- 1,8-NAPHTHYRIDINE GLUCOSAMINE DERIVATIVES, THEIR USE IN THE TREATMENT OF MICROBIAL INFECTIONS, AND A METHOD FOR PREPARATION
-
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
- -
-
-
- Design, synthesis and antimicrobial evaluation of novel glycosylated-fluoroquinolones derivatives
-
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.
- Mohammed, Aya A. M.,Okechukwu, Patrick N.,Shehadeh, Mayadah B.,Suaifan, Ghadeer A. R. Y.
-
-
- Rational Design of a DNA-Scaffolded High-Affinity Binder for Langerin
-
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
- Bachem, Gunnar,Baukmann, Hannes,Dernedde, Jens,Fuchsberger, Felix,Kim, Dongyoon,Rademacher, Christoph,Seitz, Oliver,Silberreis, Kim,Wamhoff, Eike-Christian
-
p. 21016 - 21022
(2020/09/21)
-
- GLYCOSYLATED 3-SUBSTITUTED FLUOROQUINOLONE DERIVATIVES, PREPARATION METHODS THEREOF, AND THEIR USE IN THE TREATMENT OF ANTIMICROBIAL INFECTIONS
-
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 biological evaluation of 1,8-naphthyridine glucosamine conjugates as antimicrobial agents
-
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
- Mohammed, Aya A. M.,Suaifan, Ghadeer A. R. Y.,Shehadeh, Mayadah B.,Okechukwu, Patrick N.
-
p. 179 - 186
(2019/01/04)
-
- 2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation
-
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.
- Zhao, Peng-Fei,Liu, Zai-Qun
-
p. 458 - 466
(2017/05/05)
-
- Synthesis of antimicrobial glucosamides as bacterial quorum sensing mechanism inhibitors
-
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.
- 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)
-
- Glucosamide compound and preparation and application thereof
-
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.
- -
-
-
- Design, synthesis and evaluation of a novel class of glucosamine mimetic peptides containing 1,3-dioxane
-
A number of novel 2-(N-(2-(5,5-dimethyl-1,3-dioxane-2-yl)ethyl)aminoacyl)amino-2-deoxy- d-glucopyranoside were synthesized from a readily available starting material, glucosamine, 2,2-dimethyl-1,3-propanediol and 1,1,3,3-tetramethoxypropane, and evaluated
- Zeng, Li,Xu, Guichao,Gao, Pengchao,Zhang, Meng,Li, Hong,Zhang, Jianwei
-
p. 109 - 120
(2015/02/19)
-
- Synthesis and characterization of N-acyl-tetra-O-acyl glucosamine derivatives
-
Novel 1,3,4,6-tetra-O-acyl-N-acyl-d-glucosamine derivatives were synthesized from glucosamine hydrochloride (GlcN·HCl) by the acylation with pyridine as a catalyst. A derivative of tetra-O-acetyl glucosamine contained ketoprofen, a non-steroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic effects, was first synthesized. In analysis of the NMR spectra, the ratio of α:β-anomer showed that penta-acyl-d- glucosamine derivatives and N-acetylated glucosamines containing O-acyl groups have been only the α-anomer. Meanwhile, both the intermediates and the glucoconjugate compound of ketoprofen have only the β-anomer.
- Dang, Chi-Hien,Nguyen, Cong-Hao,Nguyen, Thanh-Danh,Im, Chan
-
p. 6239 - 6245
(2014/01/23)
-
- Synthesis of unnatural N-glycosyl α-amino acids via Petasis reaction
-
A convenient and efficient protocol for the synthesis of unnatural N-glycosyl α-amino acids was developed. Condensation of 1,3,4,6-tetra-O-actyl-β-d-glucosamine hydrochloride, alkenyl boronic acid, and glyoxylic acid was achieved in CH2Cl2
- Tao, Chuan-Zhou,Zhang, Zhong-Tang,Wu, Jian-Wei,Li, Rong-Hua,Cao, Zhi-Ling
-
p. 532 - 534
(2014/05/06)
-
- Synthesis and antifungal activity of d-glucopyranosyl ureas and d-glucofurano-imidazolidine-2-ones
-
A series of N-β-d-glucopyranosyl-N'-substituted phenyl ureas were synthesized by reaction of glucosyl isocyanate with arylamines and glycosamine with aryl isocyanates, and a series of d-glucofurano-imidazolidine-2-ones were obtained via deacetylation of glycosylureas. Although some of the compounds have already been described, most were prepared for the first time in this work. The structures of all the compounds synthesized were confirmed by IR, 1H NMR, and, in part, by 13C NMR. Antifungal activity of the title compounds was determined against four kinds of plant pathogenic fungi, Sclerotinia sclerotiorum, Fusarium graminearum, Fusarium oxysporum, and Bipolaris maydis. Preliminary bioassay indicates that most of glycosylureas had some activity against S. sclerotiorum; for some, the antifungal activity was strong. However, most of the imidazolidine-2-ones had weak antifungal activity.
- Tang, Xuan,Xue, Feng,Ma, Hongju,Cao, Xiufang,Chen, Changshui,Li, Xuegang
-
p. 805 - 820
(2013/06/05)
-
- Schiff bases from d-glucosamine and aliphatic ketones
-
Despite the comprehensive literature and enormous versatility of chiral imines derived from aminosugars and aldehydes, the corresponding counterparts generated from ketones remain an underestimated research subject. Filling in the gap, this manuscript she
- Perez, Esther M.S.,Avalos, Martin,Babiano, Reyes,Cintas, Pedro,Light, Mark E.,Jimenez, Jose L.,Palacios, Juan C.,Sancho, Ana
-
scheme or table
p. 23 - 32
(2011/03/19)
-
- 2,2′-Bipyridine-3,3′-dicarboxylic carbohydrate esters and amides. Synthesis and preliminary evaluation as ligands in Cu(II)-catalysed enantioselective electrophilic fluorination
-
A series of 10 new carbohydrate-substituted bipyridines were prepared from 2,2′-bipyridine-3,3′-dicarboxylic acid, itself easily available from ortho-phenanthroline. As a preliminary exploration of their use as chiral ligands, Cu(II)-catalysed asymmetric electrophilic fluorination of model β-ketoesters using these simple and easily accessible chiral bipyridines was studied. Only modest enantioselectivity was observed in this reaction, although the ee was in a similar range as those provided by known and more elaborate ligands.
