66728-98-1

Usage

Uses

Used in Pharmaceutical Synthesis:
4-Bromo-1-chloroisoquinoline is used as a key intermediate for the development of various pharmaceuticals. Its unique structure allows for the creation of new drugs with potential therapeutic applications, including the treatment of diseases and disorders.
Used in Agrochemical Synthesis:
In the agrochemical industry, 4-Bromo-1-chloroisoquinoline serves as an essential building block for the synthesis of pesticides and other crop protection agents. Its incorporation into these compounds can enhance their effectiveness in controlling pests and diseases, thereby improving crop yields and quality.
Used as a Reagent in Organic Chemistry:
4-Bromo-1-chloroisoquinoline is utilized as a reagent in various organic chemistry reactions, particularly in the formation of carbon-carbon and carbon-heteroatom bonds. Its reactivity and functional groups make it a valuable tool for chemists in the synthesis of complex organic molecules and the development of new chemical processes.
Handling and Storage:
Due to its potential hazards and reactivity, 4-Bromo-1-chloroisoquinoline is typically handled and stored under controlled conditions. Proper safety measures, such as the use of protective equipment and adherence to handling protocols, are essential to minimize risks associated with its use in research and industrial applications.

InChI:InChI=1/C9H5BrClN/c10-8-5-12-9(11)7-4-2-1-3-6(7)8/h1-5H

Upstream product

• 3749-21-1 4-bromoisoquinoline N-oxide 
• 19493-44-8 1-chloroisoquinoline 
• 3951-95-9 4-bromo-1,2-dihydroisoquinolin-1-one 
• 1532-97-4 4-bromoisoquinoline 
• 491-30-5 1-hydroxyisoquinoline 
• 491-30-5 1-isoquinolone 
• 3951-95-9 4-Bromo-1-hydroxyisoquinoline 

Downstream Products

• 746668-73-5 4-bromo-1-methoxyisoqionoline 
• 104704-41-8 4-amino-1-methylisoquinoline 
• 104704-48-5 C₁₅H₁₈N₂O₄ 
• 36556-06-6 5,6,7,8-tetrahydroisoquinoline 
• 26345-15-3 5,6,7,8-tetrahydro-isoquinolin-1-ol 
• 848841-48-5 4-boronic acid-1-chloro-isoquinoline 
• 1071541-73-5 4-(4-bromoisoquinolin-1-ylamino)phenol hydrochloride 
• 374555-10-9 1-chloro-4-benzylisoquinoline 
• 848841-61-2 4-benzyloxy-6-(1-chloro-isoquinolin-4-yl)-quinazoline 
• 351324-72-6 1-chloroisoquinoline-4-carbaldehyde 
• 1057681-00-1 6-[4-(1-benzylisoquinolin-4-yl)piperazin-1-yl]nicotinonitrile 
• 1374249-66-7 4-bromo-1-{4-(methoxycarbonyl)phenylcarbonyl}isoquinoline 
• 1353487-23-6 2-[1-[4-[2-(4-chlorophenyl)ethylcarbamoyl]benzoyl]isoquinolin-4-yl]oxyacetic acid 
• 1374249-71-4 tert-butyl 1-(4-{2-[(4-chlorophenyl)ethylamino]carbonyl}phenylcarbonyl)isoquinolin-4-yloxyacetate 

Relevant academic research and scientific papers

Discovery and biological evaluation of phthalazines as novel non-kinase TGFβ pathway inhibitors

TGFβ is crucial for the homeostasis of epithelial and neural tissues, wound repair, and regulating immune responses. Its dysregulation is associated with a vast number of diseases, of which modifying the tumor microenvironment is one of vital clinical interest. Despite various attempts, there is still no FDA-approved therapy to inhibit the TGFβ pathway. Major mainstream approaches involve impairment of the TGFβ pathway via inhibition of the TGFβRI kinase. With the purpose to identify non-receptor kinase-based inhibitors to impair TGFβ signaling, an in-house chemical library was enriched, through a computational study, to eliminate TGFβRI kinase activity. Selected compounds were screened against a cell line engineered with a firefly luciferase gene under TGFβ-Smad-dependent transcriptional control. Results indicated moderate potency for a molecule with phthalazine core against TGFβ-Smad signaling. A series of phthalazine compounds were synthesized and evaluated for potency. The most promising compound (10p) exhibited an IC50 of 0.11 ± 0.02 μM and was confirmed to be non-cytotoxic up to 12 μM, with a selectivity index of approximately 112-fold. Simultaneously, 10p was confirmed to reduce the Smad phosphorylation using Western blot without exhibiting inhibition on the TGFβRI enzyme. This study identified a novel small-molecule scaffold that targets the TGFβ pathway via a non-receptor-kinase mechanism.

