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Synthesis and biological evaluation of heterocyclic compounds, analogs of lignans, obtained by microwave-assisted multi-component reactions


Lignans are a class of natural products of great synthetic and pharmacological interest due to the wide variety of structures and biological properties they exhibit. However, despite its wide occurrence in nature only some of them are found in sufficient quantities for performing biological assays or structural modification to produce biologically more potent derivatives. In this way, total synthesis methods can be used to obtain lignans and analogues in quantities necessary to perform those tests. Therefore, this research project aims to study the obtaining of heterocyclic analogs of lignans aryltetralinic and arylnaphthalenic for multicomponent reactions assisted by microwave irradiation (MW) using as components the tetronic acid, an aromatic aldehyde and phenolic derivatives for obtaining heterocyclic analog with oxygen at position 7 of the aryltetralinic skeleton. To obtain the heterocyclic analogues with nitrogen at position 7 of aryltetralinic and arylnaphthalenic skeletons will be used the same reagents above substituting the phenolic derivatives by anilinic derivatives. The reaction conditions for obtaining these compounds will be studied through variations of solvents, reagents, temperature and reaction times. The products obtained after purification will be submitted to analysis of NMR and MS to determination of their structures. The different compounds obtained will be evaluated in several in vitro and in vivo biological assays initially to determine their anti-inflammatory, analgesic, antimicrobial, cytotoxic and antiparasitary properties. Compounds that show biological response may undergo structural modification by reactions of reduction, alkylation, adding and removing groups bonded to aromatic rings among other.The biological assays will be conducted in collaboration with researchers from the FEIS-UNESP, Universidade Estadual de Montes Claros and Universidade de Franca. The results of biological assays for anti-inflammatory activity should guide the molecular modeling studies to propose a synthesis of the most active structures in the search for new anti-inflammatory agents. This work will be developed in collaboration with Prof. Dr. João Manuel Marques Cordeiro Laboratory of Molecular Modeling DFQ-FEIS. (AU)

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Scientific publications (4)
(References retrieved automatically from Web of Science and SciELO through information on FAPESP grants and their corresponding numbers as mentioned in the publications by the authors)
BORGES, ALEXANDRE; CASOTI, ROSANA; ANDRADE E SILVA, MARCIO LUIS; DA CUNHA, NAYANE LARISSA; DA ROCHA PISSURNO, ANA PAULA; KAWANO, DANIEL FABIO; DE LAURENTIZ, ROSANGELA DA SILVA. COX Inhibition Profiles and Molecular Docking Studies of the Lignan Hinokinin and Some Synthetic Derivatives. MOLECULAR INFORMATICS, v. 37, n. 12 DEC 2018. Web of Science Citations: 1.
DA ROCHA PISSURNO, ANA PAULA; SANTOS, FERNANDA AMORIM; BOLELA BOVO CANDIDO, ANA CAROLINA; MAGALHAES, LIZANDRA GUIDI; DE LAURENTIZ, ROSANGELA DA SILVA. In vitro leishmanicidal activity of lactone 1,4-dihydroquinoline derivatives against Leishmania (Leishmania) amazonensis. MEDICINAL CHEMISTRY RESEARCH, v. 27, n. 9, p. 2224-2229, SEP 2018. Web of Science Citations: 0.
LAURENTIZ, ROSANGELA S.; GOMES, WILLIAN P.; PISSURNO, ANA P. R.; SANTOS, FERNANDA A.; SANTOS, VINICIUS CRISTIAN O.; MARTINS, CARLOS H. G. Synthesis and antibacterial activity of new lactone 1,4-dihydroquinoline derivatives. MEDICINAL CHEMISTRY RESEARCH, v. 27, n. 4, p. 1074-1084, APR 2018. Web of Science Citations: 3.
DA ROCHA PISSURNO, ANA PAULA; DE LAURENTIZ, ROSANGELA DA SILVA. Synthesis of 4-azo-butenolides. Synthetic Communications, v. 47, n. 20, p. 1874-1878, 2017. Web of Science Citations: 0.

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