5260-29-7

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 51-35-4 4R-4-hydroxyproline 

Downstream Products

• 118329-82-1 (2S,4R)-2-(hydroxymethyl)-1-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)pyrrolidine 
• 33812-99-6 3-oxo-2-[5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-3-ylidene]-butyric acid methyl ester 
• 33812-96-3 [(1S)-5-(toluene-4-sulfonyl)-2-oxa-5-aza-bicyclo[2.2.1]hept-3-ylidene]-malonic acid dimethyl ester 

Relevant academic research and scientific papers

Chemoenzymatic synthesis and cannabinoid activity of a new diazabicyclic amide of phenylacetylricinoleic acid

Endocannabinoids (eCBs) are endogenous neuromodulators of synaptic transmission. Their dysfunction may cause debilitating disorders of diverse clinical manifestation. For example, drug addiction, lack of sex desire, eating disorders, such as anorexia or bulimia and dyssomnias. eCBs also participate in the regulation of core temperature and pain perception. In this context, it is important to recognize the utility of cannabinoid receptor 1 (CB1R) agonists, natural as Δ9-tetrahydrocannabinol (THC) or synthetic as Nabilone as useful drugs to alleviate this kind of patients' suffering. Therefore, we have developed a new drug, (R,Z)-18-((1S,4S)-5-methyl-2,5-diazabicyclo[2.2.1]heptan-2-yl)-18-oxooct adec-9-en-7-yl phenylacetate (PhAR-DBH-Me), that appears to bind and activate the CB1R. This diazabicyclic amide was synthesized from phenylacetylricinoleic acid and (1S,4S)-2,5-diazabicyclo[2.2.1]heptane. To test its cannabinergic properties we evaluated its effects on core temperature, pain perception, and the sleep-waking cycle of rats. Results indicate that 20 and 40 mg/kg of PhAR-DBH-Me readily reduced core temperature and increased pain perception threshold. In addition, 20 mg/kg increased REM sleep in otherwise normal rats. All these effects were prevented or attenuated by AM251, a CB1R antagonist. Place preference conditioning studies indicated that this molecule does not produce rewarding effects. These results strongly support that PhAR-DBH-Me possesses cannabinoid activity without the reinforcement effects.

A SHORT IMPROVED SYSTHESIS OF N-SUBSTITUTED 5-AZA-2-OXA-3-OXO-BICYCLOHEPTANES

N-Substituted 5-aza-2-oxa-3-oxo-bicycloheptanes are conformationally rigid models that have been used in several 1H-NMR studies.They have previously been obtained by multistep processes.We have devised a one step synthesis for these compounds.The utility of this new route has been demonstrated for five differently N-substituted substrates.