45 Sustainable Synthesis of New Pregn-5-Ene-7-One Derivatives and Its Cytotoxic Test

Wednesday, November 4, 2009
Ballroom A+B (Camino Real Hotel)
Elena Ramirez-Lopez, Professor of Chemistry , Pharmacy, UNIVERSIDAD NACIONAL AUTONOMA DE MEXICO, Mexico D.F., Mexico
Eugene A. Bratoeff Sr., Professor of chemistry , Pharmacy, UNIVERSIDAD NACIONAL AUTONOMA DE MEXICO, Mexico D.F., Mexico
Teresa Ramirez-Apan , INSTITUTO DE QUIMICA. UNIVERSIDAD NACIONAL AUTONOMA DE MEXICO, Mexico D.F., Mexico
Guadalupe Perez-Torres , UNIVERSIDAD POPULAR DE LA CHONTALPA, CÁrdenas Tabasco, Mexico
Sabino Lopez-Lopez , UNIVERSIDAD POPULAR DE LA CHONTALPA, CÁrdenas Tabasco, Mexico
Sustainable chemistry is defined as a chemical alternative to design, manufacture and application of products and processes that reduces or eliminates the use and generation of hazardous substances. This alternative can be applied to drug synthesis like antiandrogen production. Steroidal antiandrogens  inhibits the biological effects of androgenic hormones such as testosterone (T) and dihydrotestosterone (DHT) by inhibition of DHT formation by 5-alpha-reductase enzyme or the inhibition of the DHT-receptor complex formation. Antiandrogens are widely used agents for the treatment of androgen-dependent diseases for instance hirsutism, acne, benign prostatic hypertrophy and prostate cancer. In this study we report the green synthesis and cytotoxic activity of four novel pregn-5-ene-7-one derivatives. Starting materials were the commercially available pregnenolone and 16-dehidropregnenolone acetate; these compounds upon treatment with a variety of reagents, that should be made innocuous wherever possible, afforded in high yield the desired steroidal derivatives. Synthesized steroids were tested on human cancer cell lines: prostatic (PC-3), mammary (MCF-7) and lung (SKLU-1) adenocarcinoma. The overall data indicated that the novel synthesized compounds inhibited the proliferation of almost all cancer cell lines evaluates. We observed an upper anticancer effect larger than that for the standard cyproterone acetate. In the future we will evaluate these new steroidal compounds more thoroughly to determine if they could be considered as potential drugs for the treatment of androgen-mediate diseases.
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