Synthesis of monomeric and dimeric steroids containing [1,2,4]triazolo[1,5-a]pyrimidines.
The synthesis of several monomeric and dimeric steroidal [1,2,4]triazolo[1,5-a]pyrimidines (TPs) derived from steroids are described. These derivatives were prepared from α,β-unsaturated carbonyl compounds through a Claisen Schmidt condensation and rearrangement of the spiro moiety followed by a cycloaddition with 3-amino-1,2,4-triazole. The antiproliferative activity of compounds 7, 13-15 was tested against human cancer cells; several IG50values were below 10μM.
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico.
Ailed
A
Arenas-González
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico.
Luis Antonio
LA
Mendez-Delgado
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico.
Penélope
P
Merino-Montiel
BioLab, Instituto Universitario de Bio-Orgánica "Antonio González" (IUBO-AG), Universidad de La Laguna, C/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain.
José M
JM
Padrón
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico.
Sara
S
Montiel-Smith
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico. Electronic address: jose.vega@correo.buap.mx.
José Luis
JL
Vega-Báez
Benemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, C.P. 72570 Puebla, Pue., Mexico. Electronic address: maria.meza@correo.buap.mx.
Socorro
S
Meza-Reyes
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000494:pharmacology; D045744:Cell Line, Tumor; D049109:Cell Proliferation / Q000187:drug effects; D006801:Humans; D011743:Pyrimidines / Q000737:chemistry*; D013237:Stereoisomerism; D013256:Steroids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D014230:Triazoles / Q000737:chemistry*
D000970:Antineoplastic Agents; D011743:Pyrimidines; D013256:Steroids; D014230:Triazoles
Cycloaddition; Heterocyclic compounds; Steroids; [1,2,4]Triazolo[1,5-a]pyrimidine; α,β-Unsaturated ketones