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Open AccessArticle

Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents

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Facultad de Ciencias Químicas, Benemérita Universidad Autónoma de Puebla, Ciudad Universitaria, 72570 Puebla, Pue., Mexico
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Instituto de Física “Luis Rivera Terrazas” Benemérita Universidad Autónoma de Puebla Ecocampus Valsequillo, 72960 San Pedro Zacachimalpa, Pue., Mexico
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BioLab, Instituto Universitario de Bio-Orgánica “Antonio González” (IUBO-AG), Centro de Investigaciones Biomédicas de Canarias (CIBICAN), Universidad de La Laguna, c/ Astrofísico Francisco Sánchez 2, 38206 La Laguna, Spain
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Authors to whom correspondence should be addressed.
Molecules 2019, 24(20), 3676; https://doi.org/10.3390/molecules24203676
Received: 4 September 2019 / Revised: 30 September 2019 / Accepted: 11 October 2019 / Published: 12 October 2019
(This article belongs to the Section Medicinal Chemistry)
A small and focused library of steroidal non-fused and fused pyrimidines was prepared from pregnenolone acetate and diosgenin, respectively. The key step was the cycloaddition reaction of nitrogen-containing 1,3-binucleophiles with the steroidal α,β-unsaturated ketone. Urea, thiourea and guanidine reacted in a similar manner and afforded the steroidal pyrimidines in good yields. The antiproliferative tests against human tumor cell lines gave GI50 values in the micromolar range and had no effect on healthy fibroblasts. Additional experiments indicated that the compounds did not act as P-glycoprotein substrates, thus avoiding the rise of drug resistance. The fused steroidal pyrimidinethione was selected as drug lead for further testing due to its strong antiproliferative activities within the low micromolar range. View Full-Text
Keywords: steroids; pyrimidine; heterocycle; cycloaddition reactions; antiproliferative activity steroids; pyrimidine; heterocycle; cycloaddition reactions; antiproliferative activity
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MDPI and ACS Style

Cortés-Percino, A.; Vega-Báez, J.L.; Romero-López, A.; Puerta, A.; Merino-Montiel, P.; Meza-Reyes, S.; Padrón, J.M.; Montiel-Smith, S. Synthesis and Evaluation of Pyrimidine Steroids as Antiproliferative Agents. Molecules 2019, 24, 3676.

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