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Chemical Structure| 99-92-3 Chemical Structure| 99-92-3
Chemical Structure| 99-92-3

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Synonyms: p-Aminoacetophenone

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Agarwal, Devesh S. ; Beteck, Richard M. ; Ilbeigi, Kayhan ; Caljon, Guy ; Legoabe, Lesetja J. ;

Abstract: A library of imidazo[1,2-a]pyridine-appended chalcones were synthesized and characterized using 1H NMR,13C NMR and HRMS. The synthesized analogs were screened for their antikinetoplastid activity against Trypanosoma cruzi, Trypanosoma brucei brucei, Trypanosoma brucei rhodesiense and Leishmania infantum. The analogs were also tested for their cytotoxicity activity against human lung fibroblasts and primary mouse macrophages. Among all screened derivatives, (E)-N-(4-(3-(2-chlorophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active against T. cruzi and T. b. brucei exhibiting IC50 values of 8.5 and 1.35 μM, resp. Against T. b. rhodesiense, (E)-N-(4-(3-(4-bromophenyl)acryloyl)phenyl)imidazo[1,2-a]pyridine-2-carboxamide was found to be the most active with an IC50 value of 1.13 μM. All synthesized active analogs were found to be non-cytotoxic against MRC-5 and PMM with selectivity indexes of up to more than 50.

Keywords: antikinetoplastid ; ; drug likeliness properties ; ; neglected tropical diseases (NTDs) ; Trypanosoma brucei brucei ; Trypanosoma brucei rhodesiense

Purchased from AmBeed: ; ; ; ; ; ; ; ; ; ; ; ; ; ; 1113-59-3

Klaudia T. Angula ; Lesetja J. Legoabe ; Audrey Jordaan ; Digby F. Warner ; Richard M. Beteck ;

Abstract: A recent study identified quinolone-based thiosemicarbazone with an MIC90 value of 2 µM against Mycobacterium tuberculosis (Mtb). Herein, we report further optimization of the previous hit, which led to the discovery of quinolone-tethered aminoguanidine molecules with generally good antitubercular activity. Compounds 7f and 8e emerged as the hits of the series with submicromolar antitubercular activity, exhibiting MIC90 values of 0.49/0.90 and 0.49/0.60 µM, respectively, in the 7H9 CAS GLU Tx medium. This shows a fivefold increase in antitubercular activity compared to the previous study. Target compounds were also screened against ESKAPE (Enterococcus faecium, Staphylococcus aureus, Klebsiella pneumoniae, Acinetobacter baumannii, Pseudomonas aeruginosa, and Enterobacter species) pathogens. However, the series generally exhibited poor antibacterial activities, with only compounds 8d and 8e demonstrating >50% growth inhibition of Staphylococcus aureus and Pseudomonas aeruginosa at 32 µg/ml. The compounds displayed selective antitubercular activity as they showed no cytotoxicity effects against two noncancerous human cell lines. In silico studies predict 7f to have good solubility, no inhibitory effect on cytochrome P450 isoenzymes, and to be a non-pan-assay interfering compound.

Keywords: tuberculosis ; ESKAPE pathogens ; aminoguanidine ; quinolones ; thiosemicarzone

Purchased from AmBeed: ; ; ; ; ;

Jang, Mingyeong ; Lim, Taeho ; Park, Byoung Yong ; Han, Min Su ;

Abstract: In this study, we developed a metal-free and highly chemoselective method for the reduction of aromatic nitro compounds. This reduction was performed using tetrahydroxydiboron [B2(OH)4] as the reductant and 4,4'-bipyridine as the organocatalyst and could be completed within 5 min at room temperature. Under optimal conditions, nitroarenes with sensitive functional groups, such as vinyl, ethynyl, carbonyl, and halogen, were converted into the corresponding anilines with excellent selectivity while avoiding the undesirable reduction of the sensitive functional groups.

Alternative Products

Product Details of 4'-Aminoacetophenone

CAS No. :99-92-3
Formula : C8H9NO
M.W : 135.16
SMILES Code : CC(C1=CC=C(N)C=C1)=O
Synonyms :
p-Aminoacetophenone
MDL No. :MFCD00007896
InChI Key :GPRYKVSEZCQIHD-UHFFFAOYSA-N
Pubchem ID :7468

Safety of 4'-Aminoacetophenone

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of 4'-Aminoacetophenone

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Upstream synthesis route of [ 99-92-3 ]
  • Downstream synthetic route of [ 99-92-3 ]

