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Yi-Lei Fan, Jian-Bing Wu, Xing Ke, Zhong-Ping Huang
A series of oxime-functionalized nitrofuranylamides were designed, synthesized and evaluated for their in vitro anti-mycobacterial activities against MTB H37Rv and drug-resistant clinical isolates. Among them, two compounds 7a and 7b exhibited excellent activity against the three tested strains. Both of them were comparable to the first-line anti-TB agents INH and RIF against MTB H37Rv, and were far more potent than INH and RIF against MDR-TB 16833 and 16995 strains. Thus, both of them could act as leads for further optimization...
August 1, 2018: Bioorganic & Medicinal Chemistry Letters
Daniel M Quinn
Organophosphorus agents such as sarin and soman that phosphylate the active site serine of the enzyme acetylcholinesterase are notorious and pernicious, not only because they have been used by tyrants to effect mass murder of their own populations but also because they are sought by terrorists to inflict mass casualties on civilian populations. These threats underscore the need to develop effective antidotes against such agents. Phosphylation of acetylcholinesterase produces two adducts, an initial neutral adduct that can be reactivated with oxime nucleophiles, and a subsequent monoanionic adduct (called aged acetylcholinesterase) which has proven over two generations to be impervious to reactivation...
August 15, 2018: Journal of Medicinal Chemistry
Youchao Deng, Dingding Kang, Jie Shi, Wenqing Zhou, Aijun Sun, Jianhua Ju, Xiangcheng Zhu, Ben Shen, Yanwen Duan, Yong Huang
A dozen oxime, hydrazine and hydrazide derivatives of platensimycin (PTM) analogues were synthesized, some of which showed strong antibacterial activities and were shown to be stable under the bioassay conditions. Docking analysis revealed that they have certain new interactions with β-ketoacyl-[acyl carrier protein] synthase II (FabF), suggesting that Schiff base formation on its terpene scaffold is an effective strategy to diversify PTM structure.
May 1, 2018: MedChemComm
Juan José Villaverde, Beatriz Sevilla-Morán, Carmen López-Goti, José Luis Alonso-Prados, Pilar Sandín-España
Assessment of two buffered QuEChERS (quick, easy, cheap, effective, rugged, and safe) versions (i.e., citrate and acetate) modified by including methanol to recover the residues of three cyclohexanedione oxime (CHD) herbicides and three of their byproducts from agricultural soil was performed. In this context, a full second-order face-centered factorial experimental design was developed to quantify the influences of the main five variables (i.e., extraction time, water content, soil weight, and extraction solvent volume and composition) on the target compound recoveries...
August 11, 2018: Molecules: a Journal of Synthetic Chemistry and Natural Product Chemistry
Mauricio Acelas, Vladimir V Kouznetsov, Arnold R Romero Bohórquez
A novel and highly efficient synthetic approach for the expedite construction of new octahydroacridine-isoxazole- and octahydroacridine-1,2,3-triazole-based molecular hybrids is first reported. Rapid access to the octahydroacridine core was achieved in a highly diastereoselective fashion via cationic Povarov reaction of N-propargyl anilines and citronella essential oil (Cymbopogon nardus). The subsequent 1,3-dipolar and Cu (I) catalyzed alkyne-azide cycloaddition reaction of the terminal alkyne fragment with the corresponding oxime or azide affords the desired 3,5-isoxazoles and 1,2,3-triazoles, respectively, as interesting molecular hybrid models for pharmacological studies...
August 11, 2018: Molecular Diversity
Martijn Constantijn de Koning, Gabriele Horn, Franz Worek, Marco van Grol
Organophosphorous (OP) compounds (such as nerve agents) inhibit the enzyme acetylcholinesterase (AChE) by covalent phosphylation of a key serine residue in the active site of the enzyme resulting in severe symptoms and ultimately death. OP intoxications are currently treated by administration of certain oxime compounds. The presently fielded oximes reactivate OP-inhibited AChE by liberating the phosphylated serine. Recent research towards new reactivators was predominantly devoted to design, synthesis and evaluation of new oxime-based compounds dedicated to overcoming some of the major limitations such as their intrinsic toxicity, their permanent charge which thwarts penetration of brain tissues and their inability to effectively reactivate all types of nerve agent inhibited AChEs...
August 6, 2018: European Journal of Medicinal Chemistry
Franck Le Vaillant, Marion Garreau, Stefano Nicolai, Ganna Gryn'ova, Clemence Corminboeuf, Jerome Waser
Fine-tuned organic photoredox catalysts are introduced for the metal-free alkynylation of alkylnitrile radicals generated via oxidative ring opening of cyclic alkylketone oxime ethers. The redox properties of the dyes were determined by both cyclic voltammetry and computation and covered an existing gap in the oxidation potential of photoredox organocatalysts.
