Benzenesulfonyl Chloride Research Articles

8-Iodo-4-methyl-2-oxo-2H-chromen-7-yl Benzenesulfonate

We report a straightforward and efficient synthesis of 4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3a) and 8-iodo-4-methyl-2-oxo-2H-chromen-7-yl benzenesulfonate (3b) in good yields through an O-sulfonylation reaction of 7-hydroxy-2H-chromen-2-ones 1a and 1b with benzenesulfonyl chloride 2 mediated by triethylamine in dichloromethane at ambient temperature. The aryl sulfonyl esters were characterized using spectroscopic, spectrometric, and thermal analyses.

Effect of the position of the substituent in the electrochemical reduction of nitro-substituted benzenesulfonyl chlorides

The electrochemical reduction of a series of nitro-substituted benzenesulfonyl chlorides is investigated. The results of the electrochemical study are analysed with the assistance of theoretical calculations. The study shows that the electron transfer mechanism depends on the position of the nitro substituent on the phenyl ring. The 3-nitrobenzenesulfonyl chloride follows a stepwise mechanism where the reduction leads to an intermediate radical anion. For the 4-nitrobenzenesulfonyl chloride, 2-nitrobenzenesulfonyl chloride, and 2,4-nitrobenzenesulfonyl chloride, the reduction follows a “sticky” dissociative mechanism, where the electron transfer and S–Cl bond cleavage are concerted. The dissociation products (arylsulfinyl radical and chloride anion) show strong interactions. The difference in behaviour is associated with the overlap of the π* orbital and the S–Cl σ* orbital for the latter three compounds. The through resonance stability of the arylsulfinyl radicals for the para and ortho nitro-substituted compounds facilitates the dissociation of the reduced structures. Upon reduction, the 3-nitrobenzenesulfonyl chloride and 4-nitrobenzenesulfonyl chloride, also produce the corresponding diaryl disulfones, which are easier to reduce that the parent molecules and hence induce an interesting autocatalytic mechanism. Such a mechanism, which depends on the concentration and the scan rate, does not take place with the 2-nitrobenzenesulfonyl chloride and 2,4-dinitrobenzenesulfonyl chloride due to the sterical hindrance of the nitro substituent at the ortho position, as it prevents the formation of the disulfones.

A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide: Experimental and theoretical insights

A pyrazinamide-benzenesulfonohydrazide hybrid N'-(phenylsulfonyl)pyrazine-2-carbohydrazonamide (1), which was studied by physical measurements and computational tools, is reported. Compound 1 was synthesized using a metallic Na-assisted interaction of 2-cyanopyrazine with benzenesulfonylhydrazine in dry methanol. Our newly developed synthetic approach allowed to obtain the title compound witht the yield of 74%, which is more than twice higher in comparison to the previously reported synthesis using pyrazine-2-carbohydrazonamide and benzenesulfonyl chloride. Molecules of the title compound are linked via N–H⋯O, C–H⋯Ph, S=O⋯2-pyrazine and π⋯π interactions. As it was found by the Hirshfeld surface analysis, molecules of 1 interact through H⋯X (X = H, C, N and O) contacts. Electronic properties of 1 were revealed using the Density Functional Theory (DFT) computations. 1 was expected to be a fourth-class toxicity, and it does not penetrate the blood-brain barrier, while can potentially be absorbed by the gastrointestinal tract. It was predicted that compound 1, which demonstrated the strongest activity against PLpro, Nsp3_range 207–379 MES and Nsp16_SAM site, are of interest to suppress activity of the SARS-CoV-2 proteins. Although the Ki value is slightly higher, the ligand efficiency scores for complex PLpro–1 were found to be characteristic for a Hit.

Design, Facile synthesis, and Characterization of sulfonamide derivatives combined with amino acids and other drugs targeting HER2

Researchers have discovered that tyrosine kinase plays a significant role in cancer development. As a result, certain studies focused on synthesizing sulfonamide compounds due to their potent tyrosine kinase inhibitory (TKI). The designed compounds were docked against (HER2) human epidermal growth factor receptor 2 (PDB ID: 3pp0) to identify potential prospects for new cancer drugs. Docking studies using Molegro virtual docker (MVD) revealed the most favorable binding energy among our compounds. In total, all synthesized compounds had binding energies ranging from (-112.893 to -154.396kcal/mol) corresponding to (3a and 1a) respectively. It was found that compound 1a possessed the best binding energy value of synthesized compounds (-154.396 kcal/mol) compared to the recommended drug; trastuzumab (-133,419kcal/mol). Several of the newly designed sulfonamide derivatives were synthesized. An alkaline phase was used in our synthesis to combine some amino acids, sulfamethoxazole, and sulfadiazine with benzenesulfonyl chloride derivatives. The synthesis method was simple and cheap with yields ranging between (60.4% - 80%). Nuclear magnetic resonance spectroscopy, mass spectrometry, and infrared spectroscopy were used to characterize our compounds.

