14949-01-0

Basic information

• Product Name: 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide
• Synonyms: 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide;2-Chloro-N-(sulfamoylphenyl)acetamide;2-CHLORO-4'-SULFAMOYLACETANILIDE;2-chloro-N-(4-sulfamoylphenyl)ethanamide
• CAS NO: 14949-01-0
• Molecular Formula: C₈H₉ClN₂O₃S
• Molecular Weight: 248.69
• Mol File: 14949-01-0.mol
• Article Data: 49

Chemical Properties

• Melting Point: 217 °C
• Appearance: /
• Density: 1.527 g/cm³
• Refractive Index: 1.617
• PKA: 9.87±0.12(Predicted)
• CAS DataBase Reference: 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide(14949-01-0)
• EPA Substance Registry System: 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide(14949-01-0)

Safety Data

• Hazardous Substances Data: 14949-01-0(Hazardous Substances Data)

Usage

General Description

2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide is a chemical compound with the molecular formula C8H9ClN2O3S. It is a derivative of acetamide and contains a chlorine atom, a sulfamoyl group, and a phenyl group. 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide has potential pharmaceutical applications as a sulfonamide antibiotic or antimicrobial agent due to its structural similarity to other sulfamoyl-based drugs. It may also have uses in organic synthesis as a building block or intermediate in the production of other compounds. 2-Chloro-N-(4-sulfamoyl-phenyl)-acetamide should be handled and used with care due to its potential reactivity and health hazards associated with its chemical structure.

InChI:InChI=1/C8H9ClN2O3S/c9-5-8(12)11-6-1-3-7(4-2-6)15(10,13)14/h1-4H,5H2,(H,11,12)(H2,10,13,14)

Upstream product

• 63-74-1 sulfanilamide 
• 541-88-8 Chloroacetic anhydride 
• 79-04-9 chloroacetyl chloride 
• 35303-76-5 4-(2-aminoethyl)benzenesulfonamide 

Downstream Products

• 912969-60-9 4-(4-chlorothiazol-2-ylamino)benzenesulfonamide 

Relevant articles and documents

Quinazoline-sulfonamides with potent inhibitory activity against the α-carbonic anhydrase from Vibrio cholerae

Thirteen novel sulfonamide derivatives incorporating the quinazoline scaffold were synthesized by simple, eco-friendly procedures. These compounds were tested for their ability to inhibit the α-carbonic anhydrases (CA, EC 4.2.1.1) from Vibrio cholerae (VchCA) as well as the human α-CA isoforms, hCA I and hCA II. Nine compounds were highly effective, nanomolar inhibitors of the pathogenic enzyme VchCA. Three of them were also highly effective sub-nanomolar inhibitors of the cytosolic isoform II. The best VchCA inhibitor had a KIof 2.7 nM. Many of these developed compounds showed high selectivity for inhibition of the bacterial over the mammalian CA isoforms, with one compound possessing selectivity ratios as high as 97.9 against hCA I and 9.7 against hCA II. Compound 9d was another highly effective VchCA inhibitor presenting a selectivity ratio of 99.1 and 8.1 against hCA I and hCA II, respectively. These results suggest that sulfonamides with quinazoline backbone could be considered suitable tools to better understand the role of bacterial CAs in pathogenesis.

Pharmacological and physicochemical profile of arylacetamides as tools against human cancers

Arylacetamides are widely used as synthetic intermediates to obtain medicinal substances. This work evaluated in vitro antiproliferative activity of ten 2-Chloro-N-arylacetamides on human normal and cancer cells and detailed in vivo toxicological and anticancer investigations. Initially, cytotoxic colorimetric assays were performed using tumor lines, peripheral blood mononuclear cells (PBMC) and erythrocytes. Compounds 2, 3 and 4 were tested for acute toxicity (50, 150 and 300 mg/kg) and for subacute antitumoral capacity in HCT-116 colon carcinoma-bearing xenograft mice for 15 days at 25 mg/kg/day. Most compounds revealed cytotoxic action on tumor lines and PBMC, but activity on human erythrocytes were not detected. Molecular dipole moment, lipophilicity and electronic constant of aryl substituents had effects upon in vitro antiproliferative capacity. More common in vivo acute behavioral signals with compounds 2, 3 and 4 were muscle relaxation, reduction of spontaneous locomotor activity and number of entries in closed arms and increased number of falls andtime spent in open arms, suggesting diazepam-like anxiolytic properties. Decrease of grabbing strength and overall activity were common, but palpebral ptosis and deaths occurred at 300 mg/kg only. Compounds 2 and 3 reduced colon carcinoma growth (21.2 and 27.5%, respectively, p 0.05) without causing apparent signals of organ-specific toxicity after subacute exposure. The structural chemical simplicity of arylacetamides make them cost-effective alternatives and justifies further improvements to enhance activity, selectivity and the development of pharmaceutical formulations.