July 21, 2018: Chemical Science
Aleksandr O Kokuev, Yulia A Antonova, Valentin S Dorokhov, Ivan S Golovanov, Yulia V Nelyubina, Andrey A Tabolin, Alexey Yu Sukhorukov, Sema L Ioffe
Acylation of nitronates affords α-acyloxyoxime derivatives via an umpolung functionalization of the α-position. This transformation involves generation of hitherto unknown N-acyloxy, N-oxyenamines and their fast [3,3]-sigmatropic rearrangement driven by the cleavage of the weak N-O bond. The reaction has a broad scope, and it is regioselective in the case of nitronates possessing nonsymmetrically substituted α-positions. Application to the formal total synthesis of clausenamide and cis-clausenamide is presented...
August 16, 2018: Journal of Organic Chemistry
Antonio M Echavarren, Michael E Muratore, Andrey I Knovalov, Helena Armengol-Relats
The reaction of oxime-tethered 1,6-enynes with a cationic gold(I) catalyst demonstrates a great potential for the synthesis of a range of heterocycles in a diastereospecific fashion. The control of the configuration of the oxime and the alkene of the enyne moiety is the key to obtain selectively dihydro-1,2-oxazines, isoxazoles or dihydropyrrole-N-oxides as single diastereoisomers. As supported by DFT calculations, these cascade reactions proceed stepwise, by the intramolecular addition of the O or N atom of the oxime onto cyclopropyl gold(I) carbene intermediates...
August 1, 2018: Chemistry: a European Journal
Tomasz Kosmalski, Renata Studzińska, Natalia Daniszewska, Małgorzata Ullrich, Adam Sikora, Michał Marszałł, Bożena Modzelewska-Banachiewicz
In this study, we present a convenient method for the synthesis of oxime ethers by reacting oximes with various chlorides (alkyl, functionalized alkyl, and benzyl) and with the subsequent use of a super base-pulverized potassium hydroxide in DMSO. The reactions take place at room temperature and the products are obtained in high yields. The final products were received within 2 min to 3 h. In addition, the compounds do not require chromatographic separation. The structure elucidation of the titled compounds was performed by using 1 H NMR and 13 C NMR spectroscopy as well as mass spectrometry...
July 2018: ChemistryOpen
Alaa A-M Abdel-Aziz, Adel S El-Azab, Mohamed A Abu El-Enin, Abdulrahman A Almehizia, Claudiu T Supuran, Alessio Nocentini
The synthesis, characterization and biological evaluation of a library of isoindoline-1,3-dione-based oximes and benzenesulfonamide hydrazones is disclosed. The set of hydroxyiminoethyl aromatic derivatives 10-18 was designed to assess the potentiality as zinc-binder for a feebly studied functional group in the field of carbonic anhydrase (CA, EC inhibition. Analogue phenylphthalimmides were linked to benzenesulfonamide scaffold by hydrazone spacers in the second subset of derivatives 20-28 to further investigate the application of the "tail approach" as tool to afford CA selective inhibition profiles...
October 2018: Bioorganic Chemistry
Richard J Spears, Robin L Brabham, Darshita Budhadev, Tessa Keenan, Sophie McKenna, Julia Walton, James A Brannigan, A Marek Brzozowski, Anthony J Wilkinson, Michael Plevin, Martin A Fascione
The bioconjugation of proteins with small molecules has proved an invaluable strategy for probing and perturbing biological mechanisms. The general use of chemical methods for protein functionalisation can be limited however by the requirement for complicated reaction partners to be present in large excess, and harsh conditions which are incompatible with many protein scaffolds. Herein we describe a site-selective organocatalyst-mediated protein aldol ligation (OPAL) that affords stable carbon-carbon linked bioconjugates at neutral pH...
July 7, 2018: Chemical Science
Tatiana N Pashirova, Irina V Zueva, Konstantin A Petrov, Svetlana S Lukashenko, Irek R Nizameev, Natalya V Kulik, Aleksandra D Voloshina, Laszlo Almasy, Marsil K Kadirov, Patrick Masson, Eliana B Souto, Lucia Ya Zakharova, Oleg G Sinyashin
New mixed cationic liposomes based on L-α-phosphatidylcholine and dihexadecylmethylhydroxyethylammonium bromide (DHDHAB) were designed to overcome the BBB crossing by using the intranasal route. Synthesis and self-assembly of DHDHAB were performed. A low critical association concentration (0.01 mM), good solubilization properties toward hydrophobic dye Orange OT and antimicrobial activity against gram-positive bacteria Staphylococcus aureus (MIC=7.8 μg mL-1 ) and Bacillus cereus (MIC=7.8 μg mL-1 ), low hemolytic activities against human red blood cells (less than 10%) were achieved...
