49802-71-3

Upstream product

• 3894-09-5 2-cyclohexyl-2-phenylacetic acid 
• 140-29-4 phenylacetonitrile 
• 3893-23-0 cyclohexyl phenyl acetonitrile 
• 953-91-3 cyclohexyl tosylate 
• 103-82-2 phenylacetic acid 

Downstream Products

• 108619-75-6 cyclohexyl-phenyl-acetic acid tetrahydrothiopyran-4-yl ester 
• 99553-43-2 cyclohexyl-phenyl-acetic acid-(2-pyrrolidino-ethyl ester) 
• 99553-46-5 cyclohexyl-phenyl-acetic acid-(2-piperidino-ethyl ester) 
• 116210-90-3 cyclohexyl-phenyl-acetic acid-(2-morpholino-ethylamide) 
• 113324-33-7 cyclohexyl-phenyl-acetic acid-[2-(4-methyl-piperazino)-ethyl ester]; dihydrochloride 
• 22173-05-3 cyclohexyl-phenyl-acetic acid-(2-dimethylamino-ethyl ester) 
• 4335-79-9 cyclohexyl-phenyl-acetic acid-(2-methylsulfanyl-ethyl ester) 
• 22173-12-2 cyclohexyl-phenyl-acetic acid-(β,β'-bis-diethylamino-isopropyl ester) 
• 119394-82-0 (+/-)-cyclohexyl-phenyl-acetic acid-(6exo,7exo-dimethoxy-tropane-3endo-yl ester) 
• 4413-16-5 1-ethyl-4-phenylcyclohexane 
• 5664-22-2 (+/-)-2-cyclohexyl-2-phenylacetaldehyde 
• 109701-23-7 cyclohexyl-phenyl-acetic acid-(4,5-dihydro-1H-imidazol-2-yl-methyl ester); hydrochloride 
• 40797-11-3 (+/-)cyclohexyl-phenyl-acetic acid tropane-3endo-yl ester 
• 60576-83-2 Cyclohexyl-phenyl-acetic acid 2-dimethylamino-2-phenyl-butyl ester 

Relevant academic research and scientific papers

Discovery of new C3aR ligands. Part 2: Amino-piperidine derivatives

The synthesis and structure-activity relationships against the C3a receptor of a series of substituted aminopiperidine derivatives are reported. DMPK properties and functional activities of selected compounds are described. The compounds obtained are the first non-arginine ligands of C3aR.

Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes

Imidazoline derivatives have been reported to show antihyperglycemic activity in vivo. In the present study, we first showed that there was no correlation between the in vivo antidiabetic activity and the in vitro affinities for the I1/I2

Synthesis and biological evaluation of benzimidazole derivatives as potent AMP-activated protein kinase activators

Design, synthesis and structure-activity relationships of benzimidazole derivatives as activators of the AMP-activated protein kinase (AMPK) are presented in this paper. AMPK is the central component of a protein kinase cascade that plays a key role in the regulation of energy balance. Once activated, AMPK initiates a series of responses that are aimed at restoring the energy balance of the cell and recent studies have indicated that AMPK plays an important role in regulation of the whole-body energy metabolism. The following study based on the lead compound S27847 involved modification of three regions of this compound. Preliminary structure-activity relationships are being described.

2-SULFANYL-BENZOIMIDAZOL-1-YL-ACETIC ACID DERIVATIVES AS CRTH2 ANTAGONISTS

The invention relates to 2-sulfanyl-benzoimidazol-1-yl-acetic acid derivatives and their use as potent "chemoattractant receptor-homologous molecule expressed on Th2 cells" antagonists in the treatment of prostaglandin mediated diseases, to pharmaceutical compositions containing these derivatives and to processes for their preparation.

Pharmacological studies and synthesis of morpholino alkyl derivatives

Seven morpholin derivatives were synthesized (compounds 1-7) and their behavioural effects were evaluated; the elements considered were locomotor activity, motor coordination, catalepsy, stereotyped behaviour and antinociception. All the compounds, at doses of 10-20-40 mg/kg/i.p., induced a reduction of all behavioural elements without a significant antinociceptive effect. These results indicate that these morpholin derivatives affect the central nervous system.

