82827-09-6

Basic information

• Product Name: 6-BROMO-2H-ISOQUINOLIN-1-ONE
• Synonyms: 6-BROMO-2H-ISOQUINOLIN-1-ONE;6-BROMOISOQUINOLIN-1-ONE;6-bromoisoquinolin-1(2H)-one;6-broMo-1,2-dihydroisoquinolin-1-one;6-broMo-1,2-dihydro-1-oxoisoquinoline;6-BroMo-2H-isoquinolin-1-one, 95+%;6-bromo-2H-isoquinoline-1-one
• CAS NO: 82827-09-6
• Molecular Formula: C₉H₆BrNO
• Molecular Weight: 224.05
• Mol File: 82827-09-6.mol

Chemical Properties

• Boiling Point: 442.634 °C at 760 mmHg
• Flash Point: 221.498 °C
• Appearance: /
• Density: 1.62 g/cm³
• Storage Temp.: 2-8°C
• PKA: 12.20±0.20(Predicted)
• CAS DataBase Reference: 6-BROMO-2H-ISOQUINOLIN-1-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 6-BROMO-2H-ISOQUINOLIN-1-ONE(82827-09-6)
• EPA Substance Registry System: 6-BROMO-2H-ISOQUINOLIN-1-ONE(82827-09-6)

Safety Data

• Hazardous Substances Data: 82827-09-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
6-Bromo-2H-isoquinolin-1-one is used as a reagent in the fragment-based discovery of ROCK-I inhibitors derived from 6-substituted isoquinolin-1-amine. These inhibitors play a crucial role in the development of new therapeutic agents for various diseases.
Additionally, 6-Bromo-2H-isoquinolin-1-one is also used in the discovery of novel isoquinolone PDK1 inhibitors. PDK1 (Phosphoinositide-dependent protein kinase-1) is an enzyme that plays a significant role in cell survival and growth, and its inhibition can offer a potentially new therapeutic modality for cancer treatment. By targeting PDK1, these inhibitors can help in the development of more effective cancer therapies.

Upstream product

• 14473-91-7 3-Bromocinnamic acid 
• 1220229-19-5 (E)-4-bromo-2-(2-(dimethylamino)vinyl)benzonitrile 
• 223671-16-7 6-bromoisoquinoline nitrogen oxide 
• 13162-05-5 n-vinylformamide 
• 586-76-5 4-Bromobenzoic acid 
• 586-75-4 4-chlorobenzoyl chloride 
• 108-05-4 vinyl acetate 
• 1352801-45-6 (4-bromophenyl)formamido 2,2-dimethylpropanoate 
• 1034558-65-0 (E)-1-bromo-3-(2-isocyanatovinyl)benzene 
• 205055-63-6 6-bromo-1-chloroisoquinoline 
• 34784-05-9 6-bromo-isoquinoline 

Downstream Products

• 444898-85-5 C₃₅H₂₆BrNO₈ 
• 1036712-60-3 1-benzyloxy-6-bromo-isoquinoline 
• 1036712-58-9 6-bromo-2-(4-methoxy-benzyl)-2H-isoquinolin-1-one 
• 1070294-81-3 N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((4-(2-hydroxyethyl)-1,4-diazepan-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-83-5 4-((6-(5-(cyclopropylcarbamoyl)-3-fluoro-2-methylphenyl)-2-(cyclopropylmethyl)-1-oxo-1,2-dihydroisoquinolin-4-yl)methyl)-1-(2-hydroxyethyl)-1,4-diazepane 1-oxide 
• 1070295-55-4 (S)-N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((2-(hydroxymethyl)piperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-96-0 (R)-N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)-4-methylpiperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-93-7 (R)-N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-(hydroxymethyl)piperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-72-2 N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((4-methyl-1,4-diazepan-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070295-72-5 (S)-N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((2-methylpiperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-87-9 N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((4-(methylamino)piperidin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-5-fluoro-4-methylbenzamide 
• 1070294-25-5 N-cyclopropyl-3-[2-cyclopropylmethyl-4-(4-methyl[1,4]diazepan-1-ylmethyl)-1-oxo-1,2-dihydroisoquinolin-6-yl]-4-methylbenzamide 
• 1070293-31-0 N-cyclopropyl-4-methyl-3-{1-oxo-2-[3-(2-pyrrolidin-1-ylethoxy)benzyl]-1,2-dihydroisoquinolin-6-yl}benzamide 
• 1070294-46-0 (S)-N-cyclopropyl-3-(2-(cyclopropylmethyl)-4-((3-methylpiperazin-1-yl)methyl)-1-oxo-1,2-dihydroisoquinolin-6-yl)-4-methylbenzamide 

Relevant articles and documents

Light-induced [2 + 2] cycloadditions for the construction of cyclobutane-fused pyridinyl sulfonyl fluorides

Cyclobutanes are an important class of motifs present in a wide range of natural products and other biologically significant molecules. A photocatalytic [2 + 2] cycloaddition between pyridones or isoquinolones and ethenesulfonyl fluoride was achieved, providing a portal to a class of unique cyclobutane-fused pyridinyl sulfonyl fluorides with quaternary rigid rings (30 examples). Further applications of these novel sulfonyl fluoride molecules in SuFEx click chemistry were also accomplished, providing the corresponding sulfonates and sulphonamides with reasonable yields.

