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Synthesis of novel 4-substituted pyridine-3-sulfonamide derivatives with potential anticancer activity

Jarosław J. Sławiński ,  Krzysztof Szafrański 

Medical University of Gdańsk, Department of Organic Chemistry, Gen. J. Hallera Street 107, Gdańsk 80-416, Poland

Abstract
Previously we reported a broad spectrum of biological properties and chemical behaviours of 4-substituted pyridine-3-sulfonamide [1-4]. Our current investigations are focused on the synthesis and biological evaluations of novel pyridine-3-sulfonamide derivatives containing N-[imino(pyridin-2-yl)methyl] or N-(phenylcarbamoyl) moieties, and diversified with substituent at 4 position of pyridine ring. Thus, starting 4-chloropyridine-3-sulfonamide were converted to the novel 4-(4-arylpiperazin-1-yl)-, 4-(1H-pyrazol-1-yl)- or 4-(aryl/alkylthio)pyridine-3-sulfonamides,  which were subjected to the reactions with either methyl picolinimidate or the corresponding phenyl isocyanates, to afford the desired N-(4-R1-pyridine-3-ylsulfonyl)picolinamidine (A) or N-(4-R1-pyridine-3-ylsulfonyl)-N'-phenylurea (B) derivatives, respectively.

Several compounds obtained were screened at the National Cancer Institute (Bethesda MD, USA) for their in vitro activities against NCI-60 panel of human cancer cell lines. Many of them exhibited moderate to weak ability of growth inhibition a number of cancer cell lines. Among them, N-[imino(pyridin-2-yl)methyl]- [4-(4-phenylpiperazin-1-yl)]pyridine-3-sulfonamide (A) with para-halo substituted phenyl ring showed moderate activity against many of leukemia cells, while N-(4-R1-pyridine-3-ylsulfonyl)-N'-phenylurea derivatives of thpe B possessed activity against colon, melanoma and renal cancer cell lines.

References:

[1] Brzozowski Z., Sączewski F., Sławiński J., J. Heterocyclic Chem., 45 (2008) 1407.

[2] Brzozowski Z., Sławiński J., Kędzia A., Kwapisz E., Gdaniec M., J. Heterocyclic Chem., 46 (2009) 1396.

[3] Brzozowski Z., Sławiński J., Innocenti A., Supuran C.T. Eur. J. Med. Chem. 45 (2010) 3656.

[4] Brzozowski Z., Sławiński J., Gdaniec M., Innocenti A., Supouran C.T. Eur. J. Med. Chem. 46 (2011) 4403.

 

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Presentation: Poster at VIII Multidyscyplinarna Konferencja Nauki o Leku, by Jarosław J. Sławiński
See On-line Journal of VIII Multidyscyplinarna Konferencja Nauki o Leku

Submitted: 2012-03-07 10:13
Revised:   2012-05-11 02:04