Mgr. Jindřich Karban, Ph.D.
icpf [dot] cas [dot] cz
Research interests:
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fluorinated monosaccharides
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antitumour carbohydrate – metallocene conjugates
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aziridine derivatives of aldohexoses
including mechanistic aspects of the synthesis and reactivity of these carbohydrate analogues, conformational analysis on the basis of their crystallographic and spectroscopic properties, and application in medicinal chemistry and glycobiology
Publications:
- A Convenient Route to Peracetylated 3-Deoxy-3-fluoro Analogues of D-Glucosamine and D-Galactosamine from a Černý Epoxide, Karban, J.; Horník, t.; Červenková Šťastná, L.; Sýkora, J. Synlett 2014, 25, 1253-1256. https://www.thieme-connect.de/DOI/DOI?10.1055/s-0033-1341187
- Skeletal rearrangements resulting from reactions of 1,6:2,3- and 1,6:3,4-dianhydro-β-D-hexopyranoses with diethylaminosulphur trifluoride, Karban, J.; Císařová, I.; Strašák, T.; Červenková Šťastná, L.; Sýkora, J. Org. Biomol. Chem. 2012, 10, 394-403. http://pubs.rsc.org/en/content/articlelanding/2012/ob/c1ob06336g#!divAbstract
- Synthesis of All Configurational Isomers of 1,6-Anhydro-2,3,4-trideoxy-2,3-epimino-4-fluoro-β-D-hexopyranoses, Karban, J.; Sýkora, J.; Kroutil, J.; Císařová, I.; Padělková, Z.; Buděšínský, M. J. Org. Chem. 2010, 75, 3443-3446. http://pubs.acs.org/doi/abs/10.1021/jo1000912
Carbohydrate – metallocene conjugates. Metallocenes are organometallic compounds characterized by a transition metal central atom (M) bound to cyclopentadienide (Cp-/C5H5-) ligands, the general formula of metallocenes being Cp2M. Titanocene dichloride was among the first non-platinum organometallics investigated as promising anticancer agents. Although its clinical trials were stopped because of low efficacy and other drawbacks, the last two decades have witnessed renewed research interest in anticancer metallocenes. We have recently started a programme aimed at improving cytotoxic activity and pharmacological properties of metallocenes by their conjugation to carbohydrates. Carbohydrates have typicaly 4 - 6 functional groups that can be modified to ameliorate cytotoxic profile, bioavailability, solubility, biocompatibility, and hydrophobic/hydrophilic balance of the resulting metallocene-carbohydrate conjugate.
Publications:
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Titanocene Dihalides and Ferrocenes Bearing a Pendant α-D-Xylofuranos-5-yl or α-D-Ribofuranos-5-yl Moiety. Synthesis, Characterization, and Cytotoxic Activity, Hodík, T.; Lamač, M.; Červenková Šťastná, L.; Karban, J.; Koubková, L.; Hrstka, R.; Císařová, I.; Pinkas, J. Organometallics 2014, 33, 2059-2070. http://pubs.acs.org/doi/abs/10.1021/om500200r
Aziridine derivatives of aldohexoses Aziridines are versatile synthetic intermediates. Important for their utilization in this regard is the cleavage of the three-membered aziridine ring. Cleavage of N-tosylated aziridine ring annelated to a tetrahydropyrane ring of aldohexopyranoses affords interesting analogues of aminosugars which are difficult to prepare otherwise. We studied regio- and stereoselectivity of aziridine ring cleavage fused to the tetrahydropyrane ring of 1,6-anhydro-β-D-hexopyranoses.
Publications:
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Ring-Opening Reactions of Aziridines Fused to a Conformationally Locked Tetrahydropyran Ring, Karban, J.; Kroutil, J.; Buděšínský, M.; Sýkora, J.; Císařová, I. Eur. J. Org. Chem. 2009, 6399-6406. http://onlinelibrary.wiley.com/doi/10.1002/ejoc.200900762/abstract
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Molecular structure of eight possible configurational isomers of 2,3- and 3,4-epimino derivatives of 1,6-anhydro-β-D-hexopyranoses: conformation analysis, intra- and inter-molecular hydrogen bonds, Sýkora, J.; Karban, J.; Císařová, I.; Hilgard, S. Carbohydrate Research 2008, 343, 2789-2796. http://www.sciencedirect.com/science/article/pii/S0008621508002875