88425-47-2

Usage

Uses

1-(Phenylsulfonyl)proline can be used to inhibit hepatitis B virus.

Upstream product

• 98-09-9 benzenesulfonyl chloride 
• 344-25-2 D-Prolin 
• 609-36-9 rac-Pro-OH 
• 110714-46-0 (R)-((S)-2-(6′-(acetoxymethyl)-5′-oxo-3′,5′-dihydro-2′H-spiro[[1,3]dioxolane-2,1′-indolizine]-7′-yl)-1-ethoxy-1-oxobutan-2-yl) 1-tosylpyrrolidine-2-carboxylate 

Downstream Products

• 122213-79-0 (R)-1-Benzenesulfonyl-pyrrolidine-2-carboxylic acid (S)-3,3-dimethoxy-2-(9-phenyl-9H-fluoren-9-ylamino)-propyl ester 
• 910481-98-0 (R)-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-1-(phenylsulfonyl)pyrrolidine-2-carboxamide 
• 88494-19-3 (2RS)-1-(benzenesulfonyl)pyrrolidine-2-carbonyl chloride 
• 144331-19-1 (2S,3S)-2-(1-Benzenesulfonyl-pyrrolidine-2-carbonyloxy)-3-(9-phenyl-9H-fluoren-9-ylamino)-succinic acid dimethyl ester 
• 1392300-22-9 (R)-1-(phenylsulfonyl)pyrrolidine-2-carbohydrazide 
• 860016-08-6 methyl 1-[1-benzenesulfonyl-pyrrolidine-2'(R)-carbonyl]-3-benzyloxycarbonyl-2-oxo-imidazolidine-4(S)-carboxylate 

Relevant academic research and scientific papers

Identification of Novel Fragments Binding to the PDZ1-2 Domain of PSD-95

Inhibition of PSD-95 has emerged as a promising strategy for the treatment of ischemic stroke, as shown with peptide-based compounds that target the PDZ domains of PSD-95. In contrast, developing potent and drug-like small molecules against the PSD-95 PDZ domains has so far been unsuccessful. Here, we explore the druggability of the PSD-95 PDZ1-2 domain and use fragment screening to investigate if this protein is prone to binding small molecules. We screened 2500 fragments by fluorescence polarization (FP) and validated the hits by surface plasmon resonance (SPR), including an inhibition counter-test, and found four promising fragments. Three ligand efficient fragments were shown by 1H,15N HSQC NMR to bind in the small hydrophobic P0 pockets of PDZ1-2, and one of them underwent structure-activity relationship (SAR) studies. Overall, we demonstrate that fragment screening can successfully be applied to PDZ1-2 of PSD-95 and disclose novel fragments that can serve as starting points for optimization towards small-molecule PDZ domain inhibitors.

Catalytic Access to Functionalized Allylic gem-Difluorides via Fluorinative Meyer–Schuster-Like Rearrangement

An unprecedented approach for efficient synthesis of functionalized allylic gem-difluorides via catalytic fluorinative Meyer–Schuster-like rearrangement is disclosed. This transformation proceeded with readily accessible propargylic fluorides, and low-cost B–F reagents and electrophilic reagents by sulfide catalysis. A series of iodinated, brominated, and trifluoromethylthiolated allylic gem-difluorides that were difficult to access by other methods were facilely produced with a wide range of functional groups. Importantly, the obtained iodinated products could be incorporated into different drugs and natural products, and could be expediently converted into many other valuable gem-difluoroalkyl molecules as well. Mechanistic studies revealed that this reaction went through a regioselective fluorination of alkynes followed by a formal 1,3-fluorine migration under the assistance of the B–F reagents to give the desired products.