- Assalit, Aurelie,Billard, Thierry,Chambert, Stephane,Langlois, Bernard R.,Queneau, Yves,Coe, Diane
-
experimental part
p. 593 - 601
(2009/09/05)
-
- Glucosamine and Glucosamine/Anti-Inflammatory Mutual Prodrugs, Compositions, and Methods
-
Mutual prodrugs of glucosamine, and derivatives and analogs of glucosamine and an anti-inflammatory agent, compositions thereof, and methods for, e.g., treating disorders and conditions by administration of the compositions are provided. Topical compositi
- -
-
Page/Page column Sheet 4/17; Sheet 6/17; 11
(2010/11/29)
-
- SELECTIVE GLYCOSIDASE INHIBITORS AND USES THEREOF
-
The invention provides compounds of formula (I) for selectively inhibiting glycosidases, prodrugs of the compounds, and pharmaceutical compositions including the compounds or prodrugs of the compounds The invention also provides methods of treating diseas
- -
-
Page/Page column 63-64
(2008/06/13)
-
- Synthesis and testing of beta-cell-specific streptozotoein-derived near-infrared imaging probes
-
Labeling diabetes: Streptozotocin-derived, cyanine-5.5-labeled imaging probes were synthesized and tested with the beta-cell-mimic INS-1E cell line in cell uptake assays, as well as by flow cytometry and confocal microscopy. Both probes showed superb labe
- Ran, Chongzhao,Pantazopoulos, Pamela,Medarova, Zdravka,Moore, Anna
-
p. 8998 - 9001
(2008/09/20)
-
- In the search for new anticancer drugs. 27. Synthesis and comparison of anticancer activity in vivo of amino acids, carbohydrates, and carbohydrate- amino acid conjugates containing the [N'-(2-chloroethyl)-N'- nitrosoamino]carbonyl group
-
The [N'-(2-chloroethyl)-N'-nitrosoamino]carbonyl [(2- chloroethyl)nitrosocarbamoyl, CNC] moiety containing compounds CNC- glycinamide 2d, CNC-amino acid derivatives 7a-d, and carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23, 27, and 28 were synthesized and evaluated in vivo for their anticancer activities against the murine lymphocytic leukemia P388 using the National Cancer Institute (NCI) protocol. The most active compound was 2d with a 520% increase in life span (%ILS) and 6/6 survivors after 60 days. The CNC-amino acid analogs 7a-d possessed high to moderate activities with maximum %ILS values of 270, 174, 141 and 132, respectively. Among the carbohydrate-CNC-amino acid derivatives the α-methyl glycoside derivatives 22 and 23 were most active with maximum %ILS values of 277 and 137, respectively, followed by the hemiacetal carbohydrate analogs 13 and 18 with %ILS values of 93 and 149, respectively, and the tetra-O-acetyl derivatives 27 and 28 with %ILS of 110 and 111, respectively. Compounds 7b, 18, 23 and 28 were then tested in vivo against the murine lymphoid leukemia L1210 using the NCI protocol. In this case, the hemiacetal type carbohydrate- CNC-amino analog 18 had the highest activity with a maximum %ILS value of 477 and 4/6 survivors on day 60, followed by 7b (275% ILS), 23 (152% ILS) and 28 (106% ILS). The lipophilicities of all CNC compounds were determined by the partition coefficient using the UV method. A correlation of %ILS values with log P values indicated, in general, an increase in cytotoxicity with a decrease in hydrophilicity for the carbohydrate-CNC-amino acid conjugates 13, 18, 22, 23 and the clinical drugs streptozotocin (1e), chlorozotocin (1f), and cymerin (1g).
- Sosnovsky,Gnewuch
-
p. 989 - 998
(2007/10/02)
-
- Synthetic O-glycopeptides as model substrates for glycosyltransferases
-
A new approach to O-glycopeptides of the glucosamine type is described. N-Urethane protected, peracetylated glucosamine is converted into its 1-thio (1-bromo) derivative and used for glycosylation of a variety of protected serine or threonine derivatives
- Schultz,Kunz
-
p. 1205 - 1220
(2007/10/02)
-
- The use of N-alkoxycarbonyl derivatives of 2-amino-2-deoxy-D-glucose as donors in glycosylation reactions
-
1,3,4,6-Tetra-O-acetyl-2-alkoxycarbonylamino-2-deoxy-β-D-glucopyranoses and 3,4,6-tri-O-acetyl-2-alkoxycarbonylamino-2-deoxy-α-D-glucopyranosyl bromides have been used as donors in glycosylation reactions with model alcohols. β-Glycosides were obtained in good yields and with a high degree of 1,2-trans stereoselectivity.An oxazolidone was formed as the main product from the reaction of some of the glucopyranosylbromides with alcohols of low reactivity, but the formation of all products could be interpreted by a strong participation of the alkoxycarbonylamino group.
- Boullanger, Paul,Jouineau, Martine,Bouammali, Boufelja,Lafont, Dominique,Descotes, Gerard
-
p. 151 - 164
(2007/10/02)
-