142602-27-5

Upstream product

• 2403-51-2 2-(4-methylphenyl)-1,3-dioxolane 
• 107-21-1 ethylene glycol 
• 104-81-4 4-Methylbenzyl bromide 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 104-82-5 4-Methylbenzyl chloride 

Downstream Products

• 925419-04-1 methanesulfonic acid 2-(4-methyl-benzyloxy)-ethyl ester 
• 103061-53-6 1-{[(2-bromoethyl)oxy]methyl}-4-methylbenzene 
• 842136-34-9 (4-methyl-benzyloxy)-acetaldehyde 
• 2403-51-2 2-(4-methylphenyl)-1,3-dioxolane 

Relevant academic research and scientific papers

Correlating Solution- and Solid-State Structures of Conformationally Flexible Resorcinarenes: Significance of a Sulfonyl Group in Intramolecular Self-Inclusion

The synthesis of tetramethoxyresorcinarene podands bearing p-toluene arms connected by -SO3- (1) and -CH2O- (2) linkers is presented herein. In the solid state, the resorcinarene podand 1 forms an intramolecular self-inclusion complex with the pendant p-toluene group of a podand arm, whereas the resorcinarene podand 2 does not show self-inclusion. The conformations of the flexible resorcinarene podands in solution were investigated by variable-temperature experiments using 1D and 2D NMR spectroscopic techniques as well as by computational methods, including a conformational search and subsequent DFT optimisation of representative structures. The 1H NMR spectra of 1 and 2 at room temperature show a single set of proton signals that are in agreement with C4v symmetry. At low temperatures, the molecules exist as a mixture of boat conformations featuring slow exchange on the NMR timescale. Energy barriers (ΔG≠298) of 55.5 and 52.0 kJ mol?1 were calculated for the boat-to-boat exchange of 1 and 2, respectively. The results of the ROESY experiments performed at 193 K and computational modelling suggest that in solution the resorcinarene podand 1 adopts a similar conformation to that present in its crystal structure, whereas podand 2 populates a more versatile range of conformations in solution.

Facile catalyst-free synthesis, exchanging, and hydrolysis of an acetal motif for dynamic covalent networks

Dynamic covalent networks offer the favorable features of cross-linked polymers as well as the functions of reprocessing, recycling, self-healing, reshaping, and welding; however, it is a challenge to design readily monomer-recovery, highly malleable, catalyst-free, dynamic materials. Here we report the first design of acetal dynamic networks to address this challenge. Acetal dynamic networks were built via the catalyst-free "click" addition of polyol and a commercial divinyl ether without releasing small molecules. Small-molecule model compounds demonstrated thermally-induced acetal exchange without a catalyst. There are two mechanisms for the dynamic exchange of acetal: one is the metathesis of acetal, another is transacetalization. Acetal dynamic covalent networks exhibited excellent malleability and recyclability. They presented rapid stress relaxation at high temperatures. Hot press recovery can be achieved in 10 min at 150 °C. Meanwhile, the starting material was recovered with 92% recovery in 1 h under hot water treatment at 100 °C, and could be recross-linked with a commercial divinyl ether to obtain an acetal network. The acetal networks recovered by the two methods maintained the original structure and performance. An acetal dynamic linkage will open up a new way for the development of catalyst-free dynamic covalent networks and enrich acetal chemistry.

Generation of Alkoxyl Radicals by Photoredox Catalysis Enables Selective C(sp3)-H Functionalization under Mild Reaction Conditions

Reported herein is the first visible-light-induced formation of alkoxyl radicals from N-alkoxyphthalimides, and the Hantzsch ester as the reductant is crucial for the reaction. The selective hydrogen atom abstraction by the alkoxyl radical enables C(sp3)-H allylation and alkenylation reactions under mild reaction conditions at room temperature. Broad substrate variations, including a structurally complexed steroid, undergo the C(sp3)-H functionalization reaction effectively with high regio- and chemoselectivity.

Toward the discovery of dual HCMV-VZV inhibitors: Synthesis, structure activity relationship analysis, and cytotoxicity studies of long chained 2-uracil-3-yl-N-(4-phenoxyphenyl)acetamides

The need for novel therapeutic options to fight herpesvirus infections still persists. Herein we report the design, synthesis and antiviral evaluation of a new family of non-nucleoside antivirals, derived from 1-[ω-(4-bromophenoxy)alkyl]uracil derivatives - previously reported inhibitors of human cytomegalovirus (HCMV). Introduction of the N-(4-phenoxyphenyl)acetamide side chain at N3 increased their potency and widened activity spectrum. The most active compounds in the series exhibit submicromolar activity against different viral strains of HCMV and varicella zoster virus (VZV) replication in HEL cell cultures. Inactivity against other DNA and RNA viruses, including herpes simplex virus 1/2, points to a novel mechanism of antiviral action.

Discovery of novel 1-azoniabicyclo[2.2.2]octane muscarinic acetylcholine receptor antagonists

A novel 4-hydroxyl(diphenyl)methyl substituted quinuclidine series was discovered as a very promising class of muscarinic antagonists. The structure-activity relationships of the connectivity of the diphenyl moiety to the quinuclidine core and around the ring nitrogen side chain are described. Computational docking studies using an homology model of the M3 receptor readily explained the observed structure-activity relationship of the various compounds. Compound 14o was identified as a very potent, slowly reversible M3 antagonist with a very long in vivo duration of bronchoprotection.

COMBINATION OF A MUSCARINIC RECEPTOR ANTAGONIST AND A BETA-2-ADRENOCEPTOR AGONIST

The invention provides a pharmaceutical product, kit or composition comprising a first active ingredient which is a selected muscarinic receptor antagonist selected, and a second active ingredient which is a β2-adrenoceptor agonist, of use in the treatment of respiratory diseases such as chronic obstructive pulmonary disease and asthma.

OXAZOLE AND THIAZOLE DERIVATIVES AND THEIR USES

A quaternary ammonium compound of formula (I) having M3 receptor antagonist activity; a composition comprising such a compound; the use of such a compound in therapy (such as asthma or COPD); and a method of treating a patient with such a compound.

Structure-based design of isoquinoline-5-sulfonamide inhibitors of protein kinase B

Structure-based drug design of novel isoquinoline-5-sulfonamide inhibitors of PKB as potential antitumour agents was investigated. Constrained pyrrolidine analogues that mimicked the bound conformation of linear prototypes were identified and investigated by co-crystal structure determinations with the related protein PKA. Detailed variation in the binding modes between inhibitors with similar overall conformations was observed. Potent PKB inhibitors from this series inhibited GSK3β phosphorylation in cellular assays, consistent with inhibition of PKB kinase activity in cells.

A mild and simple procedure for the reductive cleavage of acetals and ketals

A convenient, mild and simple procedure, employing sodium cyanoborohydride in the presence of either catalytic or stoichiometric amount of boron trifluoride etherate in dry THF, for the reductive cleavage of the acetals and ketals is described.