Squarate-based carbocyclic nucleosides: Syntheses,computational analyses and anticancer/antiviral evaluation |
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Authors: | Meijun Lu Qing-Bin Lu John F. Honek |
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Affiliation: | 1. Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada;2. Department of Physics and Astronomy, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada |
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Abstract: | Squaric acid and its derivatives are versatile synthons and have demonstrated applications in medicinal chemistry, notably as non-classical bioisosteric replacements for functional groups such as carboxylic acids, alpha-amino acids, urea, guanidine, peptide bonds and phosphate/pyrophosphate linkages. Surprisingly, no reports have appeared concerning its possible application as a nucleobase substitute in nucleosides. A preliminary investigation of such an application is reported herein. 3-Amino-4-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-cyclobut-3-ene-1,2-dione, 3-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-4-methoxycyclobut-3-ene-1,2-dione, and 3-hydroxy-4-((1R,4S)-4-(hydroxymethyl)cyclopent-2-en-1-yl)amino-cyclobut-3-ene-1,2-dione sodium salt were synthesized. Computational analyses of their structures and preliminary antitumor and antiviral screening results are reported. |
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Keywords: | Squaric acid Carbocyclic Nucleoside Anticancer Antiviral Bioisostere |
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