17460-45-6Relevant academic research and scientific papers
Hydrolysis of the GlcNAc oxazoline: deamidation and acyl rearrangement
Jha, Rajesh,Davis, Jeffrey T.
, p. 125 - 134 (1995)
The specific deamidation of 2-acetamido-1,3,4,6-tetra-O-acetyl-α-D-glucopyranose is achieved by p-toluenesulfonic acid-promoted hydrolysis of 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)--2-oxazoline 2 to give quantitative formation of the 1,3,4,6-tetra-O-actyl-2-amino-2-deoxy-α-D-glucopyranose p-toluenosulfonate (5d).This two-step procedure provides an amino sugar which may be readily acylated to give novel glycoconjugates.Altermatively, base-catalyzed O-1 --> N-2 acyl rearrangemet of the amino tosylate 5d gives the 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-D-glucopyranose 4 as a 9:1 mixture of α and β anomers.Thus, hydrolysis of GlcNAc oxazoline 2 gives the amino-ester 5 as the kinetic product and the amido-alcohol 4 as the thermodynamic product.Keywords: GlcNAc oxazoline; Deamidation; Acyl rearrangement
GLYCOSYLATED 3-SUBSTITUTED FLUOROQUINOLONE DERIVATIVES, PREPARATION METHODS THEREOF, AND THEIR USE IN THE TREATMENT OF ANTIMICROBIAL INFECTIONS
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, (2020/10/20)
The present disclosure relates to 3-substituted fluoroquinolone derivatives, and more particularly to glycosylated 3-substitutred fluoroquinolone derivatives, methods of preparation thereof, and uses thereof for treating microbial infections.
Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
, (2020/07/04)
Herein we report the design, synthesis and biological evaluation of structurally modified ciprofloxacin, norfloxacin and moxifloxacin standard drugs, featuring amide functional groups at C-3 of the fluoroquinolone scaffold. In vitro antimicrobial testing against various Gram-positive bacteria, Gram-negative bacteria and fungi revealed potential antibacterial and antifungal activity. Hybrid compounds 9 (MIC 0.2668 ± 0.0001 mM), 10 (MIC 0.1358 ± 00025 mM) and 13 (MIC 0.0898 ± 0.0014 mM) had potential antimicrobial activity against a fluoroquinolone-resistant Escherichia coli clinical isolate, compared to ciprofloxacin (MIC 0.5098 ± 0.0024 mM) and norfloxacin (MIC 0.2937 ± 0.0021 mM) standard drugs. Interestingly, compound 10 also exerted potential antifungal activity against Candida albicans (MIC 0.0056 ± 0.0014 mM) and Penicillium chrysogenum (MIC 0.0453 ± 0.0156 mM). Novel derivatives and standard fluoroquinolone drugs exhibited near-identical cytotoxicity levels against L6 muscle cell-line, when measured using the MTT assay.
1,8-NAPHTHYRIDINE GLUCOSAMINE DERIVATIVES, THEIR USE IN THE TREATMENT OF MICROBIAL INFECTIONS, AND A METHOD FOR PREPARATION
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Paragraph 049-050, (2020/06/10)
The present disclosure provides a compound of Formula (I) or any pharmaceutically acceptable salt thereof for use in treating a microbial infection in a subject, a method for preparing the same, and a pharmaceutical composition thereof: (I) wherein R
Rational Design of a DNA-Scaffolded High-Affinity Binder for Langerin
Bachem, Gunnar,Baukmann, Hannes,Dernedde, Jens,Fuchsberger, Felix,Kim, Dongyoon,Rademacher, Christoph,Seitz, Oliver,Silberreis, Kim,Wamhoff, Eike-Christian
supporting information, p. 21016 - 21022 (2020/09/21)
Binders of langerin could target vaccines to Langerhans cells for improved therapeutic effect. Since langerin has low affinity for monovalent glycan ligands, highly multivalent presentation has previously been key for targeting. Aiming to reduce the amoun
Design, synthesis, and biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents
Mohammed, Aya A. M.,Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Okechukwu, Patrick N.
