26059-81-4

Usage

Uses

Used in Medicinal Chemistry:
2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE is used as a key building block for the synthesis of various pharmaceuticals and bioactive compounds. Its incorporation into drug molecules enhances their therapeutic potential, making it an essential component in the development of new medications.
Used in Drug Discovery:
In the realm of drug discovery, 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE is utilized as a starting material for the creation of novel drug candidates. Its unique properties allow researchers to explore its potential in addressing unmet medical needs and developing innovative treatments.
Used in Agrochemicals:
2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE also finds applications in the agrochemical industry, where it may be employed in the development of new pesticides or other agricultural chemicals. Its unique chemical structure could contribute to the creation of more effective and targeted agrochemical products.
Used in Materials Science:
Furthermore, 2-(TRIFLUOROMETHYL)-4(3H)-QUINAZOLINONE has potential uses in materials science, where its properties could be leveraged to develop new materials with specific characteristics for various applications, such as in electronics or advanced materials research.

InChI:InChI=1/C9H5F3N2O/c10-9(11,12)8-13-6-4-2-1-3-5(6)7(15)14-8/h1-4H,(H,13,14,15)

Upstream product

• 383-63-1 ethyl trifluoroacetate, 
• 28144-70-9 anthranilic acid amide 
• 76-05-1 trifluoroacetic acid 

Downstream Products

• 52353-35-2 4-chloro-2-trifluoromethyl quinazoline 
• 927969-20-8 (2-(trifluoromethyl)quinazolin-4-yl)glycine 
• 154136-31-9 4-hydrazino-2-trifluoromethylquinazoline 

Relevant academic research and scientific papers

Quinazolines as cyclin dependent kinase inhibitors

Quinazolines have been identified as inhibitors of CDK4/D1 and CDK2/E. Aspects of the SAR were investigated using solution-phase, parallel synthesis. An X-ray crystal structure was obtained of quinazoline 51 bound in CDK2 and key interactions within the ATP binding pocket are defined.

Synthesized 2-trifluoromethylquinazolines and quinazolinones protect bv2 and n2a cells against lps-and h2 o2-induced cytotoxicity

Background: Microglia are associated with neuroinflammation, which play a key role in the pathogenesis of neurodegenerative diseases. It has been reported that some quinazolines and quinazolinones possess anti-inflammatory properties. However, the pharmacological properties of certain quinazoline derivatives are still unknown. Objective: The antioxidant, cytotoxic, and protective effects of a series of synthesized 2-trifluoromethylquinazolines (2, 4, and 5) and quinazolinones (6-8) in lipopolysaccharide (LPS)-murine microglia (BV2) and hydrogen peroxide (H2 O2 )-mouse neuroblastoma-2a (N2a) cells were investigated. Method: The antioxidant activity of synthesized compounds was evaluated with ABTS and DPPH assays. The cytotoxic activities were determined by MTS assay in BV2 and N2a cells. The production of nitric oxide (NO) in LPS-induced BV2 microglia cells was quantified. Results: The highest ABTS and DPPH scavenging activities were observed for compound 8 with 87.7% of ABTS scavenge percentage and 54.2% DPPH inhibition. All compounds were non-cytotoxic in BV2 and N2a cells at 5 and 50 μg/mL. The compounds which showed the highest protective effects in LPS-induced BV2 and H2 O2-induced N2a cells were 5 and 7. All tested com-pounds, except 4, also reduced NO production at concentrations of 50 μg/mL. The quinazolinone series 6-8 exhibited the highest percentage of NO reduction, ranging from 38 to 60%. Compounds 5 and 8 possess balanced antioxidant and protective properties against LPS-and H2 O2-induced cell death, thus showing great potential to be developed into anti-inflammatory and neuroprotective agents. Conclusion: Compounds 5 and 7 were able to protect the BV2 and N2a cells against LPS and H2 O2 toxicity, respectively, at a low concentration (5 μg/mL). Compounds 6-8 showed potent reduction of NO production in BV2 cells.

