title: Pterocarpanquinones, aza-pterocarpanquinone and derivatives: synthesis, antineoplasic activity on human malignant cell lines and antileishmanial activity on Leishmania amazonensis.
abstract: Pterocarpanquinones (1a-e) and the aza-pterocarpanquinone (2) were synthesized through palladium catalyzed oxyarylation and azaarylation of conjugate olefins, and showed antineoplasic effect on leukemic cell lines (K562 and HL-60) as well as colon cancer (HCT-8), gliobastoma (SF-295) and melanoma (MDA-MB435) cell lines. Some derivatives were prepared (3-8) and evaluated, allowing establishing the structural requirements for the antineoplasic activity in each series. Compound 1a showed the best selectivity index in special for leukemic cells while 2 showed to be more bioselective for HCT-8, SF-295 and MDA-MB435 cells. Pterocarpanquinones 1a and 1c-e, as well as 8 were the most active on amastigote form of Leishmania amazonensis in culture. Compounds 1a, 1c and 8 showed the best selectivity index.
authors: Departamento de Química, Pontifícia Universidade Católica do Rio de Janeiro, Rio de Janeiro, RJ, Brazil.
authors: Camilla D
authors: CD
authors: Buarque
authors: Gardenia C G
authors: GC
authors: Militão
authors: Daisy J B
authors: DJ
authors: Lima
authors: Leticia V
authors: LV
authors: Costa-Lotufo
authors: Cláudia
authors: C
authors: Pessoa
authors: Manoel Odorico
authors: MO
authors: de Moraes
authors: Edézio Ferreira
authors: EF
authors: Cunha-Junior
authors: Eduardo Caio
authors: EC
authors: Torres-Santos
authors: Chaquip D
authors: CD
authors: Netto
authors: Paulo R R
authors: PR
authors: Costa
mesh_terms: D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D045744:Cell Line, Tumor; D004354:Drug Screening Assays, Antitumor; D018922:HL-60 Cells; D006801:Humans; D020014:K562 Cells; D007894:Leishmania mexicana / Q000187:drug effects*; D051379:Mice; D008807:Mice, Inbred BALB C; D036343:Pterocarpans / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D011809:Quinones / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D014344:Trypanocidal Agents / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; D036343:Pterocarpans; D011809:Quinones; D014344:Trypanocidal Agents