1709-54-2

Usage

Purification Methods

Crystallise Septazen from dioxane/H2O, EtOH/H2O or Me2CO (m 174.5-175.8o). Its solubility in H2O at 37o is 0.03-0.43mg/100mL. [Beilstein 14 III 2026.]

InChI:InChI=1/C13H14N2O2S/c14-12-6-8-13(9-7-12)18(16,17)15-10-11-4-2-1-3-5-11/h1-9,15H,10,14H2

Upstream product

• 6752-38-1 4-chlorosulfonylbenzene isocyanate 
• 100-46-9 benzylamine 
• 52374-25-1 N-benzyl-4-nitrobenzenesulfonamide 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 63-74-1 sulfanilamide 
• 100-51-6 benzyl alcohol 
• 100-52-7 benzaldehyde 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 289061-13-8 N-(4-(N-benzylsulfamoyl)phenyl)acetamide 
• 56542-67-7 3-cyanobenzene sulfonyl chloride 
• 56768-47-9 Ν-benzyl-4-cyanobenzenesulfonamide 

Downstream Products

• 722494-78-2 N-chloroacetyl-sulfanilic acid benzylamide 
• 116691-41-9 N-Benzyl-4-(8-hydroxy-quinolin-5-ylazo)-benzenesulfonamide 
• 111456-16-7 coumarin-3N-(4'-(N'-benzyl)sulphonamidophenyl)carboxamide 
• 455901-11-8 N-benzyl-4-[3-(3-cyanophenyl)-ureido]-benzenesulfonamide 
• 455900-78-4 3-[3-(4-benzylsulfamoyl-phenyl)-thioureido]-benzamidine 
• 455901-02-7 N-(4-benzylsulfamoylphenyl)-N'-(3-carbamimidoyl-phenyl)-oxalamide 
• 1167997-39-8 C₃₀H₂₃N₅O₂S 
• 1160499-34-2 dimethyl (2E,4Z)-4-({[4-(benzylsulfamoyl)phenyl]amino}methylene)pent-2-enedioate 
• 1228268-29-8 N-benzyl-4-[(3,4-diphenylpyrimido[4',5':4,5]thieno[2,3-c]pyridazin-8-yl)amino]benzenesulfonamide 
• 1326238-23-6 C₃₀H₂₆N₂O₅S 
• 1366000-27-2 N-(4-benzylsulfamoyl-phenyl)-2-(1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrrolo[3,2-d]pyrimidin-5-yl)-acetamide 

Relevant academic research and scientific papers

A base labile handle for solid phase organic chemistry

Several arylsulfonamides have been synthesised on solid phase using a new base labile handle. Cleavage front the solid support is accomplished by oxidation of the sulfide to the sulfone, followed by β-elimination in base media.

Structure-activity relationships of agonists for the orphan G protein-coupled receptor GPR27

GPR27 belongs, with GPR85 and GPR173, to a small subfamily of three receptors called “Super-Conserved Receptors Expressed in the Brain” (SREB). It has been postulated to participate in key physiological processes such as neuronal plasticity, energy metabolism, and pancreatic β-cell insulin secretion and regulation. Recently, we reported the first selective GPR27 agonist, 2,4-dichloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (I, pEC50 6.34, Emax 100%). Here, we describe the synthesis and structure-activity relationships of a series of new derivatives and analogs of I. All products were evaluated for their ability to activate GPR27 in an arrestin recruitment assay. As a result, agonists were identified with a broad range of efficacies including partial and full agonists, showing higher efficacies than the lead compound I. The most potent agonist was 4-chloro-2,5-difluoro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7y, pEC50 6.85, Emax 37%), and the agonists with higher efficacies were 4-chloro-2-methyl-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7p, pEC50 6.04, Emax 123%), and 2-bromo-4-chloro-N-(4-(N-phenylsulfamoyl)phenyl)benzamide (7r, pEC50 5.99, Emax 123%). Docking studies predicted the putative binding site and interactions of agonist 7p with GPR27. Selected potent agonists were found to be soluble and devoid of cellular toxicity within the range of their pharmacological activity. Therefore, they represent important new tools to further characterize the (patho)physiological roles of GPR27.

