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https://www.readbyqxmd.com/read/28730809/ruthenium-catalyzed-1-6-aromatic-enamide-silylalkyne-cycloisomerization-approach-to-2-3-disubstituted-indoles
#1
Kohei Takamoto, Shohei Ohno, Norimichi Hyogo, Hiromichi Fujioka, Mitsuhiro Arisawa
Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives undergo a cycloisomerization in the presence of a well-defined ruthenium hydride to give a 2,3-disubstitued indole. The vinyl and silylmethyl substituents on the 2- and 3-positions of the indole can be easily converted to other functional groups.
July 21, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28730283/blockade-of-alcohol-escalation-and-relapse-drinking-by-pharmacological-faah-inhibition-in-male-and-female-c57bl-6j-mice
#2
Yan Zhou, Benjamin I Schwartz, Joanna Giza, Steven S Gross, Francis S Lee, Mary Jeanne Kreek
BACKGROUND: Anandamide (AEA)-dependent signaling is regulated by the catabolic enzyme fatty acid amide hydrolase (FAAH). Several lines of evidence have demonstrated that FAAH and AEA are involved in the behavioral effects of alcohol. Therefore, we investigated whether a selective FAAH inhibitor, URB597 (cyclohexylcarbamic acid 3'-[aminocarbonyl]-[1,1'-biphenyl]-3-yl ester), altered alcohol intake in mice in a voluntary alcohol drinking model. METHODS: Mice, subjected to 3 weeks of chronic intermittent access (IA) in a two-bottle choice paradigm with 24-h access every other day, developed rapid escalation of alcohol intake and high preference...
July 20, 2017: Psychopharmacology
https://www.readbyqxmd.com/read/28726104/n-acyl-dopamines-induce-apoptosis-in-pc12-cell-line-via-the-gpr55-receptor-activation
#3
M G Akimov, A M Ashba, N M Gretskaya, V V Bezuglov
Dopamine amides of arachidonic, docosahexaenoic, and oleic acids were found to induce apoptosis in PC12 cells, which was blocked exclusively by antagonists and preincubation agonists of the receptor GPR55, belonging to the group of non-CB1/CB2 receptors.
May 2017: Doklady. Biochemistry and Biophysics
https://www.readbyqxmd.com/read/28702662/chiral-squaramide-catalysed-enantioselective-michael-cyclization-cascade-reaction-of-3-hydroxyoxindoles-with-%C3%AE-%C3%AE-unsaturated-n-acylated-succinimides
#4
Sheng Ming, Bo-Liang Zhao, Da-Ming Du
A bifunctional squaramide-catalysed asymmetric Michael/cyclization cascade reaction of 3-hydroxyoxindoles with α,β-unsaturated N-acylated succinimides is disclosed. With quinine-derived squaramide as the catalyst, a broad range of the desired spirooxindole lactone derivatives bearing two contiguous stereocenters were obtained in good yields (up to 89%) with high diastereoselectivities (up to >95 : 5 dr) and excellent enantioselectivities (up to 99% ee).
July 12, 2017: Organic & Biomolecular Chemistry
https://www.readbyqxmd.com/read/28702008/hypersensitive-response-of-plasmid-encoded-ahl-synthase-gene-to-lifestyle-and-nutrient-by-ensifer-adhaerens-x097
#5
Yanhua Zeng, Yanli Wang, Zhiliang Yu, Yili Huang
It is known that some bacteria, especially members of the family Rhizobiaceae, have multiple N-acyl homoserine lactones (AHL) synthase genes and produce multiple AHL signals. However, how bacteria selectively utilize these multiple genes and signals to cope with changing environments is poorly understood. Ensifer adhaerens is an important microorganism in terms of biotechnology, ecology and evolutionary. In this study, we investigated the AHL-based QS system of E. adhaerens X097 and its response to different lifestyles or nutrients...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28698362/structural-insights-into-lipoprotein-n-acylation-by-escherichia-coli-apolipoprotein-n-acyltransferase
#6
Cameron L Noland, Michele D Kattke, Jingyu Diao, Susan L Gloor, Homer Pantua, Mike Reichelt, Anand K Katakam, Donghong Yan, Jing Kang, Inna Zilberleyb, Min Xu, Sharookh B Kapadia, Jeremy M Murray
Gram-negative bacteria express a diverse array of lipoproteins that are essential for various aspects of cell growth and virulence, including nutrient uptake, signal transduction, adhesion, conjugation, sporulation, and outer membrane protein folding. Lipoprotein maturation requires the sequential activity of three enzymes that are embedded in the cytoplasmic membrane. First, phosphatidylglycerol:prolipoprotein diacylglyceryl transferase (Lgt) recognizes a conserved lipobox motif within the prolipoprotein signal sequence and catalyzes the addition of diacylglycerol to an invariant cysteine...