Aromatic compounds and preparation method and application thereof

The invention discloses aromatic compounds and a preparation method and application thereof. The preparation method of the aromatic compounds includes the step of performing a cyclization reaction between an amide compound and a benzoic acid compound in the presence of a rhodium catalyst, a metal oxidant and base, wherein the aromatic compounds are isoquinolinone compounds or isocoumarin derivatives, and the amide compound is N-vinylformamide or N-vinylacetamide. Through the synergistic effect of the rhodium catalyst, the metal oxidant and the base, the isoquinolinone compounds or isocoumarinderivatives are obtained through the one-step reaction between the benzoic acid compound and the amide compound. The reaction has simple operation, the raw materials are cheap and easily available, reaction substrates can be selected flexibly according to the required isoquinolinone compounds and the isocoumarin derivatives, and the synthesized isoquinolinone compounds and the isocoumarin derivatives can be used as a backbone structure in multiple biologically active molecules and natural products, and have high practicality.

Divergent Synthesis of Isoquinolone and Isocoumarin Derivatives by the Annulation of Benzoic Acid with N-Vinyl Amide

A simple and efficient method for the synthesis of isoquinolone and isocoumarin derivatives is reported. The method for the first time provides a one-step divergent synthesis of important isoquinolone and isocoumarin skeletons from benzoic acid by switching the coupling partners. In addition, a reliable mechanism has been proposed on the basis of experimental investigations, including kinetic isotope effect experiments, 13C labeling experiments, time-tracking experiments, and competitive experiments, as well as DFT calculation studies.

Protozoan Parasite Growth Inhibitors Discovered by Cross-Screening Yield Potent Scaffolds for Lead Discovery

Tropical protozoal infections are a significant cause of morbidity and mortality worldwide; four in particular (human African trypanosomiasis (HAT), Chagas disease, cutaneous leishmaniasis, and malaria) have an estimated combined burden of over 87 million disability-adjusted life years. New drugs are needed for each of these diseases. Building on the previous identification of NEU-617 (1) as a potent and nontoxic inhibitor of proliferation for the HAT pathogen (Trypanosoma brucei), we have now tested this class of analogs against other protozoal species: T. cruzi (Chagas disease), Leishmania major (cutaneous leishmaniasis), and Plasmodium falciparum (malaria). Based on hits identified in this screening campaign, we describe the preparation of several replacements for the quinazoline scaffold and report these inhibitors' biological activities against these parasites. In doing this, we have identified several potent proliferation inhibitors for each pathogen, such as 4-((3-chloro-4-((3-fluorobenzyl)oxy)phenyl)amino)-6-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)quinoline-3-carbonitrile (NEU-924, 83) for T. cruzi and N-(3-chloro-4-((3-fluorobenzyl)oxy)phenyl)-7-(4-((4-methyl-1,4-diazepan-1-yl)sulfonyl)phenyl)cinnolin-4-amine (NEU-1017, 68) for L. major and P. falciparum.

Rhodium(III)-catalyzed C-H activation/annulation with vinyl esters as an acetylene equivalent

The behavior of electron-rich alkenes in rhodium-catalyzed C-H activation/annulation reactions is investigated. Vinyl acetate emerges as a convenient acetylene equivalent, facilitating the synthesis of sixteen 3,4-unsubstituted isoquinolones, as well as select heteroaryl-fused pyridones. The complementary regiochemical preferences of enol ethers versus enol esters/enamides is discussed.

N1-PYRAZOLOSPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS

The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt of the compound, wherein R1, R2, R3 and R4 are as described herein; pharmaceutical compositions there-of; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl- CoA carboxylase enzyme(s) in an animal

N2-PYRAZOLOSPIROKETONE ACETYL-COA CARBOXYLASE INHIBITORS

The invention provides a compound of Formula (I) or a pharmaceutically acceptable salt of said compound, wherein R1, R2, R3 and R4 are as described herein; pharmaceutical compositions thereof; and the use thereof in treating diseases, conditions or disorders modulated by the inhibition of an acetyl- CoA carboxylase enzyme(s) in an animal.

Fragment-based discovery of 6-substituted isoquinolin-1-amine based ROCK-I inhibitors

Fragment-based NMR screening of a small literature focused library led to identification of a historical thrombin/FactorXa building block, 17A, that was found to be a ROCK-I inhibitor. In the absence of an X-ray structure, fragment growth afforded 6-substituted isoquinolin-1-amine derivatives which were profiled in the primary ROCK-I IMAP assay. Compounds 23A and 23E were selected as fragment optimized hits for further profiling. Compound 23A has similar ROCK-1 affinity, potency and cell based efficacy to the first generation ROCK inhibitors, however, it has a superior PK profile in C57 mouse. Compound 23E demonstrates the feasibility of improving ROCK-1 affinity, potency and cell based efficacy for the series, however, it has a poor PK profile relative to 23A.

ISOQUINOLINONE DERIVATIVES

The present invention relates to isoquinolinone derivatives of formula (I): wherein are as herein defined; processes for their preparation, pharmaceutical compositions containing them and their use in therapy.

Diels-alder reactions of a styrene-isocyanate: Unexpected formation of a pyridinone and uracil

During the preparation of 6-bromoisoquinolinone, a novel and unexpected reaction occurred to form a pyridinone and a pyrimidine-2,4-dione. We propose a [4+2] Diels-Alder dimerization of an intermediate styrene-isocyanate to explain the observed products.