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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

General structures of 2-mercaptobenzenesulfonamides A, B, C, and D
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Fig1: General structures of 2-mercaptobenzenesulfonamides A, B, C, and D

Mentions: It has been known that aryl/heteroarylsulfonamides may act as antitumor agents through a variety of mechanisms such as cell cycle perturbation in the G1 phase, disruption of microtubules, angiogenesis inhibition, and functional suppression of the transcriptional activator NF-Y. The most prominent mechanism was the inhibition of carbonic anhydrase isozymes [18–22]. Recently, a host of structurally novel arylsulfonamide derivatives have been reported to show substantial anticancer activities in vitro and/or in vivo [23–26]. We have reported the synthesis and anticancer activity of 2-mercaptobenzenesulfonamides and subsequently extended our study to analogues with various heterocyclic ring systems attached to the benzenesulfonamide scaffold [4–6, 8, 10, 15] (Fig. 1 structure A [4–6, 8, 15], B [8], C [10]).Fig. 1


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)

General structures of 2-mercaptobenzenesulfonamides A, B, C, and D
© Copyright Policy
Related In: Results  -  Collection

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

Fig1: General structures of 2-mercaptobenzenesulfonamides A, B, C, and D
Mentions: It has been known that aryl/heteroarylsulfonamides may act as antitumor agents through a variety of mechanisms such as cell cycle perturbation in the G1 phase, disruption of microtubules, angiogenesis inhibition, and functional suppression of the transcriptional activator NF-Y. The most prominent mechanism was the inhibition of carbonic anhydrase isozymes [18–22]. Recently, a host of structurally novel arylsulfonamide derivatives have been reported to show substantial anticancer activities in vitro and/or in vivo [23–26]. We have reported the synthesis and anticancer activity of 2-mercaptobenzenesulfonamides and subsequently extended our study to analogues with various heterocyclic ring systems attached to the benzenesulfonamide scaffold [4–6, 8, 10, 15] (Fig. 1 structure A [4–6, 8, 15], B [8], C [10]).Fig. 1

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