501130-49-0

Basic information

• Product Name: 6-Bromoisoquinoline-1,3(2H,4H)-dione
• Synonyms: 6-Bromoisoquinoline-1,3(2H,4H)-dione;6-BroMo-4H-isoquinoline-1,3-dione
• CAS NO: 501130-49-0
• Molecular Formula: C9H6BrNO2
• Molecular Weight: 240.05344
• Product Categories: organic building block
• Mol File: 501130-49-0.mol

Chemical Properties

• Boiling Point: 442.5±45.0 °C(Predicted)
• Appearance: /
• Density: 1.696±0.06 g/cm3(Predicted)
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.70±0.20(Predicted)
• CAS DataBase Reference: 6-Bromoisoquinoline-1,3(2H,4H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Bromoisoquinoline-1,3(2H,4H)-dione(501130-49-0)
• EPA Substance Registry System: 6-Bromoisoquinoline-1,3(2H,4H)-dione(501130-49-0)

Safety Data

• Hazardous Substances Data: 501130-49-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
6-Bromoisoquinoline-1,3(2H,4H)-dione is used as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, contributing to the development of new drugs and pesticides. Its reactivity and potential for substitution reactions allow for the creation of a wide range of organic compounds with specific therapeutic or pesticidal properties.
Used in Research and Development:
In the field of research and development, 6-Bromoisoquinoline-1,3(2H,4H)-dione is utilized as a starting material for the synthesis of diverse functionalized isoquinoline derivatives. These derivatives can possess unique biological activities and properties, making them valuable for further exploration and potential applications in medicinal chemistry and chemical biology.
Used in Medicinal Chemistry:
6-Bromoisoquinoline-1,3(2H,4H)-dione plays a role in medicinal chemistry as a precursor for the synthesis of compounds with potential therapeutic applications. Its ability to undergo substitution reactions allows for the creation of new molecules with specific pharmacological properties, which can be further optimized for drug development.
Used in Chemical Biology:
In chemical biology, 6-Bromoisoquinoline-1,3(2H,4H)-dione is employed as a building block for the synthesis of bioactive molecules. These molecules can be used to study biological processes, target specific biological pathways, or serve as probes for understanding the mechanisms of action of various biological systems.

Upstream product

• 925672-87-3 C₁₁H₇BrN₂O₂ 
• 105942-08-3 4-bromo-6-fluorobenzonitrile 
• 925672-88-4 4-bromo-2-(cyanomethyl)benzonitrile 
• 943749-63-1 4-bromo-2-(carboxymethyl)benzoic acid 
• 57-13-6 urea 
• 698-67-9 p-bromobenzamide 
• 501130-36-5 dithiocarbonic acid S-[2-(4-bromo-benzoylamino)-2-oxo-ethyl] ester O-ethyl ester 

Downstream Products

• 552331-06-3 6-bromo-3-chloro-isoquinoline 
• 552331-05-2 6-bromo-1,3-dichloroisoquinoline 

Relevant articles and documents

Synthesis of medical intermediate disubstituted N-containing heterocycle amine compound

The invention relates to synthesis of a medical intermediate disubstituted N-containing heterocycle amine compound. The synthesis comprises the following steps: reacting 5-bromo-2-carboxy-phenylaceticacid, urea and o-dichlorobenzene as raw materials to obtain 6-bromoisoquinoline-1, 3 (2H,4H)-dione; allowing the 6-bromoisoquinoline-1, 3 (2H,4H)-dione to react with phenyl dichloro sphosphineoxide,adding tetrahydrofuran to precipitate out, adjusting the pH value, and then passing through a column to obtain 1, 3-dichloro-6-bromoisoquinoline; then adding glacial acetic acid, red phosphorus and hydroiodic acid, and after the reaction, determining whether the reaction is complete or not by TLC, subjecting the filtrate and the filter cake to repeated fine treatment to obtain 3-chloro-6-bromoisoquinoline; adding copper sulfate pentahydrate, 6-bromo-3-chloroisoquinoline and a large amount of 15% ammonia water to react in a high-pressure kettle, extracting and passing column for many times according to different requirements to obtain the final product 3-chloro-6-aminoisoquinoline.

Isoquinoline-1,3-diones as Selective Inhibitors of Tyrosyl DNA Phosphodiesterase II (TDP2)

Tyrosyl DNA phosphodiesterase II (TDP2) is a recently discovered enzyme that specifically repairs DNA damages induced by topoisomerase II (Top2) poisons and causes resistance to these drugs. Inhibiting TDP2 is expected to enhance the efficacy of clinically important Top2-targeting anticancer drugs. However, TDP2 as a therapeutic target remains poorly understood. We report herein the discovery of isoquinoline-1,3-dione as a viable chemotype for selectively inhibiting TDP2. The initial hit compound 43 was identified by screening our in-house collection of synthetic compounds. Further structure-activity relationship (SAR) studies identified numerous analogues inhibiting TDP2 in low micromolar range without appreciable inhibition against the homologous TDP1 at the highest testing concentration (111 μM). The best compound 64 inhibited recombinant TDP2 with an IC50 of 1.9 μM. The discovery of this chemotype may provide a platform toward understanding TDP2 as a drug target.

Lead identification to generate isoquinolinedione inhibitors of insulin-like growth factor receptor (IGF-1R) for potential use in cancer treatment

Insulin-like growth factor receptor (IGF-1R) is a growth factor receptor tyrosine kinase that acts as a critical mediator of cell proliferation and survival. This receptor is over-expressed or activated in tumor cells and is emerging as a novel target in cancer therapy. Efforts in our "Hit to Lead" group have generated a novel series of submicromolar IGF-1R inhibitors based on a isoquinolinedione template originating from a Lance enzyme HTS screen. Chemical triage and parallel synthesis incorporating focused library arrays were instrumental in moving these investigations through the Wyeth exploratory medicinal chemistry process. The strategies, synthesis, and SAR behind this interesting kinase scaffold will be described.

4-(Phenylaminomethylene)isoquinoline-1,3(2H,4H)-diones as potent and selective inhibitors of the cyclin-dependent kinase 4 (CDK4)

The cyclin-dependent kinases (CDKs), as complexes with their respective partners, the cyclins, are critical regulators of cell cycle progression. Because aberrant regulations of CDK4/cyclin D1 lead to uncontrolled cell proliferation, a hallmark of cancer, small-molecule inhibitors of CDK4/cyclin D1 are attractive as prospective antitumor agents. The series of 4-(phenylaminomethylene)isoquinoline-1,3(2H,4H)-dione derivatives reported here represents a novel class of potent inhibitors that selectively inhibit CDK4 over CDK2 and CDK1 activities. In the headpiece of the 4-(phenylaminomethylene) isoquinoline-1,3(2H,4H)-dione, a basic amine substitutent is required on the aniline ring for the CDK4 inhibitory activity. The inhibitory activity is further enhanced when an aryl or heteroaryl substituent is introduced at the C-6 position of the isoquinoline-1,3(2H,4H)-dione core. We present here SAR data and a CDK4 mimic model that explains the binding, potency, and selectivity of our CDK4 selective inhibitors.

An expedient synthesis of homophthalimides

The six-membered heterocyclic subunit of homophthalimides can be obtained by a direct, hitherto unprecedented, radical cyclisation onto an aromatic ring starting from a xanthate precursor.