3,4-dichloro-5-hydroxy-2(5H)-furanone (mucochloric acid) is a substrate for synthesis of compounds with interesting chemical and biological properties. The derivatives of 2(5H)-furanone are currently a large group of heterocyclic compounds, among which are natural substances, medications exhibiting various biological activity and compounds used in chemical synthesis [1-8]. The 2(5H)-furanone subunit is a leading structure in many biologically active natural substances such as antimicrobial rubrolides or basidalin. The anticancer properties in milimole concentrations of several mucochloric acid were also reported [1].

Structure of 3,4-dichloro-5-hydroxy-2(5H)-furanone (A) and tested derivatives (B).

 We synthesized set of differently substituted 2(5H)-furanone derivatives and determine their anticancer activity against model cell lines (HCT 116 wt, NHDF).

References

[1] Lattmann E. et al; J. Pharm. Pharmacol., 2004, 56, 1163-1170.

[2] Hironoby I. et al; J. Antibiot., 1983, 36(4), 448-450.

[3] Marshall J. A. et al; Org. Chem., 1996, 61, 5729-5735.

[4] Ishikawa T. et al; L Nat. Prod., 1998, 61(4), 534-537.

[5] Bellina F. et al; Curr. Org. Chem., 2004, 8, 1089-1103.

[6] Bailly F. et al., Eur. J. Med. Chem., 2008, 43, 1222-1229.

[7] Rappai J.P. et al; Bioorg. Med. Chem. Lett., 2009, 19, 764-765.

[8] Gondela E., Walczak K.Z., J. Med. Chem., 2010, 45, 3993-3997.

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