title: Synthesis and differential antiproliferative activity of Biginelli compounds against cancer cell lines: Monastrol, oxo-monastrol and oxygenated analogues.
abstract: The synthesis and differential antiproliferative activity of monastrol (1a), oxo-monastrol (1b) and eight oxygenated derivatives 3a,b-6a,b on seven human cancer cell lines are described. For all evaluated cell lines, monastrol (1a) was shown to be more active than its oxo-analogue, except for HT-29 cell line, suggesting the importance of the sulfur atom for the antiproliferative activity. Monastrol (1a) and the thio-derivatives 3a, 4a and 6a displayed relevant antiproliferative properties with 3,4-methylenedioxy derivative 6a being approximately more than 30 times more potent than monastrol (1a) against colon cancer (HT-29) cell line.
authors.affiliation: Instituto de Química, Universidade Federal do Rio Grande do Sul, CP 15003, 91501-970 Porto Alegre, RS, Brazil. dennis@iq.ufrgs.br
authors.forename: Dennis
authors.initials: D
authors.lastname: Russowsky
authors.forename: Rômulo F S
authors.initials: RF
authors.lastname: Canto
authors.forename: Sergio A A
authors.initials: SA
authors.lastname: Sanches
authors.forename: Marcelo G M
authors.initials: MG
authors.lastname: D'Oca
authors.forename: Angelo
authors.initials: A
authors.lastname: de Fátima
authors.forename: Ronaldo A
authors.initials: RA
authors.lastname: Pilli
authors.forename: Luciana K
authors.initials: LK
authors.lastname: Kohn
authors.forename: Márcia A
authors.initials: MA
authors.lastname: Antônio
authors.forename: João Ernesto
authors.initials: JE
authors.lastname: de Carvalho
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002460:Cell Line; D049109:Cell Proliferation / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D010100:Oxygen / Q000737:chemistry*; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D013871:Thiones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
chemical_list: D000970:Antineoplastic Agents; D011743:Pyrimidines; D013871:Thiones; C400223:monastrol; D010100:Oxygen