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Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives.

Brożewicz K, Sławiński J - Monatsh. Chem. (2012)

Bottom Line: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel.Most of the compounds exhibited antiproliferative activity.Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines. .

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel. Most of the compounds exhibited antiproliferative activity. Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines.

Graphical abstract: .

No MeSH data available.


MBSA scaffold [20, 21]
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Fig1: MBSA scaffold [20, 21]

Mentions: Aryl- and heteroarylsulfonamides are an important class of therapeutic agents in current medicinal science [1]. Various arylsulfonamides have been reported to possess anticancer [2–6] and/or anti-human immunodeficiency virus (HIV) properties [6, 7]. Our systematic studies on the synthesis of 1,4,2-benzodithiazine 1,1-dioxides and their subsequent transformations into 2-mercaptobenzenesulfonamide (MBSA) derivatives (Fig. 1) having a variety of heterocyclic ring systems or acyclic polynitrogen moieties at the sulfonamide functionality resulted in promising anticancer [8–13], HIV antiviral [14–16], or antibacterial agents [17] as well as potent inhibitors of transmembrane cancer-associated carbonic anhydrase isozymes hCAIX and hCAXII [18, 19].Fig. 1


Synthesis and in vitro activity of novel 2-(benzylthio)-4-chloro-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamide derivatives.

Brożewicz K, Sławiński J - Monatsh. Chem. (2012)

MBSA scaffold [20, 21]
© Copyright Policy
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4494775&req=5

Fig1: MBSA scaffold [20, 21]
Mentions: Aryl- and heteroarylsulfonamides are an important class of therapeutic agents in current medicinal science [1]. Various arylsulfonamides have been reported to possess anticancer [2–6] and/or anti-human immunodeficiency virus (HIV) properties [6, 7]. Our systematic studies on the synthesis of 1,4,2-benzodithiazine 1,1-dioxides and their subsequent transformations into 2-mercaptobenzenesulfonamide (MBSA) derivatives (Fig. 1) having a variety of heterocyclic ring systems or acyclic polynitrogen moieties at the sulfonamide functionality resulted in promising anticancer [8–13], HIV antiviral [14–16], or antibacterial agents [17] as well as potent inhibitors of transmembrane cancer-associated carbonic anhydrase isozymes hCAIX and hCAXII [18, 19].Fig. 1

Bottom Line: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel.Most of the compounds exhibited antiproliferative activity.Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines. .

View Article: PubMed Central - PubMed

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

ABSTRACT

Abstract: Two series of novel 4-chloro-2-(benzylthio)-5-(1,3,4-oxadiazol-2-yl)benzenesulfonamides and their N-aroyl derivatives have been synthesized and evaluated for in vitro anticancer activity against the full NCI-60 cell line panel. Most of the compounds exhibited antiproliferative activity. Among them a compound bearing an N-(thien-2-ylcarbonyl) moiety showed broad-spectrum activity with 50% growth inhibition (GI50) values in the range of 2.02-7.82 μM over 50 cell lines.

Graphical abstract: .

No MeSH data available.