53-31-6

Basic information

• Product Name: medibazine
• Synonyms: medibazine;1-(1,3-Benzodioxol-5-ylmethyl)-4-(diphenylmethyl)piperazine;1-(Diphenylmethyl)-4-(1,3-benzodioxol-5-ylmethyl)piperazine;S-4105
• CAS NO: 53-31-6
• Molecular Formula: C₂₅H₂₆N₂O₂
• Molecular Weight: 386.492
• EINECS: 200-168-7
• Mol File: 53-31-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 503.2°Cat760mmHg
• Flash Point: 139.9°C
• Appearance: /
• Density: 1.207g/cm³
• Vapor Pressure: 2.97E-10mmHg at 25°C
• Refractive Index: 1.633
• CAS DataBase Reference: medibazine(CAS DataBase Reference)
• NIST Chemistry Reference: medibazine(53-31-6)
• EPA Substance Registry System: medibazine(53-31-6)

Safety Data

• Hazardous Substances Data: 53-31-6(Hazardous Substances Data)

Usage

Originator

Vialibran,Servier

Uses

Medibazine is studied as a distinguishing compound with antibacterial activity by artificial neural networks.

Manufacturing Process

To a solution of 32 g piperonyl piperazine in 100 ml anhydrous toluene, 10 g sodium carbonate are added and 35.2 g benzhydryl chloride are added dropwise. The mixture is then heated to reflux for 7 hours with vigorous agitation. Then the mixture is cooled, the salt that has formed is filtered out and 100 ml water is added. The organic layer is extracted with several batches of 10% methane sulfonic acid. The acid extracts are combined and washed with ether then alkalized with sodium carbonate. The mixture is extracted with several batches of chloroform and the combined chloroform solutions are washed several times with water. After drying and solvent evaporation, the crude base of 1-diphenylmethyl-4-piperonyl-piperazineis isolated and the hydrochloride thereof is formed in acetone. After recrystallization 22.5 g of the dihydrochloride are finally obtained. M.P.: 228°C, from methanol.

Therapeutic Function

Coronary vasodilator

InChI:InChI=1/C25H26N2O2/c1-3-7-21(8-4-1)25(22-9-5-2-6-10-22)27-15-13-26(14-16-27)18-20-11-12-23-24(17-20)29-19-28-23/h1-12,17,25H,13-16,18-19H2

Upstream product

• 495-76-1 piperonol 
• 78358-16-4 1,3-benzodioxol-5-ylmethyl methanesulfonate 
• 841-77-0 diphenylmethylpiperazine 

Relevant articles and documents

Bioisosteric replacement and related analogs in the design, synthesis and evaluation of ligands for muscarinic acetylcholine receptors

Previous structure-activity relationship studies involving a series of lactone-based muscarinic ligands identified a lead compound containing a diphenylmethylpiperazine moiety (4; IC50 = 340 nM). The purpose of the present work is to investigate 1,3-benzodioxoles, 4,4-diethyl substituted tetrahydrofurans, 5-substituted oxazolidinones and chromones as bioisosteric replacements for the lactone ring in a novel series of muscarinic ligands. The approach provided compounds with improved % inhibition values and identified a non-selective muscarinic ligand with an IC50 value of 280 nM. The structure-activity relationship for this new series will be discussed. Selected compounds were evaluated in preliminary assays for subtype selectivity and were found to be non-selective.