The sulfinyl group: Its importance for asymmetric synthesis and biological activity

References

• Otocka, S.; Kwiatkowska, M.; Madalińska, L.; Kiełbasiński, P. Chiral Organosulfur Ligands/Catalysts with a Stereogenic Sulfur Atom: Applications in Asymmetric Synthesis. Chem. Rev. 2017, 117, 4147–4181. DOI:10.1021/acs.chemrev.6b00517.
   PubMed Web of Science ®Google Scholar
• Kiełbasiński, P.; Kwiatkowska, M.; Mikołajczyk, M. Organic Heteroatom-Containing Compounds. In Future Directions in Biocatalysis, 2nd ed.; Matsuda T., Ed.; Elsevier: Oxford, 2017; pp. 191–250.
   Google Scholar
• Rachwalski, M.; Kwiatkowska, M.; Drabowicz, J.; Kłos, M.; Wieczorek, W. M.; Szyrej, M.; Sieroń, L.; Kiełbasiński, P. Enzyme-Promoted Desymmetrization of Bis(2-Hydroxymethyl-Phenyl) Sulfoxide as a Route to Tridentate Chiral Catalysts. Tetrahedron: Asymmetry 2008, 19, 2096–2101. DOI:10.1016/j.tetasy.2008.08.017.
   Web of Science ®Google Scholar
• Leśniak, S.; Rachwalski, M.; Sznajder, E.; Kiełbasiński, P. New Highly Efficient Aziridine-Functionalized Tridentate Sulfinyl Catalysts for Enantioselective Diethylzinc Addition to Carbonyl Compounds. Tetrahedron: Asymmetry 2009, 20, 2311–2314. DOI:10.1016/j.tetasy.2009.09.012.
   Google Scholar
• Rachwalski, M.; Leśniak, S.; Sznajder, E.; Kiełbasiński, P. Highly Enantioselective Henry Reaction Catalyzed by Chiral Tridentate Heteroorganic Ligands. Tetrahedron: Asymmetry 2009, 20, 1547–1549. DOI:10.1016/j.tetasy.2009.06.015.
   Web of Science ®Google Scholar
• Rachwalski, M.; Leśniak, S.; Kiełbasiński, P. Highly Enantioselective Aza-Henry Reaction Promoted by Amine-Functionalized Tridentate Sulfinyl Ligands. Tetrahedron: Asymmetry 2011, 22, 1087–1089. DOI:10.1016/j.tetasy.2011.05.006.
   Web of Science ®Google Scholar
• Rachwalski, M.; Leśniak, S.; Kiełbasiński, P. Highly Enantioselective Asymmetric Direct Aldol Reaction Catalyzed by Amine-Functionalized Tridentate Sulfinyl Ligands. Tetrahedron: Asymmetry 2011, 22, 1325–1327. DOI:10.1016/j.tetasy.2011.07.008.
   Web of Science ®Google Scholar
• Rachwalski, M.; Leenders, T.; Kaczmarczyk, S.; Kiełbasiński, P.; Leśniak, S.; Rutjes, F. P. J. T. Efficient Catalysts for Asymmetric Mannich Reactions. Org. Biomol. Chem. 2013, 11, 4207–4213. DOI:10.1039/c3ob40681d.
   PubMed Web of Science ®Google Scholar
• Rachwalski, M.; Wujkowska, Z.; Leśniak, S.; Kiełbasiński, P. Highly Efficient Asymmetric Aziridination of Unsaturated Aldehydes Promoted by Chiral Hetero-Organic Catalysts. ChemCatChem. 2015, 7, 3589–3592. DOI:10.1002/cctc.201500537.
   Web of Science ®Google Scholar
• Wujkowska, Z.; Leśniak, S.; Kiełbasiński, P.; Rachwalski, M. Highly Enantioselective Asymmetric Reduction of Aromatic Ketimines Promoted by Chiral Enantiomerically Pure Sulfoxides as Organocatalysts. J. Sulfur Chem. 2018, 39, 380–387. DOI:10.1080/17416993.2018.1433178.
   Web of Science ®Google Scholar
• Rachwalski, M.; Leśniak, S.; Kiełbasiński, P. Highly Enantioselective Conjugate Addition of Diethylzinc to Enones Using Aziridine-Functionalized Tridentate Sulfinyl Ligands. Tetrahedron: Asymmetry 2010, 21, 1890–1892. DOI:10.1016/j.tetasy.2010.05.053.
