186094-06-4

Usage

Uses

Used in Organic Synthesis:
rac-4-(3’-Methoxy-α-hydroxybenzyl)-N,N-diethylbenzamide is used as an intermediate in the synthesis of various organic compounds for [application reason] its unique structural features that allow for further functionalization and modification in chemical reactions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, rac-4-(3’-Methoxy-α-hydroxybenzyl)-N,N-diethylbenzamide is used as a starting material or a building block for the development of new drugs, particularly those targeting specific biological receptors or enzymes, due to its potential to be modified and optimized for such purposes.
Used in Chemical Research:
rac-4-(3’-Methoxy-α-hydroxybenzyl)-N,N-diethylbenzamide is also utilized in chemical research as a model or reference substance for studying the properties and reactivity of similar benzamide derivatives, which can help in understanding the structure-activity relationships and guiding the design of new molecules with desired properties.

Upstream product

• 58287-77-7 N,N-diethyl-4-formylbenzamide 
• 36282-40-3 (3-methoxyphenyl)magnesium bromide 
• 2398-37-0 3-methoxyphenyl bromide 
• 1711-05-3 m-anisoyl chloride 
• 108-88-3 toluene 
• 156727-76-3 4-(3-methoxybenzoyl)benzoic acid 
• 1027905-05-0 4-(3-Methoxy-benzoyl)-benzoyl chloride 
• 82520-37-4 (4-methylphenyl)-(3-methoxyphenyl)methanone 
• 619-66-9 4-Carboxybenzaldehyde 
• 156727-77-4 N,N-diethyl-4-(3-methoxybenzoyl)benzamide 

Downstream Products

• 156727-77-4 N,N-diethyl-4-(3-methoxybenzoyl)benzamide 
• 256504-40-2 4-[(2-chloroethoxy)-3-methoxybenzyl]-N,N-diethylbenzamide 
• 150428-54-9 SNC 85 
• 155836-50-3 4-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N,N-diethylbenzamide 
• 150428-54-9 SNC 89 
• 150428-54-9 SNC 88 
• 156727-72-9 SNC 83 
• 156727-74-1 (+)-4-[(αR)-α-(2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl-3-methoxybenzyl]-N,N-diethylbenzamide 
• 156727-71-8 SNC 67 
• 156727-75-2 SNC 79 
• 1312554-93-0 4-[(10-benzyl-9,10-diazatricyclo[4.2.1.1(2,5)]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide 
• 1312555-08-0 4-[(9,10-diazatricyclo[4.2.1.1(2,5)]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide 
• 1312552-02-5 4-[(10-allyl-9,10-diazatricyclo[4.2.1.1(2,5)]dec-9-yl)-(3-methoxyphenyl)methyl]-N,N-diethylbenzamide 
• 1312552-03-6 4-[(10-allyl-9,10-diazatricyclo[4.2.1.1(2,5)]dec-9-yl)-(3-hydroxyphenyl)methyl]-N,N-diethylbenzamide 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel delta (δ) opioid receptor ligands with diazatricyclodecane skeletons

Considering the interesting pharmacological profile of the delta (δ) selective opioid agonist compound SNC-80, conformationally constrained analogs containing two diazatricyclodecane ring systems in place of dimethylpiperazine core motif were synthesized.

PHARMACEUTICAL COMPOUNDS

Diazapolycyclic compounds having affinity for the opioidergic receptors, preferably for the delta opioidergic receptors, with central and/or peripheral activity, having formula: [in-line-formulae]A1-D1-T1??(I)[/in-line-formulae] wherein: A1 is a group of formula (II): wherein: R1 is phenyl wherein one of the ring hydrogen atoms is substituted with a group selected from C(O)R′, C(O)OR′, C(O)NHR′ or C(O)NR3R4, R′, R3 and R4, being as defined in the application; R2 is phenyl, optionally substituted D1 is a diazapolycyclic group T1 is a group selected from H, alkyl, alkenyl, alkynyl and from the following optionally substituted groups: cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl or heteroarylalkyl, and their hydrates and solvates and pharmaceutically acceptable salts.

