21978-63-2

Upstream product

• 2592-95-2 benzotriazol-1-ol 
• 98-59-9 p-toluenesulfonyl chloride 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 

Downstream Products

• 859205-33-7 1-[(4-methylphenyl)sulfonyl]-1H-indole-3-carbonitrile 
• 5457-28-3 3-cyano-1H-indole 
• 4703-22-4 N-tosylpiperidine 
• 59724-69-5 (±)-methyl 2-(4-methylphenylsulfonamido)propanoate 
• 80-30-8 N-cyclohexyl-p-toluenesulfonamide 
• 1907-65-9 N-butyl-4-toluenesulfonamide 
• 2645-02-5 methyl tosylglycinate 
• 4809-56-7 N-(1-phenylethyl)-p-toluenesulfonamide 
• 1576-37-0 N-benzyl-p-toluenesulfonamide 
• 22713-34-4 1-methoxy-1H-benzo[d][1,2,3]triazole 
• 57223-16-2 1-ethoxy-1H-benzo[d]-1,2,3-triazole 
• 77204-11-6 1-allyloxy-1H-benzo[d][1,2,3]triazole 
• 4873-09-0 allyl tosylate 
• 68930-15-4 1-(benzyloxy)-1H-benzo[d][1,2,3]triazole 

Relevant academic research and scientific papers

Synthesis and evaluation of 1-hydroxybenzotriazole derivatives: Dual inhibitors of carbonic anhydrase ii and sodium hydrogen exchanger i

Ischemia reperfusion injury is responsible for impaired graft functioning in organ transplants, cerebral dysfunction, ischemic heart diseases, systemic inflammatory response syndrome, gastrointestinal dysfunction, and multiple organ dysfunction syndromes. Intracellular pH is critical for cell survival in ischemia reperfusion injury. Sodium hydrogen exchanger I and carbonic anhydrase II are critical in the regulation of intracellular pH. Inhibition of sodium hydrogen exchanger I and carbonic anhydrase II during reperfusion is found to ameliorate ischemia reperfusion injury separately. An attempt is made to synthesize dual inhibitors of sodium hydrogen exchanger and carbonic anhydrase to have better potential drug molecule in ischemia reperfusion injury treatment. The hydroxybenzotriazole is considered as a central pharmacophore for this dual activity and 12 derivatives are synthesized. All derivatives are tested for sodium hydrogen exchanger I and carbonic anhydrase II inhibitory activity. The tosylate derivative (12) is found to be the most potent derivative with IC50 158.7± 8.4 μM for carbonic anhydrase II and 31.07 ± 1.06 μM for sodium hydrogen exchanger I. Although the potency is less than standard drugs but this is the first report of dual inhibitor of carbonic anhydrase II and sodium hydrogen exchanger.

Electrochemically induced oxidative S-O coupling: synthesis of sulfonates from sulfonyl hydrazides and N-hydroxyimides or N-hydroxybenzotriazoles

The process of oxidative S-O coupling under the action of electric current was developed. Aryl, hetaryl and alkyl sulfonyl hydrazides and N-hydroxy compounds (N-hydroxyimides and N-hydroxybenzotriazoles) are applied as starting reagents for the preparation of sulfonates. The reaction is carried out under constant current conditions in an experimentally convenient undivided electrochemical cell equipped with a graphite anode and a stainless steel cathode under a high current density (60 mA cm?2). NH4Br in this process acts as a supporting electrolyte and participates in the oxidation of the starting compounds to form a coupling product. The developed strategy represents a quite atom-efficient approach: one partner loses two nitrogen and three hydrogen atoms, while another one loses only one hydrogen atom. Cyclic voltammetry and the control experiment allowed us to propose possible reaction pathways: generated through anodic oxidation molecular bromine or its higher oxidation state derivatives oxidize the starting compounds to form reactive species, which couple to form the S-O bond.

