title: New enamine derivatives of lapachol and biological activity.
abstract: A convenient synthesis of the new enamine derivatives 2-(4-morpholinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione, 2-(1-piperidinyl)-3-(3-methyl-2-butenyl)-1,4-naphtalenedione and 2-(1-pyrrolidinyl)-3-(3-methyl-2-butenyl)-1,4-naphthalenedione was carried out from natural 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthalenedione (lapachol) and morpholine, piperidine and pyrrolidine. The structures of the products were established mainly by NMR analysis, including 2D experiments. Biological activities of these products were evaluated against Artemia salina, Aedes aegypti and cytotoxicity using A549 human breast cells.
authors.affiliation: Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza, Ceará, Brazil.
authors.forename: Mailcar F
authors.initials: MF
authors.lastname: Oliveira
authors.forename: Telma G
authors.initials: TG
authors.lastname: Lemos
authors.forename: Marcos C
authors.initials: MC
authors.lastname: de Mattos
authors.forename: Taciana A
authors.initials: TA
authors.lastname: Segundo
authors.forename: Gilvandete M P
authors.initials: GM
authors.lastname: Santiago
authors.forename: Raimundo
authors.initials: R
authors.lastname: Braz-Filho
mesh_terms: D000330:Aedes / Q000187:drug effects; D000588:Amines / Q000138:chemical synthesis* / Q000494:pharmacology; D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000138:chemical synthesis* / Q000494:pharmacology / Q000627:therapeutic use; D001156:Artemia / Q000187:drug effects; D001943:Breast Neoplasms / Q000188:drug therapy; D004353:Drug Evaluation, Preclinical; D005260:Female; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000494:pharmacology; D014407:Tumor Cells, Cultured / Q000187:drug effects
chemical_list: D000588:Amines; D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; C008252:lapachol