Synthesis Characterization and Biological Activity of 4-Methyl-benzene Sulfonohydrazide Derivatives

Background: A schiff base is generally a bi- or tri-dentate ligand capable of forming stable complexes with transition metals. Schiff base complexes have synthetic flexibilities and biological activity against various diseases. Objective: In the current study, Schiff bases compounds (PV1 - PV5) were synthesized from 4-methyl-1- benzene sulfonyl chloride. Subsequently, the synthesized products were analyzed for their antibacterial activity. Methods: Schiff base is a nitrogen analog with a carbonyl group. The reaction that results in the formation of new complexes involves the condensation of carbonyl compounds with an amine group. Furthermore, thin layer chromatography, FT-IR spectroscopy, and 1H-NMR were performed for product characterization. Results: All five complexes were successfully synthesized and some of the compounds demonstrated antibacterial, antifungal, anti-inflammatory and analgesic properties. Conclusion: The results confirmed the structure and presence of functional groups as per the scheme of synthesis. These synthesized compounds have the potential to treat the studied diseases and could be used as therapeutic candidates if further research is done.

Novel benzene sulfonamides with acetylcholinesterase and carbonic anhydrase inhibitory actions.

A series of benzene sulfonamides 15-26 were synthesized and determined for their in vitro and in silico inhibitory profiles towardacetylcholinesterase (AChE) and carbonic anhydrases (CAs). Commercially available 3,4-dimethoxytoluene was reacted with chlorosulfonic acid to furnish benzene sulfonyl chloride derivatives. The reaction of substituted benzene sulfonyl chloride with some amines also including (±)-α-amino acid methyl esters afforded a series of novel benzene sulfonamides. In this study, the enzyme inhibition abilities of these compounds were evaluated against AChE and CAs. They exhibited a highly potent inhibition ability on AChE and -CAs (Ki values are in the range of 28.11 ± 4.55 nM and 145.52 ± 28.68 nM for AChE, 39.20 ± 2.10 nM to 131.54 ± 12.82 nM for CA I, and 50.96 ± 9.83 nM and 147.94 ± 18.75 nM for CA II). The present newly synthesized novel benzene sulfonamides displayed efficient inhibitory profiles against AChE and CAs, and it is anticipated that they may emerge as lead molecules for some diseases including glaucoma, epilepsy, and Alzheimer's disease.

Structure and biological property studies of the fluorinated sulfonic esters derived from 2-hydroxy-4-(hydroxy/methoxy)acetophenone as inhibitors of biochemical targets linked to type 2 diabetes mellitus

Small molecule multi-target drugs substituted with fluorine atom/s or fluorine-containing group/s continue to attract considerable interest in medicinal chemistry due to their advantages in the treatment of multifactorial diseases. In this study, fluorine-containing alkyl and benzenesulfonyl chloride building blocks were reacted with 2,4-dihydroxyacetophenone 1a or 2-hydroxy-4-methoxyacetophenone 1b to afford the corresponding sulfonic ester derivatives 2a–f and 2g–j, respectively. Detailed crystallographic characterization was performed on a representative compound from each series. The compounds were evaluated through enzymatic assays in vitro for potential to inhibit biochemical targets linked to type 2 diabetes mellitus. Compound 1a and its 4-(4-fluorophenyl)sulfonyl derivative 2d exhibited strong and significant inhibitory effect in vitro against α-glucosidase (IC50 = 0.97 ± 0.02 μM and 0.81 ± 0.07 μM, respectively) and α-amylase (IC50 = 6.89 ± 0.04 μM and 4.87 ± 0.02 μM, respectively) compared to acarbose (IC50 = 8.60 ± 0.20 μM and 1.96 ± 0.03 μM, respectively). The presence of a 4-fluorophenylsulfonyl moiety resulted in moderate inhibitory activity for 2d (IC50 = 27.05 ± 0.01 μM) against protein tyrosine phosphatase 1 beta (PTP1B) compared to the PTP1B inhibitor, suramin (IC50 = 4.63 ± 0.003 μM). The test compounds exhibited strong to moderate nitric oxide radical scavenging activity in vitro against ascorbic acid (IC50 = 5.53 ± 0.03 μM) with IC50 values in the range 0.05–19.30 μM. Compounds 1a and 2d did not inhibit superoxide dismutase (SOD) activity. Molecular docking revealed the involvement of hydrophobic, hydrophilic and electrostatic interactions with amino acid residues in the active site of the test enzymes.