Selective Toll-like receptor 7 agonists with novel chromeno[3,4-d]imidazol-4(1H)-one and 2-(trifluoromethyl)quinoline/ quinazoline-4-amine scaffolds

Toll-like receptors (TLRs) are promising targets for treatment of viral infections, autoimmune diseases, and cancers. Here, two new series of selective small-molecule TLR7 agonists with novel scaffolds and good selectivity over TLR8 are described, some with potencies in the low micromolar range. 8-Hydroxy-1-isobutylchromeno[3,4-d]imidazol-4(1H)-one (26) from the first series was designed and synthesized on the basis of previously described TLR7 antagonist 2, and is shown to be a selective TLR7 agonist (EC50, 1.8 μM). The second series was based on 2-(trifluoromethyl)quinolin-4-amine and 2-(trifluoromethyl)quinazolin-4-amine scaffolds, which were defined according to our in-house ligand-based virtual screening protocol. Further synthesis of a focused library of analogs, biological evaluation, and docking studies provided systematic exploration of the structure?activity relationships, which indicate that a secondary or tertiary amine with smaller flexible alkyl substituents up to three carbon atoms in length, or bulkier rigid aliphatic rings is required at position 4 on 2-(trifluoromethyl)quinoline/quinazoline scaffold for potent TLR7 agonist activity. The influence of selected TLR7 agonists on cytokine production is also reported showing that N-cyclopropyl-2-(trifluoromethyl)quinazolin-4-amine (46) is able to induce increased levels of IL-6 and IL-8. These data demonstrate successful in-silico definition of novel TLR7 versus TLR8-selective compounds as promising chemical probes for further development of potent small-molecule immunomodulators.

ANTIPROLIFERATIVE PYRIMIDYL, FUSED PYRIMIDYL AND PYRIMIDYL HYDRAZONES

The present invention is related to a novel series of pyrimidyl or fused pyrimidyl hydrazones. Compounds of Formula (I) wherein A is selected from the group consisting of Formulas (A1), (A2), (A3), (A4), (A5) are useful for the treatment and/or prevention of a proliferative disease.

Microwave irradiation in solvent-free conditions: Preparation of 2-substituted- 4(3H)-quinazolinones by heterocyclisation of 2-aminobenzamide with carboxylic acids

A simple and fast preparation of 2-substituted-4(3H)-quinazolinones in high yields has been developed by microwave induced heterocyclisation of 2-aminobenzamide with carboxylic acids in solvent-free conditions. In comparison, the reactions are 40-80 times faster under microwave irradiation and the yields are much higher than conventional heating.

Studies of Rutaecarpine and Related Quinazolinocarboline Alkaloids

Quinazolinocarboline alkaloids, e.g., rutaecarpine (1), can readily be synthesized by treating tryptamine with 2-(trifluoromethyl)-4H-3,1-benzoxazin-4-one (quickly generated in situ from trifluoroacetic anhydride (TFAA) and 2H-3,1-benzoxazine-2,4(1H)-dione.The product formed, 3--2-(trifluoromethyl)-4-(3H)-quinazolinone (5), is then cyclized (HCl/HOAc) to 13b-(trifluoromethyl)-13b,14-dihydrorutaecarpine (6), whereupon CF3H is eliminated by treatment with base.The sequence can conveniently be performed as a three-reaction one-pot procedure giving rutaecarpine (1) in 99percent yield within 3h.The approach can readily be extended to the synthesis of evodiamine (2), 13,13b-dehydroevodiamine (38a), and 13b,14-dihydrorutaecarpine (21).Thus treatment of 3--4(3H)-quinazolinone (19) with TFAA affected cyclization to 13b-(trifluoroacetyl)-13b,14-dihydrorutaecarpine (20), which can be readily hydrolyzed to 13b,14-dihydrorutaecarpine (21).