[1-[3-(Phenothiazin-10-yl)propyl]-4-piperidinyl]phenylmethanones, a novel class of long-acting neuroleptic agents

Boswell, Robert F.; Welstead, William J.; Duncan, Robert L.; Johnson, D.; Funderburk, William H.

doi:10.1021/jm00199a029

Cited by 23 publications

(4 citation statements)

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“…IV-[(l-Oxo-l,2,3,4-tetrahydro-2-naphthyl)acetyl]-4-(pfluorobenzoyl)piperidine (18). Route A A solution of 1.91 g (22 mmol) of (p-fluorobenzoyl)piperidine in 30 mL of anhydrous toluene was slowly added to a stirred solution of 1.97 g (8.9 mmol) of acid chloride in 130 mL of anhydrous toluene under argon atmosphere.…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Atypical Antipsychotic Profile of Some 2-(2-Piperidinoethyl)benzocycloalkanones as Analogs of Butyrophenone

Fontenla¹,

Osuna²,

Rosa³

et al. 1994

J. Med. Chem.

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Four new 2-(2-piperidinoethyl)benzocycloalkanone derivatives, 20-23, were prepared and evaluated as potential antipsychotic agents in receptor binding assays for dopamine (DA) and 5-HT2A receptors and in functional and behavioral screens. Their affinities for D2 receptors (Ki's in the nanomolar range: 46.7-70.7) and D1 receptors (Ki's in the micromolar range: 1.09-2.81) were slightly lower than that showed by haloperidol (Ki's in the nanomolar range: 5.01 and 97.72 for D2 and for D1 receptors, respectively). The ratio of pKi's values D1/D2 showed that the new molecules are more D2-selective than haloperidol. In contrast, in the [3H]-ketanserin binding assays the new compounds had greater affinity for 5-HT2A receptors (pKi's 7.89-8.60) than haloperidol (pKi 7.70) and in functional studies, endothelium-stripped aorta rings, the pA2 values (6.75-8.12) were slightly lower than that of ketanserin (8.87) in suppressing serotonin-induced contractions. The pKi's for D2 binding (and to a lesser extent pKi's for D1 binding) tend to be greater among typical (classical) than among atypical antipsychotics, while these two classes of antipsychotics exhibit no difference with regard to pKi's for 5-HT2A receptors. The ratios of pKi's for 5-HT2A/D2 receptors may be useful for rapid screening of new compounds, and its potential induction of extrapyramidal symptoms (ratio values > 1.12 were predictive of an atypical antipsychotic profile). The new molecules had a ratio value in the range 1.08-1.20, while haloperidol showed a ratio of 0.93. In the behavioral screening tests, the new molecules showed antagonist activity of amphetamine-inducing hyperactivity and apomorphine-induced climbing (predictive tests for antipsychotic activity). In the catalepsy test (predictive test for induction of extrapyramidal symptoms), the values obtained were in accordance with an atypical antipsychotic drugs profile.

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Section: Methodsmentioning

confidence: 99%

Synthesis and Atypical Antipsychotic Profile of Some 2-(2-Piperidinoethyl)benzocycloalkanones as Analogs of Butyrophenone

Fontenla¹,

Osuna²,

Rosa³

et al. 1994

J. Med. Chem.

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“…Piperidine ring is part of many biologically potent scaffolds. 97,98 Due to the significance of piperidine chemistry, the synthesis of different piperidines have taken precedence over the years. 99 A one-pot three-component strategy was developed by Khan et al for the synthesis of highly substituted piperidine moieties using TBATB as catalyst (Scheme 25).…”

Section: Synthesis Of Second-generation Brominating Agent and Its App...mentioning

confidence: 99%

Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis

et al. 2022

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“…5 Some piperidine derivatives are used as neuroleptic agents. 6 Optically active 4-substitued piperidine derivatives have been recently synthesized from meso-3-substituted glutaric anhydride with (S)-methylbenzylamine. 7 An intramolecular antiMarkovnikov hydroamination of 1-(3-aminopropyl)vinylarenes resulted in the formation of 3-arylpiperidines.…”

Section: Introductionmentioning

confidence: 99%

A convenient one pot synthesis of highly substituted piperidines through a Michael addition-aldol cyclization sequence

Ravindran¹,

Muthusubramanian²,

Perumal³

2008

Arkivoc

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[1-[3-(Phenothiazin-10-yl)propyl]-4-piperidinyl]phenylmethanones, a novel class of long-acting neuroleptic agents

Cited by 23 publications

References 1 publication

Synthesis and Atypical Antipsychotic Profile of Some 2-(2-Piperidinoethyl)benzocycloalkanones as Analogs of Butyrophenone

Synthesis and Atypical Antipsychotic Profile of Some 2-(2-Piperidinoethyl)benzocycloalkanones as Analogs of Butyrophenone

Synthetic utility of biomimicking vanadium bromoperoxidase and n-tetrabutylammonium tribromide (TBATB) in organic synthesis

A convenient one pot synthesis of highly substituted piperidines through a Michael addition-aldol cyclization sequence

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