1129-66-4

Upstream product

• 821-09-0 n-Pent-4-enyl alcohol 
• 110-82-7 cyclohexane 
• 150239-12-6 4-<1-(hydroxycyclohexyl)>pentanal 
• 1192-30-9 tetrahydrofurfuryl bromide 
• 5631-95-8 2,3-dichlorotetrahydro-2H-pyran 
• 98078-16-1 5-cyclohexyl-4-penten-1-ol 
• 34626-51-2 5-bromopentan-1-ol 
• 931-51-1 cyclohexylmagnesiumchloride 
• 10521-91-2 5-phenylpentan-1-ol 
• 557-91-5 1,1-Dibromoethane 
• 2270-20-4 5-Phenylpentanoic acid 
• 18138-76-6 tetrahydro-2-furanylmethyl(triphenyl)phosphonium bromide 
• 108-86-1 bromobenzene 
• 150238-91-8 2-(4-iodobutyl)-1,3-dioxolane 

Downstream Products

• 54089-03-1 1-bromo-5-cyclohexylpentane 
• 1439367-81-3 5-cyclohexylpentyl pyridin-2-yl carbonate 
• 1439367-82-4 5-cyclohexylpentyl 2-oxopyridine-1-carboxylate 
• 1453492-52-8 (2R,3S)-2-(5-cyclohexylpentoxycarbonylamino)-3-hydroxy-butanoic acid 
• 1034706-03-0 2-[2-(5-cyclohexylpentoxy)-2-oxoethyl]benzoic acid 
• 4354-52-3 7-cyclohexylheptanoic acid 
• 14561-42-3 2-hydroxy-3-(8-cyclohexyloctyl)-1,4-naphthoquinone 
• 16275-30-2 2-Hydroxy-3-(ω-cyclohexylhexyl)-1,4-naphthoquinone 
• 4352-53-8 9-cyclohexyl-nonanoic acid 
• 15382-70-4 1-Cyclohexyl-5-(4-amino-2-methoxy-phenoxy)-pentan 
• 101888-83-9 1-Cyclohexyl-5-(4-nitro-2-methoxy-phenoxy)-pentan 
• 1619921-82-2 ethyl 7-cyclohexylheptanoate 
• 1619921-81-1 ethyl (E)-7-cyclohexylhept-2-enoate 
• 5962-86-7 5-cyclohexylpentanal 

Relevant academic research and scientific papers

The compound, composition, and display device

PROBLEM TO BE SOLVED: To provide a compound capable of elevating an upper limit temperature where a SmC (smectic-C) phase of a liquid crystal can exist, broadening a temperature width of the SmC phase or enlarging a tilt angle of the SmC phase, and to provide a liquid crystal composition comprising the compound and a display element including the liquid crystal composition.SOLUTION: [1] The compound is expressed by general formula (i) shown below. In general formula (i), R and R' each independently represent a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 9 carbon atoms; A1, A2 and A3 each independently represent a 1,4-phenylene group or a 2,3-difluoro-1,4-phenylene group; m represents an integer of 1 to 10; and Y represents a cyclohexylene group, a phenylene group, a bicyclooctylene group or a dialkylsilylene group.

Potent α-amino-β-lactam carbamic acid ester as NAAA inhibitors. Synthesis and structure-activity relationship (SAR) studies

4-Cyclohexylbutyl-N-[(S)-2-oxoazetidin-3-yl]carbamate (3b) is a potent, selective and systemically active inhibitor of intracellular NAAA activity, which produces profound anti-inflammatory effects in animal models. In the present work, we describe structure-activity relationship (SAR) studies on 3-aminoazetidin-2-one derivatives, which have led to the identification of 3b, and expand these studies to elucidate the principal structural and stereochemical features needed to achieve effective NAAA inhibition. Investigations on the influence of the substitution at the β-position of the 2-oxo-3-azetidinyl ring as well as on the effect of size and shape of the carbamic acid ester side chain led to the discovery of 3ak, a novel inhibitor of human NAAA that shows an improved physicochemical and drug-like profile relative to 3b. This favourable profile, along with the structural diversity of the carbamic acid chain of 3b, identify this compound as a promising new tool to investigate the potential of NAAA inhibitors as therapeutic agents for the treatment of pain and inflammation.

