114703-12-7

Usage

Uses

Used in Pharmaceutical Research and Development:
7-BROMOQUINAZOLINE-2,4(1H,3H)-DIONE is used as a building block for the synthesis of pharmacologically active molecules, contributing to the development of new drugs with potential therapeutic benefits.
Used in Organic Synthesis:
As an intermediate in the production of other organic compounds, 7-BROMOQUINAZOLINE-2,4(1H,3H)-DIONE plays a crucial role in the synthesis of complex organic molecules for various applications.
Used in Biochemical Research:
7-BROMOQUINAZOLINE-2,4(1H,3H)-DIONE is employed in biochemical research to explore its potential biological activities and understand its role in various biochemical processes, which may lead to the discovery of new therapeutic targets and applications.

InChI:InChI=1/C8H5BrN2O2/c9-4-1-2-5-6(3-4)10-8(13)11-7(5)12/h1-3H,(H2,10,11,12,13)

Upstream product

• 591-19-5 m-Bromoaniline 
• 60-35-5 acetamide 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 6326-79-0 6-bromoisatin 
• 65971-74-6 N-(3-bromophenyl)-2-(hydroxyimino)ethanamide 
• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 917-61-3 sodium isocyanate 
• 57-13-6 urea 
• 20776-48-1 2-amino-6-chlorobenzoic acid 
• 304858-65-9 2-amino-4-bromobenzonitrile 
• 124-38-9 carbon dioxide 

Downstream Products

• 1374203-78-7 4-(3-{2-fluoro-4-[7-(5-methyl-furan-2-yl)4-morpholin-4-yl-quinazolin-2-yl]-phenyl}ureido)dimethyl-benzamide 
• 1374203-80-1 5-(2-(4-(3-(4-(dimethylcarbamoyl)phenyl)ureido)phenyl)-4-morpholino-quinazolin-7-yl)furan-2-carboxylic acid 
• 1374208-57-7 methyl 5-(2-(4-(3-(4-(dimethylcarbamoyl)phenyl)ureido)phenyl)-4-morpholino-quinazolin-7-yl)furan-2-carboxylate 
• 1374203-82-3 4-(3-(4-(7-(5-cyanofuran-2-yl)-4-morpholino-quinazolin-2-yl)-3-fluorophenyl)ureido)-N,N-dimethyl-benzamide 
• 1374203-83-4 4-(3-(4-(7-(5-acetylfuran-2-yl)-4-morpholino-quinazolin-2-yl)phenyl)ureido)-2-fluoro-N,N-dimethyl-benzamide 
• 1374203-87-8 N-(4-(3-(4-(7-(5-methylfuran-2-yl)-4-morpholino-quinazolin-2-yl)phenyl)ureido)phenyl)acetamide 
• 1374203-88-9 1-(4-(7-(5-methylfuran-2-yl)-4-morpholino-quinazolin-2-yl)phenyl)-3-(4-(2-oxopyrrolidin-1-yl)phenyl)urea 
• 1374203-71-0 N,N-dimethyl-4-(3-{4-[4-morpholin-4-yl-7-pyrimidin-5-yl-quinazolin-2-yl]-phenyl}-ureido)-benzamide 
• 959237-68-4 7-bromine-2,4-dichloroquinazoline 
• 1374203-73-2 4-(3-{5-[7-(3-methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridin-2-yl}-ureido)-dimethyl-benzamide 
• 1374208-37-3 4-(2-chloro-7-(3-(methylsulfonyl)phenyl)quinazolin-4-yl)morpholine 
• 1374208-38-4 5-[7-(3-methanesulfonyl-phenyl)-4-morpholin-4-yl-quinazolin-2-yl]-pyridin2-ylamine 
• 1334602-72-0 7-bromo-2,4-bis(4-methoxybenzyloxy)quinazoline 
• 1334602-73-1 2,4-bis(4-methoxybenzyloxy)-7-morpholin-4-ylquinazoline 

Relevant academic research and scientific papers

Synthesis, Inhibitory Activity, and in Silico Modeling of Selective COX-1 Inhibitors with a Quinazoline Core

Selective cyclooxygenase-1 (COX-1) inhibition has got into the spotlight with the discovery of COX-1 upregulation in various cancers and the cardioprotective role of COX-1 in control of thrombocyte aggregation. Yet, COX-1-selective inhibitors are poorly explored. Thus, three series of quinazoline derivatives were prepared and tested for their potential inhibitory activity toward COX-1 and COX-2. Of the prepared compounds, 11 exhibited interesting COX-1 selectivity, with 8 compounds being totally COX-1-selective. The IC50 value of the best quinazoline inhibitor was 64 nM. The structural features ensuring COX-1 selectivity were elucidated using in silico modeling.

