- 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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- Base Induced Condensation of Malononitrile with Erlenmeyer Azlactones: An Unexpected Synthesis of Multi-Substituted Δ2-Pyrrolines and Their Cytotoxicity
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An efficient, metal free approach to synthesize multi-substituted Δ2-pyrroline derivatives by mild base catalyzed cyclocondensation of malononitrile with Erlenmeyer azlactones via 1,2 addition was developed. The modularity of this reaction was used to assemble a range of poly-substituted pyrrolines. Further, synthesized products were screened for cytotoxic properties on different cancer cell lines such as A549 (Human lung adenocarcinoma cells), HeLa (Human cervical adenocarcinoma cells), Jurkat (Human chronic myeloid leukemia cells) and K562 (Human leukemic T cell Lymphoblast cells). Among the synthesized library of compounds, 6f and 6q displayed potent cytotoxic activity.
- Anil, Seegehalli M.,Kiran, Kuppalli R.,Rajeev, Narasimhamurthy,Sadashiva, Maralinganadoddi P.,Shobith, Rangappa,Sudhanva, Muddenahalli S.,Swaroop, Toreshettahally R.,Vinayaka, Ajjampura C.
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- Novel diamide-based benzenesulfonamides as selective carbonic anhydrase ix inhibitors endowed with antitumor activity: Synthesis, biological evaluation and in silico insights
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In this work, we present the synthesis and biological evaluation of novel series of diamide-based benzenesulfonamides 5a-h as inhibitors of the metalloenzyme carbonic anhydrase (CA, EC 4.2.1.1) isoforms hCA I, II, IX and XII. The target tumor-associated i
- Abdelrahman, Mohamed A.,Eldehna, Wagdy M.,Nocentini, Alessio,Bua, Silvia,Al-Rashood, Sara T.,Hassan, Ghada S.,Bonardi, Alessandro,Almehizia, Abdulrahman A.,Alkahtani, Hamad M.,Alharbi, Amal,Gratteri, Paola,Supuran, Claudiu T.
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- Orthopalladation of GFP-Like Fluorophores Through C–H Bond Activation: Scope and Photophysical Properties
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The luminescence of oxazolones R1-C6H4CH=CC(O)O-CN(R2) (1a–1j) and imidazolones R1-C6H4CH=CC(O)NR3CN(R2) (1k–1q) has been examined. The new GFP-like imidazo
- Collado, Sandra,Pueyo, Alejandro,Baudequin, Christine,Bischoff, Laurent,Jiménez, Ana Isabel,Cativiela, Carlos,Hoarau, Christophe,Urriolabeitia, Esteban P.
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p. 6158 - 6166
(2018/11/23)
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- Microwave-assisted efficient synthesis of azlactones using zeolite NaY as a reusable heterogeneous catalyst
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The efficient preparation of azlactones in the presence of zeolite NaY has been reported. This heterogeneous catalyst was used for efficient synthesis of azlactone derivatives with Ac2O as a condensing agent under microwave irradiation and solvent-free co
- Bodaghifard, Mohammad Ali,Moghanian, Hassan,Mobinikhaledi, Akbar,Esmaeilzadeh, Fatemeh
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p. 845 - 849
(2017/08/10)
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- Microwave-assisted efficient and mild synthesis of azlactone derivatives
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(Formula presented) A convenient and mild procedure for the synthesis of azlactones in the presence of catalytic amounts of calcium hydrogen phosphate as a green, inexpensive and environmentally benign catalyst has been demonstrated. The present protocol is operationally simple and offers some advantages such as good yields, short reaction time, simple work-up, low cost and reusability of catalyst, which makes this method mild and eco-friendly.
- Bodaghifard, Mohammad Ali,Mobinikhaledi, Akbar,Moradi, Khosro
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p. 193 - 197
(2016/07/15)
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- Resolving Electronic Transitions in Synthetic Fluorescent Protein Chromophores by Magnetic Circular Dichroism
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The detailed electronic structures of fluorescent chromophores are important for their use in imaging of living cells. A series of green fluorescent protein chromophore derivatives is examined by magnetic circular dichroism (MCD) spectroscopy, which allows the resolution of more bands than plain absorption and fluorescence. Observed spectral patterns are rationalized with the aid of time-dependent density functional theory (TDDFT) computations and the sum-over-state (SOS) formalism, which also reveals a significant dependence of MCD intensities on chromophore conformation. The combination of organic and theoretical chemistry with spectroscopic techniques also appears useful in the rational design of fluorescence labels and understanding of the chromophore's properties. For example, the absorption threshold can be heavily affected by substitution on the phenyl ring but not much on the five-member ring, and methoxy groups can be used to further tune the electronic levels.
