ChemInform Abstract: INDOLIZIN‐ANALOGA DES INDOMETHACINS

Casagrande, C; Invernizzi, Anna Gamba; Ferrini, R; Miragoli, G

doi:10.1002/chin.197214311

Cited by 6 publications

(6 citation statements)

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“…[20] The o-bromophenacyl bromides 4 were obtained from commercial sources or from previously reported [21] o-bromoacetophenones. Bromination occurred in the α-position to the keto group in the presence of B(OMe) 3 and Br 2 according to a literature method.…”

Section: Resultsmentioning

confidence: 99%

Radical Intramolecular Arylation of Pyridinium Salts: A Straightforward Entry to 7‐Hydroxypyrido[2,1‐a]isoquinolinylium Salts

et al. 2010

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Section: Resultsmentioning

confidence: 99%

Radical Intramolecular Arylation of Pyridinium Salts: A Straightforward Entry to 7‐Hydroxypyrido[2,1‐a]isoquinolinylium Salts

et al. 2010

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“…In a series of ring-hydroxylated phenoxypropanolamines, several showed marked 3-adrenoreceptor agonist properties on guinea pig cardiac muscle (165,166), although mixed agonist-antagonist actions were seen in other tests (167). Modification of the catechol substitution in this series seems quite similar to that observed with phenylethanolamines, i.e., the meta-OH may be re placed by a n 0H-simulating !f group with retention of 3-adrenergic agonist activity (33).…”

Section: Generally the S (+)-Enantiomers Have Only Weak 3-adrenergicmentioning

confidence: 84%

New Aspects of β-Adrenergic Bronchodilator Drugs

Kaiser¹

1980

ACS Symposium Series

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Although bronchoconstriction caused by contraction of bron chiolar muscles is only one of several factors involved in asthma, drugs that induce relaxation of these muscles are frequently used in therapy. Agents that cause bronchiolar muscle relaxation may act by several different modes as suggested by the biochemical mechanism of smooth muscle relaxation (1). Such agents include a group of adrenergic receptor agonists. In mild and occasional episodic asthma, bronchoconstriction and its resultant symptoms are easily reversed by administration of effective β-adrenorecep tor activators. Such agents also find some utility in alleviation of respiratory distress in emphysema and bronchitis. Some more recent aspects of such adrenergic bronchodilators, i.e., compounds that are structurally related to the natural hormones and neuro transmitters norepinephrine (1a) and epinephrine (1b), are the subject of this review.Classification of adrenergic receptors into α and β subtypes (2) is now generally accepted. On the basis of differences in response to selective agonists (3, 4, 5) and antagonists (6, 7), Lands and his associates (3, 4, 5, 8) further subdivided the β receptors into two groups, i.e., β 1 and β 2 -drenoreceptors. Acti vation of β 2 -drenoreceptors causes relaxation of smooth muscle in bronchi, uterus and vasculature, decreases tension in some skele tal muscle, and mediates glycolysis and glycogenolysis.Responses mediated by interaction with 3i~adrenoreceptors are increased force and rate of contraction of cardiac muscle, dilation of coro nary blood vessels (9, 10), relaxation of smooth muscle in the alimentary tract, and lipolysis.Epinephrine, administered either by injection or inhalation, is still employed to relieve bronchoconstriction in bronchial asthma. Isoproterenol (lc), the prototype of 3-adrenergic recep tor agonists, because of its greater potency and selectivity has largely replaced epinephrine as an inhaled bronchodilator. This synthetic analog of epinephrine also lacks selectivity.It is almost equally effective in activating both βχ and $2~a c * rener gi c receptors. Thus, it not only produces a powerful bronchodilating 0-8412-0536-l/80/47-118-251$08.25/0

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“…2-(3-Methyl-1,4-dioxo-1,4-dihydr0-2-naphthyl)acetylthiophene (13).-After the dropwise addition of bromine (56 g) to 2acetylthiophene (42 g) in stirred tetrachloromethane (300 ml) the mixture was refluxed for 40 rnin and the solvent removed under reduced pressure. The residue in ether (sodium dried, 200 ml) was added to pyridine (32 g) also in ether (300 ml) and stirred for 5 min after which tarry material was removed by filtration through a loose glass-wool plug.…”

Section: Methodsmentioning

confidence: 99%

Pyridinium ylides in syntheses of naphthopyrandiones and in regioselective syntheses of acylated anthraquinones related to fungal and bacterial metabolites

Aldersley¹,

Chishti²,

Dean³

et al. 1990

J. Chem. Soc., Perkin Trans. 1

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Improvements have been made in the use of acylated pyridinium ylides for the transformation of 2methyl-l,4-naphthoquinone into derivatives (1 5) and (1 6) of naphtho[2,3-c] pyran-5,l O-dione, containing furan and thiophene groups. The substitution and cyclisation steps can be combined effectively by using 2-phenoxymethyl-instead of 2-methyl-naphthoquinone. The use of better leaving groups than phenoxy (especially 4-nitrophenoxy) allows the quinone to react with two proportions of ylide and leads regiospecifically to 1 -aroyl-2-arylanthracene-9,1 O-diones such as (20a). If the leaving group is nuclear bromine as in 2-bromo-3-methyl-l,4-naphthoquinone, another reaction with 2 mot equiv. of ylide leads to complex red intermediates of type (31) which in contact with alumina are quantitatively converted into the regioisomeric 2-aroyl-3-arylanthracene- 9,l O-diones such as (22a).The structures have been determined by standard methods but special features of the NMR spectra are reported including a case of extreme line broadening by traces of iron. Mechanisms are suggested for the diverse reactions between the quinones and the ylides.A small but significant group of natural products is based upon the naptho[2,3-c]pyran nucleus and contains members with antitumour and/or antibacterial activities2 We have improved and extended the route to such compounds from naphthoquinones and pyridinium y l i d e ~, ~ and found that it can be extended to regiospecific syntheses of acylated anthraquinones similar to antibiotic X-1488 1 C (Streptomyces) and altersolanol B4 and related to some of the highly physiologically active naphthacene quinones.' Results and DiscussionPaper 9/04753K

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ChemInform Abstract: INDOLIZIN‐ANALOGA DES INDOMETHACINS

Abstract: Das Nitro‐picolin‐N‐oxid (I) reagiert mit Natriummethylat zum Methoxypicolin‐N‐oxid (II), welches mit Acetanhydrid zum Methoxy‐acetoxymethyl‐pyridin (III) umgesetzt werden kann.

Cited by 6 publications

References 0 publications

Radical Intramolecular Arylation of Pyridinium Salts: A Straightforward Entry to 7‐Hydroxypyrido[2,1‐a]isoquinolinylium Salts

Radical Intramolecular Arylation of Pyridinium Salts: A Straightforward Entry to 7‐Hydroxypyrido[2,1‐a]isoquinolinylium Salts

New Aspects of β-Adrenergic Bronchodilator Drugs

Pyridinium ylides in syntheses of naphthopyrandiones and in regioselective syntheses of acylated anthraquinones related to fungal and bacterial metabolites

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