62717-14-0Relevant articles and documents
Synthesis of methyl 2,3-dihydro-2-benzofurancarboxylates from o-allylphenols via 2-(phenylthiomethyl)-2,3-dihydrobenzofurans
Yodo, Mitsuaki,Harada, Hiroshi
, p. 2361 - 2368 (2007/10/02)
A method for synthesizing methyl 2,3-dihydro-2-benzofurancarboxylates rom o-allylphenols is described.The reaction of 6allyl-2,3-dichlorophenol (3) with benzenesulfenyl chloride (PhSCl) in acetonitrile gave a mixture of PhSCl -adducts, which was heated in aqueous acetonitrile then with sodium bicarbonate to obtain 6,7-dichloro-2-(phenylmethyl)-2,3-dihydrobenzofuran (6). α-Dichlorination of the phenylthiomethyl group of 6 and subsequent methanolysis gave the methyl ester 5 in high yield.The generality of this synthetic method was examined by the conversion of o-allylphenols 11 having various substituents on the benzene ring into the corresponding methyl ester 23.Cyclization of 11 to sulfides 12 could be achived similerly to the case of 3.However, in the subsequent conversions of 12 to 23, selective α-dichlorination followed by methanolysis could be achived only with 12 substituted with an electron-withdrawing group such as a chloro or nitro group.Keywords - oallylphenils; methyl 2,3-dihydro-2-benzofurancarboxylate; 2-(phenylthiomethyl)-2,3-dihydrobenzofuran; benzenesulfenyl chloride; α-chlorination; methanolysis.
α-Adrenoreceptor Reagents. 2. Effects of Modification of the 1,4-Benzodioxan Ring System on α-Adrenoreceptor Activity
Chapleo, Christopher B.,Myers, Peter L.,Butler, Richard C. M.,Davis, John A.,Doxey, John C.,et al.
, p. 570 - 576 (2007/10/02)
Modification of the 1,4-benzodioxan ring present in RX 781094 (1) has not previously been considered.This paper describes a number of analogues of this ring system, including compounds in which one of the oxygen atoms has been replaced by a methylene group and also those in which the ring size has been changed to give, for example, furan and thiophene derivatives.The dihydroxybenzofuranylimidazoline compound 7 is the only analogue possesing presynaptic antagonist potency and selectivity comparable to that of 1.In view of this result, a number of derivatives was prepared to determine the structure-activity relationships within this series.Many derivatives, as well as the parent compound 7, were found to possess presynaptic α2-adrenoreceptor antagonist and postsynaptic α1-adrenoreceptor partial agonist properties.Two of the selective presynaptic antagonists,13 and 14, possess greater potency and selectivity than that possessed by 1.The 5-chloro derivative 25 is twice as potent as 1 after oral administration but only about half as potent when given intravenously.
(Acylaryloxy)acetic Acid Diuretics. 3. 2,3-Dihydro-5-acyl-2-benzofurancarboxylic Acids, a New Class of Uricosuric Diuretics
Hoffman, William F.,Woltersdorf, Otto W.,Novello, Frederick C.,Cragoe, Edward J,Spinger, James P.,et al.
, p. 865 - 873 (2007/10/02)
The discovery that dihydroethacrynic acid and other (4-acylphenoxy)acetic acids possessed modest but significant uricosuric and diuretic activity prompted our investigation of the related 2,3-dihydro-5-acyl-2-benzofurancarboxylic acids.Synthetic routes to
6,7-Disubstituted-5-(acyl)benzofuran-2-carboxylic acids
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, (2008/06/13)
6,7-Disubstituted-5-(acyl)benzofuran-2-carboxylic acids, the pharmaceutically acceptable salt, ester and amide derivatives thereof and combinations of these compounds with antikaluretic agents are disclosed having diuretic-saluretic, uricosuric and antihy
2,3-Dihydro-6,7-disubstituted-5-acyl benzofuran-2-carboxylic acids
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, (2008/06/13)
2,3-Dihydro-6,7-disubstituted-5-(acyl)benzofuran-2-carboxylic acids, the pharmaceutically acceptable salt, ester and amide derivatives thereof and combinations of these compounds with antikaluretic agents are disclosed having diuretic-saluretic, uricosuri
5-(Hydroxy (substituted) methyl)-2,3-dihydrobenzo furan-2-carboxylic acid and its derivatives
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, (2008/06/13)
5-[Hydroxy(substituted)methyl]-2,3-dihydrobenzo-furan-2-carboxylic acids, the pharmaceutically acceptable salt, ester and amide derivatives thereof and combinations of these compounds with antikaluretic agents are disclosed having diuretic-saluretic, uricosuric and antihypertensive activity.