, p. 179 - 186 (2019/01/04)
In the quest for discovering potent antimicrobial agents with lower toxicity, we envisioned the design and synthesis of nalidixic acid-D-(+)-glucosamine conjugates. The novel compounds were synthesized and evaluated for their in vitro antimicrobial activi
Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors
Biswas, Nripendra N.,Yu, Tsz Tin,Kimyon, ?nder,Nizalapur, Shashidhar,Gardner, Christopher R.,Manefield, Mike,Griffith, Renate,Black, David StC.,Kumar, Naresh
, p. 1183 - 1194 (2017/02/18)
Bacteria communicate with one another and regulate their pathogenicity through a phenomenon known as quorum sensing (QS). When the bacterial colony reaches a threshold density, the QS system induces the production of virulence factors and the formation of biofilms, a powerful defence system against the host's immune responses. The glucosamine monomer has been shown to disrupt the bacterial QS system by inhibiting autoinducer (AI) signalling molecules such as the acyl-homoserine lactones (AHLs). In this study, the synthesis of acetoxy-glucosamides 8, hydroxy-glucosamides 9 and 3-oxo-glucosamides 12 was performed via the 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC·HCl) and N,N′-dicyclohexylcarbodiimide (DCC) coupling methods. All of the synthesized compounds were tested against two bacterial strains, P. aeruginosa MH602 (LasI/R-type QS) and E. coli MT102 (LuxI/R-type QS), for QS inhibitory activity. The most active compound 9b showed 79.1% QS inhibition against P. aeruginosa MH602 and 98.4% against E. coli MT102, while compound 12b showed 64.5% inhibition against P. aeruginosa MH602 and 88.1% against E. coli MT102 strain at 2?mM concentration. The ability of the compounds to inhibit the production of the virulence factor pyocyanin and biofilm formation in the P. aeruginosa (PA14) strain was also examined. Finally, computational docking studies were performed with the LasR receptor protein.
2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation
Zhao, Peng-Fei,Liu, Zai-Qun
, p. 458 - 466 (2017/05/05)
The Ugi four-component-reaction (Ugi 4CR) allowed synthesizing bisamide from carboxylic acid, aldehyde, amine, and isocyanide in one-pot operation. However, introducing 2-isocyano glucose into the Ugi 4CR and investigating the inhibitory effects of Ugi adducts against radical-induced oxidation of DNA remained technical challenges. We herein applied 2-isocyano glucose (acetylation of hydroxy groups) to perform a catalyst-free Ugi 4CR at room temperature. The gallic, ferulic, caffeic, or p-hydroxybenzoic acids, aniline (or benzylamine and p-aminophenol), and formaldehyde acted as reagents. In the case of inhibiting DNA oxidations induced by 2,2’-azobis(2-amidinopropane hydrochloride) (AAPH), hydroxy radical, and Cu2+/glutathione, the Ugi adduct containing glucose moiety exhibited higher antioxidative activities than the structural analog without glucose moiety involved. It was also proved that high antioxidative property was owing to hydroxy groups in glucose moiety. Therefore, sugar-appended Ugi adducts might hold promising inhibitors for DNA oxidation.
Glucosamide compound and preparation and application thereof
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Paragraph 0033, (2017/06/21)
The invention relates to a glucosamide compound and a preparation method thereof. The glucosamide compound has a structure as shown in the formula (I). In the formula (I), R is methoxy group, nitro group, amino-group, hydroxyl group, C1-4 alkyl group or halogen, n is the number of substituent groups, and n is 1 or 2. The glucosamide compound is simple to prepare, has excellent plant induced resistance activity, and can be used as a plant induced resistance agent for controlling cucumber bacterial angular leaf spot, cucumber target leaf spot and tomato late blight. The invention also relates to a plant induced resistant agent containing the compound.
Fungicidal heterocyclic aromatic amides and their compositions, methods of use and preparation
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, (2015/09/28)
Heterocyclic aromatic amides having a hydroxy group adjacent to the amide functionality are useful as antifungal agents, particularly for plants.
