Synthesis and identification of heteroaromatic<i>N</i>-benzyl sulfonamides as potential anticancer agents

Hopkins, Megan D.; Abebe, Felagot A.; Scott, Kristina A.; Ozmer, Garett L.; Sheir, Alec A.; Schroeder, Lucas J.; Sheaff, Robert J.; Lamar, Angus A.

doi:10.1039/c9ob01694e

Cited by 9 publications

(14 citation statements)

References 115 publications

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“…10 Recently in our laboratories, the synthesis and cytotoxicity screening of 24 novel heteroaryl N-benzyl sulfonamides was reported. 11 The cytotoxicity screening of the compounds (100 μM) was conducted over a 24 h exposure period using a CellTiter-Blue (Promega) assay, which is based upon the conversion of resazurin to the fluorescent resorufin by living cells. 12 During the traditional long exposure viability screening of H293 cancer cells, 6 out of the 24 compounds were identified as a hit (compounds 2, 5, 6, 7, 23, and 30), which is defined in our investigation as 50% or lower percent of DMSO control (POC) after exposure to a library compound.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…The synthesis and characterization of compounds 1−9, 11, 12, 14, 16, 18−26, 29, and 30 has been previously reported by our laboratory, and the compounds were used without additional modification. 11 Compounds 10, 13, 15, 17, 27, and 28 were synthesized following the reported procedure. 11 4-Chloro-N-[(1-methyl-1H-indazol-5-yl)methyl]benzenesulfonamide (10).…”

Section: ■ Methodsmentioning

confidence: 99%

“…11 Compounds 10, 13, 15, 17, 27, and 28 were synthesized following the reported procedure. 11 4-Chloro-N-[(1-methyl-1H-indazol-5-yl)methyl]benzenesulfonamide (10). White solid (12 mg, 28%).…”

Section: ■ Methodsmentioning

confidence: 99%

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Development of a Rapid In Vitro Screening Assay Using Metabolic Inhibitors to Detect Highly Selective Anticancer Agents

et al. 2021

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Traditional long exposure (24–72 h) cell viability assays for identification of potential drug compounds can fail to identify compounds that are: (a) biologically active but not toxic and (b) inactive without the addition of a synergistic additive. Herein, we report the development of a rapid (1–2 h) compound screening technique using a commercially available cell viability kit (CellTiter-Glo) that has led to the detection of compounds that were not identified as active agents using traditional cytotoxicity screening methods. These compounds, in combination with metabolic inhibitor 2-deoxyglucose, display selectivity toward a pancreatic cancer cell line. An evaluation of 11 mammalian cell lines against 30 novel compounds and two metabolic inhibitors is reported. The inclusion of metabolic inhibitors during an initial screening process, and not simply during mechanistic investigations of a previously identified hit compound, provides a rapid and sensitive tool for identifying drug candidates potentially overlooked by other methods.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: ■ Methodsmentioning

confidence: 99%

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Development of a Rapid In Vitro Screening Assay Using Metabolic Inhibitors to Detect Highly Selective Anticancer Agents

et al. 2021

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“…Sulfonamides are an excellent choice of compounds for the core. These compounds are widely employed as antibacterial [24], antifungal [25], anticancer [26], and antioxidant [27] drugs. However, despite a large number of studies focusing on these metallodrugs and their well-known potential, the clinical application of these drugs is surprisingly limited [14].…”

Section: Introductionmentioning

confidence: 99%

Stimulation of Sulfonamides Antibacterial Drugs Activity as a Result of Complexation with Ru(III): Physicochemical and Biological Study

Spisz

Chylewska

Królicka

et al. 2021

IJMS

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Antibiotic resistance is a global problem, and one promising solution to overcome this issue is using metallodrugs, which are drugs containing metal ions and ligands. These complexes are superior to free ligands in various characteristics including anticancer properties and mechanism of action. The pharmacological potential of metallodrugs can be modulated by the appropriate selection of ligands and metal ions. A good example of proper coordination is the combination of sulfonamides (sulfamerazine, sulfathiazole) with a ruthenium(III) ion. This work aimed to confirm that the activity of sulfonamides antibacterial drugs is initiated and/or stimulated by their coordination to an Ru(III) ion. The study determined the structure, electrochemical profile, CT-DNA affinity, and antimicrobial as well as anticancer properties of the synthesized complexes. The results proved that Ru(III) complexes exhibited better biological properties than the free ligands.

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“…37 As a result, it is viable to expand a sequence of sulfonamides with alkyl amide side chain amendment on carboxyl for enhanced antibacterial e ciency. Sulfonamides have medicinal applications and many of them are broadly utilized in therapeutic as antimicrobial 38 , antitumor [39][40] , anticancer 41 , antiviral 42 , anti-HIV 43 , antidiabetic 44 , antimalarial 45 , antitubercular 46 , analgesic 47 , antioxidant 48 , antihypertensive 49 , antileishmanial 50 , anti-in ammatory 51 , anticonvulsant 52 , diuretic 53 , anti-carbonic anhydrase 54 and antiplatelet. 55…”

Section: Introductionmentioning

confidence: 99%

New Insights Into the Promising Antibacterial Activity of Thiophene or Chromene Moiety Containing Aryl Sulfonamide

Rathore¹,

Kumar²,

Prakash³

et al. 2021

Preprint

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Background: Aryl sulfonamides bearing thiophene and chromene moieties have been reviewed for their antibacterial activity and their synthetic methods. Heterocyclic moiety containing aryl sulfonamide compounds are dispersed in nature and are crucial for life. Diverse investigational strategies towards a structural relationship that cognizance upon the exploration of optimized candidates have grown to be extremely crucial.Method: Literature research tells that for a series of thiophene or chromene moiety containing aryl sulfonamide compoundsare vital in medicinal and industrial chemistry.Aryl sulfonamidescontainingheterocyclic moieties display pharmacological activities against pathogenic microbes.Result:Recent various disciplinary reported articles had been cited in this review article to define the potentialantibacterial properties of thiophene-arylsulfonamide and chromene-arylsulfonamide. Conclusion: The finding of this review confirms the importance of aryl sulfonamidescontaining thiophene or chromene moiety as potential antibacterial agents. These final resultswill give ideasto the synthesis and developmentof reactions leading to the potential derivativesfor betterpharmacological applications.

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Synthesis and identification of heteroaromaticN-benzyl sulfonamides as potential anticancer agents

Abstract: The regioselective incorporation of a sulfonamide unit to a broad range of heteroarene scaffolds has been developed. Synthesized N-benzyl sulfonamides have been screened against a variety of cancer cell lines for cytotoxicity effects.

Cited by 9 publications

References 115 publications

Development of a Rapid In Vitro Screening Assay Using Metabolic Inhibitors to Detect Highly Selective Anticancer Agents

Development of a Rapid In Vitro Screening Assay Using Metabolic Inhibitors to Detect Highly Selective Anticancer Agents

Stimulation of Sulfonamides Antibacterial Drugs Activity as a Result of Complexation with Ru(III): Physicochemical and Biological Study

New Insights Into the Promising Antibacterial Activity of Thiophene or Chromene Moiety Containing Aryl Sulfonamide

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