Design, synthesis, and biological evaluation of benzenesulfonyl chloride-substituted evodiamine derivatives as potential PGAM1 inhibitors

Evodiamine (EVO) is a quinazoline carboline alkaloid isolated from the fruits of the traditional Chinese herb Evodiae fructus. In the present study, we synthesized thirty EVO derivatives (9–38) with various benzenesulfonyl groups by sulfonylation of the amino group of 3-NH-EVO and thirty benzenesulfonyl chloride substituents. The results of the MTT assay showed that most of the compounds had good antitumor activity on H460, PC9, PC9/GR, H1299 and SW620 cancer cells as well as on normal LO2 cells. Among them, compounds 9, 18 and 28 were more potent than other compounds on H460 cell lines with an IC50 value of 9.1 M, 10.5 M and 9.5 M, respectively, even more potent than the positive PGMI-004A with one IC50 of 31.1 M. The enzymatic activity of representative compounds was further evaluated against phosphoglycerate mutase 1 (PGAM1). The results showed that compound 11 with an IC50 of 0.062 μM and compound 34 with an IC50 of 0.059 μM were similar to the positive drug’s IC50 of 0.052 μM. These results indicated that these compounds could be developed into potential PGAM1 inhibitors. In addition, compounds 9, 18, and 28 could induce apoptosis, block the cell cycle at the G2/M stage, lead to bursting of reactive oxygen species, and induce mitochondrial dysfunction. Overall, the present work showed that the benzenesulfonyl chloride-substituted evodiamine derivatives have good antitumor activity against tumor cells and show promise as anticancer agents.

Antimicrobial, antioxidant, mechanistic, docking simulation, and electrochemical studies for grafting polymerization of novel sulphonated gelatin derived from chicken feet

In this elucidation, alternative collagen sources were investigated. Chicken foot waste is one of the alternate sources due to its high collagen protein concentration. Herein, high-quality collagen was produced from chicken foot by-products from natural sources. NaOH and acetic acid were used in the extraction procedure, and the extracted collagen was hydrolyzed to form gelatin with a yield of 10%. Furthermore, we study the effect of gelatin on the olefinic benzene-sulfonamide interactions through graft polymerization. Firstly, the nucleophilic substitution reaction of the benzenesulfonyl chloride derivative with aminoacetophenone in pyridine affords the corresponding (E)-N-(4-(3-(4-bromophenyl) acryloyl) phenyl)-4-methyl benzene sulfonamide (4) (Br-PS) in excellent yield. Furthermore, the graft polymerization of Br-PS via free radical polymerization onto the skeleton of gelatin gave the corresponding poly (E)-N-(4-(3-(4-bromophenyl) acryloyl) phenyl)-4-methyl benzene sulfonamide-grafted gelatin [poly (Br-PS)-g-Gelatin] in good yield. The obtained compounds were elucidated using spectral analysis such as FT-IR, 1HR, SEM, and TGA and displayed diverse interactions because of the presence of various NH, CO, OH, and CH = functional groups, which can make different hydrogen bond interactions. We confirmed these proposed structures through the DFT/B3LYP/6–31(G) premise set and showed different descriptors for them. Moreover, the new synthesized Poly (Br-PS)-g-Gelatin has good electrochemical properties. However, cyclic voltammetry gives a well-known hysteresis-type loop, which is significant for a supercapacitor. Furthermore, the synthesized polymer was stable electrochemically at different scan rates, and there was no damage to the composition electrode surface. Additionally, (Br-PS), Gelatin, and poly (Br-PS)-g-Gelatin exhibited antimicrobial and antioxidant activity, which was affirmed by molecular docking simulations with diverse proteins.

