- Design, Synthesis, and Antimicrobial Activity of Novel Fluorine-Containing Imidazolones
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Abstract: A simple synthetic protocol have been developed for the preparation of novelN-(4-benzylidene-5-oxo-2-phenyl-4,5-dihydro-1H-imidazol-1-yl)-N′-phenylthiourea derivatives by the reaction of4-benzylidene-2-phenyl-4,5-dihydro-1,3-oxazol-5-ones with N
- Desai,Wadekar,Mehta,Pandit
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p. 976 - 985
(2021/08/09)
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- Benzothiazol clubbed imidazol-4-ones as anti-fungal, anti-tubercular and anti-HIV-1 agents: Their synthesis and molecular docking study
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Background: The present work describes antimicrobial, antimycobacterium and anti HIV-1 evaluation of newly synthesized 5-(4-Substituted-benzylidene)-3-[4-(5-methyl-benzothiazol2-yl)-phenyl]-2-phenyl-3,5-dihydro-imidazol-4-one (4a-o). The docking studies were performed in order to predict the potential binding affinities. Objective: The major aim of this study is to develop the new class of bezylidine candidate clubbed with benzothiazole with less toxicity and improved potency as antimicrobial, antitubercular and anti HIV-1. Methods: The titled compounds were characterized by spectral studies (IR, 1H NMR, 13C NMR and Mass). In vitro antimycobacterium activity was carried out using Lowenstein-Jensen medium method and antimicrobial activity using the broth microdilution method. The anti HIV-1 reverse transcriptase activity was determined by the colorimetric MTT method and inhibition of virusinduced cytopathogenicity in MT-4 cells. Results: Compound 4i (50 μM) showed better antifungal activity against A. clavatus. Compound 4g (50 μM) with 95% inhibition demonstrated good activity against M. tuberculosis H37Rv. Compound 4k showed CC50 (50 μM) against MT-4 (CD4+ Human T-cells containing an integrated HTLV-1 genome) cells by 50%, while 16 μM concentration value EC50 from the HIV-1 induced cytopathogenicity. Molecular docking study suggested that 4k interacted with the target with binding energy by Vina score (-10.3 Kcal/mol) Conclusion: The preliminary in vitro evaluation results revealed that some of the compounds have promising antimicrobial activities as well as antitubercular potency. Among the various substituents on benzylidene, the nitro group was the most beneficial for improving the anti-HIV-1 activity. Docking result suggested that 4k compound could be acting as a non-competitive or weak inhibitor of Reverse Transcriptase (RT).
- Patel, Navin B.,Shaikh, Asif R.,Patel, Vatsal M.,Lara-Ramirez, Edgar E.,Rivera, Gildardo
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p. 382 - 391
(2019/06/18)
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- Silica-supported Solvent Approaches More Facile than the Conventional for Erlenmeyer Synthesis with Our Pyridinium Salts
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The synthesis of pyridinium salts by both conventional/silica-supported muffle furnace and microwave approaches is described. We have optimized the Erlenmeyer synthesis of azalactone with various concentrations of our synthesized pyridinium salts. Among t
- Manikandan, Chitrarasu,Ganesan, Kilivelu
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p. 929 - 934
(2018/02/19)
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- Sulfanilic acid-catalyzed green synthesis of 4-Arylidene-2-phenyl-5(4H)-Oxazolones
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This study is focused on the catalytic activity of sulfanilic acid (SA) in the straightforward synthesis of 4-Arylidene-2-phenyl-5(4H)-oxazolones via condensation of aromatic aldehydes, hippuric acid, and acetic anhydride under green experimental conditio
- Kiyani, Hamzeh,Aslanpour, Shiva
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p. 297 - 303
(2018/02/22)
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- Greener approach: Ionic liquid [Et3NH][HSO4]-catalyzed multicomponent synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones under solvent-free condition
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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.
- Jadhav, Santosh A.,Sarkate, Aniket P.,Farooqui, Mazahar,Shinde, Devanand B.
