959237-68-4

Basic information

• Product Name: 2,4-DICHLORO-7-BROMOQUINAZOLINE
• Synonyms: 2,4-DICHLORO-7-BROMOQUINAZOLINE;7-Bromo-2,4-dichloroquinazoline
• CAS NO: 959237-68-4
• Molecular Formula: C₈H₃BrCl₂N₂
• Molecular Weight: 277.94
• Mol File: 959237-68-4.mol

Chemical Properties

• Boiling Point: 330.2±24.0 °C(Predicted)
• Appearance: /
• Density: 1.851±0.06 g/cm3(Predicted)
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• PKA: -1.17±0.30(Predicted)
• CAS DataBase Reference: 2,4-DICHLORO-7-BROMOQUINAZOLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 2,4-DICHLORO-7-BROMOQUINAZOLINE(959237-68-4)
• EPA Substance Registry System: 2,4-DICHLORO-7-BROMOQUINAZOLINE(959237-68-4)

Safety Data

• Hazardous Substances Data: 959237-68-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,4-DICHLORO-7-BROMOQUINAZOLINE is used as a chemical intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 2,4-DICHLORO-7-BROMOQUINAZOLINE is utilized as an intermediate in the production of agrochemicals. Its reactivity and structural attributes make it instrumental in formulating effective compounds for agricultural applications, such as pesticides and herbicides, thereby supporting crop protection and yield enhancement.
Used in Organic Synthesis:
2,4-DICHLORO-7-BROMOQUINAZOLINE is employed as a building block in organic synthesis for creating a diverse range of organic compounds. Its versatility in chemical reactions enables the production of specialized molecules for various applications across different industries, including but not limited to, materials science, chemical research, and the development of new chemical entities.

Upstream product

• 20776-48-1 2-amino-6-chlorobenzoic acid 
• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 65971-74-6 N-(3-bromophenyl)-2-(hydroxyimino)ethanamide 
• 6326-79-0 6-bromoisatin 
• 114703-12-7 7-bromoquinazoline-2,4(1H,3H)-dione 
• 591-19-5 m-Bromoaniline 

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 
• 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 

Relevant articles and documents

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.

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.

CD73 INHIBITORS

Disclosed are compounds that are inhibitors of CD73 and are useful in treating CD73-associated diseases or conditions, and compositions containing the compounds.

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

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.

HEPARANASE INHIBITORS AND USE THEREOF

The invention relates to functionalized quinazoline compounds, pharmaceutical compositions comprising such compounds, and the use of such compounds as heparanase inhibitors for the treatment of diseases or conditions related to heparanse activity.

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.

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.

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.

Morpholinylquinazolines

The invention relates to compounds of the formulae (I), (II) and (III) in which R1, R2, R3, R4, Y, W1, W2, L, A, Alk, Cyc, Ar, Het1, Het2, Hal and n have the meaning indicated in claim 1, and/or physiologically acceptable salts, tautomers and stereo-isomers thereof, including mixtures thereof in all ratios. The compounds of the formula (I) can be used for the inhibition of serine/threonine protein kinases and for the sensitisation of cancer cells to anticancer agents and/or ionising radiation. The invention also relates to the use of the compounds of the formula (I) in the prophylaxis, therapy or progress control of cancer, tumours, metastases or angiogenesis disorders, in combination with radiotherapy and/or an anticancer agent. The invention furthermore relates to a process for the preparation of the compounds of the formula (I) by reaction of compounds of the formulae (II) and (III) and optionally conversion of a base or acid of the compounds of the formula (I) into one of their salts.