Synthesis and antiproliferative evaluation of novel 2-(4H-1,2,4-triazole-3-ylthio)acetamide derivatives as inducers of apoptosis in cancer cells

In this study, a series of thiosemicarbazide derivatives 12–14, 1,2,4-triazol-3-thione derivatives 15–17 and compounds bearing 2-(4H-1,2,4-triazole-3-ylthio)acetamide structure 18–32 have been synthesized starting from phenolic compounds such as 2-naphthol, paracetamol and thymol. Structures and purity of the target compounds were confirmed by the use of their chromatographic and spectral data besides microanalysis. All of the synthesized new compounds 12–32 were evaluated for their anti-HIV activity. Among these compounds, three representatives 18, 19 and 25 were selected and evaluated by the National Cancer Institute (NCI) against the full panel of 60 human cancer cell lines derived from nine different cancer types. Antiproliferative effects of the selected compounds were demonstrated in human tumor cell lines K-562, A549 and PC-3. These compounds inhibited cell growth assessed by MTT assay. Compound 18, 19 and 25 exhibited anti-cancer activity with IC50values of 5.96?μM (PC-3?cells), 7.90?μM (A549/ATCC cells) and 7.71?μM (K-562?cells), respectively. After the cell viability assay, caspase activation and Bcl-2 activity of the selected compounds were measured and the loss of mitochondrial membrane potential (MMP) was detected. Compounds 18, 19 and 25 showed a significant increase in caspase-3 activity in a dose-dependent manner. This was not observed for caspase-8 activity with compound 18 and 25, while compound 19 was significantly elevated only at the dose of 50?μM. In addition, all three compounds significantly decreased the mitochondrial membrane potential and expression of Bcl-2.

Discovery of a novel series of indolylchalcone-benzenesulfonamide hybrids acting as selective carbonic anhydrase II inhibitors

The primary sulfonamide group is one of the most efficient zinc binding group (ZBG) for designing carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. In the present study primary sulfonamide linked with indolylchalcone were designed. The newly synthesized molecules (5a-r) were examined against four human (h) CA isoforms (hCA I, hCA II, hCA IX and hCA XIII). These sulfonamides showed good inhibition activity against isoforms hCA I, hCA II and hCA XIII. Compound 5i (2.3 nM), 5m (2.4 nM), 5o (3.6 nM) and 5q (7.0 nM) were more potent than standard drug AAZ (12.1 nM) against isoform hCA II, respectively. Most of the other compounds in the present series inhibited hCA XIII and hCA IX in the range of 50 nM ? 100 nM.

N-Aryl mercaptoacetamides as potential multi-target inhibitors of metallo-β-lactamases (MBLs) and the virulence factor LasB fromPseudomonas aeruginosa

Increasing antimicrobial resistance is evolving to be one of the major threats to public health. To reduce the selection pressure and thus to avoid a fast development of resistance, novel approaches aim to target bacterial virulence instead of growth. Another strategy is to restore the activity of antibiotics already in clinical use. This can be achieved by the inhibition of resistance factors such as metallo-β-lactamases (MBLs). Since MBLs can cleave almost all β-lactam antibiotics, including the “last resort” carbapenems, their inhibition is of utmost importance. Here, we report on the synthesis andin vitroevaluation ofN-aryl mercaptoacetamides as inhibitors of both clinically relevant MBLs and the virulence factor LasB fromPseudomonas aeruginosa. All testedN-aryl mercaptoacetamides showed low micromolar to submicromolar activities on the tested enzymes IMP-7, NDM-1 and VIM-1. The two most promising compounds were further examined in NDM-1 expressingKlebsiella pneumoniaeisolates, where they restored the full activity of imipenem. Together with their LasB-inhibitory activity in the micromolar range, this class of compounds can now serve as a starting point for a multi-target inhibitor approach against both bacterial resistance and virulence, which is unprecedented in antibacterial drug discovery.

Design, synthesis and mechanistic study of new benzenesulfonamide derivatives as anticancer and antimicrobial agentsviacarbonic anhydrase IX inhibition

Changes in gene expression cause uncontrolled cell proliferation and consequently tumor hypoxia. The tumor cells shift their metabolism to anaerobic glycolysis with a significant modification in pH. Therefore, an over expression of carbonic anhydrase IX (CA IX) genes was detected in many solid tumors. Accordingly, selective inhibition of CA IX can be a useful target for discovering novel antiproliferative agents. The present study described the synthesis of new aryl thiazolone-benzenesulfonamides4a-jas well as their carbonic anhydrase IX inhibitory effect. All the designed derivatives were evaluated for their anti-proliferative activity against triple-negative breast cancer cell line (as MDA-MB-231) and another breast cancer cell line (MCF-7) in addition to normal breast cell line MCF-10A. Compounds4b-c,4e,4g-hshowed significant inhibitory effect against both cancer cell lines at concentration ranges from 1.52-6.31 μM, with a high selectivity against breast cancer cell lines ranges from 5.5 to 17.5 times. Moreover, three sulfonamides derivatives4e,4gand4hshowed excellent enzyme inhibition against CA IX with IC5010.93-25.06 nM and against CA II with IC501.55-3.92 μM that revealed their remarkable selectivity for CA IX over CA II. Additionally,4ewas able to induce apoptosis in MDA-MB-231 with a significant increase in the annexin V-FITC percent by 22 fold as compared with control. Cellular uptake on MDA-MB-231 cell lines were carried out using HPLC method on the three active compounds (4e,4gand4h). On the other hand inhibition of one or more CAs present in bacteria was reported to interfere with bacterial growth. So, the new benzenesulfonamides were evaluated against their antibacterial and anti-biofilm activities. Analogues4e,4gand4hexhibited significant inhibition at 50 μg mL?1concentration with 80.69%, 69.74% and 68.30% againstS. aureuscompared to the positive control CIP which was 99.2%, while compounds4gand4hshowed potential anti-biofilm inhibition 79.46% and 77.52% againstK. pneumonia. Furthermore, the designed compounds were docked into CA IX (human) protein (PDB ID: http://xlink.rsc.org/?pdb=5FL6">5FL6) and molecular modeling studies revealed favorable binding interactions for the active inhibitors. Finally, the predictive ADMET studies showed that, compounds4e,4gand4hpossessed promising pharmacokinetic properties.