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p. 1676 - 1683
(2017/09/08)
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- Synthesis of Erlenmeyer-Pl?chl azlactones promoted by 5-Sulfosalicylic acid
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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
- Kiyani, Hamzeh,Aslanpour, Shiva
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p. 1314 - 1321
(2017/07/18)
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- One flask synthesis of esters of the corresponding 3-substituted 2-benzoylamino acrylic acids using 2-oxazolin-5-ones as synthons
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A modified route for the fast and facile synthesis of an alkyl 3-substituted 2- benzoylamino acrylate (4) is hereby developed. All the required steps are carried out in the same flask.
- Ahmed, Md. Mizanur,Borthakur, Somadrita,Tripathy, Pradeep K.
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p. 371 - 372
(2019/01/21)
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- Synthesis and quantitative structure-activity relationships study for phenylpropenamide derivatives as inhibitors of hepatitis B virus replication
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A series of new phenylpropenamide derivatives containing different substituents was synthesized, characterized and evaluated for their anti-hepatitis B virus (HBV) activities. The quantitative structure eactivity relationships (QSAR) of phenylpropenamide compound have been studied. The 2D-QSAR models, based on DFT and multiple linear regression analysis methods, revealed that higher values of total energy (TE) and lower entropy (Sθ) enhanced the anti-HBV activities of the phenylpropenamide molecules. Predictive 3D-QSAR models were established using SYBYL multifit molecular alignment rule. The optimum models were all statistically significant with cross-validated and conventional coefficients, indicating that they were reliable enough for activity prediction.
- Yang, Jing,Ma, Min,Wang, Xue-Ding,Jiang, Xing-Jun,Zhang, Yuan-Yuan,Yang, Wei-Qing,Li, Zi-Cheng,Wang, Xi-Hong,Yang, Bin,Ma, Meng-Lin
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- A green protocol for Erlenmeyer-Pl?chl reaction by using iron oxide nanoparticles under ultra sonic irradiation
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Azlactones have been prepared via Erlenmeyer synthesis from aromatic aldehydes and hippuric acid using Fe2O3 nanoparticles under ultrasonic irradiation. Short reaction times, easy and quick isolation of the products, and excellent yi
- Ahmadi, Seyed Javad,Sadjadi, Sodeh,Hosseinpour, Morteza
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p. 408 - 412
(2013/01/15)
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- Ammonium metavanadate an efficient catalyst for Erlenmeyer synthesis
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An efficient method to synthesize azalactone derivatives using ammonium metavanadate (NH4VO3) as catalyst was performed in the absence of solvent. This method is environmentally friendly and affords the product azalactones in high yi
- Madje, Balaji,Ubale, Milind,Bharad, Jagdish,Shingare, Murlidhar
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p. 1295 - 1299
(2013/01/15)
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- Alum an efficient catalyst for erlenmeyer synthesis
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A new and efficient method to synthesize azlactone derivatives using alum ascatalyst was performed in the absence of additional solvent. This method is environmentally friendly and affords the product azlactones in high yields after simple workup.
- Madje, Balaji R.,Ubale, Milind B.,Bharad, Jagdish V.,Shingare, Murlidhar S.
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experimental part
p. 158 - 161
(2012/01/06)
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- Catalyzing the Erlenmeyer Pl?chl reaction: organic bases versus sodium acetate
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An evaluation of organic base versus sodium acetate as the base in the Erlenmeyer Pl?chl reaction was performed. Aldehyde substituents play an important role in these reactions. Organic bases afford fast reactions, but other side reactions were observed. Alternatively, in the presence of solvent, sodium acetate could be used in catalytic amounts rather than the typical stoichiometric quantities. This Letter reports the comparative results for the use of organic bases versus sodium acetate in Erlenmeyer Pl?chl reactions.