July 24, 2018: Colloids and Surfaces. B, Biointerfaces
Christina M Wilhelm, Thomas H Snider, Michael C Babin, Gennady E Platoff, David A Jett, David T Yeung
Organophosphorus (OP) compounds, including pesticides and chemical warfare nerve agents (CWNA), are threats to the general population as possible weapons of terrorism or by accidental exposure whether through inadvertent release from manufacturing facilities or during transport. To mitigate the toxicities posed by these threats, a therapeutic regimen that is quick-acting and efficacious against a broad spectrum of OPs is highly desired. The work described herein sought to assess the protective ratio (PR), median effective doses (ED50 ), and therapeutic index (TI = oxime 24-h LD50 /oxime ED50 ) of MMB4 DMS, HLö-7 DMS, and 2-PAM Cl against the OPs sarin (GB), VX, and phorate-oxon (PHO)...
July 26, 2018: Neurotoxicology
Hany A M El-Sherief, Bahaa G M Youssif, Syed Nasir Abbas Bukhari, Ahmed H Abdelazeem, Mohamed Abdel-Aziz, Hamdy M Abdel-Rahman
A series of novel compounds carrying 1,2,4-triazole scaffold were prepared and evaluated for their antiproliferative activities against NCI 60 cell line. Compounds 10 (a, c), 11 (a-d), and 14 (a-e) were selected for evaluation at single concentration of 10 μM towards panel of sixty cancer cell lines. Some of nitric oxide (NO) donating triazole/oxime hybrids 11a-d showed antiproliferative activity better than their corresponding ketones. On the other hand, the thiazolo [3,2-b][1,2,4]-triazoles 14a-e showed remarkable antiproliferative activities against the same cell lines...
July 10, 2018: European Journal of Medicinal Chemistry
Vučinić Slavica, Bokonjić Dubravko, Jokanović Milan
Based on human toxicity studies, by appropriate regulatory decisions, the number of organophosphates (OP) on Serbian market has reduced significantly over the last two decades, followed by a gradual decrease in the number of poisonings by organophoshates, treated at the National Poison Control Centre (NPCC). METHODOLOGY: The aim of this retrospective study is to present data regarding the clinical management of poisoning with OP pesticides at the NPCC, that we collected during the 17 years period (1998-2014)...
July 25, 2018: Toxicology
Hend A A Ezelarab, Samar H Abbas, Heba A Hassan, Gamal El-Din A Abuo-Rahma
Fluoroquinolones remain one of the most important kind of antibacterial agents used nowadays. The emergence of more virulent and resistant strains of bacteria by the development of either mutated DNA-binding proteins or efflux pump mechanism for drugs is considered the main problem associated with the therapeutic use of these drugs. This situation participated in pushing researchers to design new fluoroquinolone derivatives, mainly with different substituents at C-7 to withstand these resistant strains of bacteria and to obtain a wider spectrum of activity including activity against anaerobic organisms...
July 26, 2018: Archiv der Pharmazie
Na Wang, Jian Wang, Yu-Long Guo, Lei Li, Yan Sun, Zhuang Li, Hong-Xia Zhang, Zhen Guo, Zhong-Liang Li, Xin-Yuan Liu
An efficient protocol for oximinotrifluoromethylation of unactivated alkenes was developed via trifluoromethyl radical-induced intramolecular remote oximino migration under mild reaction conditions, providing a wide range of β-trifluoromethylated oximes. Other fluoroalkyl radicals were also applicable for this transformation. This method provided access to synthetically challenging medium-sized ring scaffolds and the 6,7,5-fused lactam skeleton.
August 7, 2018: Chemical Communications: Chem Comm
Shuai Chen, Wei-Hui Fang, Lei Zhang, Jian Zhang
Six crystalline polyoxo-titanium clusters (PTCs) derived from oximes, namely, Ti4 (μ4 -O)(OMe)6 (L1)4 (PTC-125; H2 L1 = salicylaldoxime), H[Ti5 (μ2 -O)(μ3 -O)2 (OMe)3 (L1)6 ] (PTC-126), Ti6 (μ2 -O)(μ3 -O)2 (O i Pr)10 (OAc)2 (L2)2 (PTC-127; H3 L2 = salicylhydroxamic acid; HOAc = acetic acid), Ti7 (μ3 -O)2 (OEt)18 (L2)2 (PTC-128), Ti12 (μ2 -O)4 (μ3 -O)4 (OEt)20 (L2)4 (PTC-129), and Ti18 (μ2 -O)10 (μ3 -O)8 (μ4 -O)2 (OEt)30 (L3)2 (PTC-130; HL3 = acetoxime) have been solvothermally synthesized and structurally characterized...
August 6, 2018: Inorganic Chemistry
Dietrich E Lorke, Georg A Petroianu
Organophosphorus compounds (OPCs), inhibitors of acetylcholinesterase (AChE), are useful agents as pesticides, but also represent a serious health hazard. Standard therapy with atropine and established oxime-type enzyme reactivators (pralidoxime, obidoxime) is unsatisfactory. Better therapeutic results are obtained, when reversible AChE inhibitors are administered before OPC exposure. This review summarizes the history of such a pretreatment approach and sums up a set of experiments undertaken in search of compounds that are efficacious when given before a broad range of OPCs...
July 19, 2018: Journal of Applied Toxicology: JAT
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