2208-20-0

Basic information

• Product Name: 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide
• Synonyms: 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide;Naphthol AS-AN (C.I. 37516);3-Hydroxy-N-(4-nitrophenyl)-2-naphthamide;C.I.37516;C.I.Azoic Coupling Component 27;N-(4-Nitrophenyl)-3-hydroxynaphthalene-2-carboxamide;Naphthol AS-AN;3-hydroxy-N-(4-nitrophenyl)-2-Naphthalenecarboxamide
• CAS NO: 2208-20-0
• Molecular Formula: C₁₇H₁₂N₂O₄
• Molecular Weight: 308.29
• Mol File: 2208-20-0.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 465.5°Cat760mmHg
• Flash Point: 235.3°C
• Appearance: /
• Density: 1.449g/cm³
• Vapor Pressure: 2.76E-09mmHg at 25°C
• Refractive Index: 1.755
• CAS DataBase Reference: 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide(2208-20-0)
• EPA Substance Registry System: 3-hydroxy-N-(4-nitrophenyl)naphthalene-2-carboxamide(2208-20-0)

Safety Data

• Hazardous Substances Data: 2208-20-0(Hazardous Substances Data)

Usage

Preparation

4-Nitrobenzenamine and 3-Hydroxy-2-naphthoic acid condensation.

InChI:InChI=1/C17H12N2O4/c20-16-10-12-4-2-1-3-11(12)9-15(16)17(21)18-13-5-7-14(8-6-13)19(22)23/h1-10,20H,(H,18,21)

Upstream product

• 1734-00-5 3-hydroxy-2-naphthoyl chloride 
• 100-01-6 4-nitro-aniline 
• 92-70-6 3-Hydroxy-2-naphthoic acid 

Downstream Products

• 1174069-52-3 C₂₀H₁₆N₂O₅ 
• 53891-03-5 3-hydroxy-[2]naphthoic acid-(4-amino-anilide) 
• 17851-66-0 3-hydroxy-4-phenylazo-[2]naphthoic acid-(4-nitro-anilide) 
• 17809-74-4 3-hydroxy-4-(4-nitro-phenylazo)-[2]naphthoic acid-(4-nitro-anilide) 

Relevant articles and documents

3-Hydroxynaphthalene-2-carboxanilides and their antitrypanosomal activity

Abstract: Series of ring-substituted 3-hydroxynaphthalene-2-carboxanilides were screened for their in vitro activity against wild-type S427 (bloodstream form) of Trypanosoma brucei brucei. 3-Hydroxy-N-(3-trifluoromethylphenyl)- and 3-hydroxy-N-(4-trifluoromethylphenyl)naphthalene-2-carboxamides showed the highest biological activity (MIC?=?1.56 and 2.08?μmol/dm3, respectively). Antitrypanosomal activity was correlated with the experimentally determined lipophilicity and acid–base dissociation constants of the compounds as well as with the calculated electronic properties of individual anilide substituents expressed as Hammett’s σ parameters. The substitution in the meta- or para-position of anilide of derivatives with higher lipophilicity by an electron-withdrawing moiety is favourable for higher activity. The optimum thermodynamic pKa T value was found to be ca. 7.5. The structure–activity relationships of all compounds are discussed. Graphical abstract: [Figure not available: see fulltext.].

Antibacterial and herbicidal activity of ring-substituted 3-hydroxynaphthalene-2-carboxanilides

In this study, a series of twenty-two ring-substituted 3-hydroxy- Nphenylnaphthalene- 2-carboxanilides were prepared and characterized. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. Primary in vitro screening of the synthesized compounds was also performed against four Staphylococcus strains and against two mycobacterial species. 3-Hydroxy-N-(2-methoxyphenyl)naphthalene-2-carboxamide showed high biological activity (MIC = 55.0 μmol/L) against S. aureus as well as methicillinresistant strains. N-(2-Fluorophenyl)-3-hydroxynaphthalene-2- carboxamide showed higher activity (MIC = 28.4 μmol/L) against M. marinum than the standard isoniazid and 3-hydroxy-N-(4-nitrophenyl)naphthalene-2- carboxamide expressed higher activity (MIC = 13.0 μmol/L) against M. kansasii than the standard isoniazid. Cytotoxicity assay of effective antimicrobial compounds was performed using the human monocytic leukemia THP-1 cell line. The PET-inhibiting activity expressed by IC50 value of the most active compound 3-hydroxy-N-(3-nitrophenyl)naphthalene-2-carboxamide was 16.9 μmol/L. The structure-activity relationships of all compounds are discussed.

Naphthalene carboxamides as inhibitors of human cytomegalovirus DNA polymerase

ortho-Hydroxynaphthalene carboxamides have been identified as inhibitors of HCMV DNA polymerase. SAR investigations have demonstrated that both the amide and hydroxy functionalities are required for activity. Substitution on the naphthalene ring has led to inhibitors with submicromolar IC50s against HCMV polymerase. These compounds have been found to be >100-fold selective for inhibition of HCMV polymerase versus human alpha polymerase and display antiviral activity in a cell-based plaque reduction assay. (C) 2000 Elsevier Science Ltd.