NDLI: Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones

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Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones

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Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones

Content Provider	Springer Nature Link
Author	Rządkowska, Marzena Szacoń, Elżbieta Kaczor, Agnieszka A. Fidecka, Sylwia Kędzierska, Ewa Matosiuk, Dariusz
Copyright Year	2014
Abstract	A series of 24 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones was designed as antinociceptive compounds acting through opioid receptors with additional serotoninergic activity. The compounds, similarly as previously published series, lack the protonable nitrogen atom which is a part of classical opioid receptor pharmacophore and is necessary to interact with the conserved Asp(3.32) in the opioid receptor binding pocket. The compounds were obtained in one-step cyclocondensation of 1-aryl-4,5-dihydro-1H-imidazol-2-amines diethyl 2-benzylmalonate or diethyl 2-(2-chlorobenzyl)malonate under basic conditions. Almost all the tested compounds exerted strong antinociceptive activity, but surprisingly, it was not reversed by naloxone; thus, it is not mediated through opioid receptors. It makes it possible to conclude that addition of one more aromatic moiety to the non-classical opioid receptor pharmacophore results in the compounds which are not opioid receptor ligands. The lack of activity of one of the tested compounds may be attributed to low blood–brain barrier permeation or unfavorable distribution of electrostatic potential and HOMO and LUMO orbitals.
Starting Page	4221
Ending Page	4237
Page Count	17
File Format	PDF
ISSN	10542523
Journal	Medicinal Chemistry Research
Volume Number	23
Issue Number	9
e-ISSN	15548120
Language	English
Publisher	Springer US
Publisher Date	2014-03-27
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Antinociceptive compounds Central nervous system activity Imidazo[1,2-a]pyrimidines Pharmacology/Toxicology Biochemistry Cell Biology
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Pharmacology, Toxicology and Pharmaceutics

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ORIGINAL RESEARCH Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo [1,2-a]pyrimidine-5(1H)-ones

Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones

Synthesis, central nervous system activity and structure–activity relationship of N-substituted derivatives of 1-arylimidazolidyn-2-ylideneurea and products of their cyclization

6-(2-Chlorobenzyl)-1-(4-chlorophenyl)-7-hydroxy-2,3-dihydro-1H-imidazo[1,2-a]pyrimidin-5-one

Reaction of 2-alkylthio-6-amino-pyrimidin-4(3H)-ones with ethyl bromopyruvate. Synthesis of furo-[2,3-d]-pyrimidine and furo[3,2-e]imidazo-[1,2-c]pyrimidine carboxylates

Synthesis of new derivatives of 2,3-dicyano-imidazo (1,2-a)pyrimidine from 4-hydroxy-6-methylpyran-2-ones

N-Aryl-7-hydroxy-5-oxo-2,3-dihydro-1H,5H-pyrido-[3,2,1-ij]quinoline-6-carboxamides. The Synthesis and Effects on Urinary Output

QSAR study of a series of 2,3-dihydroimidazo[1,2-c]pyrimidines as antibacterial agents

Synthesis and biological evaluation of 7-N-(n-alkoxyphthalimido)-2-hydroxy-4- aryl-6-aryliminothiazolidino [2,3-b] pyrimidines and related compounds

Synthesis, central nervous system activity, and structure–activity relationship of 1-aryl-6-benzyl-7-hydroxy-2,3-dihydroimidazo[1,2-a]pyrimidine-5(1H)-ones

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