Synthesis, Computational Docking, and Antimycobacterial Study of Novel N'-phenyl-4-pyrrol-1-yl-benzenesulfonamide Derivatives

Fresh sequences of pyrrole linked N'-phenyl-4-pyrrolyl-benzenesulfonamide derivatives were synthesized by different synthetic methods. Synthesis of the N'-phenyl-4-(1H-pyrrol-1-yl) benzenesulfonamides 5(a-e)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N'-phenylbenzenesulfonamides 6(a-e) was achieved by refluxing 2,5-dimethoxytetrahydrofuran/hexane 2,5-dione separately in presence of acetic acid. Further, synthesis of N-(4-(N'-phenylsulfamoyl)phenyl)-4-(1H-pyrrol-1-yl)benzamides 8(a-b)/4-(2,5-dimethyl-1H-pyrrol-1-yl)-N-(4-(N'-phenylsulfamoyl)phenyl)benzamides 10(a-b) was achieved by cold stirring of 4-(1H-pyrrol-1-yl)benzoic acid (7)/2,5-dimethyl-1H-pyrrol-1-yl)benzoic acid (9) correspondingly in the presence of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, N', N'-diisopropylethylamine, and Dimethylformamide. In vitro anti-tubercular study of afresh compounds has shown good minimum inhibitory concentration values (0.4-12.5 μg/mL) counter to Mycobacterium tuberculosis H37Rv, while the corresponding study of reported molecules for antibacterial activity disclosed considerable inhibition values (0.4-25 μg/mL) counter to Escherichia coli (Gram-ve) than Staphylococcus aureus (Gram +ve).

Discovery of secondary sulphonamides as IDO1 inhibitors with potent antitumour effects in vivo

Indoleamine 2,3-dioxygenase 1 (IDO1) as a key rate-limiting enzyme in the kynurenine pathway of tryptophan metabolism plays an important role in tumour immune escape. Herein, a variety of secondary sulphonamides were synthesised and evaluated in the HeLa cell-based IDO1/kynurenine assay, leading to the identification of new IDO1 inhibitors. Among them, compounds 5d, 5l and 8g exhibited the strongest inhibitory effect with significantly improved activity over the hit compound BS-1. The in vitro results showed that these compounds could restore the T cell proliferation and inhibit the differentiation of na?ve CD4+ T cell into highly immunosuppressive FoxP3+ regulatory T (Treg) cell without affecting the viability of HeLa cells and the expression of IDO1 protein. Importantly, the pharmacodynamic assay showed that compound 5d possessed potent antitumour effect in both CT26 and B16F1 tumours bearing immunocompetent mice but not in immunodeficient mice. Functionally, subsequent experiments demonstrated that compound 5d could effectively inhibit tumour cell proliferation, induce apoptosis, up-regulate the expression of IFN-γ and granzyme B, and suppress FoxP3+ Treg cell differentiation, thereby activate the immune system. Thus, compound 5d could be a potential and efficacious agent for further evaluation.

Effect of photodynamic antibacterial chemotherapy combined with antibiotics on Gram-positive and gram-negative bacteria

The well-known and rapidly growing phenomenon of bacterial resistance to antibiotics is caused by uncontrolled, excessive and inappropriate use of antibiotics. One of alternatives to antibiotics is Photodynamic Antibacterial Chemotherapy (PACT). In the present study, the effect of PACT using a photosensitizer Rose Bengal alone and in combination with antibiotics including methicillin and derivatives of sulfanilamide synthesized by us was tested against antibiotic-sensitive and antibiotic-resistant clinical isolates of Gram-positive S. aureus and Gram-negative P. aeruginosa. Antibiotic-sensitive and resistant strains of P. aeruginosa were eradicated by Rose Bengal under illumination and by sulfanilamide but were not inhibited by new sulfanilamide derivatives. No increase in sensitivity of P. aeruginosa cells to sulfanilamide was observed upon a combination of Rose Bengal and sulfanilamide under illumination. All tested S. aureus strains (MSSA and MRSA) were effectively inhibited by PACT. When treated with sub-MIC concentrations of Rose Bengal under illumination, the minimum inhibitory concentrations (MIC) of methicillin decreased significantly for MSSA and MRSA strains. In some cases, antibiotic sensitivity of resistant strains can be restored by combining antibiotics with PACT.