DBU coupled ionic liquid-catalyzed efficient synthesis of quinazolinones from CO2 and 2-aminobenzonitriles under mild conditions

Efficient and green strategy for the chemical conversion and fixation of CO2 is an attractive topic. In this work, we reported an efficient catalytic system of organic base coupled ionic liquids that could catalyse the synthesis of quinazolinones via cyclization of 2-aminobenzonitriles with CO2 under mild conditions (e.g., 60 °C, 0.1 MPa). It was found that 1,8-diazabicyclo[5.4.0]undec-7-ene coupled 1-butyl-3-methylimidazole acetate ionic liquids (DBU/[Bmim][OAc]) displayed excellent performance in catalysing the reactions of CO2 with 2-aminobenzonitriles, and a series of quinazolinones were obtained in high yields at atmospheric pressure. Moreover, the ILs had high stability and reusability, and can be reused at least five times without considerable decrease in catalytic activity. This protocol could also be conducted on a gram scale, and may have promising and practical applications in the production of quinazolinones.

[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.

DIACYLGLYCEROL KINASE MODULATING COMPOUNDS

The present disclosure provides diacylglycerol kinase modulating compounds, and pharmaceutical compositions thereof, for treating cancer, including solid tumors, and viral infections, such as HIV or hepatitis B virus infection. The compounds can be used alone or in combination with other agents.

N2N N4-disubstituted quinazoline-2,4-diamines and uses thereof

Described herein are quinazoline-based compounds and formulations thereof. In some embodiments, the compounds and/or formulations thereof can be effective to inhibit and/or kill A. baumannii. Also described herein are methods of treating a subject in need thereof by administering to the subject in need thereof a quinazoline-based compound and/or formulation thereof to the subject in need thereof.

HETEROCYCLIC COMPOUNDS AS PRMT5 INHIBITORS

The present disclosure describes novel PRMT5 inhibitors and methods for preparing them. The pharmaceutical compositions comprising such PRMT5 inhibitors and methods of using them for treating cancer, infectious diseases, and other PRMT5 associated disorde

Characterizing the antimicrobial activity of N2,N4-disubstituted quinazoline-2,4-diamines toward multidrug-resistant Acinetobacter baumannii

We previously reported a series of N2,N4-disubstituted quinazoline-2,4- diamines as dihydrofolate reductase inhibitors with potent in vitro and in vivo antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) strains. In this work, we extended our previous study to the Gram-negative pathogen Acinetobacter baumannii. We determined that optimized N2,N4-disubstituted quinazoline-2,4-diamines are strongly antibacterial against multidrug-resistant A. baumannii strains when the 6-position is replaced with a halide or an alkyl substituent. Such agents display potent antibacterial activity, with MICs as low as 0.5 μM, while proving to be strongly bactericidal. Interestingly, these compounds also possess the potential for antibiofilm activity, eradicating 90% of cells within a biofilm at or near MICs. Using serial passage assays, we observed a limited capacity for the development of resistance toward these molecules (4-fold increase in MIC) compared to existing folic acid synthesis inhibitors, such as trimethoprim (64-fold increase) and sulfamethoxazole (128-fold increase). We also identified limited toxicity toward human cells, with 50% lethal doses (LD50s) of ≤23 μM for lead agents 4 and 5. Finally, we demonstrated that our lead agents have excellent in vivo efficacy, with lead agent 5 proving more efficacious than tigecycline in a murine model of A. baumannii infection (90% survival versus 66%), despite being used at a lower dose (2 versus 30 mg kg-1). Together, our results demonstrate that N2,N4-disubstituted quinazoline-2,4-diamines have strong antimicrobial and antibiofilm activities against both Gram-positive organisms and Gram-negative pathogens, suggesting strong potential for their development as antibacterial agents.

Discovery and SAR of a novel series of Natriuretic Peptide Receptor-A (NPR-A) agonists

Novel thienopyrimidine compounds 2 and 3 were discovered from high-throughput screening as Natriuretic Peptide Receptor A (NPR-A) agonists. Scaffold hopping of a thienopyrimidine ring to a quinazoline ring, introduction of the basic functional group and optimization of the substituent on the 6-position of the benzene ring of quinazoline led to improved agonistic activity. We discovered compound 48, which showed potent agonistic activity for NPR-A with an EC50 value of 0.073 μM, indicating 350-fold potency compared to the hit compound 3.

Discovery of 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine as a Potent IKur Inhibitor

A new series of phenylquinazoline inhibitors of Kv 1.5 is disclosed. The series was optimized for Kv 1.5 potency, selectivity versus hERG, pharmacokinetic exposure, and pharmacodynamic potency. 5-Phenyl-N-(pyridin-2-ylmethyl)-2-(pyrimidin-5-yl)quinazolin-4-amine (13k) was identified as a potent and ion channel selective inhibitor with robust efficacy in the preclinical rat ventricular effective refractory period (VERP) model and the rabbit atrial effective refractory period (AERP) model.

Substituted Amino-Pyrimidine Derivatives

The present application provides novel substituted quinazoline and pyrido-pyrimidine compounds and pharmaceutically acceptable salts, prodrugs, and solvates thereof. Also provided are methods for preparing these compounds. These compounds are useful in co-regulating PI3K and/or mTOR activity by administering a therapeutically effective amount of one or more of the compounds to a patient. By doing so, these compounds are effective in treating conditions associated with the dysregulation of the PI3K/AKT/mTOR pathway. Advantageously, these compounds perform as dual PI3K/mTOR inhibitors. A variety of conditions can be treated using these compounds and include diseases which are characterized by inflammation or abnormal cellular proliferation. In one embodiment, the disease is cancer.