Diazacyclic compounds having affinity for opioid receptors

Diazapolycyclic compounds having affinity for the opioidergic receptors, preferably for the delta opioidergic receptors, with central and/or peripheral activity, having formula: ???????? A1-D1-T1?????(I) wherein: - A1 is a group of formula (II): wherein: R1 is phenyl wherein one of the ring hydrogen atoms is substituted with a group selected from C(O)R', C(O)OR', C(O)NHR' or C(O)NR3R4, R', R3 and R4, being as defined in the application; R2 is phenyl, optionally substituted - D1 is a diazapolycyclic group - T1 is a group selected from H, alkyl, alkenyl, alkynyl and from the following optionally substituted groups: cycloalkyl, heterocycloalkyl, aryl, heteroaryl, cycloalkylalkyl, heterocycloalkylalkyl, arylalkyl or heteroarylalkyl, and their hydrates and solvates and pharmaceutically acceptable salts.

New diarylmethylpiperazines as potent and selective nonpeptidic δ opioid receptor agonists with increased in vitro metabolic stability

Nonpeptide δ opioid agonists are analgesics with a potentially improved side-effect and abuse liability profile, compared to classical opioids. Andrews analysis of the NIH nonpeptide lead SNC-80 suggested the removal of substituents not predicted to contribute to binding. This approach led to a simplified lead, N,N-diethyl-4-[phenyl(1-piperazinyl)methyl]benzamide (1), which retained potent binding affinity and selectivity to the human δ receptor (IC50 = 11 nM, μ/δ = 740, κ/δ > 900) and potency as a full agonist (EC50 = 36 nM) but had a markedly reduced molecular weight, only one chiral center, and increased in vitro metabolic stability. From this lead, the key pharmacophore groups for δ receptor affinity and activation were more clearly defined by SAR and mutagenesis studies. Further structural modifications on the basis of 1 confirmed the importance of the N,N-diethylbenzamide group and the piperazine lower basic nitrogen for δ binding, in agreement with mutagenesis data. A number of piperazine N-alkyl substituents were tolerated. In contrast, modifications of the phenyl group led to the discovery of a series of diarylmethylpiperazines exemplified by N,N-diethyl-4-[1-piperazinyl(8-quinolinyl)-methyl]benzamide (56) which had an improved in vitro binding profile (IC50 = 0.5 nM, μ/δ = 1239, EC50 = 3.6 nM) and increased in vitro metabolic stability compared to SNC-80.

Probes for narcotic receptor mediated phenomena. 26. Synthesis and biological evaluation of diarylmethylpiperazines and diarylmethylpiperidines as novel, nonpeptidic δ opioid receptor ligands

We recently reported (+)-4-[(αR)-α-{(2S,5R)-4-allyl-2,5- dimethyl-1-piperazinyl}-3-methoxybenzyl]-N,N-diethylbenzamide (1b, SNC80) as a novel nonpeptidic δ receptor agonist and explored the structure-activity relationships (SAR) of a series of related der

Probes for narcotic receptor mediated phenomena. 23. Synthesis, opioid receptor binding, and bioassay of the highly selective δ agonist (+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]N,N- diethylbenzamide (SNC 80) and related novel nonpeptide δ opioid receptor ligands

The highly selective delta (δ) opioid receptor agonist SNC 80 [(+)-4- [(αR)-α-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-methoxybenzyl]-N,N- diethylbenzamide, (+)-21] and novel optically pure derivatives were synthesized from the enantiomers of 1-allyl-trans-2,5-dimethylpiperazine (2). The piperazine (±)-2 was synthesized, and its enantiomers were obtained on a multigram scale in >99% optical purity by optical resolution of the racemate with the camphoric acids. The absolute configuration of (+)-2 was determined to be 2S,5R by X-ray analysis of the salt with (+)-camphoric acid. Since the chirality of the starting material was known, and the relative configuration of compounds (-)-21, (-)-22, and (+)-23 were obtained by single-crystal X- ray analysis, the assignment of the absolute stereochemistry of the entire series could be made. Radioreceptor binding studies in rat brain preparations showed that methyl ethers (+)-21 (SNC 80) and (-)-25 exhibited strong selectivity for rat δ receptors with low nanomolar affinity to 6 receptors and only micromolar affinity for rat mu (μ) opioid receptors. Compounds (- )-21, (-)-22, and (-)-23 showed micromolar affinities for δ opioid receptors. The unsubstituted derivative (+)-22 and the fluorinated derivative (-)-27 showed >2659- and >2105-fold δ/μ binding selectivity, respectively. The latter derivatives are the most selective ligands described in the new series. Studies with some of the compounds described in the isolated mouse vas deferens and guinea pig ileum bioassays revealed that all were agonists with different degrees of selectivity for the δ opioid receptor. These data show that (+)-21 and (+)-22 are potent δ receptor agonists and suggest that these compounds will be valuable tools for further study of the δ opioid receptor at the molecular level, including its function and role in analgesia and drug abuse.