Selectivity in new .beta.-adrenergic blocking agents. (3-Amino-2-hydroxypropoxy)benzamides

Shtacher, Gad; Erez, Mordechai; Cohen, Sasson

doi:10.1021/jm00263a024

Cited by 23 publications

(5 citation statements)

References 6 publications

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“…2 Recently it has been shown that it is possible to increase the cardioselectivity in a series of l-aryloxy-3-[(aryloxyalkyl)amino]-2-propanols3 by the proper choice of the amino substituent. It appears that the p-acylamino substituent is responsible for the cardioselectivity in this series and this has been substantiated by other workers.…”

mentioning

confidence: 99%

Cardioselective .beta.-adrenergic blocking agents. 1. 1-[(3,4-Dimethoxyphenethyl)amino]-3-aryloxy-2-propanols

Hoefle¹,

Hastings²,

Meyer³

et al. 1975

J. Med. Chem.

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A series of 1-amino-3-aryloxy-2-propanols has been synthesized and examined for cardioselective beta-blockade. The introduction of the (3,4-dimethoxyphenethyl)amino group lead to the most cardioselective agents. Structure-activity relationships are discussed. Of the compounds tested 1-[(3,4-dimethoxyphenethyl)amino]-3-(m-tolyloxy)-2-propanol was selected for clinical trial because of optimal potency and selectivity.

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mentioning

confidence: 99%

Cardioselective .beta.-adrenergic blocking agents. 1. 1-[(3,4-Dimethoxyphenethyl)amino]-3-aryloxy-2-propanols

Hoefle¹,

Hastings²,

Meyer³

et al. 1975

J. Med. Chem.

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“…These data are supported by some studies which showed that biological activity exerted by some amide derivatives on the cardiovascular system is through adrenergic activation using a heart failure model 43 . In addition, it is important to mention that some studies indicating that several benzamides derivatives can interact with the β 2 -adrenergic receptor 44 and can produce changes in left ventricular pressure 45 46 47 48 . For this reason, in this research the biological activity produced by 4-hydroxy-furanyl-benzamide derivative on left ventricular pressure was evaluated in the absence or presence of butaxamine (β 2 -adrenergic receptor inhibitor) 49 .…”

Section: Discussionmentioning

confidence: 99%

Biological Activity of a 4-Hydroxy-Furanyl-Benzamide Derivative on Heart Failure

et al. 2022

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Background There are studies that suggest that some benzamide derivatives may exert effects on heart failure; however, their molecular mechanism is not very clear. Objective The aim of this research was to evaluate the biological activity of a 4-hydroxy-furanyl-benzamide derivative against heart failure translated as area infarct. Methods Biological activity produced by 4-hydroxy-furanyl-benzamide derivative against heart failure was determinate using an ischemia-reperfusion injury model. In addition, the effects exerted by the 4-hydroxy-furanyl-benzamide derivative on left ventricular pressure (LVP) was evaluated in the absence or presence of some drugs such as yohimbine, butaxamine, methoctramine and L-NAME using a model of rat heart isolated. Results The results showed that 4-hydroxy-furanyl-benzamide derivative decrease both infarct area and LVP. However, the effect produced by 4-hydroxy-furanyl-benzamide derivative on LVP was inhibited in the presence of both methoctramine and L-NAME. Conclusions All these data suggest that biological activity produced by 4-hydroxy-furanyl-benzamide derivative on left ventricular pressure is through of both M2-muscarinic receptor and nitric oxide synthase enzyme activation. It is important to mention that this phenomenon results as a decrease of both infarct area and heart failure.

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“…The epoxypropanes were prepared according to published procedures. 7 The compounds were purified by column chromatography on neutral alumina grade II. The eluting solvents were mixtures of petroleum ether (bp 40-60 °C) and chloroform.…”

Section: Methodsmentioning

confidence: 99%

Cardioselectivity as a function of molecular structure in .beta.-adrenoceptor blocking agents of the 1-(para-substituted aryloxy)-3-(isopropylamino)propan-2-ol type

Erez¹,

Shtacher²,

Weinstock³

1978

J. Med. Chem.

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The relationship between molecular structure and cardioselectivity is described in the 1-(para-substituted aryl-oxy)-3-(isoprophylamino)propan-2-ol type of beta-adrenoceptor blocking agents. Cardioselectivity in the aforementioned series requires that the aromatic substitution in the position para to the amino alcohol side chain will have a minimal linear length of 5.0 A. Highest cardioselectivity is obtained when this para substituent is a rigid group coplanar with the aromatic ring. This may result from steric hindrance for binding at the beta2-adrenoceptor subtype which does not occur in the beta1 subtype. Evidence in favor of this suggestion was obtained by the finding that the trans isomer of 1-[4-(1-propenyl)-2-methoxyphenoxy]-3-(isopropylamino)propan-2-ol is cardioselective (beta1/beta2 = 25), whereas the cis isomer is beta2 selective (beta1/beta2 = 0.1).

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Selectivity in new .beta.-adrenergic blocking agents. (3-Amino-2-hydroxypropoxy)benzamides

Cited by 23 publications

References 6 publications

Cardioselective .beta.-adrenergic blocking agents. 1. 1-[(3,4-Dimethoxyphenethyl)amino]-3-aryloxy-2-propanols

Cardioselective .beta.-adrenergic blocking agents. 1. 1-[(3,4-Dimethoxyphenethyl)amino]-3-aryloxy-2-propanols

Biological Activity of a 4-Hydroxy-Furanyl-Benzamide Derivative on Heart Failure

Cardioselectivity as a function of molecular structure in .beta.-adrenoceptor blocking agents of the 1-(para-substituted aryloxy)-3-(isopropylamino)propan-2-ol type

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