14663-53-7

Basic information

• Product Name: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID
• Synonyms: CHEMBRDG-BB 4001974;(4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID;(4-OXOQUINAZOLIN-3(4H)-YL)ACETIC ACID;AKOS BB69;ASISCHEM D51303;OTAVA-BB 7010160005;3(4H)-quinazolineacetic acid, 4-oxo-;(4-Oxo-3(4H)-quinazolinyl)acetic acid
• CAS NO: 14663-53-7
• Molecular Formula: C₁₀H₈N₂O₃
• Molecular Weight: 204.18
• Mol File: 14663-53-7.mol

Chemical Properties

• Melting Point: 237-294 °C
• Boiling Point: 444.6°Cat760mmHg
• Flash Point: 222.7°C
• Appearance: /Solid
• Density: g/cm³
• Vapor Pressure: 1.1E-08mmHg at 25°C
• Storage Temp.: 2-8°C
• PKA: 3.61±0.10(Predicted)
• CAS DataBase Reference: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID(14663-53-7)
• EPA Substance Registry System: (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID(14663-53-7)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 14663-53-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID is used as a key compound in the study of antibiotic formation by Streptomyces echinatus, a genus of bacteria known for producing a wide range of bioactive secondary metabolites, including antibiotics. The compound plays a crucial role in understanding the biosynthetic pathways and mechanisms involved in the production of these antibiotics, which can lead to the development of new and more effective antimicrobial agents.
Used in Research and Development:
In the field of research and development, (4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID serves as an important tool for studying the structure-activity relationships of various quinazoline-based compounds. This knowledge can be applied to the design and synthesis of novel therapeutic agents with improved pharmacological properties, such as enhanced potency, selectivity, and reduced side effects.
Used in Chemical Synthesis:
(4-OXO-4H-QUINAZOLIN-3-YL)-ACETIC ACID can also be utilized as a building block or intermediate in the synthesis of more complex quinazoline-based molecules. These molecules may have potential applications in various industries, such as pharmaceuticals, agrochemicals, and materials science, where they can be used as active ingredients or components in the development of new products.

InChI:InChI=1/C10H8N2O3/c13-9(14)5-12-6-11-8-4-2-1-3-7(8)10(12)15/h1-4,6H,5H2,(H,13,14)/p-1

Upstream product

• 2981-86-4 3-(2-hydroxyethyl)quinazolin-4(3H)-one 
• 16347-69-6 2-(4-oxo-(4H)-quinazoline-3-yl)acetate ethyl ester 
• 28144-70-9 anthranilic acid amide 
• 491-36-1 4-Hydroxyquinazoline 
• 526-21-6 N-(2-aminobenzoyl)-glycine 
• 118-48-9 isatoic anhydride 
• 82185-40-8 2-amine-N-(methoxycarbonylmethyl)benzamide 
• 64-18-6 formic acid 
• 54368-19-3 3-methoxycarbonylmethyl-3,4-dihydro-4(1H)-quinazoline 
• 79-08-3 bromoacetic acid 

Downstream Products

• 54368-19-3 3-methoxycarbonylmethyl-3,4-dihydro-4(1H)-quinazoline 
• 108086-38-0 2-(4-oxoquinazolin-3(4H)-yl)-N-phenylacetamide 
• 783371-69-7 3,4-dihydro-3-[(1R,2S,5R)-menthoxycarbonylmethyl]-4(1H)-quinazolinone 

Relevant articles and documents

The unambiguous synthesis and NMR assignment of 4-alkoxy and 3-alkylquinazolines

Contrary to a number of reports, alkylations of the privileged 3,4-dihydroquinazoline scaffold provide N3-alkylated products, and not 4-alkoxyquinazolines. To correctly assign the structure, 13C NMR shifts of the -Z-CHn- (Z=O, N) fragment are necessary; resonances in the 45-55 ppm range are indicative of N3-alkylation. Treatment of 3,4-dihydroquinazoline-4-one with p-TsCl afforded the N3-tosylated compound, whose reaction with an amine yielded the corresponding N3-alkyl derivative. A mechanism corroborated by 15N-labeling involving pyrimidine ring opening and recyclisation is proposed. Finally, the unambiguous preparation of 4-alkoxyquinazolines is described via treatment of 3,4-dihydroquinazoline-4-ones with PCl5 followed by an alkoxide.

Novel bronchodilatory quinazolines and quinoxalines: Synthesis and biological evaluation

A series of heterocyclic derivatives analogous to (-)vasicinone, in which the vasicinone C-ring was replaced with alkyl chain terminated by tertiary amine was prepared. N3, C4-O, C4-S or C4-N were used as the sites of attachment. The 4-[3-(1-piperidyl)propylsulfanyl]derivatives displayed bronchodilatory effect at low micromolar concentrations on isolated rat trachea, and low toxicity both on Balb/c 3T3 mouse fibroblast cells and in mice.

Optimization of a Novel Quinazolinone-Based Series of Transient Receptor Potential A1 (TRPA1) Antagonists Demonstrating Potent in Vivo Activity

There has been significant interest in developing a transient receptor potential A1 (TRPA1) antagonist for the treatment of pain due to a wealth of data implicating its role in pain pathways. Despite this, identification of a potent small molecule tool possessing pharmacokinetic properties allowing for robust in vivo target coverage has been challenging. Here we describe the optimization of a potent, selective series of quinazolinone-based TRPA1 antagonists. High-throughput screening identified 4, which possessed promising potency and selectivity. A strategy focused on optimizing potency while increasing polarity in order to improve intrinisic clearance culminated with the discovery of purinone 27 (AM-0902), which is a potent, selective antagonist of TRPA1 with pharmacokinetic properties allowing for >30-fold coverage of the rat TRPA1 IC50 in vivo. Compound 27 demonstrated dose-dependent inhibition of AITC-induced flinching in rats, validating its utility as a tool for interrogating the role of TRPA1 in in vivo pain models.

Development of 2-(4-oxoquinazolin-3(4 H)-yl)acetamide derivatives as novel enoyl-acyl carrier protein reductase (InhA) inhibitors for the treatment of tuberculosis

InhA, the enoyl acyl carrier protein reductase of Mycobacterium tuberculosis (MTB) is an attractive target for developing novel anti-tubercular agents. Twenty eight 2-(4-oxoquinazolin-3(4H)-yl)acetamide derivatives were synthesized and evaluated for their in vitro MTB InhA inhibition. Compounds were further evaluated for their in vitro activity against drug sensitive and resistant MTB strains and cytotoxicity against RAW 264.7 cell line. Compounds were docked at the active site of InhA to understand their binding mode and differential scanning fluorimetry was performed to ascertain their protein interaction and stability.

Synthesis of 2,3-dihydro-4(1H)-quinazolinones

An improved procedure for the synthesis of 2-substituted 2,3-dihydro-4(1H)-quinazolinones through diastereomer separation of the corresponding quinazolinones derivatives is presented. The determination of their absolute configurations was obtained by X-Ra