Zhang et al., 2013 - Google Patents

Design, synthesis, and antibacterial activities of conformationally constrained kanamycin A derivatives

Zhang et al., 2013

Document ID
18303924919102871314
Author
Zhang W
Chen Y
Liang Q
Li H
Jin H
Zhang L
Meng X
Li Z
Publication year
Publication venue
The Journal of Organic Chemistry

External Links

Snippet

A series of conformationally constrained kanamycin A derivatives with a 2′-hydroxyl group in ring I and a 5-hydroxyl group in ring II tethered by carbon chains were designed and synthesized. Pivotal 5, 2′-hydroxyl groups were exposed, and the kanamycin A …
Continue reading at pubs.acs.org (other versions)

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H5/00—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium
    • C07H5/04—Compounds containing saccharide radicals in which the hetero bonds to oxygen have been replaced by the same number of hetero bonds to halogen, nitrogen, sulfur, selenium, or tellurium to nitrogen
    • C07H5/06—Aminosugars
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings

Similar Documents

Publication Publication Date Title
Haddad et al. Design of novel antibiotics that bind to the ribosomal acyltransfer site
Zhang et al. Design, synthesis, and antibacterial activities of conformationally constrained kanamycin A derivatives
Alper et al. Probing the specificity of aminoglycoside− ribosomal RNA interactions with designed synthetic analogs
Bastida et al. Exploring the use of conformationally locked aminoglycosides as a new strategy to overcome bacterial resistance
Zhang et al. Surprising alteration of antibacterial activity of 5′′-modified neomycin against resistant bacteria
Pokrovskaya et al. Design, synthesis, and evaluation of novel fluoroquinolone− aminoglycoside hybrid antibiotics
Sucheck et al. Design of bifunctional antibiotics that target bacterial rRNA and inhibit resistance-causing enzymes
Dondoni et al. C-glycoside clustering on calix [4] arene, adamantane, and benzene scaffolds through 1, 2, 3-triazole linkers
Matsushita et al. Design, multigram synthesis, and in vitro and in vivo evaluation of propylamycin: a semisynthetic 4, 5-deoxystreptamine class aminoglycoside for the treatment of drug-resistant enterobacteriaceae and other gram-negative pathogens
Wong et al. A library approach to the discovery of small molecules that recognize RNA: use of a 1, 3-hydroxyamine motif as core
Kistemaker et al. Stereoselective ribosylation of amino acids
Fridman et al. A new class of branched aminoglycosides: pseudo-pentasaccharide derivatives of neomycin B
Sati et al. Modification at the 2′-position of the 4, 5-series of 2-deoxystreptamine aminoglycoside antibiotics to resist aminoglycoside modifying enzymes and increase ribosomal target selectivity
Meiers et al. Directing drugs to bugs: antibiotic-carbohydrate conjugates targeting biofilm-associated lectins of Pseudomonas aeruginosa
Griffith et al. Model for antibiotic optimization via neoglycosylation: synthesis of liponeoglycopeptides active against VRE
Quirke et al. Apralogs: apramycin 5-O-glycosides and ethers with improved antibacterial activity and ribosomal selectivity and reduced susceptibility to the aminoacyltransferase (3)-IV resistance determinant
Mandhapati et al. Structure-based design and synthesis of apramycin–paromomycin analogues: Importance of the configuration at the 6′-position and differences between the 6′-amino and hydroxy series
Baussanne et al. Synthesis and antimicrobial evaluation of amphiphilic neamine derivatives
Liautard et al. Convergent and stereoselective synthesis of iminosugar-containing Gal f and UDP-Gal f mimicks: Evaluation as inhibitors of UDP-Gal mutase
Fosso et al. Structure–activity relationships for antibacterial to antifungal conversion of kanamycin to amphiphilic analogues
Matsushita et al. Influence of 4′-O-glycoside constitution and configuration on ribosomal selectivity of paromomycin
Dinh et al. Design, synthesis, and evaluation of the multidrug resistance-reversing activity of D-glucose mimetics of hapalosin
Bradley et al. Application of Ugi reactions in synthesis of divalent neoglycoconjugates: Evidence that the sugars are presented in restricted conformation
Sonousi et al. Effects of the 1-N-(4-Amino-2 S-hydroxybutyryl) and 6′-N-(2-Hydroxyethyl) substituents on ribosomal selectivity, cochleotoxicity, and antibacterial activity in the sisomicin class of aminoglycoside antibiotics
Wander et al. Synthetic (N, N-dimethyl) doxorubicin glycosyl diastereomers to dissect modes of action of anthracycline anticancer drugs