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Phenol groups bearing drugs suffer rapid first-pass metabolism to glucuronide and sulfate conjugates, resulting in low bioavailability and low plasma concentrations.
An isosteric and biocompatible replacement of phenyl rings is the BCP moiety (bicyclo[1.1.1]pentane). This hypothesis has been successfully demonstrated in the case of Resveratrol: BCP-Resveratrol shows significantly improved half-life in plasma and intrinsic clearance. Metabolite formation, like glucuronide and sulfate conjugation is drastically reduced.
• Toward Resolving the Resveratrol Conundrum: Synthesis and in Vivo Pharmacokinetic Evaluation of BCP−Resveratrol; Yi Ling Goh, Yan Ting Cui, Vishal Pendharkar, and Vikrant A. Adsool; ACS Med. Chem. Lett. 2017; 8: 516−520. DOI: 10.1021/acsmedchemlett.7b00018
• A practical metal-free homolytic aromatic alkylation protocol for the synthesis of 3-(pyrazin-2-yl)bicyclo[1.1.1]pentane-1-carboxylic acid; Navanita T. Thirumoorthi and Vikrant A. Adsool; Org. Biomol. Chem. 2016; 14: 9485-9489. DOI: 10.1039/c6ob01799a
• Expedient synthesis of 3-phenylbicyclo[1.1.1]pentan-1-amine via metal-free homolytic aromatic alkylation of benzene; Navanita T. Thirumoorthi, Chew Jia Shen and Vikrant A. Adsool; Chem. Commun. 2015; 51: 3139-3142. DOI: 10.1039/c4cc09655j
• Radical fluorination powered expedient synthesis of 3-fluorobicyclo[1.1.1]pentan-1-amine; Yi Ling Goh and Vikrant A. Adsool; this: Org. Biomol. Chem., 2015, 13, 11597- . DOI: 10.1039/c5ob02066b
• A New Route to Bicyclo[1.1.1]pentan-1-amine from 1 Azido-3-iodobicyclo[1.1.1]pentane; Yi Ling Goh, Eric K.W. Tam, Paul H. Bernardo, Choon Boon Cheong, Charles W. Johannes, Anthony D. William, and Vikrant A. Adsool; Org. Lett. 2014; 16: 1884−1887. DOI: org/10.1021/ol500635p.
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