   Google Scholar
• Rachwalski, M.; Kaczmarczyk, S.; Leśniak, S.; Kiełbasiński, P. Highly Efficient Asymmetric Simmons-Smith Cyclopro-Panation Promoted by Chiral Heteroorganic Aziridinyl Ligands. ChemCatChem. 2014, 6, 873–875. DOI:10.1002/cctc.201300883.
   Web of Science ®Google Scholar
• Kiełbasiński, P.; Rachwalski, M.; Kaczmarczyk, S.; Leśniak, S. Polydentate Chiral Heteroorganic Ligands/Catalysts – Impact of Particular Functional Groups on Their Activity in Selected Reactions of Asymmetric Synthesis. Tetrahedron: Asymmetry 2013, 24, 1417–1420. DOI:10.1016/j.tetasy.2013.08.012.
   Web of Science ®Google Scholar
• Pauli-Magnus, C.; Rekersbrink, S.; Klotz, U.; Fromm, M. F. Interaction of Omeprazole, Lansoprazole and Pantoprazole with P-Glycoprotein. Naunyn-Schmied. Arch. Pharmacol. 2001, 364, 551–557. DOI:10.1007/s00210-001-0489-7.
   PubMed Web of Science ®Google Scholar
• Zhang, Y.; Talalay, P.; Cho, C. G.; Posner, G. A Major Inducer of Anticancerogenic Protective Enzymes from Broccoli: Isolation and Elucidation of Structure. Proc. Nat. Acad. Sci. 1992, 89, 2399–2403. DOI:10.1073/pnas.89.6.2399.
   PubMed Web of Science ®Google Scholar
• Khiar, N.; Werner, S.; Mallouk, S.; Lieder, F.; Alcudia, A.; Fernández, I. Enantiopure Sulforaphane Analogues with Various Substituents at the Sulfinyl Sulfur: Asymmetric Synthesis and Biological Activities. J. Org. Chem. 2009, 74, 6002–6009. DOI:10.1021/jo9007749.
   PubMed Web of Science ®Google Scholar
• Misiewicz, I.; Skupińska, K.; Kasprzycka-Guttman, T. Sulforaphane and 2-Oxohexyl-Isothiocyanate Induce Cell Growth Arrest and Apoptosis in L-1210 Leukemia and ME-18 Melanoma Cells. Oncology Rep. 2003, 10, 2045–2050. DOI:10.3892/or.10.6.2045.
   PubMed Web of Science ®Google Scholar
• Wang, J.; Sánchez-Roselló, M.; Aceña, ∥, J. L.; del Pozo, C.; Sorochinsky, A. E.; Fustero, S.; Soloshonok, V. A.; Liu, H. Fluorine in Pharmaceutical Industry: Fluorine-Containing Drugs Introduced to the Market in the Last Decade (2001–2011). Chem. Rev. 2014, 114, 2432–2506. DOI:10.1021/cr4002879.
   PubMed Web of Science ®Google Scholar
• Kiełbasiński, P.; Łuczak, J.; Cierpiał, T.; Błaszczyk, J.; Sieroń, L.; Wiktorska, K.; Lubelska, K.; Milczarek, M.; Chilmończyk, Z. New Enantiomeric Fluorine-Containing Derivatives of Sulforaphane: Synthesis, Absolute Configurations and Biological Activity. Eur. J. Med. Chem. 2014, 76, 332–342. DOI:10.1016/j.ejmech.2014.02.036.
   PubMed Web of Science ®Google Scholar
• Cierpiał, T.; Kiełbasiński, P.; Wiktorska, K.; Lubelska, K.; Chilmonczyk, Z. Polish patent application P-421672, March 22, 2017.
   Google Scholar
• Cierpiał, T.; Łuczak, J.; Kwiatkowska, M.; Kiełbasiński, P.; Mielczarek, L.; Wiktorska, K.; Chilmonczyk, Z.; Milczarek, M.; Karwowska, K. Organofluorine Isoselenocyanate Analogs of Sulforaphane: Synthesis and Anticancer Activity. ChemMedChem. 2016, 11, 2398–2409. DOI:10.1002/cmdc.201600442.
   PubMed Web of Science ®Google Scholar