1640-60-4

Usage

Uses

Used in Pharmaceutical Industry:
6-Chloroquinazoline-2,4(1H,3H)-dione serves as a crucial building block for the synthesis of various biologically active molecules, contributing to the development of new pharmaceuticals with potential therapeutic applications.
Used in Antitumor Research:
6-Chloroquinazoline-2,4(1H,3H)-dione is studied for its antitumor properties, indicating its potential use in the development of new drugs for treating cancer. Its specific mechanisms and efficacy in inhibiting tumor growth are areas of ongoing research.
Used in Antiviral Research:
6-Chloroquinazoline-2,4(1H,3H)-dione is also being investigated for its antiviral activities, suggesting a possible role in creating medications to combat viral infections.
Used in Drug Development:
6-Chloroquinazoline-2,4(1H,3H)-dione's potential pharmacological properties are being explored for the development of new drugs to treat a range of diseases, highlighting its versatility and importance in medicinal chemistry.

InChI:InChI=1/C8H5ClN2O2/c9-4-1-2-6-5(3-4)7(12)11-8(13)10-6/h1-3H,(H2,10,11,12,13)

Upstream product

• 5202-89-1 4-chlorobenzenesulfonyl chloride 
• 20028-68-6 2,4,6-trichloroquinazoline 
• 57-13-6 urea 
• 635-21-2 5-chloroanthranilic acid 
• 5922-60-1 2-amino-5-chlorobenzonitrile 
• 68-12-2 N,N-dimethyl-formamide 
• 917-61-3 sodium isocyanate 
• 5202-85-7 2-Amino-5-chlorobenzamide 
• 2516-95-2 5-chloro-2-nitrobenzoic acid 
• 134-20-3 2-carbomethoxyaniline 
• 3603-10-9 ethyl 6-chloro-4-oxo-4H-benzo[d][1,3]oxazine-2-carboxylate 
• 75-44-5 phosgene 
• 590-28-3 potassium cyanate 
• 124-38-9 carbon dioxide 

Downstream Products

• 20028-68-6 2,4,6-trichloroquinazoline 
• 192570-38-0 1-(3,5-di-O-p-toluoyl-2-deoxy-α,β-D-erythro-pentofuranosyl)-6-chloro-quinazoline-2,4(3H)-dione 
• 221043-13-6 4-allylamino-2,6-dichloroquinazoline 

Relevant academic research and scientific papers

Ionic liquid[DBUH][BO2]: an excellent catalyst for chemical fixation of CO2under mild conditions

The green basic IL[DBUH][BO2]was easily synthesized for the first time and used to catalyze the cycloaddition of CO2and epoxides under solvent- and halogen-free conditions at atmospheric pressure and room temperature with high target product yields. Moreover, this IL could be easily recovered and reused at least five times without activity loss. The basic anion and the cation with N-H had excellent synergistic catalytic effects on promoting these reactions. Particularly, this basic IL, the anion of which had a strong nucleophilic ability, was also very effective for the reactions of CO2and 2-aminobenzonitriles into quinazoline-2,4(1H,3H)-diones, giving the desired products in high yields at atmospheric pressure and room temperature.

Efficient synthesis of 2-oxazolidinones and quinazoline-2,4(1H,3H)-diones from CO2 catalyzed by tetrabutylammonium fluoride

By employing tetrabutylammonium fluoride (TBAF) as a catalyst, the various carboxylative cyclizations of the propargylic amines having internal alkynes with CO2 proceeded to afford the corresponding 2-oxazolidinones. In this case, it was also found that the generated 2-oxazolidinones were tautomerized into the corresponding 2-oxazolones due to the basicity of TBAF. In addition, we performed the synthesis of quinazoline-2,4(1H,3H)-dione from 2-aminobenzonitrile and CO2 by using TBAF as a catalyst.

Ionic liquid immobilized onto fibrous nano-silica: A highly active and reusable catalyst for the synthesis of quinazoline-2,4(1 H,3 H)-diones

In this study, a novel fibrous nano-silica (KCC-1) supported ionic liquid (KCC-1/IL) with high surface area and easy accessibility of active sites was successfully developed by a facile approach. The synthesized KCC-1/IL nanocatalyst exhibited excellent catalytic activity for the synthesis of quinazoline-2,4(1 H,3 H)-diones from CO2 and 2-aminobenzonitriles under mild conditions to the easy accessibility of the active sites. A high catalytic activity and ease of recovery from the reaction mixture by using filtration and several reuses without any significant loss in performance are additional eco-friendly attributes of this catalytic system.

Application of quinazoline and pyrido[3,2-: D] pyrimidine templates to design multi-targeting agents in Alzheimer's disease

A quinazoline and pyrido[3,2-d]pyrimidine based compound library was designed, synthesized and evaluated as multi-targeting agents aimed at Alzheimer's disease (AD). The SAR studies identified compound 8h (8-chloro-N2-isopropyl-N4-ph

Amino-functionalized carbon nanofibres as an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles

Carbon nanofibres (CNFs) functionalized with 4-amino-2,6-dimethylpyridine were found to be an efficient metal free catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitriles using water as a reaction medium. The presence of water they exhibited a remarkable enhancement in reaction rates and provided high to excellent yield of the products. After completion of the reaction, the catalyst was easily separated by centrifugation and was successfully reused for several runs without showing any significant decrease in catalytic activity.