SUBSTITUTED ARYLMETHYLUREAS AND HETEROARYLMETHYLUREAS, ANALOGUES THEREOF, AND METHODS USING SAME

The present invention includes substituted arylmethyl ureas and heteroarylmethyl-ureas, and compositions comprising the same, that can be used to treat or prevent hepatitis B virus (HBV) infections in a patient.

Novel 3-methylindoline inhibitors of EZH2: Design, synthesis and SAR

EZH2 (enhancer of zeste homologue 2) is the catalytic subunit of the polycomb repressive complex 2 (PRC2) that catalyzes the methylation of lysine 27 of histone H3 (H3K27). Dysregulation of EZH2 activity is associated with several human cancers and theref

Regioselective Chlorination of Quinoline N-Oxides and Isoquinoline N-Oxides Using PPh3/Cl3CCN

A novel method for the regioselective C2-chlorination of heterocyclic N-oxides has been developed. PPh3/Cl3CCN were used as chlorinating reagents and the desired N-heterocyclic chlorides were obtained smoothly in satisfactory yields. The reactions proceeded in a highly efficient and selective manner across a broad range of substrates demonstrating excellent functional group tolerance. In addition, this chlorination reaction can be used for the modification of N-heterocyclic scaffolds of appealing ligands and pharmaceuticals.

A practical and mild chlorination of fused heterocyclic N-oxides

Fused azine N-oxides were selectively chlorinated at C2 in moderate to excellent yields, employing Vilsmeier reagent as both the activating agent and the nucleophilic chloride source. Remarkable features of the method include simple operation, mild reaction conditions, a wide substrate scope, and the use of only stoichiometric amount of POCl3. The potential extension of this method to a one-pot oxidation/chlorination sequence that obviates the need for isolation of the N-oxide intermediates is also validated.

Microwave-assisted synthesis of quinoline, isoquinoline, quinoxaline and quinazoline derivatives as CB2 receptor agonists

Quinoline, isoquinoline, quinoxaline, and quinazoline derivatives were synthesized using microwave-assisted synthesis and their CB1/CB2 receptor activities were determined using the [35S]GTPγS binding assay. Most of the prepared quinoline, isoquinoline, and quinoxalinyl phenyl amines showed low-potency partial CB2 receptor agonists activity. The most potent CB2 ligand was the 4-morpholinylmethanone derivative (compound 40e) (-log EC 50 = 7.8; Emax = 75%). The isoquinolin-1-yl(3- trifluoromethyl-phenyl)amine (compound 26c) was a high efficacy CB2 agonist (-log EC50 = 5.8; Emax = 128%). No significant CB1 receptor activation or inactivation was shown in these studies, except 40e, which showed weak CB1 agonist activity (CB1 -log EC50 = 5.0). These ligands serve as novel templates for the development of selective CB2 receptor agonist.

Simple synthesis of 4-substituted 1(2H)-isoquinolinones via electrophilic trapping of lithiated mono- and dianion precursors

Synthetic routes have been developed to access 4-substituted 1(2H)-isoquinolinones from readily available precursors. This is achieved via electrophilic trapping of di- and monolithium anions derived from alkyllithium exchange of 4-bromo-1(2H)-isoquinolinones and corresponding 4-bromo-1- methoxyisoquinolines, respectively. Products derived from the latter are then hydrolyzed to the target 4-substituted 1(2H)-isoquinolinones. The methodology has potential application to access 4-substituted 1(2H)-isoquinolinones with additional substituents in either ring. Copyright Taylor & Francis Group, LLC.

The synthesis of a novel inhibitor of B-Raf kinase

A scaleable synthetic route to [4,7′]bis-isoquinolinyl-1-yl-(2-tert- butyl-pyrimidine-5-yl)amine (1), an inhibitor of B-Raf kinase is described. The key step in the synthesis is the Pd-catalyzed Negishi coupling of 4-bromo-1-chloroisoquinoline with triflu

1,4-DISUBSTITUTED ISOQUINILONE DERIVATIVES AS RAF-KINASE INHIBITORS USEFUL FOR THE TREATMENT OF PROLIFERATIVE DISEASES

This invention relates to compounds of formula (I) wherein the variable substituents are described herein. The compounds are useful for the treatment of conditions and diseases characterized by an aberrant MAP kinase signaling pathway, such as cancer.

Amide compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use

Amide compounds that modulate and/or inhibit the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction in order to modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer as well as other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.