.uff.br; nascimentovanessa@id.uff.br

https://orcid.org/0000-0002-2042-3778

Luana S. M. Forezi

https://orcid.org/0000-0002-7657-4268

Vanessa Nascimento ^**e-mail: fcsilva@id.uff.br; nascimentovanessa@id.uff.br

https://orcid.org/0000-0001-9413-7638

*e-mail: fcsilva@id.uff.br; nascimentovanessa@id.uff.br

Editors handled this article: Teodoro S. Kaufman and Brenno A. D. Neto (Associate)

Author Contributions

Pâmella S. Cordeiro, Ingrid C. Chipoline, Ruan C. B. Ribeiro, David R. Pinho were responsible for the bibliographic search, writing original draft and drawing of the schemes; Vitor F. Ferreira, Fernando C. da Silva, Luana S. M. Forezi and Vanessa Nascimento for investigation, project administration resources, writing original draft and writing-review and editing writing.

Pâmella S. Cordeiro was born in Niterói-RJ in 1996. She received her Bachelor’s degree in Chemistry in 2019 from Universidade Federal Fluminense. In the same year she started doctoral studies in the Postgraduate Program in Chemistry at Universidade Federal Fluminense. Her line of research is based on the green synthesis of organocompounds with biological potential.

Ingrid C. Chipoline was born in Niterói-RJ in 1993. In 2016, she graduated in Industrial Chemistry from Universidade Federal Fluminense. Two years later she obtained her Master’s degree in Chemistry from the same institution. She is currently in her final year of doctoral studies in the Postgraduate Program in Chemistry at Universidade Federal Fluminense. Her project is based on the synthesis of organochalcogenic compounds and their application in medicinal chemistry and organic catalysis.

Ruan C. B. Ribeiro is graduated in Chemistry from Universidade Federal Fluminense (2014), where he gained experience in Chemistry Education, participating in the Institutional Program for Teaching Initiation Scholarships (PIBID). He holds a Master’s degree in Chemistry (2017) from the Postgraduate Program in Chemistry at the Institute of Chemistry at the Universidade Federal Fluminense. He is currently pursuing a doctorate in Chemistry in the Postgraduate Program in Chemistry at the Universidade Federal Fluminense, where he is developing a project with an emphasis on bioactive substances at the Applied Organic Synthesis Laboratory (LabSOA).

David R. Pinho is a pharmacy student at Universidade Federal Fluminense. He is currently a scientific initiation scholarship holder in a project financed by the Carlos Chagas Filho Research Support Foundation of the State of Rio de Janeiro (FAPERJ). His work has an emphasis on the synthesis of compounds containing organochalcogen menadione hybrids with potential bioactivity, being developed at the Laboratory of Applied Organic Synthesis (LabSOA).

Vitor F. Ferreira received his Bachelor’s degree in Chemistry in 1976 and a Master’s degree in Natural Product Chemistry in 1980, both from the Federal University of Rio de Janeiro. In 1984 he finished his PhD in Organic Chemistry at the University of California, San Diego. In 1986 he became Professor of Organic Chemistry in the Organic Chemistry Department of Universidade Federal Fluminense (UFF), in Niterói-RJ, and in 1995 became full Professor. In 1998 he spent one year in postdoctoral research at the University of Oklahoma. Professor Ferreira is currently a full Professor at the Pharmaceutical Technology Department of UFF, researching the synthesis of small molecules, with a focus on the development of new methods in organic synthesis in the search for bioactive compounds and their pharmaceutical formulation. He is a full member of the Brazilian Academy of Science and was president of the Brazilian Chemical Society from 2012 to 2014. He is currently the advisor to the presidency of the “Fundação Carlos Chagas Filho de Amparo à Pesquisa do Estado do Rio de Janeiro (FAPERJ)”.

Fernando C. da Silva received his Bachelor’s degree in Industrial Chemistry in 2002 and his PhD in 2007, both from Universidade Federal Fluminense. He then completed a postdoctoral stage at the University of Aveiro (Portugal) at the Laboratory of Synthesis of Porphyrin Compounds. Currently, he is an Associate Professor in the Department of Organic Chemistry of Universidade Federal Fluminense. He was an affiliate member of the Brazilian Academy of Science 2016-2020 and his research interests focus on the synthesis of quinones, 1,2,3-triazoles, coumarins, carbohydrates, diazo compounds, β-enaminones and porphyrins.

Luana S. M. Forezi received her Bachelor’s degree in Chemistry in 2008 from the Federal University of Juiz de Fora and her MSc (2011) and PhD (2014), with a period at the University of Aveiro (Portugal), at the Laboratory of Synthesis of Porphyrin Compounds, both at Universidade Federal Fluminense. She carried out two postdoctoral studies: one at the Federal University of Rio de Janeiro (2015) and another at the Fluminense Federal University (2015-2020). Since 2020, she has been adjunct Professor in the Department of Organic Chemistry at Universidade Federal Fluminense. Her the research interests focus on the synthesis of coumarins, 1,2,3-triazoles and quinones.

Vanessa Nascimento was born in Marau (RS State), Brazil. In 2009 she obtained her BSc degree in Industrial Chemistry from the Federal University of Santa Maria. She then moved to the Federal University of Santa Catarina, where she received her MSc (2011) and PhD degrees (2015) at the Selenium and Tellurium Derivatives Synthesis Laboratory and with a period at the Università degli Studi di Perugia in the Santi’s group. She then completed a postdoctoral stage at UFSC (2015-2016) in the Catalysis and Interfacial Phenomena Laboratory. Since 2016 she has been adjunct Professor in the Department of Organic Chemistry at Universidade Federal Fluminense. Her research focuses mainly on the synthesis and applications of pillararenes and organochalcogenides.

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