title: 11a-N-Tosyl-5-deoxi-pterocarpan (LQB-223), a promising prototype for targeting MDR leukemia cell lines.
abstract: Aza-deoxi-pterocarpans (1) were synthesized through palladium-catalyzed aza-arylation of dihydronaphtalen, and showed antineoplastic effect on MDR leukemic cell lines (K562, Lucena-1 and FEPS). Compounds 1c-d were prepared to identify the pharmacophoric group responsible for the activity as well as compounds 2a-c were prepared to evaluate the structural requirements in the D-ring. LQB-223 (1b) is the most promising antileukemic agent since it was the most active on MDR cells without detectable toxicity to normal immune system cells.
authors.affiliation: Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rua Marquês de São Vicente 225, Gávea-Rio de Janeiro, RJ 22435-900, Brazil. Electronic address: camilla-buarque@puc-rio.br.
authors.forename: Camilla D
authors.initials: CD
authors.lastname: Buarque
authors.affiliation: Laboratório de Imunologia Tumoral, Instituto de Bioquímica Médica Leopoldo de Meis, Centro de Ciências da Saúde, Bloco H, Universidade Federal do Rio de Janeiro, RJ 21941-590, Brazil; Laboratório de Química Bioorgânica, Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Bloco H, Universidade Federal do Rio de Janeiro, RJ 21941-590, Brazil. Electronic address: salustiano@bioqmed.ufrj.br.
authors.forename: Eduardo J
authors.initials: EJ
authors.lastname: Salustiano
authors.affiliation: Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rua Marquês de São Vicente 225, Gávea-Rio de Janeiro, RJ 22435-900, Brazil.
authors.forename: Kevin C
authors.initials: KC
authors.lastname: Fraga
authors.affiliation: Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rua Marquês de São Vicente 225, Gávea-Rio de Janeiro, RJ 22435-900, Brazil.
authors.forename: Bruna R M
authors.initials: BR
authors.lastname: Alves
authors.affiliation: Laboratório de Química Bioorgânica, Núcleo de Pesquisas de Produtos Naturais, Centro de Ciências da Saúde, Bloco H, Universidade Federal do Rio de Janeiro, RJ 21941-590, Brazil.
authors.forename: Paulo R R
authors.initials: PR
authors.lastname: Costa
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D002453:Cell Cycle / Q000187:drug effects; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D002470:Cell Survival / Q000187:drug effects; D004305:Dose-Response Relationship, Drug; D018432:Drug Resistance, Multiple / Q000187:drug effects*; D004354:Drug Screening Assays, Antitumor; D006801:Humans; D020014:K562 Cells; D008214:Lymphocytes / Q000187:drug effects; D051379:Mice; D015394:Molecular Structure; D036343:Pterocarpans / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship
chemical_list: C000593733:11a-N-tosyl-5-deoxi-pterocarpan; D000970:Antineoplastic Agents; D036343:Pterocarpans
keywords: Antileukemic activity; Aza-arylation; Aza-heck; Sulfonamide