Novel Phenoxazinones as potent agonist of PPAR-α: Design, synthesis, molecular docking and in vivo studies

Background: The use of statin, a 3-hydroxy-3-methylglutaryl coenzyme A reductase inhibitor for the treatment of dyslipidemia has been associated with dose limiting hepatoxicity, mytotoxicity and tolerability due to myalgias thereby necessitating the synthesis of new drug candidates for the treatment of lipid disorder. Methods: The reaction of appropriate benzenesulphonamide with substituted phenoxazinone in the presence of phenylboronic acid gave the targeted compounds. The molecular docking study were carried out using autodock tool against peroxisome proliferator activated receptor alpha. The in vivo lipid profile were assayed using conventional methods. The kidney and liver function test were carried out to assess the effect of the derivatives on the organs. The LD50 of the most active derivatives were determined using mice. Results: The targeted compounds were successfully synthesized in excellent yields and characterized using spectroscopic techniques. The results of the molecular docking experiment showed that they were good stimulant of peroxisome proliferator activated receptor alpha. Compound 9f showed activity at Ki of 2.8 nM and binding energy of 12.6 kcal/mol. All the compounds tested reduced triglyceride, total cholesterol, low density lipoprotein cholesterol and very low density lipoprotein cholesterol level in the mice model. Some of the reported compounds also increased high density lipoprotein cholesterol level in the mice. The compounds did not have appreciable effect on the kidney and liver of the mice used. The LD50 showed that the novel compounds have improved toxicity profile. Conclusion: The synthesis of fifteen new derivatives of carboxamides bearing phenoxazinone and sulphonamide were successful. The compounds possessed comparable activity to gemfibrozil. The reported compounds had better toxicity profile than gemfibrozil and could serve as a replacement for the statins and fibrate class of lipid agents.

α-Amino Acid Sulfonamides as Versatile Sulfonylation Reagents: Silver-Catalyzed Synthesis of Coumarins and Oxindoles by Radical Cyclization

We developed a silver-catalyzed strategy for the generation of sulfonyl radicals from sulfonamides derived from α-amino acids. The reaction proceeded via a decarboxylation, N–S bond cleavage and radical cyclization sequence and allows the difunctionalization of alkynes and the synthesis of 3-sulfonylated coumarins. The reaction tolerated a broad scope of substrates and functional groups and could be extended to the synthesis of oxindoles and an isoquinolinedione by the capturing of the sulfonyl radical with an alkene moiety. Moreover, the proposed mechanism was supported experimentally and by DFT calculations.

New antiprotozoal agents: Synthesis and biological evaluation of different 4-(7-chloroquinolin-4-yl) piperazin-1-yl)pyrrolidin-2-yl)methanone derivatives

In an endeavor to develop efficacious antiprotozoal agents 4-(7-chloroquinolin-4-yl) piperazin-1-yl)pyrrolidin-2-yl)methanone derivatives (5–14) were synthesized, characterized and biologically evaluated for antiprotozoal activity. The compounds were scre

BINHIBITORS OF HEPATITIS B VIRUS CONVALENTLY CLOSED CIRCULAR DNA FORMATION AND THEIR METHOD OF USE

Pharmaceutical compositions of the invention comprise covalently closed circular DNA formation inhibitors having a disease-modifying action in the treatment of diseases associated with the formation of covalently closed circular DNA that include hepatitis B infection, and any disease involving formation of covalently closed circular DNA.

Synthesis and structure-activity relationships of o-sulfonamido- arylhydrazides as inhibitors of LL-diaminopimelate aminotransferase (LL-DAP-AT)

Recently, ll-diaminopimelate aminotransferase (ll-DAP-AT), a pyridoxal-5′-phosphate (PLP)-dependent enzyme, was reported to catalyze a key step in the biosynthesis of l-lysine in plants and Chlamydia. Previous screening of a 29201-compound library against

Synthesis, calpain inhibitory activity, and cytotoxicity of P 2-substituted proline and thiaproline peptidyl aldehydes and peptidyl α-ketoamides

Calpain is a cytosolic cysteine endopeptidase that has been implicated in a number of disorders including cancer. We have synthesized and studied the μ-calpain inhibitory activity and cytotoxicity of peptidyl aldehydes and peptidyl α-ketoamides with N-sub

Cell adhesion inhibitors

Cell adhesion inhibitors can interact with VLA-4 molecules and inhibits VLA-4 dependent cell adhesion. An inhibitor including a polyethylene glycol moiety can have advantageous pharmaceutical properties.

ASYMMETRIC SYNTHESIS OF (S)-CAMPTOTHECIN

The title compound was synthesized via a novel diastereoselective ethylation process from indolizine derivative 5a bearing N-tosyl-(R)-proline.