- 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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- 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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- An ionic liquid gel: A heterogeneous catalyst for Erlenmeyer-Plochl and Henry reactions
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An ionic liquid gel has been prepared by entrapping 1-butyl-3-methylimidazolium hydroxide ([Bmim]OH) in an aqueous agar gel. The ionic liquid gel has been characterized by Fourier transform infrared (FT-IR), Fourier transform Raman (FT-Raman) spectroscopy, scanning electron microscopy (SEM), thermogravimetric analysis (TGA) and energy dispersive X-ray analysis (EDX). The ionic liquid gel has been successfully employed as a heterogeneous catalyst in the Erlenmeyer-Plochl reaction involving aldehydes, hippuric acid and acetic anhydride as well as in the Henry reaction between aldehydes and nitromethane in ethanol at room temperature. The heterogeneity of the ionic liquid gel has been confirmed by conducting hot filtration tests and leaching studies. Additionally, the ionic liquid gel could be easily recovered by simple filtration and reused five times without significant loss in catalytic activity.
- Jagadale, Megha,Naikwade, Altafhusen,Salunkhe, Rajashri,Rajmane, Mohan,Rashinkar, Gajanan
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p. 10993 - 11005
(2018/07/06)
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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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- Synthesis, in-vitroreverse transcriptase inhibitory activity and docking study of some new imidazol-5-one analogs
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Non-nucleoside reverse transcriptase inhibitors have a definitive role and most commonly used in treatment of HIV-1 infection. A new series of 4-ethylidene/substituted-benzylidene-1-(4-hydroxy/chloro-6-methylpyrimidin-2-yl) -2-ethyl/phenyl-1H-imidazol-5(4H)-one were designed, synthesized, and evaluated for HIV-1 reverse transcriptase (RT) inhibitory activity. The results of in-vitro HIV-1 RT assay showed that some of the new compounds, such as 4c, 4d, 4e, 5a, and 5e effectively inhibit HIV-1 RT activity. 1-(4-Chloro-6- methylpyrimidin-2-yl)-4-(furan-2-ylmethylene)-2-methyl-1H-imidazol-5(4H)-one (5e) exerted most potent in-vitro HIV-1 RT inhibitory activity, among the group of compounds. Molecular docking studies were carried out to explore the binding affinity of imidazole-5-one analogs in active site of HIV-1 RT enzyme. Springer Science+Business Media 2014.
- Mokale, Santosh N.,Lokwani, Deepak K.,Shinde, Devanand B.
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p. 3752 - 3764
(2014/08/05)
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- Synthesis, characterization and anticonvulsant activity of substituted imidazolinone derivatives
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The reaction of glycine with benzoylchloride gave 2-benzamidoacetic acid (1) which on reaction with substituted benzaldehydes in presence of acetic anhydride and anhydrous sodium acetate gave 4-benzylidene-2-phenyloxazol-5(4H)-one derivatives (2a-h). 4-Ni
- Sudha, B. Naga,Subbaiah, N. Yella,Raghavendra,Srikanth,Reddy, C.Venkataramana,Manasa
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p. 159 - 162
(2019/01/21)
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- Synthesis, biological activity and docking study of imidazol-5-one as novel non-nucleoside HIV-1 reverse transcriptase inhibitors
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A novel series of substituted imidazol-5-ones were designed, synthesized and evaluated for in vitro reverse transcriptase (RT) inhibition activity using reverse transcriptase assay kit (Roche, Colorimetric). It has been observed from in vitro screening that newly synthesized compounds possess RT inhibitory activity. Docking study was performed to study the binding orientation and affinity of synthesized compounds for RT enzyme.
- Mokale, Santosh N.,Lokwani, Deepak,Shinde, Devanand B.
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experimental part
p. 3119 - 3127
(2012/06/29)
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- Synthesis, in silico metabolic and toxicity prediction of some novel imidazolinones derivatives as potent anticonvulsant agents
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A series of 1,2,4-trisubstituted 5-imidazolinone derivatives were synthesized by Erlenmeyer condensation of benzoylglycine (hippuric acid) with different aldehydes in the presence of sodium acetate and acetic anhydride. The derivatives of the compounds we
- Hari Narayana Moorthy,Saxena, Vipin,Karthikeyan,Trivedi, Piyush
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experimental part
p. 201 - 207
(2012/07/13)
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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 one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins
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The first example of an ionic liquid-promoted one-pot synthesis of 3-benzamidocoumarins from salicylaldehydes and 2-pheny-1,3-oxazolan-5-one via Knoevenagel condensation-ring transformation cascades has been reported. No by-product formation, operational
- Yadav, Lal Dhar S.,Singh, Santosh,Rai, Vijai K.
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experimental part
p. 2208 - 2212
(2009/08/07)
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- Alcohol uncaging with fluorescence reporting: Evaluation of o-acetoxyphenyl methyloxazolone precursors
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(Chemical Equation Presented) This paper evaluates a series of photolabile protecting groups with built-in fluorescence reporting. They rely on readily available o-acetoxyphenyl methyloxazolones as activated precursors. Alcohol substrates are easily caged. The resulting photoactivable esters exhibit large one- and two-photon uncaging cross sections. The alcohol substrates are quantitatively released in a 1:1 molar ratio with a strongly fluorescent coumarin coproduct that serves as a reporter to quantify substrate delivery.
- Gagey, Nathalie,Emond, Matthieu,Neveu, Pierre,Benbrahim, Chouaha,Goetz, Bernard,Aujard, Isabelle,Baudin, Jean-Bernard,Jullien, Ludovic
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supporting information; experimental part
p. 2341 - 2344
(2009/06/06)
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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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- Efficient and chemoselective conversion of aryl aldehydes to their azalactones catalysed by Bi(III) salts under solvent free conditions
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Bi(NO3)3.5H2O, Bi(TFA)3 and Bi(OTf)3 were found to be highly powerful and practical catalysts for the synthesis of azalactones under solvent free conditions with excellent yields. In addition, high ch
- Khodaei, Mohammad Mehdi,Khosropour, Ahmad Reza,Jomor, Saied Jabar Hoseini
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p. 638 - 641
(2007/10/03)
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- 4-(2'-Hydroxyphenylmethylene)-2-phenyloxyzol-5(4H)-one: A Comedy of Errors
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Eighteen publications since 1955 have described properties and reactions of the title compound.All these reports are erroneous and refer, variously, to three other substances.All literature reports of the analogous 4-(2'-hydroxyphenylmethylene)-2-methyloxazol-5(4H)-one also need revision.A convenient synthesis of the title compound 3 (R=H), its chemical and physical properties, and its rearrangement to 3-benzoylamino-1-benzopyran-2-one 1, are reported here for the first time.A mechanism is presented for the observed course of Ploechl-Erlenmeyer syntheses with salicylaldehyde and with 2-acetoxybenzaldehyde.
- Cornforth, Sir John,Ming-hui, Du
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p. 2183 - 2187
(2007/10/02)
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- Solvatochromic Behaviour and Prototropic Studies of Some Oxazolones of Electron Donor-Acceptor Type
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Solvatochromic and halochromic behaviour in the u.v.-vis absorption spectra of some substituted 4-arylidene-2-aryloxazol-5-ones (1-5) are studied.Positive and negative solvatochromism, depending on the substituent present, are observed in different hydrog
- Antonious, M. S.,Habashy, M. M.,El-Sayed, Y. A.
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p. 563 - 570
(2007/10/02)
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