7597-81-1

Usage

Uses

Used in Organic Synthesis:
2-(4-Methoxybenzylidene)imino-2-deoxy-1,3,4,6-Tetra-O-acetyl-β-D-glucopyranose is used as a synthetic intermediate for the preparation of various organic compounds. Its unique structure allows for selective reactions and transformations that can lead to the formation of a wide range of products, making it a versatile building block in the field of organic chemistry.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-(4-Methoxybenzylidene)imino-2-deoxy-1,3,4,6-Tetra-O-acetyl-β-D-glucopyranose is used as a key component in the synthesis of drug candidates. Its ability to form stable intermediates and participate in complex reactions can contribute to the development of new medicines with improved therapeutic properties.
Used in Chemical Research:
2-(4-Methoxybenzylidene)imino-2-deoxy-1,3,4,6-Tetra-O-acetyl-β-D-glucopyranose is also utilized in chemical research for studying reaction mechanisms and exploring new synthetic pathways. Its reactivity and structural features make it an interesting subject for academic and industrial research, potentially leading to breakthroughs in synthetic chemistry.
Used in Material Science:
In the field of material science, 2-(4-Methoxybenzylidene)imino-2-deoxy-1,3,4,6-Tetra-O-acetyl-β-D-glucopyranose can be employed in the development of novel materials with specific properties. Its participation in the synthesis of polymers, coatings, or other materials can result in products with unique characteristics, such as improved stability, reactivity, or biocompatibility.

InChI:InChI=1/C22H27NO10/c1-12(24)29-11-18-20(30-13(2)25)21(31-14(3)26)19(22(33-18)32-15(4)27)23-10-16-6-8-17(28-5)9-7-16/h6-10,18-22H,11H2,1-5H3/b23-10+

Upstream product

• 35946-64-6 2-deoxy-2-(4-methoxybenzylidene)amino-D-glucose 
• 108-24-7 acetic anhydride 
• 51471-40-0 2--2-deoxy-D-glucopyranose 
• 51471-40-0 6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol 
• 123-11-5 4-methoxy-benzaldehyde 
• 52010-97-6 4-(hydroxylmethyl)benzaldehyde 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 14131-63-6 D-glucosamine hydrochloride 
• 14131-62-5 D-glucosamine hydrochloride 

Downstream Products

• 225242-73-9 phenyl(2-trifluoracetamido-2-deoxy-3,4,6-tri-O-acetyl-1-thio-D-glucopyranoside) 
• 225242-75-1 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-benzenesulfinyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester 
• 10022-13-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose 
• 82219-35-0 2-<-L-alanyl>amino>-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 129729-40-4 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-D-glucopyranose 
• 1374661-93-4 4-((3aR,5S,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)hepta-1,6-dien-4-ol 
• 1374661-94-5 1-((3aR,5S,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)cyclopent-3-enol 
• 1374661-95-6 1-((3aR,5S,6S,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-2-(methylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-5-yl)cyclopentanol 
• 1374661-99-0 (3aR,5R,6R,7R,7aR)-6,7-bis(4-methoxybenzyloxy)-N-methyl-5-(prop-1-en-2-yl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine 
• 1374661-98-9 (3aR,5S,6S,7R,7aR)-5-(2-fluoropropan-2-yl)-6,7-bis(4-methoxybenzyloxy)-N-methyl-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-amine 
• 1374768-63-4 (3aR,5R,6S,7R,7aR)-5-(acetoxymethyl)-2-(2-(benzyloxy)ethylamino)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diyl diacetate 
• 1374768-64-5 (3aR,5R,6S,7R,7aR)-2-(2-(benzyloxy)ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazole-6,7-diol 
• 1374768-65-6 tert-butyl 2-(benzyloxy)ethyl((3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)carbamate 
• 1374768-66-7 tert-butyl 2-(benzyloxy)ethyl((3aR,5R,6S,7R,7aR)-5-((tert-butyldimethylsilyloxy)methyl)-6,7-dihydroxy-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d]thiazol-2-yl)carbamate 

Relevant academic research and scientific papers

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

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.

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

GOLD COMPOSITIONS AND METHODS OF USE THEREOF

Gold compounds and pharmaceutically acceptable salts thereof are disclosed. Certain compounds and salts are active as antibacterial, antifungal, and/or anti-parasitic agents. The disclosure provides pharmaceutical compositions containing the gold compounds. Methods of using the gold compounds to treat bacterial infections are disclosed.

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.

Synthesis and Structure-Activity Relationship Study of Antimicrobial Auranofin against ESKAPE Pathogens

Auranofin, an FDA-approved arthritis drug, has recently been repurposed as a potential antimicrobial agent; it performed well against many Gram-positive bacteria, including multidrug resistant strains. It is, however, inactive toward Gram-negative bacteria, for which we are in dire need of new therapies. In this work, 40 auranofin analogues were synthesized by varying the structures of the thiol and phosphine ligands, and their activities were tested against ESKAPE pathogens. The study identified compounds that exhibited bacterial inhibition (MIC) and killing (MBC) activities up to 65 folds higher than that of auranofin, making them effective against Gram-negative pathogens. Both thiol and the phosphine structures influence the activities of the analogues. The trimethylphosphine and triethylphosphine ligands gave the highest activities against Gram-negative and Gram-positive bacteria, respectively. Our SAR study revealed that the thiol ligand is also very important, the structure of which can modulate the activities of the AuI complexes for both Gram-negative and Gram-positive bacteria. Moreover, these analogues had mammalian cell toxicities either similar to or lower than that of auranofin.

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

Total Synthesis of a Densely Functionalized Plesiomonas shigelloides Serotype 51 Aminoglycoside Trisaccharide Antigen

Plesiomonas shigelloides, a pathogen responsible for frequent outbreaks of severe travelers' diarrhea, causes grave extraintestinal infections. Sepsis and meningitis due to P. shigelloides are associated with a high mortality rate as antibiotic resistance increases and vaccines are not available. Carbohydrate antigens expressed by pathogens are often structurally unique and are targets for developing vaccines and diagnostics. Here, we report a total synthesis of the highly functionalized trisaccharide repeating unit 2 from P. shigelloides serotype 51 from three monosaccharides. A judicious choice of building blocks and reaction conditions allowed for the four amino groups adorning the sugar rings to be installed with two N-acetyl (Ac) groups, rare acetamidino (Am), and d-3-hydroxybutyryl (Hb) groups. The strategy for the differentiation of amino groups in trisaccharide 2 will serve well for the syntheses of other complex glycans.

Asymmetric organocatalytic synthesis of tertiary azomethyl alcohols: key intermediates towards azoxy compounds and α-hydroxy-β-amino esters

A series of peracylated glycosamine-derived thioureas have been synthesized and their behavior as bifunctional organocatalysts has been tested in the enantioselective nucleophilic addition of formaldehyde tert-butyl hydrazone to aliphatic α-keto esters fo

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.