[ 99-92-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 591-50-4 ]
  • [ 99-92-3 ]
  • [ 23600-83-1 ]
YieldReaction ConditionsOperation in experiment
53.4% With copper; potassium carbonate In <i>N</i>-methyl-acetamide 368.1
1-(4-anilinophenyl)ethanone
4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml).
15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper in powder form and a catalytic quantity of copper iodide are added.
The reaction mixture is taken to reflux for 12 hours.
After leaving the reaction medium to return to ambient temperature, it is filtered on celite and poured into ice-cold water.
After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum.
The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent.
Melting point: 105° C.
References: [1] Organometallics, 2012, vol. 31, # 21, p. 7336 - 7338.
[2] Patent: US2004/132788, 2004, A1, .
[3] Patent: US2005/38087, 2005, A1, .
  • 2
  • [ 591-50-4 ]
  • [ 12775-96-1 ]
  • [ 99-92-3 ]
  • [ 23600-83-1 ]
YieldReaction ConditionsOperation in experiment
53.4% With potassium carbonate In <i>N</i>-methyl-acetamide 335.1
1-(4-anilinophenyl)ethanone
4-amino-acetophenone (4.87 g; 36.0 mmol) is dissolved in dimethylformamide (75 ml).
15 g (0.108 mol) of potassium carbonate (previously dried at 170° C. under an argon atmosphere), 7.236 g (36.0 mmol) of iodobenzene, 0.4 g of copper powder and a catalytic quantity of copper iodide are added.
The reaction mixture is taken to reflux for 12 hours.
After leaving the reaction medium to return to ambient temperature, the latter is filtered on celite and poured into ice-cooled water.
After extraction with ethyl acetate, the organic phase is washed with water before being dried over magnesium sulphate, filtered and concentrated under vacuum.
The product obtained is purified by crystallization from heptane in order to produce a yellow solid with a yield of 53.4percent.
Melting point: 105° C.
References: [1] Patent: US2004/132788, 2004, A1, .
[2] Patent: US2005/38087, 2005, A1, .
  • 3
  • [ 99-92-3 ]
  • [ 108-90-7 ]
  • [ 23600-83-1 ]
References: [1] Chemistry - A European Journal, 2012, vol. 18, # 1, p. 145 - 151.
[2] Chemistry - A European Journal, 2012, vol. 18, # 3, p. 804 - 807.
[3] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1967 - 1973.
[4] Synlett, 2005, # 2, p. 275 - 278.
  • 4
  • [ 108-86-1 ]
  • [ 99-92-3 ]
  • [ 23600-83-1 ]
References: [1] Chemistry - A European Journal, 2006, vol. 12, # 13, p. 3636 - 3646.
[2] Journal of Organic Chemistry, 2005, vol. 70, # 20, p. 8107 - 8109.
  • 5
  • [ 99-92-3 ]
  • [ 88284-48-4 ]
  • [ 23600-83-1 ]
References: [1] Journal of Organic Chemistry, 2006, vol. 71, # 8, p. 3198 - 3209.
  • 6
  • [ 99-92-3 ]
  • [ 98-80-6 ]
  • [ 23600-83-1 ]
References: [1] Green Chemistry, 2018, vol. 20, # 21, p. 4891 - 4900.
[2] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 17, p. 8301 - 8313.
[3] Journal of Medicinal Chemistry, 2004, vol. 47, # 12, p. 3212 - 3219.
  • 7
  • [ 99-92-3 ]
  • [ 100-63-0 ]
  • [ 23600-83-1 ]
References: [1] European Journal of Organic Chemistry, 2013, # 30, p. 6779 - 6783.
  • 8
  • [ 603-33-8 ]
  • [ 99-92-3 ]
  • [ 23600-83-1 ]
References: [1] RSC Advances, 2016, vol. 6, # 18, p. 14531 - 14537.
  • 9
  • [ 99-92-3 ]
  • [ 100-58-3 ]
  • [ 92-52-4 ]
  • [ 23600-83-1 ]
References: [1] Organic Letters, 2012, vol. 14, # 21, p. 5570 - 5573,4.
  • 10
  • [ 99-92-3 ]
  • [ 108-95-2 ]
  • [ 23600-83-1 ]
References: [1] Angewandte Chemie - International Edition, 2015, vol. 54, # 48, p. 14487 - 14491[2] Angew. Chem., 2015, vol. 127, # 48, p. 14695 - 14699,5.
  • 11
  • [ 99-92-3 ]
  • [ 23600-83-1 ]
References: [1] Journal of the Chemical Society, 1955, p. 1278,1280.
[2] Bollettino Scientifico della Facolta di Chimica Industriale di Bologna, 1959, vol. 17, p. 33,37,41.
  • 12
  • [ 99-92-3 ]
  • [ 157014-41-0 ]
References: [1] Journal of the American Chemical Society, 1997, vol. 119, # 10, p. 2453 - 2463.
[2] Patent: WO2011/12577, 2011, A1, .
 

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