Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of alpha 1 and alpha 2 adrenergic activities.

doi:10.1021/JM00158A016

Paper

Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of alpha 1 and alpha 2 adrenergic activities.

Published Aug 1, 1986 · J. Debernardis, M. Winn, D. Arendsen

Journal of medicinal chemistry

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12

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0

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Abstract

A series of modifications to positions 1, 2, and 4 of the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin (1, A-54741) succeeded in improving the separation of the potent alpha 1 and alpha 2 adrenergic agonism observed for the parent compound 1. In particular 5,6-dihydroxy-4,4-dimethyl-1-(2-imidazolinyl)tetralin (7) was found to be a specific alpha 1 adrenergic agonist, and 7,8-dihydroxy-4-(2-imidazolinyl)chroman (2) was found to have improved alpha 2 adrenergic agonistic selectivity relative to the parent compound 1.

Study Snapshot

Modifications to the tetralin ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin improved the separation of alpha 1 and alpha 2 adrenergic activities, resulting in improved alpha 1 and alpha 2 agonistic selectivity

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Conformationally defined adrenergic agents. 3. Modifications to the carbocyclic ring of 5,6-dihydroxy-1-(2-imidazolinyl)tetralin: improved separation of alpha 1 and alpha 2 adrenergic activities.

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References

Citations

Spirotetrahydronaphthalene analogues of sympathomimetic catecholamines. Synthesis and adrenergic activity of 5,6‐ and 6,7‐dihydroxy‐3,4‐dihydrospiro[naphthalen‐1(2H)‐3′ ‐piperidines]

DDSNPs 5 and 6 show low ability to interact with both and adrenoceptors compared to reference compounds 2, 3, and 4.

Characterization of human recombinant α2A‐adrenoceptors expressed in Chinese hamster lung cells using intracellular Ca2+ changes: evidence for cross‐talk between recombinant α2A‐ and native α1‐adrenoceptors

Human 2Aadrenoceptors in Chinese hamster lung cells exhibit co-activation with native 1adrenoceptors, resulting in intracellular calcium release.

Synthesis and α-adrenergic and I1-imidazoline activity of 3-phenylpiperidines dimethyl-substituted on the phenyl ring

Dimethylphenyl-substituted 3-phenylpiperidines show good activity at 2-adrenergic receptors and I1-imidazoline receptors, providing a unique template for designing 2-AR ligands.

Conformationally restrained analogues of sympathomimetic catecholamines. Synthesis and adrenergic activity of 5,6- and 6,7-dihydroxy-3,4-dihydrospiro[naphthalen-1(2H)-2',5'-morpholines].

The new compounds 10 and 11 show low ability to interact with - and -adrenoceptors compared to their morpholine and tetrahydronaphthalene analogues.

Synthesis and α-adrenergic activity of 2- and 6-methyl-substituted (3,4-dihydroxyphenyl)-3-piperidinols

2- and 6-methyl-substituted (3,4-dihydroxyphenyl)-3-piperidinols provide a more refined understanding of steric requirements for 1- and 2-adrenergic receptor activation.

X-ray analysis, theoretical studies and α-adrenergic biopharmacological properties of 1-(2,5-dimethoxyphenyl)-2-aminoethanol and its morpholine analogue

The pharmacological activity of 1-(2,5-dimethoxyphenyl)-2-aminoethanol 3a and its morpholine analogue 3b differs between stimulant and blocking effects on 1-receptors, with rotameric positions of the phenyl

Selective Alpha Adrenergic Agents – Differentiation of Receptor Subtypes

Selective alpha-2 adrenergic agents, derived from conformational biases in phenethylamine structures, show potential therapeutic utility in nasal congestion, glaucoma, and depression.