Biomaterial Database

Synthesis and dopamine receptor binding of 4-(2-aminoethyl)-1H-pyrazole and its N,N-dialkyl derivatives. 1993

F Claudi, and G Giorgioni, and A Di Stefano, and A Cagnotto, and M Skorupska

Department of Chemical Sciences, University of Camerino, Italy.

The agnostic activity of Quinpirole (3a) at the D2 dopamine (DA) receptor suggested that the dopaminergic pharmacophore embedded in 3a was the 4-(2-aminoethyl)-1H-pyrazole (5) moiety. On that basis we have synthesized some derivatives of 5 bearing on the amino group alkyl and alkylaryl substituents. The affinities of 5 and its derivatives for the D1 and D2 DA receptor subtypes were evaluated in rat striatum by binding assays. None of these compounds show affinity for the D1 receptor. In the D2 binding assay only the N,N-di-(2-phenylethyl) (5i) and N-n-propyl-N-[2-(3-hydroxyphenyl)ethyl] (5j) derivatives show affinities comparable to that of Quinpirole. These results do not support the postulate that the 4-(2-aminoethyl)-1H-pyrazole is a bioisostere of the catechol nucleus of DA.

UI	MeSH Term	Description	Entries
D008297	Male		Males
D011720	Pyrazoles	Azoles of two nitrogens at the 1,2 positions, next to each other, in contrast with IMIDAZOLES in which they are at the 1,3 positions.
D011954	Receptors, Dopamine	Cell-surface proteins that bind dopamine with high affinity and trigger intracellular changes influencing the behavior of cells.	Dopamine Receptors,Dopamine Receptor,Receptor, Dopamine
D000818	Animals	Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA.	Animal,Metazoa,Animalia
D013329	Structure-Activity Relationship	The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups.	Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D015259	Dopamine Agents	Any drugs that are used for their effects on dopamine receptors, on the life cycle of dopamine, or on the survival of dopaminergic neurons.	Dopamine Drugs,Dopamine Effect,Dopamine Effects,Dopaminergic Agents,Dopaminergic Drugs,Dopaminergic Effect,Dopaminergic Effects,Agents, Dopamine,Agents, Dopaminergic,Drugs, Dopamine,Drugs, Dopaminergic,Effect, Dopamine,Effect, Dopaminergic,Effects, Dopamine,Effects, Dopaminergic
D051381	Rats	The common name for the genus Rattus.	Rattus,Rats, Laboratory,Rats, Norway,Rattus norvegicus,Laboratory Rat,Laboratory Rats,Norway Rat,Norway Rats,Rat,Rat, Laboratory,Rat, Norway,norvegicus, Rattus