ADENINE DERIVATIVES AS PROTEIN KINASE INHIBITORS

The present invention relates to a compound suitable for use as a kinase inhibitor according to general formula (I) [compound (C), herein after], or the N- oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof, formula (I) wherein A, R1, R2, R3, R3', R4, R4', X, Y, Z, T are as defined in the claims. The invention further relates to an in vitro method of inhibiting protein kinase activity which comprises contacting a protein kinase with a compound of formula (I), or the N-oxide, pharmaceutically acceptable salt, pharmaceutically acceptable solvate, or stereoisomer thereof. The invention further relates to the compounds of formula (I) per se, as well as to their use as a medicament, and for use or in a method of treatment of a disease mediated by a protein kinase selected from cancer, inflammatory disorders, cardiovascular diseases, viral induced diseases, circulatory diseases, fibro-proliferative diseases and pain sensitization disorders.

Cyclometalated palladium pre-catalyst for N-alkylation of amines using alcohols and regioselective alkylation of sulfanilamide using aryl alcohols

Simple pyrazole based palladacycle-phosphine with a high turnover has been developed and applied for the N-alkylation of amines and sulfanilamide using alcohols as substrates by hydrogen borrowing strategy. N-alkylation of primary and secondary amines resulted in high isolated yields at 100–130 °C, under solvent free conditions. More challenging secondary aliphatic as well as aromatic alcohols were also successfully utilized as alkylating agents under similar reaction conditions. The turn over number reached up to 43000 for N-benzylation of aniline using benzyl alcohol. Notably, regioselective N-alkylation of 2-aminobenzothiazole and 4-aminobenzenesulfonamide to the corresponding 2-N-(alkylamino)azoles and 4-amino-(N-alkyl)benzenesulfonamides using alcohols as alkylating agents have been achieved using our new pre-catalyst-phosphine system.

Synthesis process of sulfonamide compounds in microwave system

The invention discloses a synthesis process of sulfonamide compounds in a microwave system. The synthesis process is realized by the following steps: by using CuCl as a catalyst and FeCl3 as an oxidant, carrying out carbon-hydrogen activating and carbon-nitrogen coupling reaction in a DMF (Dimethyl Formamide) by substituting sulfanilamide and methylbenzene through microwave heating and efficient catalysis for 10 to 60 minutes; extracting a product by using ethyl acetate; carrying out vacuum concentration; carrying out column chromatographic purification on a product to obtain the sulfonamide compounds. The synthesis process is a method for efficiently preparing the sulfonamide compounds, which is environment-friendly and is simple and convenient to operate. Compared with the prior art, the synthetic process disclosed by the invention has the advantages of remarkably-increased reaction speed compared with that under a conventional heating condition, mild reaction conditions, simple operation, high yield, safety, low cost and environmental protection.

Potent and selective N-(4-sulfamoylphenyl)thiourea-based GPR55 agonists

To date, many known G protein-coupled receptor 55 (GPR55) ligands are those identified among the cannabinoids. In order to further study the function of GPR55, new potent and selective ligands are needed. In this study, we utilized the screening results from PubChem bioassay AID 1961 which reports the results of Image-based HTS for Selective Agonists of GPR55. Three compounds, CID1792579, CID1252842 and CID1011163, were further evaluated and used as a starting point to create a series of nanomolar potency GPR55 agonists with N-(4-sulfamoylphenyl)thiourea scaffold. The GPR55 activity of the compounds were screened by using a commercial β-arrestin PathHunter assay and the potential compounds were further evaluated by using a recombinant HEK cell line exhibiting GPR55-mediated effects on calcium signalling. The designed compounds were not active when tested against various endocannabinoid targets (CB1R, CB2R, FAAH, MGL, ABHD6 and ABHD12), indicating compounds' selectivity for the GPR55. Finally, structure-activity relationships of these compounds were explored.

Amino-(N-alkyl) benzsulfamide synthesis method

The invention discloses an amino-(N-alkyl) benzsulfamide synthesis method. The method comprises the steps of adding aminobenzenesul fonamide, an iridium complex catalyst, alkali, compound alcohol and the solvent tert-amyl alcohol into a reaction container for reaction lasting several hours at 120-150 DEG C, then reducing temperature to room temperature, conducting rotary evaporation to remove the solvent, and then conducting column separation to obtain the target compound. Commercial aminobenzenesul fonamide and nearly non-toxic compound alcohol are used as starting materials, only water is generated as reaction byproduct, and no environment harm is done; reaction atom economy is high.