Disubstituted beta-lactones as inhibitors of N-acylethanolamine acid amidase (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

CARBAMATE DERIVATIVES OF LACTAM BASED N-ACYLETHANOLAMINE ACID AMIDASE (NAAA) INHIBITORS

Described herein are compounds and pharmaceutical compositions which inhibit N-acylethanolamine acid amidase (NAAA). Described herein are methods for synthesizing the compounds set forth herein and methods for formulating these compounds as pharmaceutical compositions which include these compounds. Also described herein are methods of inhibiting NAAA in order to sustain the levels of palmitoylethanolamide (PEA) and other N-acylethanolamines (NAE) that are substrates for NAAA, in conditions characterized by reduced concentrations of NAE. Also, described here are methods of treating and ameliorating pain, inflammation, inflammatory diseases, and other disorders in which modulation of fatty acid ethanolamides is clinically or therapeutically relevant or in which decreased levels of NAE are associated with the disorder.

3-Aminoazetidin-2-one derivatives as N-acylethanolamine acid amidase (NAAA) inhibitors suitable for systemic administration

N-Acylethanolamine acid amidase (NAAA) is a cysteine hydrolase that catalyzes the hydrolysis of endogenous lipid mediators such as palmitoylethanolamide (PEA). PEA has been shown to exert anti-inflammatory and antinociceptive effects in animals by engaging peroxisome proliferator-activated receptor α (PPAR-α). Thus, preventing PEA degradation by inhibiting NAAA may provide a novel approach for the treatment of pain and inflammatory states. Recently, 3-aminooxetan-2-one compounds were identified as a class of highly potent NAAA inhibitors. The utility of these compounds is limited, however, by their low chemical and plasma stabilities. In the present study, we synthesized and tested a series of N-(2-oxoazetidin-3-yl)amides as a novel class of NAAA inhibitors with good potency and improved physicochemical properties, suitable for systemic administration. Moreover, we elucidated the main structural features of 3-aminoazetidin-2-one derivatives that are critical for NAAA inhibition. Stability is the key: α-Amino-β-lactams were synthesized as amide derivatives, and the effect of the azetidin-2-one ring, the stereochemistry at the α-position, and the functionalization of the α-amino group were studied with regard to N-acylethanolamine acid amidase inhibitory potency and hydrolytic and plasma stability.

Copper nanoparticle-catalyzed cross-coupling of alkyl halides with Grignard reagents

A cross-coupling reaction between alkyl bromides and chlorides and various Grignard reagents was carried out in the presence of commercially available copper or copper oxide nanoparticles as a catalyst and an alkyne additive. The catalytic system shows high activity, a broad scope, and good functional group tolerance.

DISUBSTITUTED BETA-LACTONES AS INHIBITORS OF N-ACYLETHANOLAMINE ACID AMIDASE (NAAA)

The present invention provides compounds and pharmaceutical compositions for inhibiting N-acylethanolamine acid amidase (NAAA). Inhibition of NAAA is contemplated as a method to sustain the levels of palmitoylethanolamide (PEA) and oleylethanolamide (OEA), two substrates of NAAA, in conditions characterized by reduced concentrations of PEA and OEA. The invention also provides methods for treating inflammatory diseases and pain, and other disorders in which decreased levels of PEA and OEA are associated with the disorder.

Role of the CAI-1 fatty acid tail in the Vibrio cholerae quorum sensing response

Quorum sensing is a mechanism of chemical communication among bacteria that enables collective behaviors. In V. cholerae, the etiological agent of the disease cholera, quorum sensing controls group behaviors including virulence factor production and biofilm formation. The major V. cholerae quorum-sensing system consists of the extracellular signal molecule called CAI-1 and its cognate membrane bound receptor called CqsS. Here, the ligand binding activity of CqsS is probed with structural analogues of the natural signal. Enabled by our discovery of a structurally simplified analogue of CAI-1, we prepared and analyzed a focused library. The molecules were designed to probe the effects of conformational and structural changes along the length of the fatty acid tail of CAI-1. Our results, combined with pharmacophore modeling, suggest a molecular basis for signal molecule recognition and receptor fidelity with respect to the fatty acid tail portion of CAI-1. These efforts provide novel probes to enhance discovery of antivirulence agents for the treatment of V. cholerae.

New masked δ-lithiocarbonyl compounds: Preparation and synthetic applications

The reaction of 2-(4-chlorobutyl)-1,3-dioxolanes (1a-c) or 2-(4-chlorobutyl)-2-ethyl-1,3-dithiane (1d) with an excess of lithium powder and a catalytic amount of naphthalene (8 mol %) in THF at - 78°C leads to a solution of the corresponding masked lithiu

Anti-inflammatory furanones

New 5-hydroxy-2-furanone compounds having anti-inflammatory, immunosuppressive and anti-proliferative activity and are useful in treating psoriasis and modifying calcium homeostasis.