573675-55-5

Usage

Uses

Used in Pharmaceutical Industry:
7-Bromo-4-chloroquinazoline is used as an intermediate in the production of pharmaceuticals, particularly for the development of anticancer agents and anti-inflammatory drugs. Its unique chemical properties allow it to be incorporated into the molecular structures of these drugs, enhancing their therapeutic effects and targeting specific biological pathways.
Used in Agrochemical Industry:
In the agrochemical industry, 7-Bromo-4-chloroquinazoline is utilized in the production of herbicides and insecticides. Its ability to target and disrupt essential biological processes in pests and weeds makes it a valuable component in the development of effective and targeted agrochemicals.
As a Heterocyclic Building Block:
7-Bromo-4-chloroquinazoline is used as a heterocyclic building block for the synthesis of a variety of compounds with diverse applications. Its unique structure allows chemists to modify and functionalize it, creating new molecules with specific properties and functions.
In Medicinal Chemistry Research:
7-Bromo-4-chloroquinazoline is employed in medicinal chemistry research as a starting material for the design and synthesis of novel therapeutic agents. Its versatility and reactivity make it an attractive candidate for the development of new drugs with improved efficacy and selectivity.
In Drug Discovery and Development:
7-Bromo-4-chloroquinazoline is used in drug discovery and development processes to identify and optimize potential drug candidates. Its unique chemical properties and ability to interact with various biological targets make it a valuable tool in the search for new and effective treatments for various diseases and conditions.
In Chemical Synthesis:
7-Bromo-4-chloroquinazoline is utilized in various chemical synthesis processes, including the preparation of complex organic molecules and the modification of existing compounds. Its reactivity and compatibility with a wide range of reagents make it a useful building block in the synthesis of diverse chemical entities.

InChI:InChI=1/C8H4BrClN2/c9-5-1-2-6-7(3-5)11-4-12-8(6)10/h1-4H

Upstream product

• 194851-16-6 7-bromoquinazolin-4(3H)-one 
• 135484-83-2 2-amino-4-bromo-benzoic acid methyl ester 
• 20776-50-5 2-amino-4-bromobenzoic acid 
• 194851-16-6 7-bromo-4-hydroxyquinazoline 

Downstream Products

• 1334602-74-2 4-(4-chloroquinazolin-7-yl)morpholine 
• 1334602-75-3 7-bromo-4-((4-methoxybenzyl)oxy)quinazoline 
• 1186390-25-9 sodium methyl 4-(4-(5-(2-(3-fluorophenylamino)-2-oxoethyl)-1H-pyrazol-3-ylamino)quinazolin-7-yl)benzoate 
• 1186390-31-7 2-(4-(4-(4-(5-(2-(3-fluorophenylamino)-2-oxoethyl)-1H-pyrazol-3-ylamino)quinazolin-7-yl)benzoyl)piperazin-1-yl)ethyl dihydrogen phosphate 
• 1186390-17-9 C₃₈H₄₅FN₈O₃Si 
• 1186390-26-0 2-(3-(7-(4-(4-(cyclopropylmethyl)piperazine-1-carbonyl)phenyl)quinazolin-4-ylamino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide 
• 1186390-09-9 N-(3-fluorophenyl)-2-(3-(7-(4-(4-(2-hydroxyethyl)piperazine-1-carbonyl)phenyl)quinazolin-4-ylamino)-1H-pyrazol-5-yl)acetamide 
• 1186390-07-7 (S)-N-(3-fluorophenyl)-2-(3-(7-(4-(3-fluoropyrrolidin-1-ylsulfonyl)phenyl)quinazolin-4-ylamino)-1H-pyrazol-5-yl)acetamide 
• 1186390-24-8 methyl 4-(4-(5-(2-(3-fluorophenylamino)-2-oxoethyl)-1H-pyrazol-3-ylamino)quinazolin-7-yl)benzoate 
• 1186390-14-6 2-(3-(7-bromoquinazolin-4-ylamino)-1H-pyrazol-5-yl)-N-(3-fluorophenyl)acetamide 
• 1186390-23-7 N-(3-fluorophenyl)-2-(3-(quinazolin-4-ylamino)-1H-pyrazol-5-yl)acetamide 

Relevant academic research and scientific papers

Discovery of BPR1R024, an Orally Active and Selective CSF1R Inhibitor that Exhibits Antitumor and Immunomodulatory Activity in a Murine Colon Tumor Model

Colony-stimulating factor-1 receptor (CSF1R) is implicated in tumor-associated macrophage (TAM) repolarization and has emerged as a promising target for cancer immunotherapy. Herein, we describe the discovery of orally active and selective CSF1R inhibitors by property-driven optimization of BPR1K871 (9), our clinical multitargeting kinase inhibitor. Molecular docking revealed an additional nonclassical hydrogen-bonding (NCHB) interaction between the unique 7-aminoquinazoline scaffold and the CSF1R hinge region, contributing to CSF1R potency enhancement. Structural studies of CSF1R and Aurora kinase B (AURB) demonstrated the differences in their back pockets, which inspired the use of a chain extension strategy to diminish the AURA/B activities. A lead compound BPR1R024 (12) exhibited potent CSF1R activity (IC50 = 0.53 nM) and specifically inhibited protumor M2-like macrophage survival with a minimal effect on antitumor M1-like macrophage growth. In vivo, oral administration of 12 mesylate delayed the MC38 murine colon tumor growth and reversed the immunosuppressive tumor microenvironment with the increased M1/M2 ratio.

