54255-50-4

Basic information

• Product Name: Ethanone, 1-(3-amino-4-hydroxyphenyl)- (9CI)
• Synonyms: Ethanone, 1-(3-amino-4-hydroxyphenyl)- (9CI)
• CAS NO: 54255-50-4
• Molecular Formula: C₈H₉NO₂
• Molecular Weight: 151.16256
• Product Categories: ACETYLGROUP
• Mol File: 54255-50-4.mol
• Article Data: 8

Chemical Properties

• Melting Point: 98 °C
• Boiling Point: 361.5±27.0 °C(Predicted)
• Appearance: /
• Density: 1.242±0.06 g/cm3(Predicted)
• PKA: 7.96±0.18(Predicted)
• CAS DataBase Reference: Ethanone, 1-(3-amino-4-hydroxyphenyl)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-(3-amino-4-hydroxyphenyl)- (9CI)(54255-50-4)
• EPA Substance Registry System: Ethanone, 1-(3-amino-4-hydroxyphenyl)- (9CI)(54255-50-4)

Safety Data

• Hazardous Substances Data: 54255-50-4(Hazardous Substances Data)

Usage

Preparation

Also obtained by reduction of 4-hydroxy-3-nitro-acetophenone by catalytic hydrogenation with hydrogen in the presence of, ? Pd/C in ethanol; ? Pt on carbon disulfide in ethanol.

Upstream product

• 75-36-5 acetyl chloride 
• 614-80-2 2-(acetylamino)phenol 
• 6322-56-1 4'-hydroxy-3'-nitroacetophenone 
• 99-93-4 4-Hydroxyacetophenone 
• 5467-64-1 2-acetamidophenyl acetate 
• 74896-30-3 1-<3-(acetylamino)-4-hydroxyphenyl>ethanone 

Downstream Products

• 74896-30-3 1-<3-(acetylamino)-4-hydroxyphenyl>ethanone 
• 871946-59-7 N-(5-acetyl-2-hydroxyphenyl)-2,2-dichloroacetamide 
• 179469-61-5 3-azido-4-methoxyacetophenone 
• 100361-20-4 1-(2-phenylbenzo[d]oxazol-5-yl)ethan-1-one 
• 308851-67-4 1-(3,4-dihydro-2H-benzo[b][1,4]oxazin-6-yl)ethanone 
• 848133-76-6 7-ethoxy-6-acetylamino-4-chloro-quinoline-3-carbonitrile 
• 1201080-09-2 N-(3-cyano-7-ethoxy-4-oxo-1,4-dihydroquinolin-6-yl)acetamide 
• 1201079-10-8 1-(5-acetamido-4-ethoxy-2-nitrophenyl)ethanone 
• 1201079-07-3 1-(3-acetamido-4-ethoxyphenyl)ethanone 

Relevant articles and documents

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Synthesis, protease inhibition, and antileishmanial activity of new benzoxazoles derived from acetophenone or benzophenone and synthetic precursors

Abstract: This work reports the synthesis, protease inhibition, and antileishmanial activity of ten benzoxazole derivatives, which were obtained in a three-step synthetic route from 4-hydroxy-acetophenone and 4-hydroxy-benzophenone. These benzoxazoles, the synthetic intermediates, and the starting ketones were evaluated for their inhibitory effect on the activity of cysteine (papain, rCPB2.8, and rCPB3.0) and serine (trypsin) proteases. All compounds showed significant values of IC50 against these enzymes (in the range of 0.0086–0.7612 μM for papain and 0.0075–0.5032 μM for trypsin), being more active than the standard inhibitors (1.7821 and 7.2318 μM, for E64 and TLCK, respectively). Following, all compounds were evaluated in vitro for their leishmanicidal activity against promastigote form of Leishmania amazonensis. The most active compounds were further evaluated against amastigote form and for its toxicity against murine macrophages. The benzoxazole 4d, a benzophenone derivative, and the intermediate 4-hydroxy-3-nitroacetophenone 2b showed significant antileishmanial activity (IC50 = 90.3 μM and IC50 = 130.9 μM, respectively) with selectivity indexes (5.22 and 18.09, respectively) compared to or better than those of two established leishmanicidal drugs, pentamidine (0.58) and amphotericin B (5.31). Graphical Abstract: [InlineMediaObject not available: see fulltext.].

Regulatory molecules for the 5-HT3 receptor ion channel gating system

Substituted benzoxazole derivatives which possess a nitrogen-containing heterocycle at C2 are selective partial agonists of the 5-HT3 receptor. Alteration of substituents on the benzoxazole nucleus affords both agonist-like and antagonist-like compounds, and uniquely modifies the function of the 5-HT3 receptor ion channel gating system. SAR and corroborative computational docking study for these partial agonists successfully explained structure and function of the 5-HT3 receptor.