3306-69-2

Usage

Uses

Used in Pharmaceutical Industry:
2-Azabicyclo[2.2.2]octan-3-one is used as a key intermediate in the synthesis of quinoline and quinoxaline compounds. These compounds are known to inhibit platelet-derived growth factor and/or tyrosine kinases, which play a crucial role in cell proliferation and differentiation. By inhibiting these factors, these compounds can potentially be used in the development of treatments for various diseases, including cancer and fibrosis.
Additionally, 2-azabicyclo[2.2.2]octan-3-one is used in the preparation of phenyl derivatives containing inhibitors of coagulation factor. These inhibitors can be employed for prophylaxis and/or therapy of thromboembolic disorders, which are conditions characterized by the formation of blood clots in the blood vessels. By inhibiting coagulation factors, these phenyl derivatives can help prevent the formation of blood clots and reduce the risk of thromboembolic events.

InChI:InChI=1/C7H11NO/c9-7-5-1-3-6(8-7)4-2-5/h5-6H,1-4H2,(H,8,9)

Upstream product

• 1776-53-0 4-aminocyclohexanecarboxylic acid 
• 3685-23-2 cis-4-aminocyclohexane-1-carboxylic acid 
• 62456-15-9 methyl (1s,4s)-4-aminocyclohexane-1-carboxylate 
• 150-13-0 4-amino-benzoic acid 
• 61367-16-6 cis-4-aminocyclohexanecarboxylic acid methyl ester hydrochloride 
• 17159-79-4 ethyl 4-oxocyclohexane-1-carboxylate 
• 51498-33-0 ethyl 4-amino-1-cyclohexanecarboxylate 

Downstream Products

• 74403-57-9 2-benzyl-2-aza-bicyclo[2.2.2]octan-3-one 
• 102012-20-4 2-benzhydryl-2-aza-bicyclo[2.2.2]octan-3-one 
• 280-38-6 isoquinuclidine 
• 30134-98-6 ((1r,4r)-4-aminocyclohexyl)methanol 
• 46410-64-4 2-benzyl-2-aza-bicyclo[2.2.2]octane 
• 102155-99-7 2-benzhydryl-2-aza-bicyclo[2.2.2]octane 
• 87640-24-2 cis-4-<(phenylmethyl)amino>cyclohexanecarboxylic acid 
• 102003-92-9 benzyl-cyclohex-3-enylmethyl-methyl-amine 

Relevant academic research and scientific papers

Rapid and Mild Lactamization Using Highly Electrophilic Triphosgene in a Microflow Reactor

Lactams are cyclic amides that are indispensable as drugs and as drug candidates. Conventional lactamization includes acid-mediated and coupling-agent-mediated approaches that suffer from narrow substrate scope, much waste, and/or high cost. Inexpensive, less-wasteful approaches mediated by highly electrophilic reagents are attractive, but there is an imminent risk of side reactions. Herein, a methods using highly electrophilic triphosgene in a microflow reactor that accomplishes rapid (0.5–10 s), mild, inexpensive, and less-wasteful lactamization are described. Methods A and B, which use N-methylmorpholine and N-methylimidazole, respectively, were developed. Various lactams and a cyclic peptide containing acid- and/or heat-labile functional groups were synthesized in good to high yields without the need for tedious purification. Undesired reactions were successfully suppressed, and the risk of handling triphosgene was minimized by the use of microflow technology.

Inhibitors of protein kinases

Compounds of general Formula (I): wherein R1, R2, R3, Ra, A, B and x are as defined herein are inhibitors of protein kinases in particular members of the cyclin-dependent kinase family and/or the glycogen synthase kinase 3 family and are useful in preventing and/or treating any type of pain, inflammatory disorders, cancer, immunological diseases, proliferative diseases, infectious diseases, cardiovascular diseases, metabolic disorders, renal diseases, neurologic and neuropsychiatric diseases and neurodegenerative diseases.

COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF

Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.

Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: The synthesis and biological activities of RPR127963 an orally bioavailable inhibitor

RPR127963 demonstrates an excellent pharmacokinetic profile in several species and was found to be efficacious in the prevention of restenosis in a Yucatan mini-pig model upon oral administration of 1-5 mg/kg. The in vitro selectivity profile and SAR of t

An improved preparation of 2-azabicyclo[2.2.2]octane

An improved preparative four-step synthesis to isoquinuclidine tosylate salt 4 has been demonstrated in 70% overall yield from p-aminobenzoic acid (PABA) 1. Hydrogenation of PABA 1 affords 4-aminocyclohexane carboxylic acid 2 as an 80 : 20 mixture of cis- and trans-isomers. Heating the mixture at 250°C effected epimerization and cyclization to provide the bicyclic lactam 3. Subsequent Red-A1 reduction and treatment with tosic acid furnished the desired bicyclic amine, tosylate salt 4.

Isoquinuclidine-based expectorants. Synthesis and biological activities of N-alkoxybenzylisoquinuclidines

N-Di-, trialkoxybenzylisoquinuclidines and related compounds were synthesized and evaluated for expectorant activities. Structure-activity relationship investigations in this series showed that both the trialkoxyphenyl ring and the basic nitrogen atom at the benzylic position were necessary for activity. N-Trialkoxybenzylisoquinuclidines 7a, 7c, 7d, 7f and 7g significantly increased bronchial secretion, and ethoxy derivative 7c showed the highest activity in these compounds. The n-propyloxy derivatives 7d and 7f also accelerated bronchoalveolar surfactant secretion with about two to four times more activity than ambroxol (7d and 7f; ED50 = 27.5 and 15.5 mg/kg po, respectively); however, compounds 7a, 7c and 7g were less active than ambroxol. Compounds 7d and 7f were selected for further examination. These compounds displayed antioxidant activity in vitro (7d and 7f; IC50 = 48.0 and 66.0 μM, respectively). Compound 7d also showed inhibition on bradykinin- or antigen-induced airway inflammation in guinea pigs. These findings suggest that compounds 7d and 7f are potent expectorants with antiinflammatory activity.

Approaches towards the synthesis of fluoro(cyclo)alkylamines

The synthesis of fluoro(cyclo)alkylamines 1-amino-6-fluorohexane (1), 1-amino-7-fluoroheptane (2), cis/trans-4-fluorocyclohexylamine (3a,b) and cis-4-fluoromethylcyclohexylamine (4) has been investigated for use as synthons for histamine receptor ligands for use in PET.

TRANSFORMATIONS MICROBIOLOGIQUES-3 APPROCHE DE LA TOPOLOGIE DU SITE HYDROXYLANT DE BEAUVERIA SULFURESCENS

Hydroxylation of some bi- or tricyclic amides or lactams, the determination of the absolute configuration of the alcohols obtained and the topology of the hydroxylating site of Beauveria sulfurescens based on these absolute configurations, are discussed.

NMR AND RAMAN SPECTROSCOPIC STUDY OF COMPLEX FORMATION BETWEEN 2-METHYL-2-AZABICYCLO--OCTA-3-ONE AND TiCl4

From analysis of 1H and 13C NMR and Raman specroscopic data, in CDCl3 and 1,1,2,2-tetrachloroethane-d2 solution, the lactam 2-methyl-2-azabicyclo--octa-3-one (L) was found to form complexes with TiCl4 (M) of overall composition M2/