July 11, 2017: Proceedings of the National Academy of Sciences of the United States of America
https://www.readbyqxmd.com/read/28697551/n-acyl-homoserine-lactone-dynamics-during-biofilm-formation-of-a-1-2-4-trichlorobenzene-mineralizing-community-on-clay
#7
Hongjie Sheng, Mourad Harir, Lisa A Boughner, Xin Jiang, Philippe Schmitt-Kopplin, Reiner Schroll, Fang Wang
In Gram-negative bacteria, quorum sensing systems are based on the N-acyl-homoserine lactone (AHL) molecule. The objective of this study was to investigate the role of quorum sensing systems during biofilm formation by a microbial community while degrading the pollutant. Our model system included 1,2,4-trichlorobenzene (1,2,4-TCB) and its mineralizing Gram-negative bacterial community to investigate the relationships between AHL dynamics, cell growth and pollutant degradation. Biomineralization of 1,2,4-TCB was monitored for both the planktonic bacterial community with and without sterile clay particles in liquid cultures...
July 6, 2017: Science of the Total Environment
https://www.readbyqxmd.com/read/28690598/large-diversity-and-original-structures-of-acyl-homoserine-lactones-in-strain-mola-401-a-marine-rhodobacteraceae-bacterium
#8
Margot Doberva, Didier Stien, Jonathan Sorres, Nathalie Hue, Sophie Sanchez-Ferandin, Véronique Eparvier, Yoan Ferandin, Philippe Lebaron, Raphaël Lami
Quorum sensing (QS) is a density-dependent mechanism allowing bacteria to synchronize their physiological activities, mediated by a wide range of signaling molecules including N-acyl-homoserine lactones (AHLs). Production of AHL has been identified in various marine strains of Proteobacteria. However, the chemical diversity of these molecules still needs to be further explored. In this study, we examined the diversity of AHLs produced by strain MOLA 401, a marine Alphaproteobacterium that belongs to the ubiquitous Rhodobacteraceae family...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28685594/disruption-of-the-quorum-sensing-regulated-pathogenic-traits-of-the-biofilm-forming-fish-pathogen-aeromonas-hydrophila-by-tannic-acid-a-potent-quorum-quencher
#9
Bhakti Patel, Supriya Kumari, Rajanya Banerjee, Mrinal Samanta, Surajit Das
The quorum sensing (QS) phenomenon regulates a myriad of pathogenic traits in the biofilm forming fish pathogen, Aeromonas hydrophila. Blocking the QS mechanism of A. hydrophila is a novel strategy to prevent disease in fish. This study evaluated the effect of tannic acid, a QS inhibitor, on A. hydrophila-associated QS regulated phenomena. A streaking assay with Chromobacterium violaceum (CVO26) reported the presence of N-acyl homoserine lactone (AHL) in A. hydrophila, which was confirmed by HPLC and GC-MS analysis...
July 7, 2017: Biofouling
https://www.readbyqxmd.com/read/28681186/oleic-derivatives-of-dopamine-and-respiration
#10
Dominika Zajac, Agnieszka Stasinska, Mieczyslaw Pokorski
Ventilatory inhibition is considered an undesirable pharmacological side effect of pharmacotherapy in neurodegenerative conditions underlain by brain dopamine deficiency. In this context, oleic derivatives of dopamine or N-acyl-dopamines are novel substances that may be of high therapeutic interest as having the ability to cross the blood-brain barrier and acting in dopamine-like manner. In the present study we seek to define the influence of N-acyl-dopamines on lung ventilation and its hypoxic responses in the rat...
