Synthesis and cytotoxicity of new aminoterpenylquinones.
Several 6(7)-alkyl-1,4-naphthoquinones (NQ) have been prepared by cycloaddition reactions between the monoterpene alpha-myrcene and p-benzoquinones and halogen and nitrogen-containing functional groups have been introduced at the C-2 position of the naphthoquinone ring via nucleophilic addition or substitution reactions. These substituents at positions 2/3 of the NQ clearly influence the cytotoxic potency of this type of compound. Of particular interest is substitution by arylamino, specifically p-oxyarylamino, groups, which considerably enhance their bioactivity and selectivity.
Miguel del Corral
José M
JM
Departamento de Química Farmacéutica, Facultad de Farmacia, Universidad de Salamanca, E-37007 Salamanca, Spain. jmmcs@usal.es
Castro
María Angeles
MA
Gordaliza
Marina
M
Martín
María Luz
ML
Gualberto
Simone A
SA
Gamito
Ana María
AM
Cuevas
Carmen
C
San Feliciano
Arturo
A
D009682:Magnetic Resonance Spectroscopy; D011809:Quinones / Q000138:chemical synthesis* / Q000633:toxicity; D013055:Spectrophotometry, Infrared; D013729:Terpenes / Q000737:chemistry*
D011809:Quinones; D013729:Terpenes