104478-99-1

Basic information

• Product Name: ASISCHEM U63903
• Synonyms: ASISCHEM U63903;N-(4-Amino-2-methylphenyl)benzamide;Albb-006194
• CAS NO: 104478-99-1
• Molecular Formula: C₁₄H₁₄N₂O
• Molecular Weight: 226.28
• Mol File: 104478-99-1.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 317.7°C at 760 mmHg
• Flash Point: 145.9°C
• Appearance: /
• Density: 1.21g/cm³
• Vapor Pressure: 0.000379mmHg at 25°C
• Refractive Index: 1.671
• CAS DataBase Reference: ASISCHEM U63903(CAS DataBase Reference)
• NIST Chemistry Reference: ASISCHEM U63903(104478-99-1)
• EPA Substance Registry System: ASISCHEM U63903(104478-99-1)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 104478-99-1(Hazardous Substances Data)

Usage

InChI:InChI=1/C14H14N2O/c1-10-9-12(15)7-8-13(10)16-14(17)11-5-3-2-4-6-11/h2-9H,15H2,1H3,(H,16,17)

Upstream product

• 65-85-0 benzoic acid 
• 99-52-5 2-methyl-4-nitro-benzenamine 
• 98-88-4 benzoyl chloride 
• 104478-92-4 N-(2-methyl-4-nitrophenyl)benzamide 

Downstream Products

• 438209-04-2 N-[4-({[(5-chloro(2-thienyl))sulfonyl]amino}carbonylamino)-2-methylphenyl]benzamide 
• 104479-08-5 C₁₉H₂₀N₄O₅ 

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.

Platelet ADP receptor inhibitors

Novel compounds of formulae (I) to (VIII), which more particularly include sulfonylurea derivatives, sulfonylthiourea derivatives, sulfonylguanidine derivatives, sulfonylcyanoguanidine derivatives, thioacylsulfonamide derivatives, and acylsulfonamide derivatives which are effective platelet ADP receptor inhibitors. These derivatives may be used in various pharmaceutical compositions, and are particularly effective for the prevention and/or treatment of cardiovascular diseases, particularly those diseases related to thrombosis. The invention also relates to a method for preventing or treating thrombosis in a mammal comprising the step of administering a therapeutically effective amount of a compound of formulae (I) to (VIII), or a pharmaceutically acceptable salt thereof.

Design, anticonvulsive and neurotoxic properties of retrobenzamides / N- (nitrophenyl)benzamides and N-(aminophenyl)benzamides

Design, anticonvulsant properties in maximal electroshock-reduced seizures [MES] and seizures reduced by subcutaneous administration of pentetrazole (scPtz), and neurotoxicity of retrobenzamides (N- (nitrophenyl)benzamides and N-(aminophenyl) benzamides are reported. These data are further compared with those on carbamazepine, phenytoin, ameltolide and other reference compounds. Studies on retrobenzamides in mice dosed intraperitoneally point out a good anticonvulsant potential in the MES test for the amino derivatives (N-(aminophenyl)benzamides) and moderate activity for corresponding 'nitro' derivatives. In rats dosed orally, aminoretrobenzamides were, however, less active in the MES test than in mice dosed intraperitoneally. Differences between experimental animal species and administration routes lead to hypothesize rapid metabolization of compounds, reduced intestinal resorption and increased removal from body. The presence of a methyl substitution on the N-phenyl moiety of aminoretrobenzamides attenuated these discrepancies between mice and rats. Present results indicate that pharmacological values - including the dose offering anticonvulsant protection in 50 % of tested animals (ED50) and protective indices - obtained on some retrobenzamides may compete with phenytoin and carbamazepine values. By contrast with phenytoin, some retrobenzamides further exhibit activity in the scPtz test.