76088-98-7

Usage

Uses

Used in Pharmaceutical Industry:
7-Fluoroquinazoline-2,4(1H,3H)-dione is used as a building block for the synthesis of various pharmaceuticals and bioactive compounds. Its unique structure and potential biological activities make it a valuable component in the development of new drugs and therapeutic agents.
Used in Medicinal Chemistry:
7-Fluoroquinazoline-2,4(1H,3H)-dione is used as a starting material in medicinal chemistry for the preparation of compounds with potential therapeutic applications. Its anti-inflammatory, anti-cancer, and anti-microbial properties contribute to its potential as a precursor for the development of new drugs and therapeutic agents.
Used in Organic Synthesis:
7-Fluoroquinazoline-2,4(1H,3H)-dione is used as a key intermediate in organic synthesis, allowing for the creation of a wide range of chemical compounds with diverse applications. Its unique structure and properties make it a versatile building block for the synthesis of various organic compounds.

InChI:InChI=1/C8H5FN2/c9-7-2-1-6-4-10-5-11-8(6)3-7/h1-5H

Upstream product

• 446-32-2 4-fluoroanthranilic acid 
• 57-13-6 urea 
• 590-28-3 potassium cyanate 
• 124-38-9 carbon dioxide 
• 80517-22-2 2-amino-4-fluorobenzonitrile 

Downstream Products

• 1007308-74-8 C₈H₄FN₃O₄ 
• 174566-15-5 2,4,-dichloro-7-fluoroquinazoline 
• 956101-10-3 2-chloro-7-fluoro-quinazoline 
• 1007308-75-9 C₈H₂Cl₂FN₃O₂ 

Relevant academic research and scientific papers

Design, synthesis and evaluation of anti-proliferative activity of 2-aryl-4-aminoquinazoline derivatives as EGFR inhibitors

A class of 2-aryl-4-aminoquinazoline derivatives (7a-7j, 8a-8h, 9a-9h and 10a-10k) were designed, synthesized and evaluated as EGFR inhibitors. The anti-proliferative activity of compounds in vitro showed that compound 9e was considered to be a promising derivative. Compared with the lead compound Angew2017-7634-1, 9e exhibited excellent inhibitory activity against A549, NCI-H460 and H1975 cell lines, with IC50 values of 14.33 ± 1.16 μM, 17.81 ± 1.25 μM and 13.41 ± 1.14 μM, respectively. Moreover, 9e could effectively inhibit against Ba/F3-EGFRDel19/T790M/C797S cell lines. In the kinase experiment, the most promising compound 9e exhibited excellent enzymatic inhibitory activity and selectivity for EGFRL858R/T790M, with an IC50 value of 0.74 μM. Further activity studies showed that 9e could not only induce remarkable cell-apoptosis of A549, but also block A549 cell lines in S-phase in a concentration-dependent manner. Furthermore, molecular docking study revealed the binding mode of 9e. All in all, we analyzed the structure–activity relationship of the target compounds, and explored their mechanism of action.

Targeting sars-cov-2 polymerase with new nucleoside analogues

Despite the fact that COVID-19 vaccines are already available on the market, there have not been any effective FDA-approved drugs to treat this disease. There are several already known drugs that through drug repositioning have shown an inhibitory activity against SARS-CoV-2 RNA-dependent RNA polymerase. These drugs are included in the family of nucleoside analogues. In our efforts, we synthesized a group of new nucleoside analogues, which are modified at the sugar moiety that is replaced by a quinazoline entity. Different nucleobase derivatives are used in order to increase the inhibition. Five new nucleoside analogues were evaluated with in vitro assays for targeting polymerase of SARS-CoV-2.

Facile and efficient synthesis of quinazoline-2,4(1H,3H)-diones through sequential hydrogenation condensation

The heterocyclizations from various methyl (2-nitrobenzoyl)carbamates to substituted quinazoline-2,4(1H,3H)-diones under hydrogenation conditions were investigated in this study. In the presence of p-toluenesulfonic acid monohydrate in methanol, various q

Preparation method of quinazoline diketone derivative

The invention belongs to the technical field of medicine, and especially relates to a preparation method of a quinazoline diketone derivative. The preparation method is friendly to the environment; synthesis requirements are low; and operation method is simple. The preparation method comprises following steps: (1) acetonitrile with excellent dissolvability is taken as a solvent, isocyanic acid is prepared via acidification of potassium isocyanate with 2.0 times equivalent weight, and reaction is carried out for 2h at 50 DEG C; (2) 1.88g PPh3 is dissolved in 15ml of methylbenzene, 0.8ml of ethyl bromoacetate is added, reaction is carried out at room temperature for one night; (3) NaOH is added into an obtained reaction liquid, when alkali adding amount is 4 times equivalent weight, it is shown by LC-MS that cyclization reaction is completed, hydrochloric acid is added so as to adjust pH value to 1, the solvent is recovered via decompression, and the quinazoline diketone derivative is obtained via silica-gel column chromatography separation.

