127168-84-7

Usage

Uses

Used in Pharmaceutical Industry:
5-Bromoisoindoline is used as a key intermediate in the synthesis of 2,3-dihydro-1H-isoindoles, which are known for their high affinity and selectivity for the dopamine D3 receptor. These synthesized compounds have potential applications in the treatment of various neurological and psychiatric disorders, such as schizophrenia, Parkinson's disease, and drug addiction, by modulating the dopaminergic system.

InChI:InChI=1/C8H8BrN/c9-8-2-1-6-4-10-5-7(6)3-8/h1-3,10H,4-5H2

Upstream product

• 6941-75-9 5-Bromoisoindoline-1,3-dione 
• 1423-27-4 2-(trifluoromethyl)phenylboronic acid 
• 24424-99-5 di-tert-butyl dicarbonate 
• 64990-51-8 hydrochloric acid 1,4-dioxane 
• 85-44-9 phthalic anhydride 
• 69189-19-1 4-bromo-1,2-bis-bromomethyl-benzene 
• 583-71-1 4-bromo-o-xylene 
• 127168-85-8 2-(p-toluenesulfonyl)-5-bromoisoindoline 
• 86-90-8 4-bromophthalic anhydride 

Downstream Products

• 437651-72-4 {4-[2-(5-bromo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester 
• 201940-08-1 5-bromo-1,3-dihydro-isoindole-2-carboxylic acid tert-butyl ester 
• 905273-91-8 tert-butyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-dihydro-2H-isoindole-2-carboxylate 
• 437652-06-7 4-[2-(5-bromo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclohexylamine 
• 405150-03-0 5-bromo-2-trityl-2,3-dihydro-1H-isoindole 
• 913000-29-0 (5-bromo-1,3-dihydro-isoindol-2-yl)-(5-isopropyl-2,4-dimethoxyphenyl)-methanone 
• 913000-21-2 (2,4-bis-benzyloxy-5-isopropenylphenyl)-(5-bromo-1,3-dihydroisoindol-2-yl)methanone 
• 1181690-78-7 (R)-5-(4-(2-(2-methylpyrrolidin-1-yl)ethyl)phenyl)isoindoline 
• 1208147-37-8 C₂₆H₁₇BrCl₂N₄O 
• 1240040-82-7 ethyl N-[4-(1-{1-(4-chlorophenyl)-2-oxo-2-[5-bromo-1,3-dihydro-2H-isoindol-2-yl]ethyl}butyl)benzoyl]-β-alaninate 
• 1126832-42-5 2,4-bisbenzyloxy-N-butyl-5-(5-bromo-1,3-dihydroisoindole-2-carbonyl)-N-methylbenzamide 
• 253801-14-8 tert-butyl 5-(hydroxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate 

Relevant academic research and scientific papers

2-Amino-2,3-dihydro-1 H-indene-5-carboxamide-Based Discoidin Domain Receptor 1 (DDR1) Inhibitors: Design, Synthesis, and in Vivo Antipancreatic Cancer Efficacy

A series of 2-amino-2,3-dihydro-1H-indene-5-carboxamides were designed and synthesized as new selective discoidin domain receptor 1 (DDR1) inhibitors. One of the representative compounds, 7f, bound with DDR1 with a Kd value of 5.9 nM and suppre

Development of Dihydroxyphenyl Sulfonylisoindoline Derivatives as Liver-Targeting Pyruvate Dehydrogenase Kinase Inhibitors

Pyruvate dehydrogenase kinases 1-4 (PDK1-4) negatively control activity of the pyruvate dehydrogenase complex (PDC) and are up-regulated in obesity, diabetes, heart failure, and cancer. We reported earlier two novel pan-PDK inhibitors PS8 [4-((5-hydroxyisoindolin-2-yl)sulfonyl)benzene-1,3-diol] (1) and PS10 [2-((2,4-dihydroxyphenyl)sulfonyl)isoindoline-4,6-diol] (2) that targeted the ATP-binding pocket in PDKs. Here, we developed a new generation of PDK inhibitors by extending the dihydroxyphenyl sulfonylisoindoline scaffold in 1 and 2 to the entrance region of the ATP-binding pocket in PDK2. The lead inhibitor (S)-3-amino-4-(4-((2-((2,4-dihydroxyphenyl)sulfonyl)isoindolin-5-yl)amino)piperidin-1-yl)-4-oxobutanamide (17) shows a ～8-fold lower IC50 (58 nM) than 2 (456 nM). In the crystal structure, the asparagine moiety in 17 provides additional interactions with Glu-262 from PDK2. Treatment of diet-induced obese mice with 17 resulted in significant liver-specific augmentation of PDC activity, accompanied by improved glucose tolerance and drastically reduced hepatic steatosis. These findings support 17 as a potential glucose-lowering therapeutic targeting liver for obesity and type 2 diabetes.

