- 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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- Stereoselective Intermolecular [2 + 2] Cycloadditions of Erlenmeyer-Pl?chl Azlactones Using Visible Light Photoredox Catalysis
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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.
- Marra, Isabellar F. S.,De Almeida, Angelina M.,Silva, Larissa P.,De Castro, Pedro P.,Corrêa, Charlane C.,Amarante, Giovanni Wilson
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p. 15144 - 15154
(2018/12/14)
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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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- New compounds having skin whitening, antioxidant and PPAR activity, and medical use thereof
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PURPOSE: A novel compound with skin whitening, antioxidation, and PPAR activation effects, and a medical use thereof are provided to be used for a pharmaceutical composition or a cosmetic product. CONSTITUTION: A compound is denoted by chemical formula 1. A skin whitening composition contains the compound as an active ingredient. An antioxidative composition for preventing or treating oxidative diseases contains the compound of chemical formula 1 as an active ingredient. The oxidative diseases are selected among skin aging, pigmentation, wrinkling, psoriasis, or eczema. The composition prevents or treats diseases which are regulated by PPAR(peroxisome proliferator-activated receptor) activity. The PPAR includes PPAR alpha or PPAR gamma.
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Paragraph 0498; 0509; 0513
(2017/04/14)
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- A convenient synthesis of 4-arylidene-2-phenyl-5(4H)-oxazolones under solvent-assisted grinding
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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
- Pattarawarapan, Mookda,Jaita, Subin,Phakhodee, Wong
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supporting information
p. 3171 - 3174
(2016/07/06)
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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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- NOVEL COMPOUND HAVING SKIN-WHITENING, ANTI-OXIDIZING AND PPAR ACTIVITIES AND MEDICAL USE THEREFOR
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Provided are a novel compound having skin-whitening, anti-oxidizing and PPAR activities and a medical use thereof, and the compound has skin-whitening activities for the suppression of tyrosinase, and accordingly, is useful for use in skin-whitening pharmaceutical composition or cosmetic products; has anti-oxidant activities, and accordingly, is useful for the prevention and treatment of skin-aging; and has PPAR activities, and in particular, PPARα and PPARγ activities, and accordingly, is useful for use in pharmaceutical compositions or health foods which are effective for the prevention and treatment of obesity, metabolic disease, or cardiovascular disease.
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Paragraph 0312; 0315; 0318; 0320
(2014/02/16)
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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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- Pseudo-peptides derived from isomannide: Inhibitors of serine proteases
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In this paper, we describe the synthesis of a novel class of pseudo-peptides derived from isomannide and several oxazolones as potential inhibitors of serine proteases as well as preliminary pharmacological assays for hepatitis C. Hepatitis C, dengue and West Nile fever are among the most important flaviviruses that share one important serine protease enzyme. Serine proteases belong to the most studied class of proteolytic enzymes and are a primary target in the drug development field. Several pseudo-peptides were obtained in good yields from the reaction of isomannide and oxazolones, and their anti-HCV potential using the HCV replicon-based assay was shown.
- Barros, Thalita G.,Pinheiro, Sergio,Williamson,Tanuri, Amilcar,Gomes Jr.,Pereira, Helena S.,Brindeiro,Neto, Jose B. A.,Antunes,Muri, Estela M. F.
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scheme or table
p. 701 - 709
(2010/08/05)
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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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- Novel synthesis of unsaturated 5(4H)-oxazolone derivatives with using palladium(II) acetate as a catalyst and microvawe irradiation in solvent-free condition
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Unsaturated 5(4H)-oxazolones have emerged as an important class of synthons. These compounds have prepared with using palladium(II) acetate under free-solvent conditions with excellent yields and microwave irradiation.
- Hamidian, Hooshang,Tikdari, Ahmad Momeni
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- Three distinct reactions of 3,4-dihydroisoquinolines with azlactones: Novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-ones
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(Diagram presented) A facile and direct synthetic entry to tricyclic imidazoloisoquinolin-3-ones and benzo[a]quinolizin-4-ones is reported based on the ring annulation of 1-unsubstituted and 1-substituted dihydroisoquinolines with azlactones under neutral
- Worayuthakarn, Rattana,Thasana, Nopporn,Ruchirawat, Somsak
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p. 5845 - 5848
(2007/10/03)
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- Calcium acetate catalyzed synthesis of 4-arylidene-2-phenyl-5(4H)- oxazolones under solvent-free conditions
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Eight 4-arylidene-2-phenyl-5(4H)-oxazolones (azlactones) have been prepared via Erlenmeyer synthesis from aromatic aldehydes and hippuric acid using calcium acetate under solvent-free conditions with microwave irradiation.
- Paul, Satya,Nanda, Puja,Gupta, Rajive,Loupy, André
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p. 425 - 427
(2007/10/03)
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- Synthesis and immunomodulatory properties of selected oxazolone derivatives
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Eleven oxazolone derivatives were synthesized and characterized by 1H NMR, EI, IR and UV spectroscopic and CHN analysis. Three compounds, 4-[(E)-(4-nitrophenyl)methylidene]-2-phenyl-1,3-oxazol-5(4H)-one (11), 4-[(E)-(4-methoxyphenyl)methylidene]-2-methyl-1,3-oxazol-5-one (12) and 4-[(E)-(4-nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) were screened for phagocyte chemiluminescence, neutrophil chemotaxis, T-cell proliferation, cytokine production from mononuclear cells and cytotoxicity. 4-[(E)-(4-Nitrophenyl)methylidene]-2-methyl-1,3-oxazol-5(4H)-one (13) was found to be the most potent immunomodulator in the series.
- Mesaik, Muhammad A.,Rahat, Shagufta,Khan, Khalid M.,Zia-Ullah,Choudhary, Muhammad I.,Murad, Shahnaz,Ismail, Zakiah,Atta-ur-Rahman,Ahmad, Aqeel
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p. 2049 - 2057
(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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- 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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- A modified synthesis of (±)-β-aryllactic acids
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The synthesis of racemic forms of the reportedly active principle of Danshen, namely (±)-β-(3,4-dihydroxyphenyl)lactic acid [(±)3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid] and its seven racemic derivatives is reported.
- Wong,Xu,Chang,Lee
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p. 793 - 797
(2007/10/02)
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- Synthesis of (S)-3,4-dihydroxyphenylalanine (L-DOPA) and unnatural α-amino acids via enzymatic resolution using alcalase
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Enzymatic resolution has been used for the synthesis of L-DOPA with high optical purity.N-Acetyl-(R,S)-3,4-methylenedioxyphenylalanine methyl ester (2b) on enzymatic resolution by alcalase (Subtilisin Carlsberg) yields N-acetyl-(S)-3,4-methylenedioxyphenylalanine (3b) which upon acid treatment affords (S)-3,4-dihydroxyphenylalanine (L-DOPA) (4).Several optically active unnatural N-acetylated and N-benzoylated α-amino acids have been prepared by similar enzymatic resolution.
- Tyagi, O D,Boll, P M,Parmar, V S,Taneja, Poonam,Singh, S K
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p. 851 - 854
(2007/10/02)
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- Preparation and Thermal Ring-closure of β-Aryl Vinyl Carbodi-imides: Synthesis of Isoquinoline Derivatives
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Reaction of the iminophosphoranes (7)-(9), derived from α-azidocinnamates and triphenylphosphine, with aromatic isocyanates gives either 1-arylaminoisoquinoline-3-carboxylates (10)-(12) or the corresponding carbodi-imides (14)-(18) which by thermal treatm
- a. Jose
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p. 1727 - 1731
(2007/10/02)
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