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Chemical name: N-alpha-(9-Fluorenylmethyloxycarbonyl)-3-(bicyclo[1.1.1]pentan-1-yl)-L-alanine // Synonyms: Fmoc-Ala(BCP)-OH, 3-Bicyclo[1.1.1]pent-1-yl-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid
|Molecular weight:||377,43 g/mol|
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. Y. L. Goh, Y. T. Cui, V. Pendharkar, and V. A. Adsool; ACS Med. Chem. Lett. 2017; 8: 516-520. https://doi.org/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. N. T. Thirumoorthi, V. A. Adsool; Org. Biomol. Chem. 2016; 14: 9485-9489. https://doi.org/10.1039/c6ob01799a.
Expedient synthesis of 3-phenylbicyclo[1.1.1]pentan-1-amine via metal-free homolytic aromatic alkylation of benzene. N. T. Thirumoorthi, C. J. Shen, V. A. Adsool; Chem. Commun. 2015; 51: 3139-3142. https://doi.org/10.1039/C4CC09655J.
Radical fluorination powered expedient synthesis of 3-fluorobicyclo[1.1.1]pentan-1-amine. Y. L. Goh and V. A. Adsool; Org. Biomol. Chem. 2015; 13: 11597-11601. https://doi.org/10.1039/C5OB02066B.
A New Route to Bicyclo[1.1.1]pentan-1-amine from 1-Azido-3-iodobicyclo[1.1.1]pentane. Y. L. Goh, E. K. W. Tam, P. H. Bernardo, C. B. Cheong, C. W. Johannes, A. D. William, and V. A. Adsool; Org. Lett. 2014; 16: 1884-1887. https://doi.org/10.1021/ol500635p.
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