Development of Chemotherapeutic Agents to Treat Prostate Cancer: Synthesis of 5-amino-3(trifluoromethyl)picolinonitrile, a Key Intermediate for Anti-Androgen Compounds, and Synthesis of 5,6-dihydropyridine-2(1H)-one, a Key Intermediate of Piperlongumine and its Derivatives
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Authors
Lenning, Jacob C.
Issue Date
2015
Type
Thesis
Language
en_US
Keywords
Alternative Title
Abstract
Prostate cancer is one of the most prevalent cancers as 16% of men will develop prostate cancer in their lifetime. Due to this, much research is devoted to developing new and more effective prostate cancer treatments. Second generation anti-androgens are the most recent advancement in chemotherapeutic agents, while the anti-cancer potential of piperlongumine and its derivatives is just beginning to be discovered through cell culture experimentation. For such testing, it is necessary to obtain the required compounds in cost effective manners. Thus, synthetic routes were explored to determine whether the synthesis or the purchase of two important intermediates for prostate cancer research was more cost effective. 5,6-dihydropyridine-2(1H)-one, a key intermediate of piperlongumine and its derivatives, was successfully synthesized from commercially available 𝛿-valerolactam. However, 5-amino-3(trifluoromethyl)picolinonitrile, a key intermediate for second generation anti-androgen agents, was not successfully synthesized from commercially available 3-bromopyridine due to a failed trifluoromethyl substitution. 3-bromo-5-nitropicolinonitrile was the nearest precursor to the desired anti-androgen intermediated that was obtained. Nonetheless, the precursor to the anti-androgen intermediate and the piperlongumine intermediate were both synthesized in cost effective manners.
Description
v, 18 p.
Citation
Publisher
Kalamazoo College
License
U.S. copyright laws protect this material. Commercial use or distribution of this material is not permitted without prior written permission of the copyright holder. All rights reserved.