Discovery of 2-(4-Substituted-piperidin/piperazine-1-yl)-N-(5-cyclopropyl-1H-pyrazol-3-yl)-quinazoline-2,4-diamines as PAK4 inhibitors with potent A549 cell proliferation, migration, and invasion inhibition activity

A series of novel 2,4-diaminoquinazoline derivatives were designed, synthesized, and evaluated as p21-activated kinase 4 (PAK4) inhibitors. All compounds showed significant inhibitory activity against PAK4 (half-maximal inhibitory concentration IC50 1 ?M). Among them, compounds 8d and 9c demonstrated the most potent inhibitory activity against PAK4 (IC50 = 0.060 ?M and 0.068 ?M, respectively). Furthermore, we observed that compounds 8d and 9c displayed potent antiproliferative activity against the A549 cell line and inhibited cell cycle distribution, migration, and invasion of this cell line. In addition, molecular docking analysis was performed to predict the possible binding mode of compound 8d. This series of compounds has the potential for further development as PAK4 inhibitors for anticancer activity.

A green, facile, and one-pot synthesis of 2,4-(1H,3H)-quinazolinediones under microwave irradiations

Quinazoline-2,4-diones are of considerable interest due to their wide pharmacological properties. Here, we have described an environmentally friendly method for the one-pot synthesis of 2,4-(1H,3H)-quinazolinediones from the reaction of anthranilic acid derivatives with urea in H2O media under microwave irradiations. This method is simple, safe, and fast which produces high yield of products without use of any catalyst. Copyright

Spidery catalyst for the synthesis of quinazoline-2,4(1H,3H)-diones

In this study, a novel fibrous nanosilica (KCC-1) based nanocatalyst (Au, Pd, and Cu) with a high surface area and easy accessibility of active sites was successfully developed by a facile approach. KCC-1 with a high surface area was functionalized with multi-carboxylic hyperbranched polyglycerol groups (HPG) acting as robust anchors so that the metal nanoparticles (Au, Pd, and Cu) were well-dispersed on the fibers of the KCC-1 microspheres without aggregation. Because of the amplification effect of HPG, high loading capacities of the nanocatalysts were achieved. The synthesized KCC-1/HPG/X nanocatalyst exhibited excellent catalytic activity for the synthesis of quinazoline-2,4(1H,3H)-diones from CO2 and 2-aminobenzonitrile under mild conditions due to the easy accessibility of the active sites. High catalytic activity and ease of recovery from the reaction mixture by using filtration after several reuses without any significant loss of performance are additional eco-friendly attributes of this catalytic system.

Alkali metal cations control over nucleophilic substitutions on aromatic fused pyrimidine-2,4-[1H,3H]-diones: Towards new PNA monomers

In this paper we report synthesis of a series of aromatic fused pyrimidine-2,4(3H)-dione-1-yl acetic acid and new PNA monomers containing these polycyclic nucleobase analogues. Introduction of a fused aromatic ring onto the 5,6-positions of the pyrimidine-2,4-[1H,3H]-diones brings about the steric effects and the charge delocalization, both weakening the nucleophilic substitutions on the 1- and 3-positions. We found that alkali metal cations play an important role in this alkylation reaction. LiOH brings out a much more efficient alkylation than NaOH does, while KOH nearly does not work on this reaction. Such influences from the alkali metal cations are probably due to that the charge-pairing interactions between the pyrimidine-2,4-dioxide anions and the alkali metal cations rearrange the charge distribution around the whole aromatic system and increase the negative charge distribution on the 1- and 3-nitrogen atoms, which then strengthens the nucleophilic reactivity on these positions.

[TBDH][HFIP] ionic liquid catalyzed synthesis of quinazoline-2,4(1H,3H)-diones in the presence of ambient temperature and pressure

The utilization of carbon dioxide under mild reaction conditions is an important aspect of the sustainable chemistry point of view. Herein, we prepared three bifunctional protic ionic liquids having 1,5,7-Triazabicyclo[4.4.0]dec-5-ene (TBD) as a cation and an alcohol anions were prepared by simple neutralization of the super base TBD with proton donor alcohols such as hexafluoroisopropanol (HFIP), TFE (2,2,2-Trifluoroethanol) and TFA (2,2,2-Trifluoroacetic acid). These PILs were used as catalysts for chemical fixation of carbon dioxide into quinazoline-2,4(1H,3H)-diones. [TBDH+][HFIP-] protic ionic liquid (PIL) shows very good result compare to other PILs. As a bifunctional ionic liquid, it simultaneously activates 2-aminobenzonitrile as well as CO2 and shows excellent performance for the conversion of 2-aminobenzonitrile to quinazoline-2,4(1H,3H)-diones in presence of CO2 balloon pressure at 35 °C temperature. Moreover, the [TBDH+][HFIP-] PIL can be recycled up to six recycle run.