183129-81-9

Upstream product

• 49594-75-4 4-(4-ethylphenyl)-4-oxobutyric acid 
• 100-41-4 ethylbenzene 

Downstream Products

• 183129-85-3 4-(4-Ethyl-phenyl)-butyraldehyde 
• 183129-92-2 {2-Amino-5-[2-(4-ethyl-phenyl)-ethyl]-thiophen-3-yl}-(2-chloro-phenyl)-methanone 
• 183130-16-7 5-(2-Chloro-phenyl)-7-[2-(4-ethyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepin-2-one 
• 183130-00-9 2-Chloro-N-{3-(2-chloro-benzoyl)-5-[2-(4-ethyl-phenyl)-ethyl]-thiophen-2-yl}-acetamide 
• 183130-08-7 2-Amino-N-{3-(2-chloro-benzoyl)-5-[2-(4-ethyl-phenyl)-ethyl]-thiophen-2-yl}-acetamide 
• 1027988-98-2 [5-(2-Chloro-phenyl)-7-[2-(4-ethyl-phenyl)-ethyl]-1,3-dihydro-thieno[2,3-e][1,4]diazepin-(2Z)-ylidene]-hydrazine 

Relevant academic research and scientific papers

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.

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.

Structural optimization of 4-(2-chlorophenyl)-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepines as antagonists for platelet activating factor: Pharmacological contribution of substituents at the 2- and 6-positions of a condensed ring system

A series of 4-(2-chlorophenyl)-9-methyl-6H-thieno [3,2-f][1,2,4]triazolo[4,3-a][1,4]diazepine derivatives bearing substituents at the 2- and 6-positions were synthesized, and evaluated in vitro for their inhibitory activity on rabbit platelet aggregation induced by platelet activating factor (PAF) and in vivo for their preventing effect on PAF-induced mortality in mice. The length of alkyl or arylalkyl side chain at the 2-position was responsible for enhancing the affinity for the PAF receptor. The simultaneous substitution at both the 2- and 6-positions resulted in a successful separation of the affinity for the PAF receptor from that for the benzodiazepine (BZ) receptor. Thus, (±)-4-(2-chlorophenyl)-2-[2-(4-isobutylphenyl)ethyl]- 6,9-dimethyl-6H-thieno[3,2-f][1,2,4]triazolo[4,3-a][1,4] diazepine (Y-24180) was confirmed to be a specific antagonist for the PAF receptor and is currently under clinical trials.