64356-57-6

Basic information

• Product Name: 2-Pyridinesulfonamide,5-amino-(9CI)
• Synonyms: 2-Pyridinesulfonamide,5-amino-(9CI);5-amino-2-pyridinesulfonamide;5-Aminopyridine-2-sulfonamide
• CAS NO: 64356-57-6
• Molecular Formula: C5H7N3O2S
• Molecular Weight: 173.195
• Product Categories: SULFONAMIDE
• Mol File: 64356-57-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 476.805 °C at 760 mmHg
• Flash Point: 242.163 °C
• Appearance: /
• Density: 1.521 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.632
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 2-Pyridinesulfonamide,5-amino-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Pyridinesulfonamide,5-amino-(9CI)(64356-57-6)
• EPA Substance Registry System: 2-Pyridinesulfonamide,5-amino-(9CI)(64356-57-6)

Safety Data

• Hazardous Substances Data: 64356-57-6(Hazardous Substances Data)

Usage

General Description

2-Pyridinesulfonamide,5-amino-(9CI), also known as 5-Aminonicotinamide, is a chemical compound with the molecular formula C5H6N4O2S. It is a derivative of nicotinamide and is commonly used in pharmaceutical research as an inhibitor of poly(ADP-ribose) polymerases (PARPs), which are enzymes involved in DNA repair and cell death. 5-Aminonicotinamide has also been studied for its potential therapeutic applications in various diseases, including cancer, diabetes, and inflammatory disorders. Its ability to modulate PARP activity makes it a promising candidate for the development of new drugs targeting these pathways. Additionally, it has been investigated for its potential role as an antioxidant and neuroprotective agent. Overall, 5-Aminonicotinamide is a versatile compound with potential applications in both basic research and drug development.

InChI:InChI=1/C5H7N3O2S/c6-4-1-2-5(8-3-4)11(7,9)10/h1-3H,6H2,(H2,7,9,10)

Upstream product

• 409112-27-2 5-acetylamino-2-pyridinesulfonyl chloride 
• 27885-57-0 2-thiol-5-acetaminopyridine 
• 2127-09-5 2-mercapto-5-nitropyridine 
• 98548-28-8 5-acetamino-2-pyridinesulfonamide 

Relevant articles and documents

Combining the tail and the ring approaches for obtaining potent and isoform-selective carbonic anhydrase inhibitors: Solution and X-ray crystallographic studies

5-(3-Tosylureido)pyridine-2-sulfonamide and 4-tosylureido- benzenesulfonamide (ts-SA) only differ by the substitution of a CH by a nitrogen atom, but they have very different inhibitory properties against the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1). By means of X-ray crystallography on the human CA II adducts of the two compounds these differences have been rationalized. As all sulfonamides, the two compounds bind in deprotonated form to the Zn(II) ion from the enzyme active site and their organic scaffolds extend throughout the cavity, participating in many interactions with amino acid residues and water molecules. However the pyridine derivative undergoes a tilt of the heterocyclic ring compared to the benzene analog, which leads to a very different orientation of the two scaffolds when bound to the enzyme. This tilt also leads to a clash between a carbon atom from the pyridine ring of the first inhibitor and the OH moiety of Thr200, leading to less effective inhibitory properties of the pyridine versus the benzene sulfonamide derivative. Indeed, ts-SA is a promiscuous, low nanomolar inhibitor of 7 out of 10 human (h) CA isoforms, whereas the pyridine sulfonamide is a low nanomolar inhibitor only of the tumor-associated hCA IX and XII, being less effective against other 9 isoforms. Thus, a difference of one atom (N vs CH) in two isostructural sulfonamides leads to drastic differences of activity, phenomenon understood at the atomic level through the high resolution crystallographic structure and kinetic measurements reported in the paper. Combining the tail and the ring approaches in the same chemotype leads to isoform-selective, highly effective sulfonamide CA inhibitors.