.beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols

Crowther, A. F.; Gilman, David J.; McLoughlin, B. J.; Smith, L. H.; Turner, R. W.; Wood, Thomas M.

doi:10.1021/jm00304a018

Cited by 23 publications

(6 citation statements)

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“…The topic of regioselective biotransformation has been extensively reviewed. 23 Recent studies of interest include the first report of enzymic hydroxylation a to an acetylenic 0022-2623/78/1821-0683$01.00/0 group24 and a careful investigation of the metabolism of 1-methylcyclohexene and related terpinoids in mammals showing high regioselectivities for allylic positions. 25 The biotransformation of /V-n-propylamphetamine by rat liver homogenates yielded ten times more N-dealkylated metabolites (resulting from C0-hydroxylation) than C3hydroxylated metabolites.26…”

Section: Methodsmentioning

confidence: 99%

Alteration of relative affinities toward myocardial and vascular .beta. adrenoceptors induced by side-chain substitution of aryloxypropanolamines

Shtacher¹,

Rubinstein²,

Somani³

1978

J. Med. Chem.

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Section: Methodsmentioning

confidence: 99%

Alteration of relative affinities toward myocardial and vascular .beta. adrenoceptors induced by side-chain substitution of aryloxypropanolamines

Shtacher¹,

Rubinstein²,

Somani³

1978

J. Med. Chem.

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“…Their cyclic system can be opened highly regioselectively by N-nucleophiles. Thus, the most common method for synthesizing phenol glycidyl ethers uses attack of the phenols at the oxirane ring of 1-chloro-2,3-epoxypropane (epichlorohydrin) to give the chlorohydrin ethers followed by dehydrochlorination by base to close the epoxide ring [4,5,26,27]. …”

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confidence: 99%

New Aloperine–Isoflavone Conjugates

2016

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The reaction of aloperine with isoflavone glycidyl ethers was investigated. A series of alkaloid-isoflavonoid conjugates were synthesized via regioselective opening of the oxirane ring by aloperine.Keywords: aloperine, isoflavone, propanolamine, isoflavone glycidyl ether.E-Adrenoblockers play an important role in the treatment of cardiovascular diseases. Their anti-ischemic, antiarrhythmic, and antihypertensive properties have been used in clinical medicine for many years. Derivatives of phenylpropanolamine and phenoxypropanolamine are typical E-adrenoreceptor blockers [1, 2]. Chromone and flavone derivatives containing a propanolamine fragment are also known to be capable of blocking E-adrenoreceptors [3,4]. Furthermore, several 7-(3-amino-2-hydroxypropoxy) flavonoid derivatives exhibited antihypertensive [5][6][7], antihyperglycemic [8], and antiproliferative [9] activity. Isoflavones containing an aminopropanol fragment showed anti-osteoporosis activity, an estrogen effect [10], and anticancer activity [11].In continuation of research on the synthesis of alkaloid-flavonoid conjugates, it seemed interesting to study the possibility of using a hydroxypropane linker to conjugate 7-hydroxyisoflavones and aloperine, which was isolated as a minor constituent from seeds and leaves of Sophora alopecuroides L. [12][13][14][15][16].Modification of this alkaloid was interesting because of its valuable biological properties. Aloperine exhibits antiinflammatory, anti-allergic [17,18], and antiviral activity [19]; inhibits proliferation of HCT116 cancer cells; initiates apoptosis; and interrupts the cell cycle [20].The phenols for conjugation with aloperine were the natural isoflavones formononetin 1a [21], 2-methylformononetin 1b [22], cladrin 1c [23], afromorsin 1d [24], cladrastin 1e [23], pseudobaptigenin 1f [25], and their derivatives 1g-j.Oxiranes are widely used to synthesize phenoxypropanolamines. Their cyclic system can be opened highly regioselectively by N-nucleophiles. Thus, the most common method for synthesizing phenol glycidyl ethers uses attack of the phenols at the oxirane ring of 1-chloro-2,3-epoxypropane (epichlorohydrin) to give the chlorohydrin ethers followed by dehydrochlorination by base to close the epoxide ring [4,5,26,27].

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“…Since, until very recently15 (see Discussion), no NMR analysis was available on /3-adrenoceptor-blocking aryloxypropanolamines, which, in general, show higher receptor affinities than arylethanolamine antagonists, it was decided to perform an IR and NMR study on toliprolol [3-(isopropylamino)-l-(3-methylphenoxy)-2-propanol; 1], the affinity of which being of the same high level as that of propranolol. 16 Our main attention was focused on the hydrohalide salts, since the high pKa values indicate the protonized form to be responsible for activity. 17 to the OH and NH2+ protons, which phenomenon gives rise to a seven-membered ring structure.…”

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confidence: 99%

.beta.-Adrenoceptor studies. 5. Proton NMR and IR spectroscopic analysis of the conformation of the hydrohalide salts of .beta.-adrenoceptor-blocking aryloxypropanolamines. Evidence for a seven-membered ring structure with participation of two hydrogen bonds

Zaagsma¹

1979

J. Med. Chem.

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.beta.-Adrenergic blocking agents. V. 1-Amino-3-(substituted phenoxy)-2-propanols

Cited by 23 publications

References 0 publications

Alteration of relative affinities toward myocardial and vascular .beta. adrenoceptors induced by side-chain substitution of aryloxypropanolamines

Alteration of relative affinities toward myocardial and vascular .beta. adrenoceptors induced by side-chain substitution of aryloxypropanolamines

New Aloperine–Isoflavone Conjugates

.beta.-Adrenoceptor studies. 5. Proton NMR and IR spectroscopic analysis of the conformation of the hydrohalide salts of .beta.-adrenoceptor-blocking aryloxypropanolamines. Evidence for a seven-membered ring structure with participation of two hydrogen bonds

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