Recent advances of the Povarov reaction in medicinal chemistry

Ouldouz Ghashghaei; Carme Masdeu; Concepción Alonso; Francisco Palacios; Rodolfo Lavilla

doi:10.1016/j.ddtec.2018.08.004

Recent advances of the Povarov reaction in medicinal chemistry

Drug Discov Today Technol. 2018 Nov:29:71-79. doi: 10.1016/j.ddtec.2018.08.004. Epub 2018 Aug 28.

Authors

Ouldouz Ghashghaei¹, Carme Masdeu², Concepción Alonso², Francisco Palacios³, Rodolfo Lavilla⁴

Affiliations

¹ Laboratory of Medicinal Chemistry, Faculty of Pharmacy and Food Sciences and Institute of Biomedicine (IBUB), University of Barcelona, Av. de Joan XXIII, 27-31, 08028 Barcelona, Spain.
² Departamento de Química Orgánica I, Facultad de Farmacia, University of the Basque Country, UPV/EHU Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain.
³ Departamento de Química Orgánica I, Facultad de Farmacia, University of the Basque Country, UPV/EHU Paseo de la Universidad 7, 01006 Vitoria-Gasteiz, Spain. Electronic address: francisco.palacios@ehu.eus.
⁴ Laboratory of Medicinal Chemistry, Faculty of Pharmacy and Food Sciences and Institute of Biomedicine (IBUB), University of Barcelona, Av. de Joan XXIII, 27-31, 08028 Barcelona, Spain. Electronic address: rlavilla@ub.edu.

PMID: 30471676
DOI: 10.1016/j.ddtec.2018.08.004

Abstract

The Povarov multicomponent reaction consists on the condensation of an aniline, an aldehyde, and an activated olefin to generate a tetrahydroquinoline adduct with 3 diversity points. Hereby, we report the main features of this transformation and its uses in medicinal chemistry. Relevant examples of the impact of Povarov adducts in different therapeutic areas are provided.

Publication types

Review

MeSH terms

Aldehydes / chemistry*
Alkenes / chemistry*
Aniline Compounds / chemistry*
Anti-Infective Agents / chemical synthesis
Antineoplastic Agents / chemical synthesis
Catalysis
Chemistry, Pharmaceutical / methods*
Drug Discovery / methods
Neurotransmitter Agents / chemical synthesis
Quinolines / chemical synthesis*
Stereoisomerism

Substances

Aldehydes
Alkenes
Aniline Compounds
Anti-Infective Agents
Antineoplastic Agents
Neurotransmitter Agents
Quinolines
1,2,3,4-tetrahydroquinoline