56338-25-1

Upstream product

• 22071-24-5 3-benzoylbenzyl bromide 
• 579-18-0 3-benzoylbenzoic acid 
• 643-65-2 3-methyl benzophenone 
• 22071-15-4 ketoprofen 
• 66067-43-4 3-ethylbenzophenone 
• 66067-44-5 (3-acetylphenyl)(phenyl)methanone 
• 3132-99-8 m-bromobenzoic aldehyde 
• 15852-73-0 (3-Bromophenyl)methanol 
• 103978-12-7 [(3-bromobenzyl)oxy](tert-butyl)dimethylsilane 

Downstream Products

• 1621861-44-6 C₄₆H₇₃NO₁₁ 
• 1621861-47-9 C₄₉H₇₉NO₁₁ 
• 1621861-48-0 C₅₀H₈₁NO₁₁ 
• 1621861-33-3 C₂₂H₂₆O₄ 
• 1621861-27-5 C₂₅H₃₂O₄ 
• 53179-78-5 3-(2',2'-dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic acid 
• 863030-40-4 3-(α-hydroxy-4'-methylbenzyl)benzophenone 
• 52010-96-5 3-(hydroxy(phenyl)methyl)benzaldehyde 
• 71856-95-6 3-benzoylbenzaldehyde 

Relevant academic research and scientific papers

Photoactivable Glycolipid Antigens Generate Stable Conjugates with CD1d for Invariant Natural Killer T Cell Activation

Activation of invariant natural killer T lymphocytes (iNKT cells) by α-galactosylceramide (α-GC) elicits a range of pro-inflammatory or anti-inflammatory immune responses. We report the synthesis and characterization of a series of α-GC analogues with acyl chains of varying length and a terminal benzophenone. These bound efficiently to the glycolipid antigen presenting protein CD1d, and upon photoactivation formed stable CD1d-glycolipid covalent conjugates. Conjugates of benzophenone α-GCs with soluble or cell-bound CD1d proteins retained potent iNKT cell activating properties, with biologic effects that were modulated by acyl chain length and the resulting affinities of conjugates for iNKT cell antigen receptors. Analysis by mass spectrometry identified a unique covalent attachment site for the glycolipid ligands in the hydrophobic ligand binding pocket of CD1d. The creation of covalent conjugates of CD1d with α-GC provides a new tool for probing the biology of glycolipid antigen presentation, as well as opportunities for developing effective immunotherapeutics.

Palladium Catalysis Enables Benzylation of α,α-Difluoroketone Enolates

A palladium-catalyzed decarboxylative benzylation reaction of α,α-difluoroketone enolates is reported, in which the key C(α)?C(sp3) bond is generated by reductive elimination from a palladium intermediate. The transformation provides convergent access to α-benzyl-α,α-difluoroketone-based products, and should be useful for accessing biological probes.

MODIFIED GLYCOLIPIDS AND METHODS OF MAKING AND USING THE SAME

The invention is directed to compositions and methods related to proteins that are physically associated with ceramide-like glycolipids for use as activators of NKT cells. The compositions and methods of the present invention are useful for the prevention and treatment of diseases.

Chemoselective ruthenium-catalysed reduction of carboxylic acids

A very general and efficient catalytic protocol for the selective reduction of carboxylic acids to their corresponding alcohols under mild conditions is described. Various carboxylic acids, including benzoic acids, were reduced in good yields using the presented methodology. The ruthenium-catalysed method yields a highly chemoselective reduction permitting the reduction of a carboxylic acid functionality in the presence of numerous other potentially reducible moieties.

Application of complementary mass spectrometric techniques to the identification of ketoprofen phototransformation products

Ketoprofen (KP) is a nonsteroidal anti-inflammatory drug, which during UV irradiation rapidly transforms into benzophenone derivatives. Such transformation products may occur after topical application of KP, which is then exposed to sunlight resulting in a photo-allergic reaction. These reactions are mediated by the benzophenone moiety independently of the amount of allergen. The same reactions will also occur during wastewater or drinking water treatment albeit their effect in the aqueous environment is yet to be ascertained. In addition, only a few such transformation products have been recognised. To enable the detection and structural elucidation of the widest range of KP transformation products, this study applies complementary chromatographic and mass spectrometric techniques including gas chromatography coupled to single quadrupole or ion trap mass spectrometry and liquid chromatography hyphenated with quadrupole-time-of-flight mass spectrometry. Based on structural information gained in tandem and multiple MS experiments, and on highly accurate molecular mass measurements, chemical structures of 22 transformation products are proposed and used to construct an overall breakdown pathway. Among the identified transformation products all but two compounds retained the benzophenone moietya€"a result, which raises important issues concerning the possible toxic synergistic effects of KP and its transformation products. These findings trigger further research into water treatment technologies that would limit their entrance into environmental or drinking waters. Copyright

Reaction mechanisms and structural characterization of the reactive intermediates observed after the photolysis of 3-(hydroxymethyl)benzophenone in acetonitrile, 2-propanol, and neutral and acidic aqueous solutions

Nanosecond time-resolved resonance Raman (ns-TR3) spectroscopy was employed to investigate the photoinduced reactions of 3-(hydroxymethyl) benzophenone (1) in acetonitrile, 2-propanol, and neutral and acidic aqueous solutions. Density functional theory calculations were utilized to help the interpretation of the experimental spectra. In acetonitrile, the neutral triplet state 1 [denoted here as (m-BPOH)3] was observed on the nanosecond to microsecond time scale. In 2-propanol this triplet state appeared to abstract a hydrogen atom from the solvent molecules to produce the aryphenyl ketyl radical of 1 (denoted here as ArPK of 1), and then this species underwent a cross-coupling reaction with the dimethylketyl radical (also formed from the hydrogen abstraction reaction) to form a long-lived light absorbing transient species that was tentatively identified to be mainly 2-(4-(hydroxy(3- (hydroxymethyl)phenyl)methylene)cyclohexa-2,5-dienyl)propan-2-ol. In 1:1 H 2O:CH3CN aqueous solution at neutral pH, (m-BPOH) 3 reacted with water to produce the ArPK of 1 and then underwent further reaction to produce a long-lived light absorbing transient species. Three photochemical reactions appeared to take place after 266 nm photolysis of 1 in acidic aqueous solutions, a photoreduction reaction, an overall photohydration reaction, and a novel photoredox reaction. TR3 experiments in 1:1 H2O:CH3CN aqueous solution at pH 2 detected a new triplet biradical species, which is associated with an unusual photoredox reaction. This reaction is observed to be the predominant reaction at pH 2 and seems to face competition from the overall photohydration reaction at pH 0.

Formal intramolecular photoredox chemistry of meta-substituted benzophenones

(Chemical Equation Presented) Photolysis of 3-(hydroxymethyl)benzophenone (1) in aqueous solution (pH -4 M) conditions. Evidence suggests that the highly efficient (Φ ～ 0.6) reaction involves a unimolecular mechanism and an overall formal intramolecular photoredox process, which requires electronic communication between the 1,3-positions of the benzene ring, an unprecedented example of the photochemical meta effect. The photoredox reaction was not observed in organic solvents, where only photoreduction of the benzophenone moiety was observed.

Trisubstituted-N-[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl] benzamides which inhibit P2X3 and P2X2/3 containing receptors

Compounds of formula (I) are novel P2X3 and P2X2/P2X3 antagonists which are useful in treating pain, urinary incontinence and bladder overactivity.