Phenacylthioimidazolines and 3-aryl-5,6-dihydroimidazo[2,1-b]thiazoles with antidepressant activity

Cj, Sharpe; Rs, Shadbolt; Ashford, A.; Jw, Ross

doi:10.1021/jm00292a023

Cited by 47 publications

(24 citation statements)

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“…containing thiazole and related heterocycles (thiadiazole and thiadiazine) exhibit antihistaminic, antithyroid, antitubercular, antifungal & antibacterial activities [1][2][3] and their synthetic importance has been greatly enhanced by the recent uses of their condensed bridgehead nitrogen heterocycles as anthelminitics, antidepressants, platelet aggregation inhibitors, antineoplastic, vulcanization accelerators and photographic sensitizers [4][5][6][7][8][9][10][11] . The indoles are already been synthesized by different method But they requires longer reaction time and tedious workup [12][13][14][15][16][17][18][19][20][21] .…”

Section: B R I D G E H E a D N I T R O G E N H E T E R O C Yclesmentioning

confidence: 99%

A Multistep Preparation of 3-Aryl-8-methoxythiazolo [3’, 2’ : 2, 3] [1, 2, 4] triazino [5, 6-b] indoles Under Microwave IR-radiations

Singh¹

2014

Orient. J. Chem

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Section: B R I D G E H E a D N I T R O G E N H E T E R O C Yclesmentioning

confidence: 99%

A Multistep Preparation of 3-Aryl-8-methoxythiazolo [3’, 2’ : 2, 3] [1, 2, 4] triazino [5, 6-b] indoles Under Microwave IR-radiations

Singh¹

2014

Orient. J. Chem

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“…The bromination of hydroxy-and dihydroxyacetophenones was performed using CuBr 2 in a CHCl 3 -EtOAc solvent mixture [8,9]. 3,4-Dimethoxyphenacylbromide was ob-tained via bromination of the corresponding acetophenone in ethanol as described for 4-methoxyacetophenone [10].…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and pharmacological activity of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals

et al. 2007

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The synthesis and pharmacological properties of a series of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals are described. It is established that most of the synthesized compounds exhibit a high antioxidant activity, possess pronounced hemorheological properties, and influence the blood glucose level.The treatment of various pathological states accompanied by the intensification of peroxidation processes [1 -3] usually involves antioxidants [4 -6]. In continuation of the search for new substances possessing antioxidant properties, we have synthesized a series of aroylmethyl derivatives of 2,3-dihydroimidazo-and 2,3,4,10-tetrahydropyrimido-[1, 2-a]benzimidazoles containing various phenolic substituents in the aroyl radical (II -V) and their open forms, representing 2-hydroxyalkylaminobenzimidazoles with 3,5-ditert-butyl-4-hydroxyphenacyl radical in position 1 (IXa, IXb). The synthesized compounds were characterized with respect to antioxidant properties and some other pharmacological effects on various models involving activation of the free-radical processes (in particular, those influencing blood rheology).Compounds II -V can be obtained by directly introducing acylmethyl groups into tricycles Ia and Ib with the aid of the corresponding substituted phenacylbromides.In contrast to smoothly proceeding reactions of tricycles Ia and Ib with 3,5-di-tert-butyl-4-hydroxyphenacylbromide leading to derivatives IV and V, the reactions with 4-hydroxy-and 3,4-dihydroxyphenacylbromides are rather ambigu-ous. These reactions yield ketones II and III heavily contaminated with resinous products, which can be separated neither by recrystallization nor by column chromatography (because of their low mobility). However, using the saponification of methoxy groups in N-para-methoxyphenacyl derivatives of these heterocycles (described in [7]) and in 4-hydroxy-and 3,4-dihydroxyphenacyl derivatives VI in concentrated NBr, we obtained the target products II and III in a rather pure form and with good yields. The restoration of ketones IV and VI by sodium borohydride in MeOH or EtOH yielded alcohols VII and VIII, respectively. n = 1 (Ia -VIIa), 2 (Ib -VIIb, IXa), 3 (IXb); Ar = C 6 H 4 OH-4 (II); C 6 H 3 (OH) 2 -3,4 (III); 3,5-di-tert-butyl-4-hydroxyphenyl (IV, V*, VIII, IX), C 6 H 3 (OCH 3 ) 2 (VI, VII); * Compound Vb contains Me groups in positions 7 and 8.

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“…Bromination of the initial methoxyacetophenones was carried out using the reaction with bromine in etherdioxane solutions [12], while oxyacetophenones were reacted with copper bromide in CHCl 3 -ethyl acetate mixture [13]. a-Chloro-3,4-dioxyacetophenone was obtained as described in [14].…”

Section: Experimental Chemical Partmentioning

confidence: 99%

Synthesis and pharmacological activity of 2-methoxyphenyl-and 2-oxyphenyl-substituted 1-dialkylaminoalkylimidazo[1,2-a]-benzimidazoles

et al. 2005

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A series of 2-methoxy-and 2-oxyphenyl-1-dialkylaminoalkylimidazo[1,2-a]benzimidazoles have been synthesized and characterized with respect to pharmacological properties. Some of the synthesized compounds exhibit antioxidant, membranotropic, antiaggregant, hemorheological, anticalmodulin, and hypotensive properties, and behave as antagonists of serotonin (5-HT 2,3 ) and purine (P2Y 1 ) receptors. The obtained data show good prospects for the synthesis and screening of biologically active substances in this class of compounds. 579 0091-150X/05/3911-0579

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Phenacylthioimidazolines and 3-aryl-5,6-dihydroimidazo[2,1-b]thiazoles with antidepressant activity

Cited by 47 publications

References 1 publication

A Multistep Preparation of 3-Aryl-8-methoxythiazolo [3’, 2’ : 2, 3] [1, 2, 4] triazino [5, 6-b] indoles Under Microwave IR-radiations

A Multistep Preparation of 3-Aryl-8-methoxythiazolo [3’, 2’ : 2, 3] [1, 2, 4] triazino [5, 6-b] indoles Under Microwave IR-radiations

Synthesis and pharmacological activity of aroylmethyl derivatives of tricyclic benzimidazole systems containing hydroxy groups in aroyl radicals

Synthesis and pharmacological activity of 2-methoxyphenyl-and 2-oxyphenyl-substituted 1-dialkylaminoalkylimidazo[1,2-a]-benzimidazoles

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