1026-04-6

Basic information

• Product Name: 2-(2-HYDROXY-PHENYL)-3H-QUINAZOLIN-4-ONE
• Synonyms: 2-(2-Hydroxyphenyl)-4(1H)-quinazolinone;2-(2-Hydroxyphenyl)quinazoline-4(3H)-one;4(1H)-Quinazolinone, 2-(2-hydroxyphenyl)-;2-(2'-hydroxyphenyl)-4-(3H)-quinazolinone
• CAS NO: 1026-04-6
• Molecular Formula: C₁₄H₁₀N₂O₂
• Molecular Weight: 238.24
• Mol File: 1026-04-6.mol
• Article Data: 42

Chemical Properties

• Boiling Point: 523.7°Cat760mmHg
• Flash Point: 227.3°C
• Appearance: /
• Density: 1.343g/cm³
• Vapor Pressure: 1.81E-08mmHg at 25°C
• Refractive Index: 1.687
• CAS DataBase Reference: 2-(2-HYDROXY-PHENYL)-3H-QUINAZOLIN-4-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(2-HYDROXY-PHENYL)-3H-QUINAZOLIN-4-ONE(1026-04-6)
• EPA Substance Registry System: 2-(2-HYDROXY-PHENYL)-3H-QUINAZOLIN-4-ONE(1026-04-6)

Safety Data

• Hazardous Substances Data: 1026-04-6(Hazardous Substances Data)

Usage

General Description

2-(2-hydroxy-phenyl)-3H-quinazolin-4-one, also known as PD153035, is a chemical compound that belongs to the quinazolinone class. It is a selective inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase, and its structural features make it a potential candidate for anti-cancer drug development. PD153035 has been studied for its ability to inhibit the proliferation and survival of various cancer cells by blocking the EGFR signaling pathway. It has also shown promising activity in preclinical models of glioblastoma and lung cancer, and its development as a targeted therapy for EGFR-dependent cancers continues to be explored. Furthermore, PD153035 has been used as a research tool to investigate the role of EGFR in cancer biology and to develop methods for targeting EGFR in cancer treatment.

InChI:InChI=1/C14H10N2O2/c17-12-8-4-2-6-10(12)13-15-11-7-3-1-5-9(11)14(18)16-13/h1-8,17H,(H,15,16,18)

Upstream product

• 70792-84-6 4-anilino-1,3<2H>benzoxazin-2-one 
• 18543-22-1 2-benzoylaminobenzamide 
• 28144-70-9 anthranilic acid amide 
• 1022-45-3 2-phenyl-1,4-dihydroquinazolin-4-one 
• 98-88-4 benzoyl chloride 
• 90-02-8 salicylaldehyde 
• 1885-29-6 anthranilic acid nitrile 
• 1310417-73-2 2-(2-bromophenyl)-quinazolin-4(3H)-one 
• 1441-87-8 salicyloyl chloride 
• 101046-14-4 2-((4-bromobenzyl)oxy)benzaldehyde 
• 3930-83-4 o-iodobenzamide 
• 118-93-4 o-hydroxyacetophenone 
• 90-01-7 salicylic alcohol 
• 610-15-1 2-nitrobenzamide 

Downstream Products

• 1218788-49-8 C₃₃H₃₆N₄O₇ 
• 1218788-42-1 C₂₇H₂₅N₃O₆ 

Relevant articles and documents

SYNTHESIS AND CYCLOISOMERIZATION OF o-CYANOPHENYL CARBANILATE

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Synthesis and use of new fluorogenic precipitating substrates

New fluorogenic esterase, glycosidase, aryl sulfatase, microsomal dealkylase, guanidinobenzoatase and alkaline phosphatase substrates have been prepared which precipitate at the site of enzyme activity, both in vitro and in vivo.

A novel HPQ-based turn-on fluorescent probe for detection of fluoride ions in living cells

2-(2′-Hydroxyphenyl)-4(3H)-quinazolinone (HPQ) has been reported as a precipitating fluorescent molecule with excellent optical properties, such as large Stokes shift and strong fluorescence intensity. HPQF, a novel HPQ-based turn-on probe for localizable detection of fluoride ions, was designed, synthesized and fully characterized by 1H NMR, 13C NMR and HRMS. As a chemogenic fluoride probe, the tert-butyldiphenylsilane moiety of HPQF can be easily cleaved by fluoride. After spontaneous 1,6-elimination, HPQ molecule was generated to emit fluorescence under the excitation light. Further study shows that HPQF exhibited high selectivity and sensitivity for detection of fluoride. In addition, HPQF was utilized for the detection of fluoride in living cells.

Electrochemical synthesis of quinazolinone: via I2-catalyzed tandem oxidation in aqueous solution

The development of protocols for synthesizing quinazolinones using biocompatible catalysts in aqueous medium will help to resolve the difficulties of using green and sustainable chemistry for their synthesis. Herein, using I2 in coordination with electrochemical synthesis induced a C-H oxidation reaction which is reported when using water as the environmentally friendly solvent to access a broad range of quinazolinones at room temperature. The reaction mechanism strongly showed that I2 cooperates electrochemically promoted the oxidation of alcohols, then effectively cyclizing amides to various quinazolinones.

Antioxidant and ros inhibitory activities of heterocyclic 2-aryl-4(3h)-quinazolinone derivatives

Background: Antioxidants are small molecules that prevent or delay the process of oxidations caused by highly reactive free radicals. These molecules are known for their ability to protect various cellular architecture and other biomolecules from oxidative stress and free radicals. Thus, antioxidants play a key role in the prevention of oxidative damages caused by highly reactive free radicals. Methods: In the present study, a series of previously synthesized heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 were screened for antioxidant activity by employing in vitro DPPH and superoxide anion radical scavenging activities. ROS inhibitory activities were also evaluated by serum-opsonized zymosan activated whole blood phagocytes and isolated neutrophils. Cytotoxicity studies were carried out by employing an MTT assay against the 3T3 cell line. Results: Most of the 2-aryl-4(3H)-quinazolinone derivatives showed potent antioxidant activities in superoxide anion radical scavenging assay with IC50 value ranging between 0.57 μM-48.93 μM, as compared to positive control quercetin dihydrate (IC50 = 94.1 ± 1.1 μM ). Compounds 5, 6, and 14 showed excellent activity in DPPH assay. Compounds 5-8, 12-15, 17, and 20 showed promising activities in the ROS inhibition assay. All compounds were found to be non-cytotoxic against the 3T3 cell line. Structure antioxidant activity has been established. Conclusion: It can be concluded that most of the heterocyclic 2-aryl-4(3H)-quinazolinone derivatives 1-25 are identified as promising antioxidant agents that are capable of fighting against free radicals and oxidative stress. Thus, they can serve as a lead towards treating oxidative stress and related pathologies.