A fast and accurate colorimetric assay for quantifying hippuric acid in human urine

Hippuric acid is an abundant metabolite in human urine. Urinary hippuric acid levels change with toxic exposure to aromatic compounds, consumption of fruits and vegetables, cancers, chronic kidney disease, schizophrenia and Crohn's disease. While urinary hippuric acid can be detected and quantified via mass spectrometry or nuclear magnetic resonance spectroscopy, a colorimetric assay would be preferable for a low-cost, point-of care clinical assay. Two colorimetric methods, that use p-dimethylaminobenzaldehyde (DMAB) or benzenesulfonyl chloride (PhSO2Cl), respectively, have been previously developed to detect hippuric acid but these assays have many limitations. We replaced PhSO2Cl with p-toluenesulfonyl chloride (p-TsCl), to create a simpler, faster and more accurate method that works with human urine. This modified colorimetric assay detects from 60 μM to 1000 μM hippuric acid in urine in 2 min. We also corrected for the effects of interfering compounds present in urine such that the assay works across many urine backgrounds. We validated this improved assay on multiple hippurate-spiked urine samples, observing an excellent correlation (R2 > 0.94) between observed and known hippurate concentrations. These data suggest that this colorimetric assay is accurate and should greatly facilitate the measurement of hippuric acid in urine to detect a variety of human conditions.

Rapid Analysis of Estrogens in Meat Samples by High Performance Liquid Chromatography with Fluorescence Detection.

A novel reagent named 4-(N-methyl-1,3-dioxo-benzoisoquinolin-6-yl-oxy)benzene sulfonyl chloride (MBIOBS-Cl) for the determination of estrogens in food samples by high-performance liquid chromatography (HPLC) with fluorescence detection has been developed. Estrogens could be easily labeled by MBIOBS-Cl in Na2CO3-NaHCO3 buffer solution at pH 10.0. The complete labeling reaction for estrogens could be accomplished within five minutes, the corresponding derivatives exhibited strong fluorescence with the maximum excitation and emission wavelengths at 249nm and 443nm, respectively. The derivatization conditions, such as the molar ratio of reagent to estrogens, derivatization time, pH, temperature, and buffers were optimized. Derivatives were sufficiently stable to be efficiently analyzed by HPLC with a reversed-phase Agilent ZORBAX 300SB-C18 column with a good baseline resolution. Excellent linear correlations were obtained for all estrogen derivatives with correlation coefficients greater than 0.9998. Ultrasonic-Assisted extraction was used to optimize the extraction of estrogens from meat samples with a recovery higher than 82%. The detection limits (LOD, S/N = 3) of the method ranged from 0.95 to 3.3μg· kg-1. The established method, which is fast, simple, inexpensive, and environment friendly, can be successfully applied for the detection of four steroidal estrogens from meat samples with little matrix interference.

Synthesis of some new substituted imines from aldehydes and ketones derived from quinolinic acid

In this paper, some substituted imines compounds have been prepared from quinolinic acid as a starting material. Firstly, the quinolinic acid was treated with acetic anhydride and acetic acid to form furo[3,4-b]pyridine-5,7-dione (1); the resulting compound was heated with urea to form 5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (2). After that, it was treated with potassium hydroxide to give potassium 5,7-dioxo-5,7-dihydropyrrolo[3,4-b]pyridin-6-dione, which was directly and easily converted to 6-(2-([1,1'-biphenyl]-4-yl)-2-oxoethyl)-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (3) by the reaction with 1-([1,1'-biphenyl]-4-yl)-2-bromoethan-1-one. Finally, the resultant compound reacted with substituted aniline to give imines (4, 5). Secondly the quinolinic acid converted to 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo[3,4-b] pyridin-6-yl) benzenesulfonyl chloride according to our previous work, then treated with p-hydroxy acetophenone or p-hydroxy benzaldehyde to form 4-substituted bezyloxy 4-(5,7-dioxo-5,7-dihydro-6H-pyrrolo[3,4-b] pyridine-6-yl) benzenesulfonate (6, 7), which were finally treated with substituted aniline to form new substituted imines (8–12).

Hemin‐Promoted Direct C−H Thiolation in the Synthesis of Diaryl Sulfides

AbstractDiaryl sulfides are a class of important synthetic chemical units. Herein, we report a new method for direct preparation of diphenyl sulfides using P‐toluenesulfonyl chloride as an effective thiophenyl radical precursor with assistance from Hemin. Various substituted anisoles and benzenesulfonyl chlorides are well tolerated, resulting in moderate to good yields of diaryl sulfides. The potential of the proposed method is validated by good yields obtained in gram scale reactions.

