New enamine derivatives of lapachol and biological activity.
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.
Oliveira
Mailcar F
MF
Departamento de Química Orgânica e Inorgânica, Universidade Federal do Ceará, Fortaleza, Ceará, Brazil.
Lemos
Telma G
TG
de Mattos
Marcos C
MC
Segundo
Taciana A
TA
Santiago
Gilvandete M P
GM
Braz-Filho
Raimundo
R
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
D000588:Amines; D000972:Antineoplastic Agents, Phytogenic; D009285:Naphthoquinones; C008252:lapachol