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Sci. Pharm. 2016, 84(3), 467-483; doi:10.3390/scipharm84030467

Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives

1
Fundação Oswaldo Cruz (Fiocruz), Instituto de Tecnologia em Fármacos Farmanguinhos, Rua Sizenando Nabuco, 100, Manguinhos 21041-250, Rio de Janeiro, Brazil
2
Instituto de Pesquisa Clínica Evandro Chagas (IPEC)Av. Brasil, 4365, Fiocruz, 21040-900 Rio de Janeiro, Brazil
3
Department of Chemistry, University of Aberdeen, Aberdeen AB2 3UE, Scotland, UK
4
CHEMSOL, 1 Harcourt Road, Aberdeen AB15 5NY, Scotland, UK
*
Author to whom correspondence should be addressed.
Academic Editor: Thomas Erker
Received: 25 August 2015 / Accepted: 18 October 2015 / Published: 18 October 2015
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Abstract

Both sonochemical and classical methodologies have been employed to convert camphor, 1,7,7-trimethylbicyclo[2.2.1]heptan-2-one, C9H16C=O, into a number of derivatives including hydrazones, C9H16C=N-NHAr 3, imines, C9H16C=N-R 7, and the key intermediate nitroimine, C9H16C=N-NO2 6. Reactions of nitroamine 6 with nucleophiles by classical methods provided the desired compounds in a range of yields. In evaluations of activity against Mycobacterium tuberculosis, compound 7j exhibited the best activity (minimal inhibitory concentration (MIC) = 3.12 µg/mL), comparable to that of the antitubercular drug ethambutol. The other derivatives displayed modest antimycobacterial activities at 25–50 µg/mL. In in vitro tests against cancer cell lines, none of the synthesized camphor compounds exhibited cytotoxic activities. View Full-Text
Keywords: camphor; sonochemistry; hydrazones; imines; tuberculosis camphor; sonochemistry; hydrazones; imines; tuberculosis
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MDPI and ACS Style

da Silva, E.T.; da Silva Araújo, A.; Moraes, A.M.; de Souza, L.A.; Silva Lourenço, M.C.; de Souza, M.V.N.; Wardell, J.L.; Wardell, S.M.S.V. Synthesis and Biological Activities of Camphor Hydrazone and Imine Derivatives. Sci. Pharm. 2016, 84, 467-483.

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