July 6, 2017: Advances in Experimental Medicine and Biology
https://www.readbyqxmd.com/read/28676791/interplay-between-4-hydroxy-3-methyl-2-alkylquinoline-and-n-acyl-homoserine-lactone-signaling-in-a-burkholderia-cepacia-complex-clinical-strain
#11
Annelise Chapalain, Marie-Christine Groleau, Servane Le Guillouzer, Aurélie Miomandre, Ludovic Vial, Sylvain Milot, Eric Déziel
Species from the Burkholderia cepacia complex (Bcc) share a canonical LuxI/LuxR quorum sensing (QS) regulation system named CepI/CepR, which mainly relies on the acyl-homoserine lactone (AHL), octanoyl-homoserine lactone (C8-HSL) as signaling molecule. Burkholderia ambifaria is one of the least virulent Bcc species, more often isolated from rhizospheres where it exerts a plant growth-promoting activity. However, clinical strains of B. ambifaria display distinct features, such as phase variation and higher virulence properties...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28670299/detection-of-diverse-n-acyl-homoserine-lactones-in-vibrio-alginolyticus-and-regulation-of-biofilm-formation-by-n-3-oxodecanoyl-homoserine-lactone-in-vitro
#12
Jianfei Liu, Kaifei Fu, Yuxiao Wang, Chenglin Wu, Fei Li, Lei Shi, Yinlin Ge, Lijun Zhou
Quorum sensing (QS) is a cell-to-cell communication system based on the exchange of small intercellular signal molecules, such as N-Acyl homoserine lactones (AHLs), which act as cell-density mediators of QS gene expression, and are highly variable both in types and amounts in most Gram-negative Proteobacteria. Understanding the regulation of AHLs may contribute to the elucidation of cell density-dependent phenomena, such as biofilm formation. Vibrio alginolyticus is among the most frequently observed marine opportunistic Vibrio pathogens...
2017: Frontiers in Microbiology
https://www.readbyqxmd.com/read/28661678/combining-eosin-y-with-selectfluor-a-regioselective-brominating-system-for-para-bromination-of-aniline-derivatives
#13
Binbin Huang, Yating Zhao, Chao Yang, Yuan Gao, Wujiong Xia
A mild, metal-free, and absolutely para-selective bromination of aniline derivatives has been developed in excellent yields, wherein the organic dye Eosin Y is employed as the bromine source in company with Selectfluor. Neither air nor moisture sensitive, this facile reaction proceeds smoothly at room temperature and completes within a short time. Mechanistic studies indicate a radical pathway; therefore, the existence of an in situ generated brominating reagent, "Selectbrom", is postulated, which may reasonably account for the unique regioselectivity for the para-bromination of N-acyl- as well as N-sulfonylanilines...
June 29, 2017: Organic Letters
https://www.readbyqxmd.com/read/28651915/novel-analogs-of-n-acylhydroxyethylaminomethyl-4h-chromen-4-one-scaffold-as-il-5-inhibitors
#14
Hyun-Sun Yang, Eeda Venkateswararao, Pulla Reddy Boggu, Vinay K Sharma, Youngsoo Kim, Sang-Hun Jung
A number of N-acyl substituted hydroxyethylaminomethyl-4H-chromen-4-ones 6a-u were prepared and evaluated for their IL-5 inhibitory activity. Among them, the compound 6r (95.0% inhibition at 30µM, IC50=10.0µM, ClogP=4.1549) showed most potent inhibitory activity. The structure activity relationship revealed that the bulkier or hydrophobic substituents at urea, carbamate or amide group resulted in good inhibitory activity against IL-5. Moreover, electron donating group at phenyl ring (6g and 6s) is much more active than electron withdrawing group (6f)...
June 15, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28651911/conformational-studies-of-gram-negative-bacterial-quorum-sensing-3-oxo-n-acyl-homoserine-lactone-molecules
#15
Darren Crowe, Alan Nicholson, Adrienne Fleming, Ed Carey, Goar Sánchez-Sanz, Fintan Kelleher
In their (1)H NMR spectra in CDCl3 3-oxo-N-acyl homoserine lactones (OHLs) show significant downfield chemical shifts of the amide NH proton when compared to the parent N-acyl homoserine lactones (AHLs). NMR spectroscopic and DFT calculation studies have shown that this is most likely due to the presence of a stabilising intramolecular H-bond from the NH to the 3-oxo group. The (1)H NMR spectra also show evidence for the enol tautomers and that the amount of enol present for a range of OHLs is 4.1-4.5% in CDCl3 and 6...
