118776-39-9

Upstream product

• 147-85-3 L-proline 
• 98-59-9 p-toluenesulfonyl chloride 
• 110771-95-4 (R)-N-tosylproline 
• 344-25-2 D-Prolin 
• 51077-01-1 L-N-tosyl-proline 

Downstream Products

• 73096-29-4 1-(toluene-4-sulfonyl)-L-prolin-anilide 
• 101603-32-1 1-[1-(toluene-4-sulfonyl)-L-prolyl]-L-proline 
• 17585-75-0 trans-4-hydroxy-1-[1-(toluene-4-sulfonyl)-L-prolyl]-L-proline 
• 67488-66-8 (2S)-1-Tosyl-2-pyrrolidyl-diazomethyl-keton 
• 130737-55-2 (E)-1-[(S)-1-(Toluene-4-sulfonyl)-pyrrolidin-2-yl]-3-trimethylsilanyl-propenone 
• 130719-35-6 (E)-4-Oxo-4-[(S)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-but-2-enoic acid ethyl ester 
• 130719-34-5 (E)-3-Phenyl-1-[(S)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propenone 
• 130719-36-7 (E)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxy]-1-[(S)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-but-2-en-1-one 
• 130719-37-8 (E)-3-(2-Methoxy-phenyl)-1-[(S)-1-(toluene-4-sulfonyl)-pyrrolidin-2-yl]-propenone 
• 107224-20-4 1-(N-tosyl-(S)-prolyl)-(R)-2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydroquinoline 
• 107224-19-1 1-(N-tosyl-(S)-prolyl)-(S)-2,5-dimethyl-6-fluoro-1,2,3,4-tetrahydroquinoline 
• 107994-07-0 Nα-(Tosyl-L-prolyl)-D,L-4-cyanphenylalanin 
• 26177-34-4 (1S,2S)-1-methyl-3,3-pentamethylenediaziridine 
• 26177-34-4 (R)-1-Methyl-1,2-diaza-spiro[2.5]octane 

Relevant academic research and scientific papers

Identification of Human Toll-like Receptor 2-Agonistic Activity in Dihydropyridine-Quinolone Carboxamides

Using a multiplexed, reporter gene-based, high-throughput screen, we identified 9-fluoro-7-hydroxy-3-methyl-5-oxo-N-(pyridin-3-ylmethyl)-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxamide as a TLR2 agonist. Preliminary structure-activity relationship studies on the carboxamide moiety led to the identification of analogues that induce chemokines and cytokines in a TLR2-dependent manner. These results represent new leads for the development of vaccine adjuvants.

Structure-Activity Relationship Studies with Tetrahydroquinoline Analogs as EPAC Inhibitors

EPAC proteins are therapeutic targets for the potential treatment of cardiac hypertrophy and cancer metastasis. Several laboratories use a tetrahydroquinoline analog, CE3F4, to dissect the role of EPAC1 in various disease states. Here, we report SAR studies with tetrahydroquinoline analogs that explore various functional groups. The most potent EPAC inhibitor 12a exists as a mixture of inseparable E (major) and Z (minor) rotamers. The rotation about the N-formyl group indeed impacts the activity against EPAC.

Stereoselective total synthesis of (S)- and (R)-nuciferine using benzyne chemistry

Total syntheses of (S)- and (R)-nuciferine were accomplished through approach involving diastereoselective reaction between a chiral dihydroisoquinoline enamide and 2-(trimethylsilyl)phenyl trifluoromethanesulfonate promoted by CsF, affording a separable mixture of diastereoisomers, which provided (S)- and (R)-nuciferine via simple and efficient transformations.

Enantiomeric resolution of [(2,2-diphenyl-1,3-dioxolan-4-yl)methyl](2-phenoxyethyl)amine, a potent α1 and 5-HT1A receptor ligand: An in vitro and computational study

In this paper, the enantiomers of (±)-1, previously studied as α1 and 5-HT1A ligands, were prepared both by resolution of the racemate and asymmetric synthesis. The enantiomeric purity and absolute configuration were determined by me

High-Performance Isocyanide Scavengers for Use in Low-Waste Purification of Olefin Metathesis Products

Three isocyanides containing a tertiary nitrogen atom were investigated for use as small-molecule ruthenium scavenging agents in the workup of olefin metathesis reactions. The proposed compounds are odorless, easy to obtain, and highly effective in removi

Synthesis, enantiomeric separation and docking studies of spiropiperidine analogues as ligands of the nociceptin/orphanin FQ receptor

A series of triazospirodecanone derivatives were synthesized as potential NOP ligands. 8-(Chroman-4-yl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (4) and its 5-fluoro analogue (18) proved to be active as agonists with EC50 values in the submicromolar range. Single enantiomers of compound 4 were separated and tested as NOP agonists; the eutomer R-(+)-4 showed a pEC 50 of 7.34. Finally docking studies were performed on the NOP receptor to identify the most significant stereospecific interactions.

N-tosyl-(S)-prolyl chloride in kinetic resolution of racemic heterocyclic amines

The kinetic resolution of racemic heterocyclic amines via acylation with N-tosyl-(S)-prolyl chloride was systematically investigated. It was established that racemic mixtures of aromatic amines could be resolved with high efficiency, while the acylation of 2- and 3-methylpiperidines occurred with low diastereoselectivity. A method for the preparation of enantiomerically pure (3R)-7,8-difluoro-3-methyl-3,4-dihydro-2H-[1,4]benzoxazine was developed.

Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(S)-prolyl chloride and its structural analogs

A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.

Diastereoselective acylation of racemic heterocyclic amines with N-tosyl-(s)-prolyl chloride and its structural analogs

A comparative study on the kinetic resolution of racemic amines (2,3-dihydro-4H-1,4-benzoxazine and 1,2,3,4-tetrahydroquinoline derivatives) via diastereoselective acylation with N-tosyl-(S)-prolyl chloride and its structural analogs was performed. The effect of resolving agent structure on the stereoselectivity of heterocyclic amine acylation was examined. The highest stereoselectivity was achieved in the case of acylation with acyl chlorides bearing a conformationally restricted pyrrolidine ring and an aromatic substituent in the protecting group at the nitrogen atom.

Does an axial propeller shape on a dirhodium(III,III) core affect equatorial ligand chirality?

The dirhodium(III,III) tetrakis(1-aza-2-cyclooctanoate) framework, which exists solely in a propeller conformation, has been prepared with nonidentical apical aryl ligands. The presence of these nonidentical ligands on the propeller conformation was expec