Design, synthesis and binding at cloned muscarinic receptors of N-[5-(1'-substituted-acetoxymethyl)-3-oxadiazolyl] and N-[4-(1'-substituted-acetoxymethyl)-2-dioxolanyl] dialkyl amines

Few muscarinic antagonists differentiate between the M4 and M2 muscarinic receptors. In a structure-activity study, aimed at discovering leads for the development of a M4 muscarinic receptor-selective antagonist, we have s

Synthesis, antimuscarinic activity and quantitative structure-activity relationship (QSAR) of tropinyl and piperidinyl esters

A series of tropinyl and piperidinyl esters was synthesized and evaluated for inhibitory activities on the endothelial muscarinic receptors of rat (M3) and rabbit (M2) aorta. Some of the esters (cyclohexylphenylglycolates and cyclohexylphenylpropionates) were found to be better antimuscarinic compounds than standard M2 and M3 inhibitors such as AFDX116 and 4-diphenylacetoxy-N-methylpiperidine (DAMP), with pKEC50 values in the range of 8-9. A few esters were found to be more selective M3 than M2 inhibitors, but these tended to have low activities. The hydrophobic, electronic and steric characteristics of these esters were correlated with antimuscarinic activity by using appropriate parameters representing hydrophobicity (HPLC capacity factor, log k(w), size (molecular volume) and electronic character (Taft's polar substituent constant δ and 13C chemical shift difference Δδ). Finally, 92% of the M2-inhibitory activities of the esters could be accounted for by the size and electronic character σ* of the side chain. In contrast, the M3-inhibitory activities of these esters were mainly attributed to the electronic nature (σ*, Δδ) of the side chain, with good activity being associated with electron-withdrawing groups. Visualization of the comparative molecular field analysis (CoMFA) steric and electrostatic fields provided further confirmation of the structure-activity relationship (SAR) derived from traditional quantitative structure-activity relationship (QSAR) approaches.

Deracemization of α-substituted arylacetic acids

Reaction of rac-α-substituted arylacetyl chlorides with (R)- and (S)-3-hydroxy-4,4-dimethyl-1-phenyl-2-pyrrolidinone under standard esterification conditions, gave esters (3R,αR)- and (3S,αS)-3, respectively, with a diastereoselectivity which diminishes on increasing the steric effect of the α-substituent. Controlled acidic hydrolysis of esters 3 afforded the corresponding acids 4 with minimal racemization. Boron tribromide demethylation of (R)- and (S)-4d gave without racemization the hydroxyacids (R)- and (S)-4e, known precursors of (R)- and (S)-iodoalphionic acid.

Synthesis, NMR spectroscopy study, and antimuscarinic activity of a series of 2-(acyloxymethyl)-1,3-dioxolanes

A series of 19-dioxolane-based ligands, bearing hydroxymethyl or ester functionalities, was synthesized and tested as potential muscarinic antagonists. The compounds display moderate to low affinity for the three receptor subtypes M1-M3/s

Cyclopropylketenes: preparation and nucleophilic additions

Phenylcyclopropylketene (4), tert-butylcyclopropylketene (5), and dicyclopropylketene (6) were formed by dehydrochlorination of the corresponding acyl chlorides by Et3N in THF, and are the first cyclopropylketenes to be isolated and purified.Reaction of 4 with n-BuLi and capture of the intermediate enolates with Me3SiCl gave the stereoisomeric silyl enol ethers c-PrCPh=C(OSiMe3)-n-Bu with a 79:21 preference for formation of the Z isomer resulting from nucleophilic attack syn to cyclopropyl, whereas the corresponding reaction of t-BuLi gave 9:91 preference for attackanti to cyclopropyl.Some isopropyl-, cyclopentyl-, and cyclohexylketenes gave comparable results.Analyses of the relative sizes of the ketene substituents in the ground state by steric parameters, and of the product stabilities by molecular mechanics, both fail to predict the observed similarities in the results with different secondary alkyl groups.The hydration reactivities of 4 and 6 show that, in neutral H2O/CH3CN, c-PrCPh=C=O is more reactive than i-PrCPh=C=O, a result ascribed as mainly due to the smaller size of cyclopropyl. c-Pr2C=C=O has the same reactivity in neutral water as Et2C=C=O, but is 22 times less reactive with acid, a result attributed to the inability of the β-cyclopropyl groups to directly stabilize the cationic transition state for protonation. Key words: cyclopropylketenes, ketenes, nucleophilic addition, hydration kinetics.