N , N -Dialkyl-4-[(8-azabicyclo[3.2.1]-oct-3-ylidene)phenylmethyl]benzamides, potent, selective δ opioid agonists

Carson, John R.; Coats, Steven J.; Codd, Ellen E.; Dax, Scott L.; Lee, Jung; Martinez, Rebecca P.; Neilson, Lou Anne; Pitis, Philip; Zhang, Sui‐Po

doi:10.1016/j.bmcl.2004.02.051

Cited by 19 publications

(4 citation statements)

References 15 publications

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“…However, the studies of other DOR-selective agonists have not revealed proconvulsant effects. 67,[70][71][72] It has been pointed out that several non-proconvulsant DOR agonists comprise diverse structural types, including morphinan, octahydroisoquinoline, tricyclic, and spiro and diarylmethylenepiperidine scaffolds, so that DOR agonistinduced convulsions may be the exception rather than the rule. 67 Sleep architecture.…”

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confidence: 99%

Delta opioid agonists: a concise update on potential therapeutic applications

Peppin

Raffa

2015

J Clin Pharm Ther

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SUMMARYWhat is known and objective: The endogenous opioid system co-evolved with chemical defences, or at times symbiotic relationships, between plants and other autotrophs and heterotrophic predators -thus, it is not surprising that endogenous opioid ligands and exogenous mimetic ligands produce diverse physiological effects. Among the endogenous opioid peptides (endomorphins, enkephalins, dynorphins and nociception/orphanin FQ) derived from the precursors encoded by four genes (PNOC, PENK, PDYN and POMC) are the pentapeptides Met-enkephalin (Tyr-Gly-Gly-Phe-Met) and Leu-enkephalin (Tyr-Gly-Gly-PheLeu). The physiological effects of the enkephalins are mediated via 7-transmembrane G protein-coupled receptors, including delta opioid receptor (DOR). We present a concise update on the status of progress and opportunities of this approach. Methods: A literature search of the PUBMED database and a combination of keywords including delta opioid receptor, analgesia, mood and individual compounds identified therein, from industry and other source, and from www.clinicaltrials.com. Results and discussion: DOR agonist and antagonist ligands have been developed with ever increasing affinity and selectivity for DOR over other opioid receptor subtypes and studied for therapeutic utility, primarily for pain relief, but also for other clinical endpoints. What is new and conclusion: Selective DOR agonists have been designed with a large increase in therapeutic window for a variety of potential CNS applications including pain, depression, and learning and memory among others. WHAT IS KNOWN AND OBJECTIVE

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confidence: 99%

Delta opioid agonists: a concise update on potential therapeutic applications

Peppin

Raffa

2015

J Clin Pharm Ther

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“…(Azaadamantanone was converted to a series of amino azacadamantane benzamides (Scheme 17a-d) were profiled for serotonin receptor activity. Aminomethyl azadaniantaiie lung cancer have been suggested [10].…”

Section: Analgesic Activitymentioning

confidence: 99%

Pharmacological Potential of Benzamide Analogues and their Uses in Medicinal Chemistry

Asif¹

2016

Mod Chem Appl

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Benzamide derivatives possess different kinds of pharmacological activities like antimicrobial, analgesic, antiinflammatory, anticancer, cardiovascular, and other biological activities. Due to these biologically significances, scientists have interesting to develop various new benzamide derivatives. There is still need to improve the already used benzamide derivatives and search for the new and more effective benzamide derivatives. This review exhibited various pharmacophoric activities of benzamides analogues which are biologically importance.

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“…Benzamides are the carbonic acid amide of benzoic acid and have also been described for exhibiting various biological activities i.e. antimicrobial [ 23 , 24 ], anti-inflammatory [ 25 ], anticancer [ 26 , 27 ], antidiabetic [ 28 ], antidepressant, antitubercular [ 29 ], anticonvulsant [ 30 ] and analgesic [ 31 ] etc. 2,4-Dichlorobenzoic acid derivatives have also been reported for their antidiabetic potential exhibiting α-glucosidase and α-amylase inhibitory activity, as described in our previous studies [ 32 , 33 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

et al. 2020

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A series of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives (5a-5v) has been synthesized and confirmed by physicochemical(R f , melting point) and spectral means (IR, 1 HNMR, 13 CNMR). The results of in vitro antidiabetic study against α-glucosidase indicated that compound 5o bearing 2-CH 3-5-NO 2 substituent on phenyl ring was found to be the most active compound against both enzymes. The electron donating (CH 3) group and electron withdrawing (NO 2) group on a phenyl ring highly favoured the inhibitory activity against these enzymes. The docking simulations study revealed that these synthesized compounds displayed hydrogen bonding, electrostatic and hydrophobic interactions with active site residues. The structure activity relationship studies of these compounds were also corroborated with the help of molecular modeling studies. Molecular dynamic simulations have been done for top most active compound for validating its α-glucosidase and α-amylase inhibitory potential, RMSD analysis of ligand protein complex suggested the stability of top most active compound 5o in binding site of target proteins. In silico ADMET results showed that synthesized compounds were found to have negligible toxicity, good solubility and absorption profile as the synthesized compounds fulfilled Lipinski's rule of 5 and Veber's rule.

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N , N -Dialkyl-4-[(8-azabicyclo[3.2.1]-oct-3-ylidene)phenylmethyl]benzamides, potent, selective δ opioid agonists

Cited by 19 publications

References 15 publications

Delta opioid agonists: a concise update on potential therapeutic applications

Delta opioid agonists: a concise update on potential therapeutic applications

Pharmacological Potential of Benzamide Analogues and their Uses in Medicinal Chemistry

Synthesis, molecular docking and molecular dynamic simulation studies of 2-chloro-5-[(4-chlorophenyl)sulfamoyl]-N-(alkyl/aryl)-4-nitrobenzamide derivatives as antidiabetic agents

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