Synthesis, Spectroscopic Analysis, Biological Evaluation, and In Silico Studies of Novel Benzenesulfonate-Derived Schiff-Mannich Bases

In the current study, 3-formyl phenyl benzenesulfonate is created by reacting 3-hydroxybenzaldehyde with benzene sulfonyl chloride, which is aided by triethylamine. Nine unique (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were formed through the reaction of a manufactured 3-formyl phenyl benzenesulfonate chemical with nine 3-alkyl(aryl)-4-amino-4,5-dihydro-1H-1,2,4-triazol-5-one, as detailed in the existing literature. Phenyl benzene sulfonate (S) compounds were purchased. Through the reaction of the Schiff bases that were made a secondary amine, such as morpholine with formaldehyde, heterocyclic Mannich bases of a unique kind were created. Five recently found (Z)-3-[(3-substituted-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds are presented in this work. By reacting phenyl benzene sulfonate (S) with morpholine in the presence of formaldehyde, five new (Z)-3-[(3-substituted-1-(morpholinomethyl)-5-oxo-1,5-dihydro-4H-1,2,4-triazol-4-yl)-iminomethyl] compounds were created. Chemical compounds fall under the category of phenylbenzene sulfonates (M). Utilizing IR, 1H NMR, and 13C NMR spectroscopy, fourteen recently novel compoundsand#39; chemical structures were examined. The ability of the freshly synthesized Schiff and morpholine-derived Mannich bases to obstruct the acetylcholinesterase enzymeand#39;s (AChE) activity was also assessed. The 1,2,4-triazole functional group was modified by adding various groups at the 1 and 3 positions, resulting in a collection of compounds (S1–9 and M1, 2, 4, 5, 7). It was determined whether these synthetic compounds could prevent the human recombinant AR enzyme from working in vitro, and the findings were validated using molecular docking, molecular mechanics, and ADME analyses. To better understand this mechanism, synthetic Schiff and Mannich base derivatives as well as the positive control substance quercetin were tested using molecular docking against the human recombinant AR enzyme in vitro. To assess the drug-like properties of Schiff and Mannich base analogs, a series of absorption, distribution, metabolism, and excretion (ADME) properties were analyzed theoretically.

Macrocyclization via remote meta-selective C-H olefination using a practical indolyl template.

The synthesis of macrocyclic compounds with different sizes and linkages remains a great challenge via transition metal-catalysed intramolecular C-H activation. Herein, we disclose an efficient macrocyclization strategy via Pd-catalysed remote meta-C-H olefination using a practical indolyl template. This approach was successfully employed to access macrolides and coumarins. In addition, the intermolecular meta-C-H olefination also worked well and was exemplified by the synthesis of antitumor drug belinostat from inexpensive and readily available benzenesulfonyl chloride. Notably, catalytic copper acetate and molecular oxygen were used in place of silver salts as oxidants. Furthermore, for the first time, the formation of a macrocyclophane cyclopalladated intermediate was detected through in situ Fourier-transform infrared monitoring experiments and ESI-MS.

Synthesis of indole derivatives as Alzheimer inhibitors and their molecular docking study

Acetylcholinesterase prevails in the healthy brain, with butyrylcholinesterase reflected to play a minor role in regulating brain acetylcholine (ACh) levels. However, BuChE activity gradually increases in patients with (AD), while AChE activity remains unaffected or decays. Both enzymes therefore represent legitimate therapeutic targets for ameliorating the cholinergic deficit considered to be responsible for the declines in cognitive, behavioural, and global functioning characteristic of AD. Current study described the synthesis of indole-based sulfonamide derivatives (1-23) and their biological activity. Synthesis of these scaffolds were achieved by mixing chloro-substituted indole bearing amine group with various substituted benzene sulfonyl chloride in pyridine, under refluxed condition to obtained desired products. All products were then evaluated for AchE and BuchE inhibitory potential compare with positive Donepezil as standard drug for both AchE and BchE having IC50 = 0.016 ± 0.12 and 0.30 ± 0.010 μM respectively. In this regard analog 9 was found potent having IC50 value 0.15 ± 0.050 μM and 0.20 ± 0.10 for both AchE and BuChE respectively. All other derivatives also found with better potential. All compounds were characterized by various techniques such as 1H, 13C-NMR and HREI-MS. In addition, biological activity was maintained to explore the bioactive nature of scaffolds and their protein-ligand interaction (PLI) was checked through molecular docking study. Communicated by Ramaswamy H. Sarma

