5427-99-6Relevant articles and documents
Design, synthesis and biological evaluation of quinoxaline compounds as anti-HIV agents targeting reverse transcriptase enzyme
Estrin, Darío,Fabian, Lucas,Gómez, Natalia,Moglioni, Albertina,Salvatori, Melina,Taverna Porro, Marisa,Turk, Gabriela
, (2019/12/30)
Infection by human immunodeficiency virus still represents a continuous serious concern and a global threat to human health. Due to appearance of multi-resistant virus strains and the serious adverse side effects of the antiretroviral therapy administered, there is an urgent need for the development of new treatment agents, more active, less toxic and with increased tolerability to mutations. Quinoxaline derivatives are an emergent class of heterocyclic compounds with a wide spectrum of biological activities and therapeutic applications. These types of compounds have also shown high potency in the inhibition of HIV reverse transcriptase and HIV replication in cell culture. For these reasons we propose, in this work, the design, synthesis and biological evaluation of quinoxaline derivatives targeting HIV reverse transcriptase enzyme. For this, we first carried out a structure-based development of target-specific compound virtual chemical library of quinoxaline derivatives. The rational construction of the virtual chemical library was based on previously assigned pharmacophore features. This library was processed by a virtual screening protocol employing molecular docking and 3D-QSAR. Twenty-five quinoxaline compounds were selected for synthesis in the basis of their docking and 3D-QSAR scores and chemical synthetic simplicity. They were evaluated as inhibitors of the recombinant wild-type reverse transcriptase enzyme. Finally, the anti-HIV activity and cytotoxicity of the synthesized quinoxaline compounds with highest reverse transcriptase inhibitory capabilities was evaluated. This simple screening strategy led to the discovery of two selective and potent quinoxaline reverse transcriptase inhibitors with high selectivity index.
SUBSTITUTED BENZIMIDAZOLIUM, PYRIDO-IMIDAZOLIUM, OR PYRAZINO-IMIDAZOLIUM COMPOUNDS AS CHEMOTHERAPEUTICS
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Paragraph 00271, (2017/08/01)
Provided herein are compounds of the formula:(I) wherein: R1, R2, R3, R4, R5, X, A1, A2, A3, and A4 are as defined herein. In some aspects, these compounds may be used to treat cancer and other hyperproliferative disease. In some aspects, compositions, methods of treatment, and methods of synthesis are also provided herein.
Synthesis of [18F]Fluoroarenes by Nucleophilic Radiofluorination of N-Arylsydnones
Narayanam, Maruthi Kumar,Ma, Gaoyuan,Champagne, Pier Alexandre,Houk, Kendall N.,Murphy, Jennifer M.
supporting information, p. 13006 - 13010 (2017/09/28)
A practical method for radiofluorination of anilines with [18F]fluoride via N-arylsydnone intermediates is described. These precursors are stable, easy to handle and facilitate direct and regioselective 18F-labeling to prepare [
Novel HDAC6 isoform selective chiral small molecule histone deacetylase inhibitors
Smil, David V.,Manku, Sukhdev,Chantigny, Yves A.,Leit, Silvana,Wahhab, Amal,Yan, Theresa P.,Fournel, Marielle,Maroun, Christiane,Li, Zuomei,Lemieux, Anne-Marie,Nicolescu, Alina,Rahil, Jubrail,Lefebvre, Sylvain,Panetta, Anthony,Besterman, Jeffrey M.,Déziel, Robert
scheme or table, p. 688 - 692 (2009/08/15)
In an effort to identify HDAC isoform selective inhibitors, we designed and synthesized novel, chiral 3,4-dihydroquinoxalin-2(1H)-one and piperazine-2,5-dione aryl hydroxamates showing selectivity (up to 40-fold) for human HDAC6 over other class I/IIa HDACs. The observed selectivity and potency (IC50 values 10-200 nM against HDAC6) is markedly dependent on the absolute configuration of the chiral moiety, and suggests new possibilities for use of chiral compounds in selective HDAC isoform inhibition.
Synthesis and evaluation of phenyl substituted sydnones as potential DPPH-radical scavengers
Mallur, Shanta G.,Tiwari,Raju, B. China,Babu, K. Suresh,Ali, A. Zehra,Sastry,Rao, J. Madhusudana
, p. 1686 - 1689 (2008/09/19)
A series of phenyl substituted sydnones has been synthesized and their radical-scavenging activity has been studied on DPPH free radical. Out of eighteen compounds screened, nine compounds show interesting activity. A mechanism is presented whereby sydnones scavenge DPPH radical through donating H-atom at 4th-position. Its strong radical-scavenging activity mainly arises from 1, 2, 3-oxadiazolium-5-olate ring. Different substituents and their positions on the phenyl ring differently influence DPPH scavenging activity and therefore, may provide clues to design and develop better free-radical scavenging sydnones with multiple activities.
Microwave-assisted synthesis of N-arylglycines: Improvement of sydnone synthesis
Azarifar, Davood,Bosra, Hassan Ghasemnejad,Zolfigol, Mohammad-Ali,Tajbaksh, Mahmood
, p. 175 - 181 (2007/10/03)
Reactions of anilines with ethyl bromoacetate under microwave irradiation have afforded N-arylglycines that are subsequently converted to their N-nitroso derivatives with a combination of silica chloride or periodic acid, wet SiO2 and sodium nitrite in CH2Cl2 with satisfactory yields. In the final step, the use of 1,3-dibromo-5,5-dimethylhydantoin (DBH) as a new and effective reagent for dehydration of N-nitroso-N-arylglycines to sydnones was successfully examined.
Synthesis and evaluation of 3-anilino-quinoxalinones as glycogen phosphorylase inhibitors
Dudash Jr., Joseph,Zhang, Yongzheng,Moore, John B.,Look, Richard,Liang, Yin,Beavers, Mary Pat,Conway, Bruce R.,Rybczynski, Philip J.,Demarest, Keith T.
, p. 4790 - 4793 (2007/10/03)
A series of 3-anilino-quinoxalinones has been identified as a new class of glycogen phosphorylase inhibitors. The lead compound 1 was identified through high throughput screening as well as through pharmacophore-based electronic screening. Modifications were made to the scaffold of 1 to produce novel analogues, some of which are 25 times more potent than the lead compound.
Soluble Polymer-Supported Synthesis of α-Amino Acid Derivatives
Hu, Chunling,Chen, Zuxing,Yang, Guichun
, p. 219 - 224 (2007/10/03)
A practical and efficient synthesis of N-substituted α-amino acid derivatives on soluble polymer support is described.
o-Nitroaniline Derivatives. Part 9. Benzimidazole N-Oxides Unsubstituted at N-1 and C-2
Harvey, Ian W.,McFarlane, Michael D.,Moody, David J.,Smith, David M.
, p. 681 - 690 (2007/10/02)
Since previous routes to the title compounds (1) have proved unsatisfactory as general methods, a simple new synthesis has been devised.N-Cyanomethyl-o-nitroanilines (5) are cyclised in basic media, giving 2-cyanobenzimidazole N-oxides (12) in good yield.Hydrolysis of these products with hydrochloric acid gives, directly, the title compounds as their hydrochloride salts (13), which may be isolated and purified, and which give the free N-oxides (1) by treatment with aqueous ammonia followed by evaporation. o-Nitrophenylglycine esters (4) may satisfactorily replace the nitriles (5) in certain cases.A modification of this kind in the related nitropyridylglycine series leads to 3H-imidazolpyridine 1-oxide (20).