- Cowie, Thomas Y.,?afa?ík, Martin,?ebestík, Jaroslav,Pohl, Radek,Bou?, Petr,?těpánek, Petr
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p. 2348 - 2354
(2016/08/27)
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- Efficient synthesis of 5(4H)-imidazolones and IN VITRO antifungal activity studies against selected phytopathogens
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A series of five new 1-(substituted phenyl)-2-phenyl-4-(substituted benzylidine)imidazole-5-one derivatives (or) 5(4H)-imidazolones I have been synthesized adopting SiO2, Al2O3-90 and Y-faujasite (Y-H type) zeolite as cata
- Voosala, Christopher,Yellajyosula, Lakshmi Narasimha Murthy,Uppuleti, Viplava Prasad,Kilaru, Padma Suhasini
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p. 2873 - 2876
(2014/06/09)
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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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- Practical synthesis of 4-benzylidene-2-phenyl-5(4H)-oxazolones
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A simple and alternative method has been developed for the synthesis of 4-benzylidene-2-phenyl-5(4H)-oxazolones via reactions of hippuric acid with various aldehydes in the presence of 2-chloro-4,6-dimethoxy-1,3,5-triazine/N- methylmorpholine at 75 °C. Co
- Siddaiah,Basha, G. Mahaboob,Sudhakar,Srinuvasarao,Kumar, Y. Santosh
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supporting information
p. 2191 - 2197
(2013/07/25)
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- Sonochemical hot-spot assisted one-pot synthesis of 4-arylmethylidene-2- phenyl-4H-oxazol-5-ones using nano-mgo as an efficient catalyst
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Twelve 4-arylmethylidene-2-phenyl-4H-oxazol-5-ones were prepared in excellent yield by sonicating a mixture of an araldehyde, hippuric acid and acetic anhydride in the presence of a green heterogeneous NanoMgO as a basic catalyst. The catalytic activity o
- Saleh Azzam, Sadeq Hamood,Chandrappa,Pasha, Mohamed Afzal
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p. 283 - 290
(2013/07/26)
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- Synthesis and evaluation of a series of novel imidazolidinone analogues of 6-aminoflavone as anticancer and anti-inflammatory agents
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The flavone moiety is a potential pharmacophore known for its diverse range of pharmacological activities. Aminoflavones have recently been the subject of considerable attention as lead molecules in several cancer research projects. Imidazolidinone heterocycles represent another biologically active scaffold with known cytotoxic properties. In an attempt to provide synergistic cytotoxic activity, these two moieties have been combined, and the resulting novel analogues evaluated for their anticancer and anti-inflammatory activities. The results revealed that the cytotoxicities of these compounds were fivefold greater than those of aminoflavone. DNA histograms obtained from cell cycle analysis in the presence of these compounds were apoptotic in their nature. Furthermore, the in vivo screening of these compounds using Ehrlich's ascites tumour model showed an increase in life span, whereas an in vivo anti-inflammatory study resulted in the enhancement of the anti-inflammatory potential. The results therefore supported the hypothesis that there is a relationship between inflammation and cancer.
- Moorkoth, Sudheer,Srinivasan,Gopalan Kutty,Joseph, Alex,Naseer
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p. 5066 - 5075
(2013/09/23)
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- Synthesis and evaluation of substituted cinnamoyl alanines for antiinflammatory, analgesic and antioxidant activities
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A series of substituted cinnamoyl alanines were synthesized by condensation of substituted 4-benzylidene-2-phenyloxazol-5-ones with alanine. The chemical structures of synthesized compounds were confirmed by means of IR, 1H NMR, mass spectral and elementa
- Rajitha,Prasad,Bharathi
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scheme or table
p. 1197 - 1204
(2012/03/11)
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- Comparison of clinoptilolite, analcime and yugawaralite for synthesis of unsaturated 5(4H)-oxazolones in solvent-free condition and microwave irrudiation
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In view of the importance of azlactones as synthons, biological importance of the compounds and the advantages offered by coupling microwave activation with dry media reactions, we report here a solvent-free procedure for the synthesis of 2-phenyl-5(4H)-o
- Fozooni, Samieh,Tikdari, Ahmad Momeni,Hamidian, Hooshang
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- An efficient synthesis of new class of pyrazolo[3,4-b]pyridine-6-one derivatives by a novel cascade reaction
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(Chemical Equation Presented) A novel cascade reaction of 4-arylidene-2-phenyl-1,3-oxazol-5(4H)-one with 3-methyl-l-phenyl-1H-pyrazol-5- amine was described and a number of new pyrazolo[3,4-b]pyridine-6-one derivatives were synthesized. This new protocol has the advantages of shorter time, higher yields, and lower cost as well as easier operation.
