15601-47-5Relevant academic research and scientific papers
5(4H)-oxazolones. Part XIII. A new synthesis of 4-ylidene-5(4H)- oxazolones by the Stille reaction
Beccalli, Egle Maria,Clerici, Francesca,Gelmi, Maria Luisa
, p. 781 - 786 (1999)
4-Chloromethylene-2-phenyl-5(4H)-oxazolone 1 was used as the starting material for the preparation of a series of 4-ylideneoxazolones 3 by the Stille reaction. When compound 1 was reacted with organostannanes 2 in the presence of the palladium catalyst, o
Synthesis and antibacterial activity of some imidazole-5-(4H)one derivatives
Saravanan, Sampath,Selvan, Perumal Senthamil,Gopal, Natesan,Gupta, Jayanta Kumar,De, Biplap
, p. 488 - 492 (2005)
In the present study, several substituted oxazolones were synthesized by condensation of benzoylglycine with different aldehydes. From such oxazolones, substituted imidazolones were synthesized by condensation with ethylenediamine, urea and 4-N,N-dimethyl
5-(4H)-oxazolones and their benzamides as potential bioactive small molecules
Bermperoglou, Eleftherios,Hadjipavlou-Litina, Dimitra,Mavridis, Evangelos,Pontiki, Eleni
, (2020/08/24)
The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer-Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94percent and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5percent. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a-4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.
Pharmaceutical composition and method of treating cancer
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Page/Page column 47, (2020/12/07)
Cytotoxic compounds containing a phenyl core, amide link(s), an imidazolinone or a propenamide moiety. Also described are pharmaceutical compositions incorporating the cytotoxic compounds and methods for treating cancer. These compounds are cytotoxic against breast, prostate, and leukemia cancer cell lines via dual inhibition of Src kinases and tubulin.
Stereoselective Intermolecular [2 + 2] Cycloadditions of Erlenmeyer-Pl?chl Azlactones Using Visible Light Photoredox Catalysis
Marra, Isabellar F. S.,De Almeida, Angelina M.,Silva, Larissa P.,De Castro, Pedro P.,Corrêa, Charlane C.,Amarante, Giovanni Wilson
, p. 15144 - 15154 (2018/12/14)
The first report of the preparation of symmetric and nonsymmetric diaminotruxinic derivatives through the photoredox [2 + 2] cycloadditions of Erlenmeyer azlactones is described, affording the desired compounds in high regio- and diastereocontrol (only head-to-head coupling). Mechanistic studies by DFT suggest that the reaction proceeds through a neutral photocatalytic pathway.
Synthesis and herbicidal activity of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives using l-proline as catalyst
Bhandari,Kasana
, p. 1717 - 1722 (2018/07/10)
A simple, efficient and environmentally benign method for the synthesis of 4-benzylidene-2-phenyl oxazol-5(4H)-one derivatives by the reaction of aromatic aldehydes and hippuric acid using acetic anhydride as dehydrating agent and L-proline as catalyst ha
Synthesis of Erlenmeyer-Pl?chl azlactones promoted by 5-Sulfosalicylic acid
Kiyani, Hamzeh,Aslanpour, Shiva
, p. 1314 - 1321 (2017/07/18)
5-Sulfosalicylic acid was found as an efficient catalyst in the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones by condensation and cyclodehydration of aromatic aldehydes with hippuric acid and acetic anhydride at room temperature. The catalyst was eas
Triphenylphosphine (PPh3) Catalyzed Erlenmeyer Reaction for Azlactones under Solvent-free Conditions
Punna Rao, Alapati Mohan Lakshmi,Sridhar Rao, Abburi,Saratchandra Babu, Mukkamala,Krishnaji Rao
supporting information, p. 429 - 435 (2017/02/03)
This study presents triphenylphosphine catalyzed process for the synthesis of azlactones and their derivatives using hippuric and substituted aromatic aldehydes. The methodology also found to be effective for the synthesis of azlactones from 5-(2,6-dichlorophenyl)-3-methyl-1,2-oxazol-4-yl carbonyl amino acetic acid and offers several advantages such as solvent-free conditions, excellent yields, simple procedure, mild conditions, and reduced environmental consequences.
Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition
Jadhav, Santosh A.,Sarkate, Aniket P.,Farooqui, Mazahar,Shinde, Devanand B.
, p. 1676 - 1683 (2017/09/08)
We have developed simple, greener, safer multicomponent synthesis series of 4-arylidene-2-phenyl-5(4H) oxazolones 4(a-r) catalyzed by Bronsted acid ionic liquid as triethylammonium hydrogen sulfate [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate with excellent yields (90–99%). The protocol offers economical, environmentally benign, solvent-free conditions, and recycle–reuse of the catalyst and easily available starting as benzoyl chloride 1, amino acid 2 and a variety of aldehydes 3. The cyclization followed by condensation of benzoyl chloride, amino acid, and a variety of aldehydes catalyzed by ILs [Et3NH][HSO4] and catalytic amount of acetic anhydride and sodium acetate. The final products were confirmed by their characterization data such as FTIR, 1H-NMR, 13C-NMR, Mass, high-resolution mass spectra and were compared with its reported method.
A convenient synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-assisted grinding
Pattarawarapan, Mookda,Jaita, Subin,Phakhodee, Wong
supporting information, p. 3171 - 3174 (2016/07/06)
A facile and effective approach for the synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones has been developed. Under solvent-assisted grinding in the presence of 2,4,6-trichloro-1,3,5-triazine, catalytic triphenylphosphine, and sodium carbonate, dehydrati
