16822-65-4

Basic information

• Product Name: 2-(4-methylpiperazin-1-yl)quinazolin-4(1H)-one
• Synonyms: 2-(4-Methylpiperazin-1-yl)quinazolin-4(1H)-one; 4(1H)-quinazolinone, 2-(4-methyl-1-piperazinyl)-
• CAS NO: 16822-65-4
• Molecular Formula: C₁₃H₁₆N₄O
• Molecular Weight: 244.2923
• Mol File: 16822-65-4.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 395.4°C at 760 mmHg
• Flash Point: 192.9°C
• Density: 1.32g/cm³
• Vapor Pressure: 1.85E-06mmHg at 25°C
• Refractive Index: 1.68
• CAS DataBase Reference: 2-(4-methylpiperazin-1-yl)quinazolin-4(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-methylpiperazin-1-yl)quinazolin-4(1H)-one(16822-65-4)
• EPA Substance Registry System: 2-(4-methylpiperazin-1-yl)quinazolin-4(1H)-one(16822-65-4)

Safety Data

• Hazardous Substances Data: 16822-65-4(Hazardous Substances Data)

Upstream product

• 13906-09-7 2-thioxo-2,3-dihydro-1H-quinazolin-4-one 
• 118-92-3 anthranilic acid 
• 28457-20-7 N-methylpiperazine carboxamidine sulfate 
• 88-65-3 2-bromobenzoic-acid 
• 118-91-2 ortho-chlorobenzoic acid 
• 118-48-9 isatoic anhydride 
• 109-01-3 1-methyl-piperazine 
• 54855-81-1 2-methylthioquinazolin-4(3H)-one 
• 16802-73-6 2-ethylsulfanyl-3H-quinazolin-4-one 

Downstream Products

• 39213-14-4 2-(4-methylpiperazin-1-yl)-4-phenoxyquinazoline 
• 129112-39-6 4-(3-Methoxy-phenoxy)-2-(4-methyl-piperazin-1-yl)-quinazoline 
• 129112-67-0 2-(4-Methyl-piperazin-1-yl)-4-p-tolyloxy-quinazoline 
• 129664-09-1 2-(4-Methyl-piperazin-1-yl)-4-pentyloxy-quinazoline; compound with (E)-but-2-enedioic acid 
• 129112-43-2 N-{4-[2-(4-Methyl-piperazin-1-yl)-quinazolin-4-yloxy]-phenyl}-acetamide 
• 129112-47-6 2-(4-Methyl-piperazin-1-yl)-6-nitro-4-phenoxy-quinazoline 
• 129112-41-0 2-(4-Methyl-piperazin-1-yl)-4-(3-trifluoromethyl-phenoxy)-quinazoline 
• 129112-42-1 1-{4-[2-(4-Methyl-piperazin-1-yl)-quinazolin-4-yloxy]-phenyl}-ethanone 
• 129112-44-3 4-(2,4-Dichloro-phenoxy)-2-(4-methyl-piperazin-1-yl)-quinazoline 
• 129112-45-4 4-(3,4-Dichloro-phenoxy)-2-(4-methyl-piperazin-1-yl)-quinazoline 
• 129112-35-2 4-(2-Chlorophenoxy)-2-(4-methyl-1-piperazinyl)quinazoline 
• 129112-40-9 4-(4-Methoxy-phenoxy)-2-(4-methyl-piperazin-1-yl)-quinazoline 
• 129112-46-5 4-(4-Chloro-3-methyl-phenoxy)-2-(4-methyl-piperazin-1-yl)-quinazoline 
• 129112-51-2 6-Chloro-2-(4-methyl-piperazin-1-yl)-4-phenoxy-quinazoline 

Relevant articles and documents

Design, synthesis, and structure-activity relationships of highly potent 5-HT3 receptor ligands

The 5-HT3 receptor, a pentameric ligand-gated ion channel (pLGIC), is an important therapeutic target. During a recent fragment screen, 6-chloro-N-methyl-2-(4-methyl-1,4-diazepan-1-yl)quinazolin-4-amine (1) was identified as a 5-HT3R hit fragment. Here we describe the synthesis and structure-activity relationships (SAR) of a series of (iso)quinoline and quinazoline compounds that were synthesized and screened for 5-HT3R affinity using a [3H]granisetron displacement assay. These studies resulted in the discovery of several high affinity ligands of which compound 22 showed the highest affinity (pKi > 10) for the 5-HT3 receptor. The observed SAR is in agreement with established pharmacophore models for 5-HT3 ligands and is used for ligand-receptor binding mode prediction using homology modeling and in silico docking approaches.

Synthesis of 2-aminoquinazoline-4(3H)-one derivatives as potential potassium channel openers

Starting from 2-thioxoquinazolin-4-one, the synthesis of 2-amino-4(3H)- one derivatives, structurally related to potassium channels openers pinacidil and diazoxide, is described.