Synthesis of 11a - Aza-5-deoxi-pterocarpans Via Palladium Aza-arylation of Dihydronaphtalen by Orto-iodoanilines Derivatives

Synthesis of 11a - Aza-5-deoxi-pterocarpans Via Palladium Aza-arylation of Dihydronaphtalen by Orto-iodoanilines Derivatives

Buarque, Camilla D.; Fraga, Kevin C. de; Costa, Paulo R. R.

Abstract:

During the course of our studies aiming the discovery of new antineoplasic and antiparasitary compounds, we recently described the synthesis of the aza-dehydropterocarpan 1a (Figure 1). In order to know more about the structural features required for the observed activities of 1a, we report in this work the synthesis of compounds 1b-d and 2a-c. Our first goal was to modify the substituent at the nitrogen atom in the C-ring (1b-c) to see if this moiety is part of the pharmacophore. In analogues 2a-b, halogen atoms at D-ring were introduced to target diverse set of relevant medicinal proteins due to halogen bond. Trying to understand more about the mechanism of the antineoplasic activity, cell death was evaluated by flow cytometry.

During the course of our studies aiming the discovery of new antineoplasic and antiparasitary compounds, we recently described the synthesis of the aza-dehydropterocarpan 1a (Figure 1). In order to know more about the structural features required for the observed activities of 1a, we report in this work the synthesis of compounds 1b-d and 2a-c. Our first goal was to modify the substituent at the nitrogen atom in the C-ring (1b-c) to see if this moiety is part of the pharmacophore. In analogues 2a-b, halogen atoms at D-ring were introduced to target diverse set of relevant medicinal proteins due to halogen bond. Trying to understand more about the mechanism of the antineoplasic activity, cell death was evaluated by flow cytometry.

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DOI: 10.5151/chempro-15bmos-BMOS2013_201397224911

Referências bibliográficas

• [1] 1Buarque, C.D.; Militão Gardênia C.G.; Lima, Dayse .J. B.; Costa-Lotufo Letícia V.; Pessoa, Cláudia.; de Moraes, Manoel Odorico, Cunha-Junior, Edézio Ferreira; Torres-Santos, Eduardo Caio; Netto, Chaquip D.; Costa, Paulo R.R.. Bioorganic And Medicinal Chemistry 2011, 19, 6885.
• [2] 2Wilcken, R.; 2Zimmermann, M. O.; Lange, A.; Joerger, A.C.and Boeckler , F. M. Principles and Applications of Halogen Bonding in Medicinal Chemistry and Chemical Biology J. Med. Chem. 2013, 56, 1363

Como citar:

Buarque, Camilla D.; Fraga, Kevin C. de; Costa, Paulo R. R.; "Synthesis of 11a - Aza-5-deoxi-pterocarpans Via Palladium Aza-arylation of Dihydronaphtalen by Orto-iodoanilines Derivatives", p-118-118. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_201397224911