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Usage

Uses

Used in Pharmaceutical Research and Drug Development:
5-FLUORO-4-HYDROXYQUINAZOLINE is used as a chemical intermediate for the synthesis of various pharmaceutical compounds due to its unique structure and properties. Its presence in the quinazoline family, along with the fluorine and hydroxyl groups, may contribute to the development of new drugs with improved efficacy and selectivity.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 5-FLUORO-4-HYDROXYQUINAZOLINE is used as a building block for the design and synthesis of novel bioactive molecules. Its unique structural features can be exploited to create new compounds with potential therapeutic applications, such as antimicrobial, antiviral, or anticancer agents.
Used in Biological Research:
5-FLUORO-4-HYDROXYQUINAZOLINE may be used in biological research to study its potential biological activities and effects on various cellular processes. This can help researchers understand its mechanism of action and identify potential therapeutic targets for the treatment of specific diseases or conditions.
Used in Drug Discovery:
As a member of the quinazoline family, 5-FLUORO-4-HYDROXYQUINAZOLINE can be used in drug discovery efforts to identify new lead compounds with potential therapeutic applications. Its unique structural features may provide insights into the design of more effective and selective drugs for various diseases.
Used in Chemical Synthesis:
5-FLUORO-4-HYDROXYQUINAZOLINE can be used as a starting material or reagent in various chemical synthesis processes. Its unique structure and properties may enable the development of new synthetic routes or methodologies for the preparation of complex organic molecules with potential applications in various industries, including pharmaceuticals, materials science, and agrochemicals.

Upstream product

• 122-51-0 orthoformic acid triethyl ester 
• 115643-59-9 2-amino-6-fluorobenzamide 
• 434-76-4 2-amino-6-fluorobenzoic acid 
• 77287-34-4 formamide 
• 64-18-6 formic acid 
• 77326-36-4 2-amino-6-fluorobenzonitrile 
• 144-62-7 oxalic acid 

Downstream Products

• 16499-60-8 4-chloro-5-fluoro-quinazoline 
• 135106-52-4 5-methoxy-4-(3H)-quinazolinone 
• 379228-40-7 4-[(2-chloro-5-methoxyphenyl)amino]quinazolin-5-ol 
• 379230-16-7 tert-butyl 4-[(4-chloroquinazolin-5-yl)oxy]piperidine-1-carboxylate 
• 179246-14-1 4-chloro-5-methoxyquinazoline 
• 1312757-87-1 C₃₀H₃₀FN₃O₅ 
• 1133219-01-8 3-cyclohexyl-5-fluoroquinazolin-4(3H)-one 

Relevant academic research and scientific papers

ERBB RECEPTOR INHIBITORS

Disclosed are compounds inhibiting ErbBs (e. g. HER2), pharmaceutically acceptable salts, hydrates, solvates or stereoisomers thereof and pharmaceutical compositions comprising the compounds. The compound and the pharmaceutical composition can effectively treat diseases associated ErbBs (especially HER2), including cancer.

Oxalic/malonic acids as carbon building blocks for benzazole, quinazoline and quinazolinone synthesis

An oxidant, base and metal free methodology has been developed for the synthesis of various 2-substituted and non-substituted benzazoles, quinazolines and quinazolinones using oxalic/malonic acids as an in situ carbon source. This methodology is applicable for a wide range of substituted o-phenylenediamine, o-aminothiophenol, o-aminophenol and o-aminobenzamide containing various functional groups and provides good to excellent yields of the corresponding product. Furthermore an easy workup procedure, high yield and easy isolation of products are key features of this methodology. The developed protocol is also applicable for the gram scale synthesis of benzimidazoles.

