Sulfur-Lone Pair Interactions

We carry out computations aimed at understanding the origins of apparently attractive interactions between sulfur atoms and oxygen or nitrogen lone pairs. We have examined cases of relevance to medicinal chemistry, organocatalysis and natural products chemistry.

Knapp, J. M.; Wood, A. B.; Phuan, P.-W.; Lodewyk, M. W.; Tantillo, D. J.; Verkman, A. S.; Kurth, M. J. J. Med. Chem. 2012, 55, 1242-1251: "Structure-Activity Relationships of Cyanoquinolines with Corrector-Potentiator Activity in (delta)F508-Cystic Fibrosis Transmembrane Conductance Regulator Protein"

Ye, L.; Hu, B.; El-Badri, F.; Hudson, B.M.; Phuan, P.-W.; Verkman, A. S.; Tantillo, D. J.; Kurth, M. J. Bioorg. Med. Chem. Lett. 2014, 24, 5840-5844: "(delta)F508-CFTR Correctors: Synthesis and Evaluation of Thiazole-Tethered Oxazoles, Oxadiazoles, and Thiadiazoles"

Abbasov, M. E.; Hudson, B. M.; Tantillo, D. J.; Romo, D. J. Am. Chem. Soc. 2014, 136, 4492-4495: "Acylammonium Salts as Dienophiles in Diels-Alder/Lactonization Organocascades," highlighted in SYNFACTS.

Coffman, K. C.; Nguyen, H. H.; Phuan, P.-W.; Hudson, B.M.; Yu, G. J.; Bagdazarian, A. L.; Montgomery, D.; Lodewyk, M. W.; Yang, B.; Yoo, C. L.; Verkman, A. S.; Tantillo, D. J.; Kurth, M. J. J. Med. Chem. 2014, 57, 6729-6738: "Constrained Bithiazoles: Small Molecule Correctors of Defective (delta)F508-CFTR Protein Trafficking"

Hudson, B. M.; Nguyen, E.; Tantillo, D. J. Org. Biomol. Chem. 2016, 14, 3975-3980: "The Influence of Intramolecular Sulfur–Lone Pair Interactions on Small-Molecule Drug Design and Receptor Binding"

Abbasov, M. E.; Hudson, B. M.; Tantillo, D. J.; Romo, D. Chem. Sci. 2017, 8, 1511-1524: "Stereodivergent, Diels-Alder-Initiated Organocascades Employing α,β-Unsaturated Acylammonium Salts: Scope, Mechanism, and Application"

Abbasov, M. E.; Hudson, B. M.; Kong, W.; Tantillo, D. J.; Romo, D. Org. Biomol. Chem. 2017, 15, 3179-3183: "Enantioselective Diels-Alder-Lactamization Organocascades Employing a Furan-Based Diene," invited contribution to themed issue on "Polycylizations in Synthesis and Biosynthesis."


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