Sulfonamides and Sulfonylated Derivatives as Anticancer Agents

Abstract

The sulfonamides constitute an important class of drugs, with several types of pharmacological agents possessing antibacterial, anti-carbonic anhydrase, diuretic, hypoglycemic and antithyroid activity among others. A host of structurally novel sulfonamide derivatives have recently been reported to show substantial antitumor activity in vitro and/or in vivo. Although they have a common chemical motif of aromatic/heterocyclic sulfonamide, there are a variety of mechanisms of their antitumor action, such as carbonic anhydrase inhibition, cell cycle arrest in the G1 phase, disruption of microtubule assembly, functional suppression of the transcriptional activator NF-Y, and angiogenesis (matrix metalloproteinase, MMP) inhibition among others. Some of these compounds selected via elaborate preclinical screenings or obtained based on computer-aided drug design, are currently being evaluated in clinical trials. This review summarizes recent classes of sulfonamides and related sulfonyl derivatives disclosed ultimately as effective tumor cell growth inhibitors, or for the treatment of different types of cancer.

Study of reactivity of cyanoacetohydrazonoethyl-N-ethyl-N-methyl benzenesulfonamide: preparation of novel anticancer and antimicrobial active heterocyclic benzenesulfonamide derivatives and their molecular docking against dihydrofolate reductase

“…Precoated silica gel plates (silica gel 0.25 mm, 60 G F 254; Merck, Germany) were used for thin layer chromatography, dichloromethane/methanol (9.5:0.5 mL) mixture was used as a developing solvent system and the spots were recorded in KBr discs using IR-470 Shimadzu spectrometer (Shi-madzu, Tokyo, Japan). 1 H, 13 C NMR spectra (in DMSO-d 6 ) were recorded on Bruker Ac-300 ultra shield NMR spectrometer (Bruker, Flawil, Switzerland, ppm) at 300 MHz, using TMS as internal standard ( 1 H and 13 C) and CFCl 3 ( 19 F). Electron impact Mass Spectra were recorded on a Shimadzu GC/MS-QP5000 instrument Shimadzu, Tokyo, Japan.…”

“…It is evident from the literature survey that benzenesulfonamides exhibited a significant anticancer and antimicrobial activity [1][2][3][4] . Furthermore, benzenesulfonamides derivatives having aromatic heterocyclic moiety possess a wide spectrum of pharmacological activities, such as anticancer [5][6][7] , anti-bacterial [8][9][10] , anti-inflammatory 11 and anti-viral 12 , hypoglycemic 13 , diuretic 14,15 , anticarbonic anhydrase 16 and anti-thyroid 17 , antimalarial 18 and antileprotic 19,20 activity. In addition, literature survey exhibited that some of the synthesized benzenesulfonamide derivatives were found to be dihydrofolate reductase (DHFR) inhibitors [21][22][23] .…”

Synthesis and antimalarial activity of novel chiral and achiral benzenesulfonamides bearing 1, 3, 4-oxadiazole moieties

“…Apart from their previous and more recently published antimalarial activity reports [3], sulfonamides have extensively been documented for their wide variety of pharmacological activities such as antimicrobial, insulin-releasing antidiabetic, carbonic anhydrase inhibitory, anti-HIV, high ceiling diuretic, antithyroid and antitumor [4 -5]. Sildenafil citrate, another sulfonamide derivative, was approved as the first drug for treating male erectile dysfunction (ED) [6] and a second generation antimitotic sulfonamide, ER-34410, evolved again from a scaffold of antibacterial-like sulfonamides, being 2-to 3-fold more potent than E7010 in a panel of various human tumor cell lines in vitro, and unlike E7010, can be administered intravenously [7,8]. Therefore, the sulfonamide moiety is a crucial functionality because of its wide variety of pharmacological activities.…”

Synthesis and Biological Activities Evaluation of Some New 1,2,4-Triazinone Derivatives Bearing Sulfonamide Moiety

“…For example, glibenclamide has found use as a hypoglycemic agent, indisulam (E7070) as an anticancer agent, amprenavir and tipranavir are used in HIV therapy, Furosemide as a diuretic, acetazolamide as a carbonic anhydrase inhibitor, and sulfathiazole, sulfaquinoxaline, silver sulfadiazine (silvadene®), sulfasalazine (azulfidine®) and sulfamethoxazole (gantanol®) as an antibacterial agents [7,10,11,[14][15][16]. In addition, dorzolamide, and brinzolamide have been launched as topically acting antiglaucoma pharmacological agents [17,18]. Till date, thousands of sulfonamide derivatives, analogues, and related compounds have been synthesized, which are effective as diuretics, antimalarial, leprosy and antithyroid agents and employed for other diseases [17,19].…”

“…In addition, dorzolamide, and brinzolamide have been launched as topically acting antiglaucoma pharmacological agents [17,18]. Till date, thousands of sulfonamide derivatives, analogues, and related compounds have been synthesized, which are effective as diuretics, antimalarial, leprosy and antithyroid agents and employed for other diseases [17,19]. Moreover, aryl sulfonamides celecoxib and vadecoxib are used as COX-II inhibitors and anticancer agents [20,21].…”