- Shi, Feng,Zhang, Junyong,Tu, Shujiang,Jia, Runhong,Zhang, Yan,Jiang, Bo,Jiang, Hong
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p. 1013 - 1017
(2008/03/29)
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- Oxazolones: New tyrosinase inhibitors; synthesis and their structure-activity relationships
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The tyrosinase inhibitory potential of seventeen synthesized oxazolone derivatives has been evaluated and their structure-activity relationships developed in the present work. All the synthesized derivatives, 3-19, demonstrated excellent in vitro tyrosina
- Khan, Khalid Mohammed,Mughal, Uzma Rasool,Khan, Mahmud Tareq Hassan,Zia-Ullah,Perveen, Shahnaz,Iqbal Choudhary, Muhammad
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p. 6027 - 6033
(2007/10/03)
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- Oxazolone analogs as amyloid aggregation inhibitors and for the treatment of alzheimer's disease and disorders related to amyloidosis
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Disclosed are compounds of the Formula I and their use in a method of inhibiting the aggregation of amyloid proteins and in a method of imaging amyloid deposits.
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- Diastereoselective Synthesis of Cularine Alkaloids via Enium Ions and an Easy Entry to Isoquinolines by Aza-Wittig Electrocyclic Ring Closure
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In preliminary communications, we reported the diastereoselective synthesis of cularine and sarcocapnine via the intramolecular ring closure of nitrenium and oxenium ions, a new highly diastereoselective reductive methylation with (+)-8-phenylmenthyl chloroacetate followed by reduction with sodium borohydride, and a facile entry to the isoquinoline precursors by aza-Wittig electrocyclic ring closure. We now report the full details of the syntheses of (+)-O-demethylcularine, (+)-cularine, (+)-sarcocapnidine, (+)-sarcocapnine, and (+)-crassifoline and describe different methods of synthesis of their precursors.
- Rodrigues, J. Augusto R.,Abramovitch, Rudolph A.,De Sousa, Joana D. F.,Leiva, Genaro C.
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p. 2920 - 2928
(2007/10/03)
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- Reactions of 2-aryl-4-arylidene-4H-oxazol-5-ones with 3-amino-1,2,4- triazole, 5-aminotetrazole, and 2-aminobenzimidazole
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The reactions of 3-amino-1,2,4-triazole, 5-aminotetrazole, and 2-aminobenzimidazole with 2-aryl-4-arylidene-4H-oxazol-5-ones (azlactones) were studied. The electron-releasing properties of the azole ring were demonstrated to influence the reaction pathway
- Chebanov,Desenko,Kuzmenko,Borovskoy,Musatov,Sadchikova
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p. 2845 - 2849
(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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- An expedient synthesis of isopropyl anisoles and veratroles
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Isopropyl-substituted anisoles and veratroles were obtained in high yields (89-93%) on the aqueous work-up of the reaction of 3-(methoxyphenyl)-2-oxopropanoic acids with iodomethane and potassium hydroxide in dimethyl sulfoxide.
- Yli-Kauhaluoma, Jari T.,Janda, Kim D.
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p. 4509 - 4510
(2007/10/02)
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- Synthesis of 2-(2-benzothiazoyl/benzoxazoylthio)-N--5-oxo-2-phenyl/methyl-1H-imidazol-1-yl>acetamides as possible anthelmintics
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Twenty new 2-(2-benzothiazolyl/benzoxazolylthio)-N--5-oxo-2-phenyl/methyl-1H-imidazol-1-yl>acetamides have been synthesised and tested for their anthelmintic activity against H. nana infection in mice.
- Husain, M Imtiaz,Kumar, Vinay
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p. 285 - 288
(2007/10/02)
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