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Molecules 2012, 17(5), 6100-6113; doi:10.3390/molecules17056100

Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents

1, 2, 2, 2, 2, 3, 1 and 1,*
1 Departamento de Química, Centro de Ciências Exatas, Universidade Estadual de Maringá, Av. Colombo, 5790, Maringá, 87020-900 PR, Brazil 2 Centro Pluridisciplinar de Pesquisas Químicas, Biológicas e Agrícolas (CPQBA), Universidade Estadual de Campinas, 6171, Campinas, 13083-970 SP, Brazil 3 Centro de Engenharias e Ciências Exatas, Universidade Estadual do Oeste do Paraná, Rua da Faculdade, 645, Toledo, 85903-000 PR, Brazil
* Author to whom correspondence should be addressed.
Received: 5 April 2012 / Revised: 5 May 2012 / Accepted: 7 May 2012 / Published: 21 May 2012
(This article belongs to the Section Medicinal Chemistry)
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In the present work, we report the synthesis and in vitro anticancer and antimicrobial activity evaluation of a new series of 1-substituted-β-carboline derivatives bearing a 4-benzylidene-4H-oxazol-5-one unity at C-3. The compound 2-[1-(4-methoxyphenyl)-9H-β-carbolin-3-yl]-4-(benzylidene)-4H-oxazol-5-one (11) was the most active derivative, exhibiting a potent cytotoxic activity against glioma (U251), prostate (PC-3) and ovarian (OVCAR-03) cancer cell lines with IC50 values of 0.48, 1.50 and 1.07 µM, respectively. An in silico study of the ADME properties of the novel synthesized β-carboline derivatives was also performed.
Keywords: b-carboline; 4H-oxazol-5-one; cytotoxic activity; antimicrobial activity b-carboline; 4H-oxazol-5-one; cytotoxic activity; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License (CC BY) which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Savariz, F.C.; Foglio, M.A.; de Carvalho, J.E.; Ruiz, A.L.T.G.; Duarte, M.C.T.; da Rosa, M.F.; Meyer, E.; Sarragiotto, M.H. Synthesis and Evaluation of New β-Carboline-3-(4-benzylidene)-4H-oxazol-5-one Derivatives as Antitumor Agents. Molecules 2012, 17, 6100-6113.

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