171880-56-1

Basic information

• Product Name: 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE
• Synonyms: 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE
• CAS NO: 171880-56-1
• Molecular Formula: C10H5BrN2O3
• Molecular Weight: 281.06
• Mol File: 171880-56-1.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE(171880-56-1)
• EPA Substance Registry System: 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE(171880-56-1)

Safety Data

• Hazardous Substances Data: 171880-56-1(Hazardous Substances Data)

Usage

Uses

Used in Organic Synthesis:
4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE is used as a building block in organic synthesis for the creation of various pharmaceuticals, agrochemicals, and dyes. Its unique structure allows for the development of a wide range of compounds with diverse applications.
Used in Research and Development:
In the field of medicinal chemistry and drug discovery, 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE is used as a reagent for chemical reactions. Its properties make it a valuable tool for researchers to explore new chemical pathways and synthesize potential drug candidates.
Used in Fluorescent Probes and Imaging Studies:
Due to its unique chemical properties, 4-BROMO-5-NITRO-ISOQUINOLINE-1-CARBALDEHYDE has potential applications in the development of fluorescent probes and materials for imaging studies. This allows researchers to visualize and study biological processes and structures with greater precision and detail.

Upstream product

• 1532-97-4 4-bromoisoquinoline 
• 171880-20-9 ethyl 2-cyano-2,2-(4-bromo-1,2-dihydroisoquinolidene)acetate 
• 104704-40-7 4-bromo-1-methylisoquinoline 
• 3749-21-1 4-bromoisoquinoline N-oxide 
• 171880-55-0 4-bromo-1-methyl-5-nitroisoquinoline 

Relevant articles and documents

Synthesis and Antitumor Activity of 4- and 5-Substituted Derivatives of Isoquinoline-1-carboxaldehyde Thiosemicarbazone

Various substituted isoquinoline-1-carboxaldehyde thiosemicarbazones (12 compounds) have been synthesized and evaluated for antineoplastic activity in mice bearing the L1210 leukemia.Condensation of 4-bromo-1-methylisoquinoline (4) with ammonium hydroxide, methylamine, ethylamine, and N-acetylethylenediamine gave the corresponding 4-amino, 4-methylamino, 4-ethylamino, and 4-N-(acetylethyl)amino derivatives, which were then converted to amides and subsequently oxidized to aldehydes followed by condensation with thiosemicarbazide to yield thiosemicarbazones 8a-c, 9a-c, and 16.Nitration of 4, followed by oxidation with selenium dioxide, produced aldehyde 18, which was then converted to the cyclic ethylene acetal 19.Condensation of 19 with morpholine followed by catalytic reduction of the nitro group and treatment with thiosemicarbazide afforded 5-amino-4-morpholinoisoquinoline-1-carboxaldehyde thiosemicarbazone (22).N-Oxidation of 1,5-dimethylisoquinoline, followed by rearrangement with acetic anhydride, gave, after acid hydrolysis, 1,5-dimethyl-4-hydroxyisoquinoline, which was converted to its acetate and then oxidized to yield 4-acetoxy-5-methylisoquinoline-1-carboxaldehyde (32).Sulfonation of 1,4-dimethylisoquinoline, followed by reaction with potassium hydroxide, acetylation, and oxidation, gave 5-acetoxy-4-methylisoquinoline-1-carboxaldehyde (40).Condensation of compounds 32 and 39 with thiosemicarbazide afforded the respective 4- and 5-acetoxy(5- and 4-methyl)thiosemicarbazones 33 and 40, which were then converted to their respective 4- and 5-hydroxy derivatives 34 and 41 by acid hydrolysis.The most active compounds synthesized were 4-aminoisoquinoline-1-carboxaldehyde thiosemicarbazone (9a) and 4- (methylamino)isoquinoline-1-carboxaldehyde thiosemicarbazone (9b), which both produced optimum percent T/C values of 177 against the L1210 leukemia in mice when used at daily dosage of 40 mg/kg for 6 consecutive days.Furthermore, when 9a was given twice daily at a dosage of 40 mg/kg for 6 consecutive days, a T/C value of 165 was obtained and 60percent of the mice were 60-day long-term survivors.