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Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro-N-(4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activity.

Sławiński J, Żołnowska B, Orlewska C, Chojnacki J - Monatsh. Chem. (2012)

Bottom Line: A series of novel 4-chloro-N-(4,5-dihydro-5-oxo-1-R(2)-1H-1,2,4-triazol-3-yl)-5-methyl-2-(R(1)-methylthio)benzenesulfonamide derivatives have been synthesized as potential anticancer agents.The in vitro antitumor activity of some compounds was evaluated in the US National Cancer Institute (NCI) against the NCI-60 cell line panel.The most prominent compound showed remarkable activity against 13 human tumor cell lines representing lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast at low micromolar GI50 level in the range of 1.9-3.0 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of novel 4-chloro-N-(4,5-dihydro-5-oxo-1-R(2)-1H-1,2,4-triazol-3-yl)-5-methyl-2-(R(1)-methylthio)benzenesulfonamide derivatives have been synthesized as potential anticancer agents. The in vitro antitumor activity of some compounds was evaluated in the US National Cancer Institute (NCI) against the NCI-60 cell line panel. The most prominent compound showed remarkable activity against 13 human tumor cell lines representing lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast at low micromolar GI50 level in the range of 1.9-3.0 μM.

No MeSH data available.


Related in: MedlinePlus

Hydrogen bonds in structure of 31Pyr. Blue lines represent hydrogen bonds; transparent yellow balls denote inversion centers in the crystal (generated using Mercury CSD 2.4 [46])
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Fig3: Hydrogen bonds in structure of 31Pyr. Blue lines represent hydrogen bonds; transparent yellow balls denote inversion centers in the crystal (generated using Mercury CSD 2.4 [46])

Mentions: The structure of the new compounds was confirmed by elemental analyses (C, H, N) and spectral (NMR, IR, MS) data presented in the experimental section. Moreover, X-ray analysis was undertaken to confirm proposed structures on the representative compound 31, which crystallized as pyridinium salt (further specified as 31Pyr, Figs. 2 and 3).Fig. 2


Synthesis and molecular structure of novel 2-(alkylthio)-4-chloro-N-(4,5-dihydro-5-oxo-1H-1,2,4-triazol-3-yl)-5-methylbenzenesulfonamides with potential anticancer activity.

Sławiński J, Żołnowska B, Orlewska C, Chojnacki J - Monatsh. Chem. (2012)

Hydrogen bonds in structure of 31Pyr. Blue lines represent hydrogen bonds; transparent yellow balls denote inversion centers in the crystal (generated using Mercury CSD 2.4 [46])
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4495025&req=5

Fig3: Hydrogen bonds in structure of 31Pyr. Blue lines represent hydrogen bonds; transparent yellow balls denote inversion centers in the crystal (generated using Mercury CSD 2.4 [46])
Mentions: The structure of the new compounds was confirmed by elemental analyses (C, H, N) and spectral (NMR, IR, MS) data presented in the experimental section. Moreover, X-ray analysis was undertaken to confirm proposed structures on the representative compound 31, which crystallized as pyridinium salt (further specified as 31Pyr, Figs. 2 and 3).Fig. 2

Bottom Line: A series of novel 4-chloro-N-(4,5-dihydro-5-oxo-1-R(2)-1H-1,2,4-triazol-3-yl)-5-methyl-2-(R(1)-methylthio)benzenesulfonamide derivatives have been synthesized as potential anticancer agents.The in vitro antitumor activity of some compounds was evaluated in the US National Cancer Institute (NCI) against the NCI-60 cell line panel.The most prominent compound showed remarkable activity against 13 human tumor cell lines representing lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast at low micromolar GI50 level in the range of 1.9-3.0 μM.

View Article: PubMed Central - PubMed

Affiliation: Department of Organic Chemistry, Medical University of Gdańsk, Gen. J. Hallera Str. 107, 80416 Gdańsk, Poland.

ABSTRACT

Abstract: A series of novel 4-chloro-N-(4,5-dihydro-5-oxo-1-R(2)-1H-1,2,4-triazol-3-yl)-5-methyl-2-(R(1)-methylthio)benzenesulfonamide derivatives have been synthesized as potential anticancer agents. The in vitro antitumor activity of some compounds was evaluated in the US National Cancer Institute (NCI) against the NCI-60 cell line panel. The most prominent compound showed remarkable activity against 13 human tumor cell lines representing lung, colon, CNS, melanoma, ovarian, renal, prostate, and breast at low micromolar GI50 level in the range of 1.9-3.0 μM.

No MeSH data available.


Related in: MedlinePlus