DIARYLTHIOHYDANTOIN COMPOUND AS ANDROGEN RECEPTOR ANTAGONIST

The present application belongs to the field of medicine. In particular, the present application relates to a diarylthiohydantoin compound as an androgen receptor antagonist or a pharmaceutically acceptable salt thereof, a preparation method of the same, a pharmaceutical composition comprising the compound, and a use thereof in treating a cell proliferative disease mediated by androgen. The compound of the present application has good antagonistic effect on androgen receptor and exhibits excellent antitumor effect.

Quinazoline DNA-PK (deoxyribonucleic acid-polyketide) inhibitor

The invention belongs to the technical field of medicines, and particularly relates to quinazoline DNAPK inhibitor compounds, pharmaceutically acceptable salts or isomers thereof, pharmaceutical compositions and preparations containing the compounds, the pharmaceutically acceptable salts or the isomers thereof, and a method for preparing the compounds, the pharmaceutically acceptable salts or theisomers thereof, as well as uses of the compounds, pharmaceutically acceptable salts thereof, or isomers thereof.

HETEROCYCLIC COMPOUNDS AS KINASE INHIBITORS FOR THERAPEUTIC USES

Heterocyclic compounds of formula I shown below and pharmaceutical compositions containing one of such compounds: Also disclosed is a method of treating a condition modulated by the colony-stimulating factor-1 receptor with one of the heterocyclic compounds.

A Scaffold-Hopping Strategy toward the Identification of Inhibitors of Cyclin G Associated Kinase

We recently reported the discovery of isothiazolo[4,3-b]pyridine-based inhibitors of cyclin G associated kinase (GAK) displaying low nanomolar binding affinity for GAK and demonstrating broad-spectrum antiviral activity. To come up with novel core structures that act as GAK inhibitors, a scaffold-hopping approach was applied starting from two different isothiazolo[4,3-b]pyridines. In total, 13 novel 5,6- and 6,6-fused bicyclic heteroaromatic scaffolds were synthesized. Four of them displayed GAK affinity with Kd values in the low micromolar range that can serve as chemical starting points for the discovery of GAK inhibitors based on a different scaffold.

Synthesis and biological evaluation of new tetramethylpyrazine-based chalcone derivatives as potential anti-Alzheimer agents

In the current study, a series of new ligustrazine-based chalcones was synthesized. For insertion of tetramethylpyrazine (TMP, also designated as ligustrazine) in chemical backbone of chalcone, a new ligustrazine-based aldehyde was prepared. New ketones were synthesized for inclusion of quinazolin-4-yl amino and pyrazin-2-yl amino moieties. The newly synthesized compounds were screened for acetylcholinesterase, butyrylcholinesterase, and monoamine oxidases (MAO) inhibitory activities and also for in vitro cytotoxicity on PC12 cells. The effect of these compounds against amyloid β-induced cytotoxicity and aggregation was also investigated. The synthesized compounds effectively inhibited the related enzymes and also exhibited neuroprotective effects. Most of the compounds displayed better inhibitory potencies against Aβ aggregation than reference compounds. Some compounds such as 11e and 16b showed very potent effects on multiple targets exhibiting behavior as multifunctional anti-Alzheimer agents.

Compounds capable of inhibiting ErbB/HDAC and preparation method thereof, and pharmaceutical composition comprising compounds and application thereof

The invention relates to compounds capable of inhibiting ErbB/HDAC and a preparation method thereof, and a pharmaceutical composition comprising the compounds and application thereof. The compounds are disclosed as Formula 1. The compounds or pharmaceutically acceptable salts, solvates, esters, acids, metabolites or prodrugs thereof, or the pharmaceutical composition comprising the compounds can be used for preparing ErbB kinases and HDAC activity inhibitors and also preparing ErbB-kinase/HDAC-activated mediated disease curatives.

Development of Specific, Irreversible Inhibitors for a Receptor Tyrosine Kinase EphB3

Erythropoietin-producing human hepatocellular carcinoma (Eph) receptor tyrosine kinases (RTKs) regulate a variety of dynamic cellular events, including cell protrusion, migration, proliferation, and cell-fate determination. Small-molecule inhibitors of Eph kinases are valuable tools for dissecting the physiological and pathological roles of Eph. However, there is a lack of small-molecule inhibitors that are selective for individual Eph isoforms due to the high homology within the family. Herein, we report the development of the first potent and specific inhibitors of a single Eph isoform, EphB3. Through structural bioinformatic analysis, we identified a cysteine in the hinge region of the EphB3 kinase domain, a feature that is not shared with any other human kinases. We synthesized and characterized a series of electrophilic quinazolines to target this unique, reactive feature in EphB3. Some of the electrophilic quinazolines selectively and potently inhibited EphB3 both in vitro and in cells. Cocrystal structures of EphB3 in complex with two quinazolines confirmed the covalent linkage between the protein and the inhibitors. A "clickable" version of an optimized inhibitor was created and employed to verify specific target engagement in the whole proteome and to probe the extent and kinetics of target engagement of existing EphB3 inhibitors. Furthermore, we demonstrate that the autophosphorylation of EphB3 within the juxtamembrane region occurs in trans using a specific inhibitor. These exquisitely specific inhibitors will facilitate the dissection of EphB3's role in various biological processes and disease contribution.

THERAPEUTIC INHIBITORY COMPOUNDS

The invention provides compounds of Formula I and Formula II: A-B-C-D-E-F-G-J (I) C-D-E-F-G-J (II) wherein A, B, C, D, E, F, G, and J have any of the values defined in the specification, and salts thereof. The compounds are useful for inhibiting plasma kallikrein, and for treating a disease or condition in an animal where inhibition of plasma kallikrein is indicated.

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.