.beta.-Adrenergic blocking agents. 11. Heterocycyclic analogs of pronethalol [2-isopropylamino-1-(2-naphthyl)ethanol]

Chodnekar, M. S.; Crowther, A. F.; Hepworth, W.; Howe, R.; McLoughlin, B. J.; Mitchell, A.; Rao, B. Dharma; Slatcher, R. P.; Smith, L. H.; Stevens, Marcus A.

doi:10.1021/jm00271a014

Cited by 22 publications

(5 citation statements)

References 5 publications

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“…Arndt and Eistert7 pioneered the field of diazomethane‐based homologations, however, as shown later by Capuano and Velter8 and, more recently by Alcaide and Almendros (with TMSCHN 2 ),9 formation of rearranged products limits the appeal of this tactic. Alternatively, Howe,10 Westwood,11 Nair12 and Hajra13 applied the Corey–Chaykovsky epoxydation14 to simple, non‐functionalized isatins , although non‐uniformly high yields were observed, probably depending on the specific nature of the substrate employed. As a consequence, to the best of our knowledge, chemoselectivity issues arising from the presence of concomitant reactive sites have not been addressed.…”

Section: Methodsmentioning

confidence: 99%

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro‐Epoxyoxindoles

et al. 2016

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An efficient, chemoselective approach to spiro-epoxyoxindoles via the addition of chloromethyllithium followed by ring-closure of the intermediate alkoxide is reported. Chemoselectivity is fully preserved in the presence of different electrophilic sites.T he synthetic potentialo fs elected spiro-epoxyindoles has been exploited in the copper(I)-catalyzed intramolecular oxyarylation of an alkyne andinthe formation of N,N-dimethylisoindigo via the addition of dihalocarbenoids.

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Section: Methodsmentioning

confidence: 99%

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro‐Epoxyoxindoles

et al. 2016

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“…(Cl9H24N203) , N; C: caled, 69.49; found, 68.94. l-(5-Benzyloxy-6-methyI-2-pyridyl)-2-fe.rt-butylaminoethanol (18). This compound was prepared from 2-(5-benzyloxy-6-methyl-2-pyridyl)-iV-tert-butyl-2-hydroxyacetamide in a manner similar to the B2H6 reduction of 9 to 10.…”

Section: Methodsmentioning

confidence: 99%

Adrenergic Agents. 7. Synthesis and β-Adrenergic Agonist Activity of Several 2-Pyridylethanolamines

Jen¹,

Frazee²,

Schwartz³

et al. 1977

J. Med. Chem.

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In a search for new selective bronchodilators, three 2-pyridylethanolamines, i.e., 2-tert-butylamino-1-(5-hydroxy-2-pyridyl)ethanol (2b), a related 6-methylsulfonylmethyl (2c), and, a 6-methyl (2d) derivative, were prepared. These compounds were examined for potential bronchodilator activity in an in vitro test for relaxation of guinea pig tracheal tissue. Potential cardiac stimulant activity was evaluated in vitro by measuring changes in the rate of spontaneously beating guinea pig right atrial muscle. Comparison of potency in the tracheal test relative to that in the atrial procedure provides a measure of selectivity. Results of this study indicate that replacement of the phenyl ring of a para-hydroxylated phenylethanolamine with a 2-pyridyl system generally results in compounds which retain a high order of potency in the tracheal test; however, selectivity for tracheobronchial vs. cardiac tissue is markedly greater for the pyridyl derivatives. The alpha-picoline, 2-tert-butylamino-1-(5-hydroxy-6-methyl-2-pyridyl) ethanol (2d), which bears labile protons at a position meta to the ethanolamine side chain, was about equipotent with the corresponding 6-unsubstituted relative 2b. The reason for the failure of these apparently appropriately located labile protons to enhance beta-adrenoreceptor agonist activity is uncertain.

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“…In all cases the structures 1b,c were obtained; Bartsch [5] has demonstrated that the correct structure for the 2,3-dihydro-1,4-benzoxazine obtained from the 2-N-tosylaminophenol is 1c and not 2c [6].…”

mentioning

confidence: 99%

Attempted synthesis of ethyl 3,4‐dihydro‐2H‐1,4‐benzoxazine‐3‐carboxylate and 3‐acetate derivatives

Mayer

Arrault

Guillaumet

et al. 2001

Journal of Heterocyclic Chem

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Ethyl 3,4‐dihydro‐2H‐1,4‐benzoxazine‐3‐carboxylate derivatives 2 were obtained and isolated in low yields from the condensation of 2‐aminophenol and ethyl 2,3‐dibromopropanoate. They can be obtained by hydrogenation of ethyl 2H‐1,4‐benzoxazine‐3‐carboxylate in satisfactory yield. Using 2‐iminophenol did not direct the condensation with ethyl 2,3‐dibromopropanoate towards 2 but was fruitfull for the preparation of ethyl 2‐(4‐benzyl‐3,4‐dihydro‐2H‐1,4‐benzoxazin‐3‐yl)acetate from ethyl bromocrotonate.

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.beta.-Adrenergic blocking agents. 11. Heterocycyclic analogs of pronethalol [2-isopropylamino-1-(2-naphthyl)ethanol]

Cited by 22 publications

References 5 publications

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro‐Epoxyoxindoles

Chemoselective Addition of Halomethyllithiums to Functionalized Isatins:A Straightforward Access to Spiro‐Epoxyoxindoles

Adrenergic Agents. 7. Synthesis and β-Adrenergic Agonist Activity of Several 2-Pyridylethanolamines

Attempted synthesis of ethyl 3,4‐dihydro‐2H‐1,4‐benzoxazine‐3‐carboxylate and 3‐acetate derivatives

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