Design, Synthesis, and Potency of Pyruvate Dehydrogenase Complex E1 Inhibitors against Cyanobacteria

Safe and effective algaecides are needed to control agriculturally and environmentally significant algal species. Four series (6, 10, 17, and 21) of 29 novel 4-aminopyrimidine derivatives were rationally designed and synthesized. A part of 10, 17, and 21 displayed potent inhibition of Escherichia coli pyruvate dehydrogenase complex E1 (E. coli PDHc-E1) (IC50 = 2.12-18.06 μM) and good inhibition of Synechocystis sp. PCC 6803 (EC50 = 0.7-7.1 μM) and Microcystis sp. FACH 905 (EC50 = 3.7-7.6 μM). The algaecidal activity of these compounds positively correlated with their inhibition of E. coli PDHc-E1. In particular, 21l and 10b exhibited potent algaecidal activity against PCC 6803 (EC50 = 0.7 and 0.8 μM, respectively), values that were 2-fold increased compared to that of copper sulfate (EC50 = 1.8 μM), and showed the best inhibition of cyanobacterium PDHc-E1 (IC50 = 5.10 and 6.06 μM, respectively). 17h and 21e, the best inhibitors of E. coli PDHc-E1, were studied by molecular docking, site-directed mutagenesis, and enzymatic assays. These results revealed that the improved inhibition of novel inhibitors compared with that of the lead compound I was due to the formation of a new hydrogen bond with Leu264 at the active site of E. coli PDHc-E1. The results proved the great potential to obtain effective algaecides via the rational design of PDHc-E1 inhibitors. [Figure Presented]

Simple, selective, and practical synthesis of 2-substituted 4(3H)-quinazolinones by Yb(OTf)3-catalyzed condensation of 2-aminobenzamide with carboxamides

A simple, selective, and practical synthetic method of 4(3H)-quinazolinones is realized by Yb(OTf)3-catalyzed condensation of 2-aminobenzamide with carboxamides. As the reaction proceeds, NH3 and H2O were formed as byproducts; however, Yb(OTf)3 can operate as an efficient Lewis acid catalyst without deactivation.

Synthesis and SAR optimization of quinazolin-4(3H)-ones as poly(ADP-ribose)polymerase-1 inhibitors

We have demonstrated that quinazolin-4(3H)-one, a nicotinamide (NI) mimic with PARP-1 inhibitory activity in the high micromolar range (IC50 = 5.75 μM) could be transformed into highly active derivatives with only marginal increase in molecular weight. Convenient one to two synthetic steps allowed us to explore extensive SAR at the 2-, and 5- through 8-positions of the quinazolin-4(3H)-one scaffold. Substitutions at the 2- and 8-positions were found to be most favorable for improved PARP-1 inhibition. The amino group at 8-position resulted in compound 22 with an IC50 value of 0.76 μM. Combination of the 8-amino substituent with an additional methyl substituent at the 2-position provided the most potent compound 31 [8-amino-2-methylquinazolin- 4(3H)-one, IC50 = 0.4 μM] in the present study. Compound 31 inhibited the proliferation of Brca1-deficient cells with an IC50 value of 49.0 μM and displayed >10-fold selectivity over wild type counterparts. Binding models of these derivatives within the active site of PARP-1 have further supported the SAR data and will be useful for future lead optimization efforts.

2,4-SUBSTITUTED QUINAZOLINES AS LIPID KINASE INHIBITORS

The invention relates to compounds of the formula (I), which are appropriate for the treatment of kinase, e.g. PI3K-related, diseases, such as proliferative diseases, inflammatory diseases, obstructive airways disorders and transplantation related disease

Synthesis of 5-and 7-fluoroquinazolin-4(1H)-ones

5-Fluoroquinazoline-2,4-diones and their 2-thio analogs were obtained from 6-fluoroanthranilic acid. Two convenient routes to 5-fluoroquinazolin-4-ones involved cyclocondensation of 6-fluoroanthranilamide with acid chlorides (anhydrides) or with aromatic (heterocyclic) aldehydes. A method for the synthesis of 7-fluoroquinazolin-4-one from 2,4-difluorobenzoic acid was proposed.