80281-50-1

Upstream product

• 90701-93-2 (E)-5-bromomethylene-2-phenyl-4,5-dihydro-oxazole 
• 146896-52-8 2-phenyl-5-methylene-4,5-dihydrooxazole 
• 98-88-4 benzoyl chloride 
• 10283-95-1 N-allylbenzamide 
• 50487-77-9 N-(2,3-dibromopropyl)benzamide 
• 55-21-0 benzamide 

Downstream Products

• 719308-17-5 3,6-diethoxy-(2R)-2-isopropyl-(5S)-5-(2-phenyl-oxazol-5-ylmethyl)-2,5-dihydro-pyrazine 
• 1201042-16-1 (R)-1-(2-phenyl-oxazol-5-ylmethyl)-3-((S)-2-phenyl-2-piperidin-1-yl-propionyloxy)-1-azonia-bicyclo[2.2.2]octane bromide 
• 838892-99-2 2-(2-phenyloxazol-5-ylmethyl)isoindole-1,3-dione 
• 80281-51-2 5-((methylthio)methyl)-2-phenyloxazole 

Relevant academic research and scientific papers

URIDINE NUCLEOSIDE DERIVATIVES, COMPOSITIONS AND METHODS OF USE

This disclosure relates to uridine nucleoside derivatives, compositions comprising therapeutically effective amounts of those nucleoside derivatives and methods of using those nucleoside derivatives or compositions in treating disorders that are responsive to compounds, such as agonists, of P2Y6 receptor, e.g., neuronal disorders, including neurodegenerative disorders (e.g., Alzheimer's disease, Parkinson's disease) and traumatic CNS injury, pain, Down Syndrome (DS), glaucoma and inflammatory conditions.

Chromium-Catalyzed Asymmetric Dearomatization-Addition Reactions of Halomethyloxazoles and Indoles

The asymmetric dearomatization-addition reaction of halomethyloxazoles and halomethylindoles with aldehydes is realized in the presence of a carbazole-based bisoxazoline CrCl 2 complex to afford the corresponding enantioenriched, hydroxylated oxazoline and indoline products. The observed excellent chemo-, regio-, diastereo- and enantioselectivities are notable advantages of this protocol. The strategy established in this study is expected to find application in the synthesis of azaheterocycles with biological significance and useful functionalities.

Lead Optimization Generates CYP11B1 Inhibitors of Pyridylmethyl Isoxazole Type with Improved Pharmacological Profile for the Treatment of Cushing's Disease

Cushing's disease, characterized by elevated plasma cortisol levels, can be controlled by inhibition of 11β-hydroxylase (CYP11B1). The previously identified selective and potent CYP11B1 inhibitor 5-((5-methylpyridin-3-yl)methyl)-2-phenylpyridine Ref 7 (IC50= 2 nM) exhibited promutagenic potential as well as very low oral bioavailability in rats (F = 2%) and was therefore modified to overcome these drawbacks. Successful lead optimization resulted in similarly potent and selective 5-((5-methoxypyridin-3-yl)methyl)-3-phenylisoxazole 25 (IC50 = 2 nM, 14-fold selectivity over CYP11B2), exhibiting a superior pharmacological profile with no mutagenic potential. Furthermore, compound 25 inhibited rat CYP11B1 (IC50 = 2 μM) and showed a high oral bioavailability (F = 50%) and sufficient plasma concentrations in rats, providing an excellent starting point for a proof-of-principle study.

NIS-mediated ring-closure/opening cascade reactions of allylamides: An expedient route to oxazolines

An unprecedented NIS-mediated ring-closure/opening cascade reaction of allylamides is developed. The substrates with various functionalities were well tolerated and the scope can be extended to allylic carboxylates. Notably, the resulting iodinated chain

Catalyst-free intramolecular oxidative cyclization of N-allylbenzamides: A new route to 2,5-substituted oxazoles

A catalyst-free intramolecular oxidative cyclization reaction of N-allylbenzamides has been developed to prepare 2,5-disubstituted oxazoles with good yields. This reaction gives an efficient synthetic strategy to form an oxazole nucleus directly from easi

Gold-catalysed synthesis of amino acid-derived 2,5-disubstituted oxazoles

Amino acid-derived propargylic amides are cyclised in a one-pot, Au(iii)-catalysed operation to yield 5-bromomethyl oxazoles. These compounds are further elaborated to bis-heterocycles, dipeptide mimics and more.

Cyclization of propargylic amides: Mild access to oxazole derivatives

The substrate scope, the mechanistic aspects of the gold-catalyzed oxazole synthesis, and substrates with different aliphatic, aromatic, and functional groups in the side chain were investigated. Even molecules with several propargyl amide groups could easily be converted, delivering di- and trioxazoles with interesting optical properties. Furthermore, the scope of the gold(I)-catalyzed alkylidene synthesis was investigated. Further functionalizations of these isolable intermediates of the oxazole synthesis were developed and chelate ligands can be obtained. The use of Barluenga's reagent offers a new and mild access to the synthetically valuable iodoalkylideneoxazoles from propargylic amides, this reagent being superior to other sources of halogens.

Intramolecular Cyclisation Using Methyl(bismethylthio)sulphonium Salts, Bromine, and Iodine. 5-Methylene-4,5-dihydro-oxazoles from 3-amidopropynes

The reaction of methyl(bismethylthio)sulphonium hexachloroantimonate (3) with acylaminopropines (1) and (2) gave (E)-5-methylthiomethylene-2-phenyl-4,5-dihydro-oxazolium (4) and (E)-2-methyl-5-methylthiomethylene-4,5-dihydro-oxazolium (7) hexachloroantimo

NEIGHBOURING GROUP PARTICIPATION IN ELECTROPHILIC ADDITION TO ACETYLENES. 5-METHYLENE OXAZOLINES FROM 3-BENZAMIDOPROPYNE.

Benzamido group participates in addition of various electrophiles to triple bond leading to 5-methylene oxazolines.