Unique reaction of cyclicimides containing double bond with chlorosulfonyl isocyanate and theoretical computations: Solvent-free reactions

The addition reactions of chlorosulfonyl isocyanate (CSI) to N-phenylmaleimide and 2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione were investigated. Interesting products were obtained from the reaction of both compounds with CSI. N-phenylmaleimide led to the formation of an electrophilic substitution product, 4-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)benzenesulfonyl chloride while 2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione led to the formation of ((3aS,7aR,E)-3-oxo-2-phenyl-2,3,3a,4,7,7a-hexahydro-1H-isoindol-1-ylidene)sulfamoyl chloride. The structure of both products was determined by using spectroscopic methods such as NMR and Mass. Theoretical studies were carried out to explain the different reactions of both compounds with similar structures. It was determined by theoretical studies that the progression of both compounds through different reactions depends on the structure of the imides used and the energy levels of the intermediates.

A silicone diphenylsulfonate for improving the flame retardancy of polycarbonate

AbstractSilicone diphenylsulfonate (SDPSF) was synthesized via nucleophilic substitution reaction between dihydroxyalkyl‐terminated silicone oil and benzene sulfonyl chloride, and its chemical structure was confirmed by Fourier transform infrared (FTIR) and 1H NMR. The effect of SDPSF on the flame retardancy, thermal stability, combustion behavior, and mechanical properties of PC/SDPSF blends were investigated. The PC/2 wt% SDPSF blend achieved the UL‐94 (3 mm) V‐0 rating and limiting oxygen index value of 30.3% together with the lowest values of the total heat release (32.2 MJ/M2), peak heat release rate (239.5 kW/M2), CO production (0.48 kg/kg), and fire growth index (1.09 kW/s·m2). It demonstrated that the SDPSF improved evidently the flame retardancy and fire safety of the polycarbonate (PC) matrix. The blend also gave a slightly reduced tensile strength (60.0 MPa) and notched impact strength (57.0 kJ/m2). The TG‐FTIR spectra of the pyrolysis gases demonstrated that the SDPSF promoted the decomposition of PC matrix on advance to release much more nonflammable gases in the early combustion process, meanwhile, the analysis of the char residues confirmed that the SDPSF facilitated the formation of compact and continuous layers with higher graphitization degree to isolate the transfer of heat and combustible volatiles.

Synthesis, Characterization and Antimicrobial Activity of N-Pyridin-3-yl-benzenesulfonamide

This study describes a simple one-pot synthesis of N-pyridin-3-yl-benzenesulfonamide and its antimicrobial activity. The reaction of benzene sulfonyl chloride with 3-aminopyridine in the presence of aqueous Na2CO3 and HCl as a scavenger furnished the sulfonamide in 93.3% yield. The structure of the synthesized compound was established using the spectral data obtained from FTIR, 1HNMR and 13CNMR). All spectrometric spectrum bands and peaks obtained were sulfonamide-related. The antibacterial test carried out against Gram-positive bacterium (Staphylococcus aureus) and Gram-negative bacteria (Salmonella typhi and Eschericha coli) tested upon at concentrations 150, 100, 50 and 25 mg/ml revealed that the synthesized N-pyridin-3yl-benzenesulfonamide possesses great antimicrobial activity.

Synthesis, Spectroscopic Analysis, and In Vitro Anticancer Evaluation of 2-(Phenylsulfonyl)-2H-1,2,3-triazole

The 1,2,3-Triazole derivatives containing the sulfonyl group have proved their biological importance in medicinal chemistry and drug design. In this sense, we describe the regioselective synthesis of 2-(phenylsulfonyl)-2H-1,2,3-triazole 3 in good yield through a classical sulfonamidation reaction of 1H-1,2,3-triazole 1 with benzenesulfonyl chloride 2 in dichloromethane using a slight excess of triethylamine at 20 °C for 3 h. This procedure is distinguished by its short reaction time, high yield, excellent regioselectivity, clean reaction profile, and operational simplicity. The sulfonamide 3 was characterized by high-resolution mass spectrometry, FT–IR, UV–Vis, 1D and 2D NMR spectroscopy, and elemental analysis. The sulfonamide 3 exhibited moderate activity against UO-31 renal, SNB-75 central nervous system, HCT-116 colon, and BT-549 breast cancer cell lines, with growth inhibition percentages (GI%) ranging from 10.83% to 17.64%.