BICYCLIC DERIVATIVE CONTAINING PYRIMIDINE RING, AND PREPARATION METHOD THEREFOR

The present invention provides: a bicyclic derivative comprising a pyrimidine ring, or a pharmaceutically acceptable salt thereof; a preparation method therefor, a pharmaceutical composition comprising the same; and a use therefor. According to the present invention, the bicyclic compound derivative comprising a pyrimidine ring, or a pharmaceutically acceptable salt thereof acts as a 5-HT4 receptor agonist, and thus can be usefully applied to the prevention or treatment of dysfunction in gastrointestinal motility, for example, gastrointestinal diseases such as gastroesophageal reflux disease (GERD), constipation, irritable bowel syndrome (IBS), dyspepsia, post-operative ileus, delayed gastric emptying, gastroparesis, intestinal pseudo-obstruction, drug-induced delayed transit, diabetic gastric atony and the like.

Efficient synthesis of quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by N-heterocyclic carbene at atmospheric pressure

Under atmospheric pressure, quinazoline-2,4(1H,3H)-diones were obtained from the reaction of 2-aminobenzonitriles with carbon dioxide (0.1 MPa) with a catalytic amount of N-heterocyclic carbene in DMSO. It was found that various electron-donating and electron-withdrawing groups such as -OMe, -F, -Cl, -Br, -CH3, -CF3 and -CN were well tolerated to give the products in almost quantitative yields.

Discovery of 1-substituted benzyl-quinazoline-2,4(1H,3H)-dione derivatives as novel poly(ADP-ribose)polymerase-1 inhibitors

Poly(ADP-ribose)polymerase-1 (PARP-1) has emerged as a promising anticancer drug target due to its key role in the DNA repair process. In this work, a novel series of 1-benzyl-quinazoline-2,4(1H,3H)-dione derivatives were designed and synthesized as human PARP-1 inhibitors, structure-activity relationships were conducted and led to a number of potent PARP-1 inhibitors having IC50 values of single or double digit nanomolar level. Compound 7j was a potent PARP-1 and PARP-2 inhibitor and it could selectively kill the breast cancer cells MX-1 and MDA-MB-468 with mutated BRCA1/2 and PTEN, respectively, in comparison with homologous recombination proficient cell types such as breast cancer cells MDA-MB-231. In addition, compound 7j displayed the strongest potentiation effect on temozolomide in MX-1 cells (PF50 = 3.77) in this series of PARP-1 inhibitors.

1-(Arylmethyl)quinazoline-2,4(1H,3H)-diones as PARP Inhibitors and the Use Thereof

Disclosed are 1-(arylmethyl)quinazoline-2,4(1H,3H)-diones thereof, represented by the Formula (I) wherein Ar, R1-R6 are defined herein. Compounds having Formula (I) are PARP inhibitors. Therefore, compounds of the invention may be us

Eco-efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones at room temperature in water

An efficient one-pot synthesis of quinazoline-2,4(1H,3H)-diones was developed. First, the reactions of anthranilic acid derivatives with potassium cyanate afforded the corresponding urea derivatives. Then, cyclization of the urea derivatives with NaOH afforded the monosodium salts of benzoylene urea. Finally, HCl treatment afforded the desired products in near-quantitative yields. This is an eco-efficient method because all the reactions were carried out in water, and the desired products were obtained simply by filtration. The aqueous filtrate was the only waste generated from the reaction. We scaled up the reaction to 1 kg starting material, thus establishing an alternative approach for the green synthesis of quinazoline-2,4(1H,3H)-diones in the chemical and pharmaceutical industries.

1-(ARYLMETHYL)QUINAZOLINE-2,4(1H,3H)-DIONES AS PARP INHIBITORS AND THE USE THEREOF

Disclosed are 1-(arylmethyl)quinazoline-2,4(1H,3H)-diones thereof, represented by the Formula (I) wherein Ar, R1-R6 are defined herein. Compounds having Formula (I) are PARP inhibitors. Therefore, compounds of the invention may be us