The design, synthesis and structure-activity relationships of novel isoindoline-based histone deacetylase inhibitors

The design, synthesis and biological evaluation of a novel series of isoindoline-based hydroxamates is described. Several analogs were shown to inhibit HDAC1 with IC50 values in the low nanomolar range and inhibit cellular proliferation of HCT116 human colon cancer cells in the sub-micromolar range. The cellular potency of compound 17e was found to have greater in vitro anti-proliferative activity than several compounds in late stage clinical trials for the treatment of cancer. The in vitro safety profiles of selected compounds were assessed and shown to be suitable for further lead optimization.

APPLICATION OF MONOCYCLIC BETA-LACTAM COMPOUND IN PHARMACY

An application of a compound represented by formula (I) and pharmaceutically acceptable salts thereof in preparation of a drug for treating pneumonia.

Isoindoline scaffold-based dual inhibitors of HDAC6 and HSP90 suppressing the growth of lung cancer in vitro and in vivo

This study reports the synthesis of a series of 2-aroylisoindoline hydroxamic acids employing N-benzyl, long alkyl chain and acrylamide units as diverse linkers. In-vitro studies led to the identification of N-benzyl linker-bearing compound (10) and long

MONOCYCLIC B-LACTAM COMPOUND FOR TREATING BACTERIAL INFECTION

Disclosed are a class of new monocyclic β-lactam compounds, an isomer thereof or pharmaceutically acceptable salts thereof, and a pharmaceutical composition comprising the compounds, and the use of same in preparing drugs for treating diseases associated

CRYSTAL OF DPP-IV LONG-ACTING INHIBITOR AND SALT

The present application relates a crystal of a compound represented by Formula (I), a salt thereof, and a crystal of the salt thereof, a method for preparing the crystal of the compound represented by Formula (I), the salt thereof, and the crystal of the

Intramolecular Reductive Cyclization of o-Nitroarenes via Biradical Recombination

A visible-light-induced/thiourea-mediated intramolecular cyclization of o-nitroarenes under mild conditions is realized for the first time, which provides an efficient and environmentally friendly way to access pharmaceutical relevant quinazolinone derivatives. The reaction can be easily extended to gram level by using a continuous-flow setup with high efficiency. Mechanistic investigation including control experiments, transient fluorescence, UV-vis spectra, and DFT calculations suggests that the formation of active biradical intermediates via intramolecular single electron transfer (SET) is key stage in the catalytic cycle.

Metal-Free Synthesis of Polycyclic Quinazolinones Enabled by a (NH4)2S2O8-Promoted Intramolecular Oxidative Cyclization

An efficient metal-free, (NH4)2S2O8 mediated intramolecular oxidative cyclization for the construction of polycyclic heterocycles was disclosed. A series of polycyclic quinazolinone derivatives with good functional group tolerance were obtained in high yields. The natural products tryptanthrin and rutaecarpine, as well as their derivatives, were easily synthesized by this strategy. A preliminary mechanism study suggested the carbon-centered radical was involved in the catalytic cycle.

GPR40 receptor stimulant, and preparation method, pharmaceutical composition and application thereof

The invention discloses a GPR40 receptor stimulant, and a preparation method, a pharmaceutical composition and application thereof. The invention particularly discloses a GPR40 receptor stimulant shown in general formula (I) and pharmacologically acceptable salt thereof, a preparation process of the compound, a pharmaceutical composition containing the compound of general formula (I), and application of the compound and the pharmaceutical composition in anti-diabetes.