Synthesis of O-benzyl hydroxamates employing the sulfonate esters of N-hydroxybenzotriazole

The direct conversion of various carboxylic acids, that include sterically hindered amino acids and di-peptides, to O-benzyl hydroxamates is demonstrated using sulfonate esters of benzotriazoles under ambient and milder conditions without significant race

Synthesis, structure, theoretical calculations and biological activity of sulfonate active ester new derivatives

A series of naphthyl and tolyl sulfonate ester were synthesized and characterized by H NMR. X-ray single crystal diffraction experiments established the molecular structure of three new sulfonate esters derivatives, and spectral data agree with these in solution. The observed hydrogen bonding is discussed on the basis of crystal structural analyses and DFT/MP2 geometry optimization quantum calculations. Antimicrobial activities were screened for selected compounds against three human cancer cell lines and Mosquito Culex pipiens larvae.

Sulfonamide synthesis using N-hydroxybenzotriazole sulfonate: An alternative to pentafluorophenyl (PFP) and trichlorophenyl (TCP) esters of sulfonic acids

The N-hydroxybenzotriazole (HOBt) sulfonate esters undergo amidation under ambient conditions in the presence of di-isopropylethyl amine. This method can be applied to varieties of amines including sterically hindered amino acid esters in less time with reasonably good yields. HOBt ester of sulfonic acids can be a replacement for pentafluorophenyl and trichlorophenyl ester as well as chloride moiety of sulfonyl chloride for amidation.

Sulfonate esters of 1-hydroxypyridin-2(1H)-one and ethyl 2-cyano-2-(hydroxyimino)acetate (Oxyma) as effective peptide coupling reagents to replace 1-hydroxybenzotriazole and 1-hydroxy-7-azabenzotriazole

A new family of sulfonate ester-type coupling reagents is described which differs in its leaving group. The sulfonate ester coupling reagents ethyl 2-cyano-2-(naphthalen-2-ylsulfonyloxyimino)acetate (NpsOXY), and ethyl 2-cyano-2-(tosyloxyimino)acetate (Ts

A simple synthesis of nitriles from aldoximes

Easily synthesized aldoximes have been converted to the corresponding nitriles under very mild conditions by a simple reaction with lH-benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP) and DBU in CH2CI2, THF, or DMF. As an alternative reagent that eliminates the formation of hexamethylphosphoramide as a byproduct, use of lH-benzotriazol-lyl-4-methylbenzenesulfonate (Bt-OTs) and DBU was investigated. Reactions with this reagent also proceeded smoothly and in good yields, although in one case N-sulfonylation was observed. An attempt to gain mechanistic insight into the BOP-mediated reaction has been made using 31P{ 1H} NMR. However, no phosphorus-bearing intermediate could be readily observed. Finally, the method has been applied to the synthesis of an antiviral 4'-cyano adenosine analogue from a commercial precursor using a single saccharide protecting group.

Organophosphorus and Nitro-Substituted Sulfonate Esters of 1-Hydroxy-7-azabenzotriazole as Highly Efficient Fast-Acting Peptide Coupling Reagents

Organophosphorus esters 9, 10, 14, and 15 prepared via reaction of diethyl- and diphenylphosphoryl chloride, di(o-tolyl)phosphinyl chloride, and 2,8-dimethylphenoxaphosphinyl chloride with HOAt are excellent coupling reagents for peptide synthesis which are generally superior to their uronium/guanidinium analogues and HOBt- or HODhbt-derived phosphate ester counterparts in minimizing loss of configuration during segment coupling. The phosphinyl analogues are more shelf-stable than the phosphoryl systems. The new reagents have been tested in segment couplings leading to two tripeptides (20, 21) and a hexapeptide 22. Outstanding utility is also shown for the solid-phase assembly of the ACP decapeptide. Similar results were obtained with the 2- and 4-nitro- and 2,4-dinitrophenylsulfonyl esters derived from HOAt.