8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones: Dual-acting 5-HT1 receptor antagonists and serotonin reuptake inhibitors—Part II

Bromidge, Steven M.; Bertani, Barbara; Borriello, Manuela; Bozzoli, Andrea; Faedo, Stefania; Gianotti, Massimo; Gordon, Laurie J.; Hill, Matthew; Zucchelli, Valeria; Watson, Jeannette M.; Zonzini, Laura

doi:10.1016/j.bmcl.2009.02.056

Cited by 18 publications

(13 citation statements)

References 17 publications

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“…During the last twenty years several chemical scaffolds are known to bind 5-HT 1A R sites, among these, arylpiperazine derivatives represent one of the most studied skeletons [ 8 , 9 , 10 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

et al. 2012

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A series of novel benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one derivatives 6a–f, 7a–f and their corresponding alcohols 8a–f were synthesized and evaluated for their affinity towards 5-HT1A receptors. The influence of arylpiperazine moiety and benzo[b]thiophene ring substitutions on binding affinity was studied. The most promising analogue, 1-(benzo[b]thiophen-2-yl)-3-(4-(pyridin-2-yl)piperazin-1-yl)propan-1-one (7e) displayed micromolar affinity (Ki = 2.30 μM) toward 5-HT1A sites. Docking studies shed light on the relevant electrostatic interactions which could explain the observed affinity for this compound.

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Section: Introductionmentioning

confidence: 99%

Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

et al. 2012

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“…SB-269970 and SB-656104-A are 5-HT 7 receptor antagonists that exhibit antidepressant-like activity . Moreover, recent studies suggest that selective blockade of 5-HT 7 R may have a synergistic effect with the inhibition of 5-HT reuptake in animal model of depression .…”

Section: Introductionmentioning

confidence: 99%

“…Other studies have shown the antidepressant efficacy of dual 5-HT1/SSRIs compounds. 17 One of the most important advantages of these compounds is that they may behave as novel antidepressantlike agents with a faster onset of action. 18 …”

Section: Introductionmentioning

confidence: 99%

Novel Benzo[b]thiophene Derivatives as New Potential Antidepressants with Rapid Onset of Action

et al. 2011

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ABSTRACT. We report benzo [b]thiophene derivatives synthesized according to a dual strategy. 8j, 9c, and 9e with affinity values toward 5-HT 7 R and 5-HTT were selected to probe using the forced swimming text (FST). The results showed significant antidepressant activity after chronic treatment. 9c was effective in reducing the immobility time in FST even after acute treatment. These findings identify these compounds as a new class of antidepressants with a rapid onset of action.

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“…This special reactivity allows this class of compounds to be useful as antimicrobial [1], anti-platelet aggregation [2], human leukocyte elastase inhibitors [3], receptor agonist active [4], receptor antagonist active [5-9], pesticides [10], tissue culture protective and in vivo model of neurodegeneration [11] and improve the umbilical vein endothelial cells [12]. In this paper, we report both the uses of 2-ethoxy-(4 H )-3,1-benzoxazin-4-one (1, Scheme 1) in the synthesis of some quinazolinone derivatives and the screening of antimicrobial activity of some of the newly synthesized derivatives against Gram-negative and Gram-positive bacteria as well as fungi by means of the disc diffusion method.…”

Section: Introductionmentioning

confidence: 99%

The Uses of 2-Ethoxy-(4H)-3,1-benzoxazin-4-one in the Synthesis of Some Quinazolinone Derivatives of Antimicrobial Activity

et al. 2011

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The behavior of 2-ethoxy-(4H)-3,1-benzoxazin-4-one (1) towards nitrogen nucleophiles, e.g. ethanolamine, aromatic amines (namely: p-toluidine, p-anisidine, p-hydroxyaniline, o-hydroxyaniline, o-bromoaniline, o-phenylenediamine, p-phenylenediamine, o-tolidinediamine) p-aminobenzoic acid, glucosamine hydrochloride, 2-aminonicotinic acid, 1-naphthalenesulfonic acid hydrazide, n-decanoic acid hydrazide, benzoic acid hydrazide, semicarbazide, aminoacids (e.g. D,L-alanine, L-asparagine, L-arginine) and derivatives of 2-aminothiodiazole has been investigated. The behavior of the benzoxazinone towards a selected sulfur nucleophile, L-cysteine, has also been discussed. Formation of an amidine salt as a reaction intermediate has been assumed. The effect of solvent in some reactions has been elucidated. The structures of all the novel quinazoline and quinazolinone derivatives, obtained by heterocyclic ring opening and ring closure were inferred by the IR, MS as well as 1H-NMR spectral analysis. Moreover, the antimicrobial potential of some of the new synthesized derivatives has been evaluated.

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8-[2-(4-Aryl-1-piperazinyl)ethyl]-2H-1,4-benzoxazin-3(4H)-ones: Dual-acting 5-HT1 receptor antagonists and serotonin reuptake inhibitors—Part II

Cited by 18 publications

References 17 publications

Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

Synthesis, Docking Studies and Biological Evaluation of Benzo[b]thiophen-2-yl-3-(4-arylpiperazin-1-yl)-propan-1-one Derivatives on 5-HT1A Serotonin Receptors

Novel Benzo[b]thiophene Derivatives as New Potential Antidepressants with Rapid Onset of Action

The Uses of 2-Ethoxy-(4H)-3,1-benzoxazin-4-one in the Synthesis of Some Quinazolinone Derivatives of Antimicrobial Activity

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