16064-19-0

Basic information

• Product Name: 6,7,8-Trimethoxyquinazolin-4(3H)-one
• Synonyms: 6,7,8-Trimethoxyquinazolin-4(3H)-one;6,7,8-trimethoxyquinazolin-4(1H)-one
• CAS NO: 16064-19-0
• Molecular Formula: C₁₁H₁₂N₂O₄
• Molecular Weight: 236.22
• Mol File: 16064-19-0.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 6,7,8-Trimethoxyquinazolin-4(3H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 6,7,8-Trimethoxyquinazolin-4(3H)-one(16064-19-0)
• EPA Substance Registry System: 6,7,8-Trimethoxyquinazolin-4(3H)-one(16064-19-0)

Safety Data

• Hazardous Substances Data: 16064-19-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6,7,8-Trimethoxyquinazolin-4(3H)-one is used as a pharmaceutical candidate for its potential antibacterial properties, offering a new avenue for the development of antibiotics to combat resistant bacterial strains.
6,7,8-Trimethoxyquinazolin-4(3H)-one is also used as an anticancer agent, given its potential to target and inhibit the growth of cancer cells, making it a valuable asset in the ongoing search for novel and effective cancer treatments.
Furthermore, 6,7,8-Trimethoxyquinazolin-4(3H)-one is utilized in drug discovery and development processes, where its unique structure and properties are explored for the creation of new therapeutic agents to address various health conditions.

Upstream product

• 61948-85-4 3,4,5-trimethoxyanthranilic acid 
• 77287-34-4 formamide 
• 5035-82-5 methyl 3,4,5-trimethoxyanthranilate 
• 66907-52-6 3,4,5-trimethoxy-2-nitrobenzoic acid 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 118-41-2 Eudesmic acid 
• 5081-42-5 3,4,5-trimethoxy-2-nitrobenzoic acid methyl ester 
• 161078-64-4 2-<1-(6,7,8-trimethoxyquinazolin-4-yl)hydrazino>-ethanol 

Downstream Products

• 33371-00-5 4-chloro-6,7,8-trimethoxy-quinazoline 
• 99109-03-2 4-(3-Chloro-4-nitrophenyl)thio-6,7,8-trimethoxyquinazoline 

Relevant articles and documents

Synthesis and bioactivities of 6,7,8-trimethoxy-N-aryl-4-aminoquinazoline derivatives

A series of 4-aminoquinazoline derivatives is prepared by the nucleophilic substitution reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl amine. The structures of the compounds are confirmed by elemental analysis, IR, and 1H NMR spectral data. The compounds are also evaluated for their ability to inhibit tumor cells PC3, A431, Bcap-37, and BGC823 by MTT assays. Among them, 6b and 6e are found as potent inhibitors, with IC50 values ranging from 5.8 to 9.8 μM, in vitro assay.

Microwave assisted synthesis of novel 6,7,8-trimethoxy N-substituted-4- aminoquinazoline compounds

(Chemical Equation Presented) A fast, efficient and convenient reaction of 6,7,8-trimethoxy-4-chloroquinazoline and aryl (or benzyl) amines was achieved under microwave irradiation in isopropyl alcohol, providing a simple method for synthesis of novel 6,7,8-trimethoxy N-substituted-4-aminoquinazoline compounds in good yield in short time. The title compounds were evaluated for their in vitro anti-proliferative activities against PC3 cell by MTT method.

Synthesis and antitumor activity of novel 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives

A series of 6,7,8-trimethoxy N-aryl-substituted-4-aminoquinazoline derivatives were synthesized as epidermal growth factor receptor (EGFR) inhibitors, and their antitumor activities were assessed in the gastric cancer cell line SGC7901 using MTT assay. All compounds of Tg1–14 were found to inhibit SGC7901 cell proliferation, and compound Tg11 (IC50 = 0.434 μM) was found to be slightly more effective against SGC7901 cells than epirubicin (IC50 = 5.16 μM). This suggests that compound Tg11 can be used as a new substitution structure to develop more efficacious antitumor agents. Western blot analysis showed that treatment with Tg11 (40 μM for 30 min) resulted in near complete inhibition of EGF-induced ERK1/2 phosphorylation, indicating that its anti-proliferative effect is largely associated with inhibition of ERK1/2 activation. These data imply that Tg11 is a potential anticancer agent capable of inhibiting cell proliferation.

Small-molecule phosphodiesterase probes: Discovery of potent and selective CNS-penetrable quinazoline inhibitors of PDE1

PDE1 is a family of calcium-activated, dual substrate phosphodiesterases expressed in both the CNS and periphery that play a role in the integration of intracellular calcium and cyclic nucleotide signaling cascades. Exploration of the potential in targeting this family of enzymes to treat neuropsychiatric disorders has been hampered by a lack of potent, selective, and brain penetrable PDE1 inhibitors. To identify such compounds we used high-throughput screening, structure-based design, and targeted synthetic chemistry to discover the 4-aminoquinazoline 7a (PF-04471141) and the 4-indanylquinazoline 27 (PF-04822163) each of which are PDE1 inhibitors that readily cross the blood brain barrier. These quinazoline-based PDE1-selective inhibitors represent valuable new tools to study the biological processes regulated by PDE1 and to begin to determine the potential therapeutic utility of such compounds to treat neuropsychiatric disorders.

Design and application of a rigid quinazolone scaffold based on two-face Bim α-helix mimicking

Based on our previous discovery of an anthraquinone scaffold mimicking two faces of Bim α-helix, we derived a quinazolone scaffold through structure simplification and optimization. It was inferred that a rigid bicyclic ring was necessary and efficient to maintain the two-faced binding mode. A novel dual inhibitor 6c [6,7,8-trihydroxy-3-(2-hydroxy-5-methylbenzyl)-2-phenylquinazolin- 4(3H)-one] was obtained based on this scaffold. 6c exhibited dual binding activity with Ki values of 0.123 μM for Mcl-1 and 0.179 μM for Bcl-2.

Synthesis and biological activity of novel N-substituted 4-amino-6,7,8-trimethoxyquinazoline compounds

A series of N-substituted 4-amino-6,7,8-trimethoxyquinazoline derivatives has been synthesized from 4-chloro-6,7,8-trimethoxyquinazoline and aryl (or benzyl) amines using 2-propanol as a solvent. The starting material 4-chloro-6,7,8-trimethoxyquinazoline has been synthesized from natural gallic acid by a novel route. Their structures have been verified by elemental analysis and IR, 1H, and 13C NMR spectroscopy. The title compounds have been evaluated for their in vitro antiproliferative activities against some cancer cells by the MTT method. Unfortunately, most of the compounds tested have exhibited a weaker anticancer activity than the reference standard drug PD153035.

Microwave-assisted Niementowski reaction. Back to the roots

In a search to speed up an aspect of the drug discovery processes, the Niementowski synthesis of the 3H-quinazolin-4-one core was reinvestigated using microwave irradiation. The experimental methodology and microwave conditions described here are well established, allowing significant rate enhancements and good yields compared to conventional reaction conditions.

Tyrphostins IV - Highly potent inhibitors of EGF receptor kinase. Structure-activity relationship study of 4-anilidoquinazolines

Potent 4-anilido-substituted quinazolines which potently inhibit epidermal growth factor receptor (EGFR) kinase were prepared. Structure-activity relationship studies reveal high sensitivity to substitution at the aniline ring.