June 8, 2017: Bioorganic & Medicinal Chemistry
https://www.readbyqxmd.com/read/28641003/synthesis-and-anti-inflammatory-evaluation-of-2-aminobenzaldehydes-via-ir-iii-catalyzed-c-h-amidation-of-aldimines-with-acyl-azides
#16
Saegun Kim, Prashant Chakrasali, Hyo Sun Suh, Neeraj Kumar Mishra, Taeyoung Kim, Sang Hoon Han, Hyung Sik Kim, Byung Mu Lee, Soo Bong Han, In Su Kim
The aldimine-directed C-H amidation of various arenes with N-acyl azides as amidation surrogates under cationic iridium(III) catalysis is described. This transformation efficiently provides a range of 2-aminobenzaldehyde derivatives with excellent site selectivity and functional group compatibility. The resulting 2-aminobenzaldehyde framework provides facile access to a range of biologically interesting heterocycles. In addition, all synthetic compounds were screened for anti-inflammatory activity against interleukin-1β (IL-1β) and tumor necrosis factor alpha (TNF-α) with lipopolysaccharide (LPS)-induced RAW264...
June 30, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28632928/n-acylsulfonamides-synthetic-routes-and-biological-potential-in-medicinal-chemistry
#17
REVIEW
Alessandra Ammazzalorso, Barbara De Filippis, Letizia Giampietro, Rosa Amoroso
Sulfonamide is a common structural motif in naturally occurring and synthetic medicinal compounds. The rising interest in sulfonamides and N-acyl derivatives is attested by the large number of drugs and lead compounds identified in last years, explored in different fields of medicinal chemistry and showing biological activity. Many acylsulfonamide derivatives were designed and synthesized as isosteres of carboxylic acids, being the characteristics of these functional groups very close. Starting from chemical routes to N-acylsulfonamides, this review explores compounds of pharmaceutical interest, developed as enzymatic inhibitors or targeting receptors...
June 20, 2017: Chemical Biology & Drug Design
https://www.readbyqxmd.com/read/28596183/leptogenic-effects-of-n-acyl-phosphatidylethanolamine-nape-requires-activity-of-n-acylphosphatidylethanolamine-hydrolyzing-phospholipase-d-nape-pld
#18
Zhongyi Chen, Yongqin Zhang, Lilu Guo, Noura Dosoky, Lorenzo De Ferra, Scott Peters, Kevin D Niswender, Sean S Davies
Food intake induces synthesis of N-acylphosphatidylethanolamines (NAPEs) in the intestinal tract. While NAPEs exert leptin-like (leptogenic) effects including reduced food intake and weight gain, the mechanisms by which NAPEs induce these leptogenic effects remain unclear. One key question is whether intestinal NAPEs act directly on cognate receptors or first require conversion to N-acylethanolamides (NAEs) by NAPE-hydrolyzing phospholipase D (NAPE-PLD). Previous studies using Nape-pld-/- mice were equivocal because intraperitoneal injection of NAPEs led to non-specific, aversive effects...
June 8, 2017: Journal of Lipid Research
https://www.readbyqxmd.com/read/28594179/organocatalytic-direct-n-acylation-of-amides-with-aldehydes-under-oxidative-conditions
#19
Chenguang Zheng, Xiang Liu, Cheng Ma
The direct oxidative N-acylation reaction of primary amides with aryl/α,β-unsaturated aldehydes was achieved in the presence of azolium salt C3 and an inorganic base using 3,3',5,5'-tetra-tert-butyldiphenoquinone as the oxidant, thus providing an efficient approach for the synthesis of three types of imide compounds including N-sulfonylcarboxamides, N-sulfinylcarboxamides, and dicarboxyimides in good yield.
June 13, 2017: Journal of Organic Chemistry
https://www.readbyqxmd.com/read/28591636/n-acyl-taurines-and-acylcarnitines-cause-an-imbalance-in-insulin-synthesis-and-secretion-provoking-%C3%AE-cell-dysfunction-in-type-2-diabetes
#20
Michaela Aichler, Daniela Borgmann, Jan Krumsiek, Achim Buck, Patrick E MacDonald, Jocelyn E Manning Fox, James Lyon, Peter E Light, Susanne Keipert, Martin Jastroch, Annette Feuchtinger, Nikola S Mueller, Na Sun, Andrew Palmer, Theodore Alexandrov, Martin Hrabe de Angelis, Susanne Neschen, Matthias H Tschöp, Axel Walch
The processes contributing to β cell dysfunction in type 2 diabetes (T2D) are uncertain, largely because it is difficult to access β cells in their intact immediate environment. We examined the pathophysiology of β cells under T2D progression directly in pancreatic tissues. We used MALDI imaging of Langerhans islets (LHIs) within mouse tissues or from human tissues to generate in situ-omics data, which we supported with in vitro experiments. Molecular interaction networks provided information on functional pathways and molecules...
June 6, 2017: Cell Metabolism
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