Syntheses and 5-HT2 antagonist activity of bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives.

doi:10.1021/JM00079A026

Paper

Syntheses and 5-HT2 antagonist activity of bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives.

Published 1992 · Yoshifumi Watanabe, H. Usui, Shozo Kobayashi

Journal of medicinal chemistry

Q1 SJR score

33

Citations

0

Influential Citations

Full textSemantic Scholar

Abstract

A series of bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives with a 4-[bis(4-fluoro-phenyl)methylene]piperidine or 4-(4-fluorobenzoyl)piperidine group has been prepared and tested for 5-HT2 and alpha 1 receptor antagonist activity. Among the compounds prepared, 2-[2-[4-[bis(4-fluorophenyl)methylene]-piperidin-1-yl]ethyl]- 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyridin-3(2H)-one (7b) had the most potent 5-HT2 antagonist activity, which was greater than ritanserin (2), while 7b did not show alpha 1 antagonist activity in vivo. The central 5-HT2 receptor antagonism was approximately 1/30 that of 2 when tested for the ability to block head twitches induced by 5-hydroxytryptophan. Compound 21b, 3-[2-[4-(4-fluorobenzoyl)piperidin-1-yl]ethyl]-6,7,8,9-tetrahydro- 2H- pyrido[1,2-a]-1,3,5-triazine-2,4(3H)-dione also displayed potent 5-HT2 antagonist activity. The compound had moderate alpha 1 receptor antagonism, and the potency inhibiting head twitches was about one-third that of ketanserin (1). These results indicate that 5,6,7,8-tetrahydro-1,2,4-triazolo[4,3-a]pyrimidin-3(2H)-one and 6,7,8,9-tetrahydro-2H-pyrido-[1,2-a]-1,3,5-triazine-2,4(3H)-dione ring systems are useful components of 5-HT2 antagonists.

In Vitro Study

Study Snapshot

Bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives with a 4-(4-fluorobenzoyl)piperidine group show potent 5-HT2 antagonist activity, with potential as useful

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

Sign up to use Study Snapshot

Consensus is limited without an account. Create an account or sign in to get more searches and use the Study Snapshot.

Create an account

Paper

Syntheses and 5-HT2 antagonist activity of bicyclic 1,2,4-triazol-3(2H)-one and 1,3,5-triazine-2,4(3H)-dione derivatives.

Sign up to use Study Snapshot

References

Citations

The Structural and Optical Properties of 1,2,4-Triazolo[4,3-a]pyridine-3-amine

The new triazolopyridine derivative (1,2,4-triazolo[4,3-a]pyridin-3-amine) has a unique molecular structure and spectroscopic properties, with potential applications in organic electronics and photocatalysis.

Synthesis, Molecular Docking and In Vitro Screening of Some Newly Synthesized Triazolopyridine, Pyridotriazine and Pyridine–Pyrazole Hybrid Derivatives

Newly synthesized triazolopyridine, pyridotriazine, and pyridine-pyrazole hybrid derivatives show moderate to good binding energies to GlcN-6-P synthase and exhibit antimicrobial and antioxidant activity.

Oxidant‐Mediated Nitrogenation and Recyclization of Imidazo[1,2‐a]pyridines with Sodium Azide: Synthesis of 4H‐Pyrido[1,2‐a][1,3,5]triazin‐4‐ones

This study presents a straightforward approach for the synthesis of 4H-pyrido[1,2a][1,3,5]triazin4ones using readily available imidazo[1,2a]pyridines and sodium azide under aerobic oxidative conditions, achieving gram-scale

Brain serotoninergic nervous system is involved in bombesin‐induced frequent urination through brain 5‐HT7 receptors in rats

Bombesin-induced frequent urination in rats is mediated by brain 5HT7 receptors, suggesting a potential role for serotonin in bladder dysfunction under stress conditions.

On the reactivity of pyrido[3′,2′:4,5]furo(thieno)[3,2-d]pyrimidin-7(8)-ones with some alkyl mono- and di-halides: synthesis of new heterocyclic systems containing thiazolo[3,2-a]pyrimidine and pyrimido[2,1-b]thiazine moiety

This study synthesized new compounds with promising antimicrobial activity against Staphylococcus aureus by combining thiazolo[3,2-a]pyrimidine and pyrimido[2,1-b]thiazine moiety.

Synthesis of Diverse Nitrogen-Enriched Heterocyclic Scaffolds Using a Suite of Tunable One-Pot Multicomponent Reactions

Tunable one-pot multicomponent reactions enable the synthesis of diverse nitrogen-enriched heterocycles, potentially aiding in drug discovery efforts.

Mannich reaction in the synthesis of N,S-containing heterocycles. 16.*Synthesis of derivatives of tetra-hydropyrido[1,2-a][1,3,5]triazine and 5,6,12,13-tetra-hydro-1H,8H-dipyrido[1,2-a:1',2'-e][1,3,5,7]tetrazocine

The Mannich reaction can synthesize N,S-containing heterocycles, with structures and yields largely dependent on the initial amine and reaction conditions.

Synthetic routes towards thiazolo〔1,3,5〕triazines (review)

Synthetic approaches to thiazolo[3,2-a][1,3,5]triazines and polyfused systems bearing this heterocyclic core since 1887, with potential applications as biologically active agents.

Synthesis and Biological Activity of Novel Phenyltriazolinone Derivatives

Novel phenyltriazolinone derivatives with a strobilurin pharmacophore show moderate herbicidal activity at 150 g ai/ha, offering potential for new herbicides targeting the protoporphyrinogen oxidase enzyme.