Synthesis of novel 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4]diazepines under microwave irradiation as potential anti-tumor agents.
A new series of 6,6a,7,8-tetrahydro-5H-naphtho[1,2-e]pyrimido[4,5-b][1,4]diazepines 4a-f and 5a-f were efficiently synthesized in good yields from the reaction of E-2-arylidene-1-tetralones 1 and the respective tri- or tetraaminopyrimidines 2 or 3 under microwave irradiation using DMF as solvent and catalytic amounts of BF(3).OEt(2). Six of the obtained compounds were selected and tested by the National Cancer Institute (NCI-USA) against 60 different tumor cell lines. In particular, compounds 5a, 5c and 5e presented remarkable anti-tumor activity against melanoma cancer in SK-MEL-5 cell line.
Insuasty
Braulio
B
Heterocyclic Compounds Research Group, Department of Chemistry, Universidad del Valle, A.A. 25360 Cali, Colombia. brainsu@univalle.edu.co
García
Angélica
A
Quiroga
Jairo
J
Abonia
Rodrigo
R
Nogueras
Manuel
M
Cobo
Justo
J
D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D002384:Catalysis; D045744:Cell Line, Tumor; D006801:Humans; D020128:Inhibitory Concentration 50; D008872:Microwaves; D012997:Solvents / Q000737:chemistry; D044024:Tetralones / Q000737:chemistry
D000970:Antineoplastic Agents; D001381:Azepines; D012997:Solvents; D044024:Tetralones