BIOMAT Database Logo BIOMAT Database Logo

Structure-activity relationship studies of CNS agents. Part 10(1): 1-Aryl-2-[3-(4-aryl-1-piperazinyl)propyl]-1,4-dihydro-3(2H)-isoquino linones: two modes of the interaction with the 5-HT1A receptor site. 1994

J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Department of Medicinal Chemistry, Polish Academy of Sciences, Kraków.

The synthesis and 5-HT1A and 5-HT2 receptor affinities of 1-aryl-2-[3-(4-aryl-1-piperazinyl)propyl]-1,4-dihydro-3(2H)- isoquinolinones 7-28 are reported. The two derivatives 7 and 13 were the most potent 5-HT1A ligands (Ki 1.72 +/- 0.07 and 2.75 +/- 0.59 nM, respectively) of all the investigated compounds. It has been found that the effect of the substituent in the 1-arylpiperazine portion is opposite to the observed in simple 1-arylpiperazine. The molecular modelling results indicate that the investigated derivatives may interact with 5-HT1A sites in two different ways: as ordinary 4-substituted 1-arylpiperazines, or in such a manner that the aryl substituent at position 1 of the 3(2H)-isoquinolinone moiety and N-4 piperazine atom mimics remarkably well the bioactive conformation of simple 1-arylpiperazines.

UI MeSH Term Description Entries
D007546 Isoquinolines A group of compounds with the heterocyclic ring structure of benzo(c)pyridine. The ring structure is characteristic of the group of opium alkaloids such as papaverine. (From Stedman, 25th ed)
D007650 Ketanserin A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients. 3-(2-(4-(4-Fluorobenzoyl)piperidinol)ethyl)-2,4(1H,3H)-quinazolinedione,R-41,468,R-41468,R 41,468,R 41468,R41,468,R41468
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D010879 Piperazines Compounds that are derived from PIPERAZINE.
D011619 Psychotropic Drugs A loosely defined grouping of drugs that have effects on psychological function. Here the psychotropic agents include the antidepressive agents, hallucinogens, and tranquilizing agents (including the antipsychotics and anti-anxiety agents). Psychoactive Agent,Psychoactive Agents,Psychoactive Drug,Psychopharmaceutical,Psychopharmaceuticals,Psychotropic Drug,Psychoactive Drugs,Agent, Psychoactive,Agents, Psychoactive,Drug, Psychoactive,Drug, Psychotropic,Drugs, Psychoactive,Drugs, Psychotropic
D011985 Receptors, Serotonin Cell-surface proteins that bind SEROTONIN and trigger intracellular changes which influence the behavior of cells. Several types of serotonin receptors have been recognized which differ in their pharmacology, molecular biology, and mode of action. 5-HT Receptor,5-HT Receptors,5-Hydroxytryptamine Receptor,5-Hydroxytryptamine Receptors,Receptors, Tryptamine,Serotonin Receptor,Serotonin Receptors,Tryptamine Receptor,Tryptamine Receptors,Receptors, 5-HT,Receptors, 5-Hydroxytryptamine,5 HT Receptor,5 HT Receptors,5 Hydroxytryptamine Receptor,5 Hydroxytryptamine Receptors,Receptor, 5-HT,Receptor, 5-Hydroxytryptamine,Receptor, Serotonin,Receptor, Tryptamine,Receptors, 5 HT,Receptors, 5 Hydroxytryptamine
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
D017366 Serotonin Receptor Agonists Endogenous compounds and drugs that bind to and activate SEROTONIN RECEPTORS. Many serotonin receptor agonists are used as ANTIDEPRESSANTS; ANXIOLYTICS; and in the treatment of MIGRAINE DISORDERS. 5-HT Agonists,5-Hydroxytryptamine Agonists,Serotonin Agonists,5-HT Agonist,5-Hydroxytrytamine Agonist,Receptor Agonists, Serotonin,Serotonergic Agonist,Serotonergic Agonists,Serotonin Agonist,Serotonin Receptor Agonist,5 HT Agonist,5 HT Agonists,5 Hydroxytryptamine Agonists,5 Hydroxytrytamine Agonist,Agonist, 5-HT,Agonist, 5-Hydroxytrytamine,Agonist, Serotonergic,Agonist, Serotonin,Agonist, Serotonin Receptor,Agonists, 5-HT,Agonists, 5-Hydroxytryptamine,Agonists, Serotonergic,Agonists, Serotonin,Agonists, Serotonin Receptor,Receptor Agonist, Serotonin
D017371 8-Hydroxy-2-(di-n-propylamino)tetralin A serotonin 1A-receptor agonist that is used experimentally to test the effects of serotonin. 8-OH-DPAT,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (+-)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (R)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrobromide, (S)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrochloride, (R)-Isomer,,8-Hydroxy-2-(di-n-propylamino)tetralin Hydrochloride, (S)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (+-)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (R)-Isomer,8-Hydroxy-2-(di-n-propylamino)tetralin, (S)-Isomer

Related Publications

J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents. Part VII. The effect of the imidazole fragment in 2-substituted 1-[3-(4-aryl-1-piperazinyl)propyl]imidazoles on their interaction modes with 5-HT1A and 5-HT2 receptors.
January 1992, Polish journal of pharmacology and pharmacy,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
5-HT1A and 5-HT2A receptor affinity and functional profile of some N-[3-(4-aryl-1-piperazinyl)propyl] derivatives of indolin-2(1H)-one, quinolin-2(1 H)-one and isoquinolin-1(2H)-one. Part 30: Structure-activity relationship studies of CNS agents.
June 1997, Die Pharmazie,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents. Part 4: 2-[3-(4-aryl-1-piperazinyl)propyl]-1,2,3,4-tetrahydro-beta-carbolin+ ++ -1-one derivatives as potential central anti-serotonin agents.
April 1992, Die Pharmazie,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents. XII. 1-[4-(4-aryl-1-piperazinyl)butyl]-3,4-dihydro-2(1H)-quinolinones: new 5-HT1A, 5-HT2 and D2 ligands with a potential antipsychotic activity.
April 1994, Drug design and discovery,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
3,4-Dihydro-3-amino-2H-1-benzopyran derivatives as 5-HT1A receptor ligands and potential anxiolytic agents. 1. Synthesis and structure--activity relationship studies.
June 1994, Journal of medicinal chemistry,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents, Part 20: 9-(omega-[1-(m-chlorophenyl)-4-piperazinyl]alkyl]-1,2,3,4-tetra-hydro- beta-carbolines: new 5-HT1A and 5-HT2A receptor ligands.
March 1995, Die Pharmazie,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents. Part 24: New analogs of N-tert.-butyl-3-[4-(2-methoxyphenyl)-1-piperazinyl]-2-phenylpropanamide (WAY-100135).
February 1996, Die Pharmazie,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
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.
April 2009, Bioorganic & medicinal chemistry letters,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Synthesis, 5-hydroxytryptamine1A receptor affinity and docking studies of 3-[3-(4-aryl-1-piperazinyl)-propyl]-1H-indole derivatives.
January 2012, Chemical & pharmaceutical bulletin,
J L Mokrosz, and A J Bojarski, and M Maćkowiak, and Z Bielecka, and J Boksa
Structure-activity relationship studies of CNS agents, XV: N-[omega-(4-aryl-1-piperazinyl)alkyl]-2-oxo-1,2,3,4-tetrahydroquinoline s and -4-oxo-1,2,3,4-tetrahydropyrazino[1,2-a]indoles: new, highly potent 5-HT1A ligands.
August 1994, Archiv der Pharmazie,
Copied contents to your clipboard!