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Usage

Uses

Used in Pharmaceutical Research:
3-Cinnolinecarboxaldehyde is used as a key intermediate in the synthesis of schizocommunin (272119-70-7), a compound of interest in pharmaceutical research. Schizocommunin is being studied for its potential therapeutic properties and applications in medicine.
In the field of organic chemistry, 3-cinnolinecarboxaldehyde serves as a versatile building block for the development of new compounds with diverse biological activities. Its unique structure allows for various chemical reactions, enabling the creation of a wide range of derivatives with potential applications in drug discovery and medicinal chemistry.
Furthermore, 3-cinnolinecarboxaldehyde can be utilized in the synthesis of other cinnoline-based compounds, which may exhibit interesting pharmacological properties. These compounds can be explored for their potential use in treating various diseases and conditions, contributing to the advancement of healthcare and pharmaceutical sciences.

InChI:InChI=1/C9H6N2O/c12-6-8-5-7-3-1-2-4-9(7)11-10-8/h1-6H

Upstream product

• 3879-35-4 D-tagatose phenylosazone 
• 17460-12-7 (1R,2S,3R)-1-cinnolin-3-ylbutane-1,2,3,4-tetrol 
• 104680-31-1 methyl 4-chlorocinnoline-3-carboxylate 

Downstream Products

• 1398582-88-1 3-({(cinnolin-3-ylcarbonyl)[(1R)-1-(4-fluorophenyl)ethyl]amino}methyl)benzoic acid 
• 1398584-10-5 C₂₆H₂₂FN₃O₃ 
• 90418-63-6 cinnoline-3-carboxylic acid 
• 1421236-89-6 (R)-N-((1R,2R)-3-((S)-4-benzyl-5,5-dimethyl-2-oxooxazolidin-3-yl)-1-(cinnolin-3-yl)-2-methyl-3-oxopropyl)-2-methylpropane-2-sulfinamide 

Relevant academic research and scientific papers

Total synthesis of schizocommunin and revision of its structure

A proposed structure for schizocommunin (Z)-1hydroxy and its geometric isomer (E)-1hydroxy, which exist in a keto form, has been synthesized. However, the spectroscopic data of (Z)-1keto and (E)-1keto were not consistent with those reported for natural schizocommunin. After reinvestigating the spectral data for natural schizocommunin, we synthesized the quinazolinone derivative (Z)-2 as a revised structure for schizocommunin. All of the spectral data of (Z)-2 were completely identical to those reported for natural schizocommunin. (Z)-2 showed moderate antiproliferative activity.

Synthesis of Bioderived Cinnolines and Their Flow-Based Conversion into 1,4-Dihydrocinnoline Derivatives

Starting from phenylhydrazine and glucose, a versatile cinnoline scaffold was obtained on a multigram scale and further derivatized. A simple continuous-flow hydrogenation process permits the conversion of selected cinnolines into their 1,4-dihydrocinnoline counterparts. These products are generated in high yields and high purities with residence times of less than one minute and, along with their cinnoline precursors, are expected to serve as valuable heterocyclic building blocks for future medicinal chemistry programs.