47226-27-7

Basic information

• Product Name: N-(2,4-dinitrophenyl)-2-hydroxybenzamide
• Synonyms: N-(2,4-dinitrophenyl)-2-hydroxybenzamide
• CAS NO: 47226-27-7
• Molecular Weight: 303.231
• Mol File: 47226-27-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: N-(2,4-dinitrophenyl)-2-hydroxybenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,4-dinitrophenyl)-2-hydroxybenzamide(47226-27-7)
• EPA Substance Registry System: N-(2,4-dinitrophenyl)-2-hydroxybenzamide(47226-27-7)

Safety Data

• Hazardous Substances Data: 47226-27-7(Hazardous Substances Data)

Upstream product

• 97-00-7 1-chloro-2,4-dinitro-benzene 
• 65-45-2 salicylamide 
• 69-72-7 salicylic acid 
• 97-02-9 2,4-Dinitroanilin 
• 7504-64-5 2-(2,4-dinitro-phenoxy)-benzoic acid 
• 438540-50-2 2-(2,4-dinitro-phenoxy)-benzoic acid amide 

Relevant articles and documents

Reversible small molecule inhibitors of MAO A and MAO B with anilide motifs

Background: Ligands consisting of two aryl moieties connected via a short spacer were shown to be potent inhibitors of monoamine oxidases (MAO) A and B, which are known as suitable targets in treatment of neurological diseases. Based on this general blueprint, we synthesized a series of 66 small aromatic amide derivatives as novel MAO A/B inhibitors. Methods: The compounds were synthesized, purified and structurally confirmed by spectroscopic methods. Fluorimetric enzymological assays were performed to determine MAO A/B inhibition properties. Mode and reversibility of inhibition was determined for the most potent MAO B inhibitor. Docking poses and pharmacophore models were generated to confirm the in vitro results. Results: N-(2,4-Dinitrophenyl)benzo[d][1,3]dioxole-5-carboxamide (55, ST-2043) was found to be a reversible competitive moderately selective MAO B inhibitor (IC50 = 56 nM, Ki = 6.3 nM), while N-(2,4-dinitrophenyl)benzamide (7, ST-2023) showed higher preference for MAO A (IC50 = 126 nM). Computational analysis confirmed in vitro binding properties, where the anilides examined possessed high surface complementarity to MAO A/B active sites. Conclusion: The small molecule anilides with different substitution patterns were identified as potent MAO A/B inhibitors, which were active in nanomolar concentrations ranges. These small and easily accessible molecules are promising motifs, especially for newly designed multitargeted ligands taking advantage of these fragments.