33371-00-5

Basic information

• Product Name: 4-chloro-6,7,8-trimethoxyquinazoline
• Synonyms: 4-chloro-6,7,8-trimethoxyquinazoline
• CAS NO: 33371-00-5
• Molecular Formula: C₁₁H₁₁ClN₂O₃
• Molecular Weight: 254.66964
• EINECS: 251-481-0
• Mol File: 33371-00-5.mol
• Article Data: 9

Chemical Properties

• Boiling Point: 372.5 °C at 760 mmHg
• Flash Point: 179.1 °C
• Appearance: /
• Density: 1.313g/cm³
• Vapor Pressure: 2.05E-05mmHg at 25°C
• Refractive Index: 1.587
• CAS DataBase Reference: 4-chloro-6,7,8-trimethoxyquinazoline(CAS DataBase Reference)
• NIST Chemistry Reference: 4-chloro-6,7,8-trimethoxyquinazoline(33371-00-5)
• EPA Substance Registry System: 4-chloro-6,7,8-trimethoxyquinazoline(33371-00-5)

Safety Data

• Hazardous Substances Data: 33371-00-5(Hazardous Substances Data)

Usage

General Description

4-Chloro-6,7,8-trimethoxyquinazoline is a chemical compound with the molecular formula C11H11ClN2O3. It belongs to the quinazoline class of organic compounds and is a derivative of quinazoline with a chlorine atom and three methoxy groups attached to the six, seven, and eight positions of the quinazoline ring. 4-Chloro-6,7,8-trimethoxyquinazoline has potential pharmaceutical applications, particularly in the field of medicinal chemistry, due to its structural features and potential biological activities. It may be used as a precursor in the synthesis of other organic compounds or as a building block in the development of new drugs. Additionally, it may also have applications in the field of agrochemicals and material science. Overall, 4-Chloro-6,7,8-trimethoxyquinazoline is a versatile chemical with potential uses in various industries and research fields.

InChI:InChI=1/C11H11ClN2O3/c1-15-7-4-6-8(13-5-14-11(6)12)10(17-3)9(7)16-2/h4-5H,1-3H3

Upstream product

• 16064-19-0 6,7,8-Trimethoxy-4(3H)-quinazolinone 
• 66907-52-6 3,4,5-trimethoxy-2-nitrobenzoic acid 
• 5081-42-5 3,4,5-trimethoxy-2-nitrobenzoic acid methyl ester 
• 1916-07-0 3,4,5-trimethoxybenzoic acid methyl ester 
• 118-41-2 Eudesmic acid 
• 5035-82-5 methyl 3,4,5-trimethoxyanthranilate 
• 61948-85-4 3,4,5-trimethoxyanthranilic acid 
• 77287-34-4 formamide 

Relevant articles and documents

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.

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.