- Cleary, Thomas,Rawalpally, Thimma,Kennedy, Nicole,Chavez, Flavio
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supporting information; experimental part
p. 1533 - 1536
(2010/06/13)
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- Molecular iodine-catalyzed, mild, effective, ecofriendly, microwave-assisted, one-pot synthesis of 5-arylmethylidene-2-phenyloxazol-4-ones (Azalactones) under solvent-free conditions
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Fourteen azalactones have been synthesized in excellent yields under solvent-free conditions by heating an aldehyde, hippuric acid, and acetic anhydride in the presence of molecular iodine as a catalyst in a microwave oven. The short reaction time, cleaner reaction, and easy workup make this protocol practical and economically attractive. Copyright
- Reddy, M. B. Madhusudana,Pasha
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experimental part
p. 1895 - 1898
(2010/09/07)
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- Synthesis and antimicrobial activity of some 2-phenyl-1-[4-phenyl-1,3- thiazol-2-yl]-4-(substituted benzylidene)- imidazoline-5-ones
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A series of thiazolyl imidazolinones have been synthesized and screened for their antimicrobial activity. Few of the compounds have shown promising activity against Gram positive organisms when compared with the standard drug.
- Rao, Gopal Krishna,Rajasekaran,Pai, P. N. Sanjay,Murthy, M. Srinivasa,Sengupta, Joydeep,Devi, Kalpana
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experimental part
p. 303 - 304
(2011/12/15)
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- Synthesis, characterization and biological activity of 5-arylidene-3-(6,7-dicloro-1,3-benzothiazol-2-yl)-phenyl-3,5-dihydro-4H-imidazol-4-ones
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Some novel 5-arylidene-3-(6,7-dichloro-1,3-benzothiazol-2-yl)-2-phenyl-3,5-dihydro-4H-imidazol-4-ones (6a-q) have been synthesized and characterized by elemental analyses, IR, NMR, and mass spectra. The products have been evaluated for antibacterial and a
- Baldaniya
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scheme or table
p. 81 - 84
(2011/01/03)
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- A new, efficient and chemoselective one-pot protocol for synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones from aryl aldehyde bisulfite adducts promoted by POCl3
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(Chemical Equation Presented) A one-pot procedure for the synthesis of 4-arylidene-2-phenyl-5(4H)oxazolones directly from aryl aldehyde bisulfite adducts in the absence of Ac2O in good to excellent yields using phosphoryl chloride is reported. In addition, the observed chemoselectivity can be considered as a noteworthy advantage of this method.
- Khosropour, Ahmad R.,Khodaei, Mohammad M.,Hoseini Jomor, Seyed J.
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p. 683 - 686
(2008/09/21)
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- Synthesis and pharmacological evaluation of imidazole derivatives of some non-steroidal anti-inflammatory drugs
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A series of imidazole derivatives of NSAIDs (4a-l) have been prepared by condensation of NSAIDs hydrazides (1,2) with substituted oxazolones and evaluated for anti-inflammatory and gastrointestinal toxicity, which showed good anti-inflammatory activity and reduced gastrointestinal toxicity as compared to parent drug.
- Parcha, Versha,Kaur, Jaswinder,Gupta, Vinay,Anroop
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experimental part
p. 321 - 325
(2009/06/25)
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- Synthesis of some novel imidazolinones as potent anticonvulsant agents
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Imidazolinone derivatives of IIa-IIc, IIIa-IIIf and IVa-IVf have been synthesised by the condensation of some known sulpha drugs with 5-oxazolone derivatives, which were prepared by Erlenmeyer condensation of benzoyl glycine with different aldehydes in th
- Joshi, Hashmukh,Upadhyay, Paresh,Karia, Denish,Baxi
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p. 837 - 840
(2007/10/03)
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- Bismuth (III) acetate: A new catalyst for preparation of azlactones via the Erlenmeyer synthesis
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Bismuth(III) acetate catalyzes the synthesis of azlactones from aromatic aldehydes in moderate to good yields via the Erlenmeyer synthesis. The relatively low toxicity and low cost of bismuth(III) acetate make this procedure particularly attractive.
- Monk, Keith A.,Sarapa, Dusan,Mohan, Ram S.
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p. 3167 - 3170
(2007/10/03)
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