Reductive alkylation of the glycopeptide antibiotic eremomycin and its derivatives

Pavlov, A. Y.; Berdnikova, T. F.; Olsuf'eva, E. N.; Orlova, G. I.; Preobrazhenskaya, M. N.

doi:10.1007/bf02219465

Cited by 2 publications

(1 citation statement)

References 2 publications

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“…The methods of modification of C-terminal carboxyl group of eremomycin were developed: esterification (with diazoalkanes or alkyl halides) (Fig. 1, modification Ea) [20,21] and amidation (with amines in the presence of DPPA, PyBOP, HBTU, or TBTU) (Fig. 1, modification Eb) [22][23][24] without using the protection of other reactive groups (amine, hydroxy, etc).…”

Section: Mementioning

confidence: 99%

Structure-activity relationships in a series of semisynthetic polycyclic glycopeptide antibiotics

Olsuf'eva

Preobrazhenskaya

2006

Russ J Bioorg Chem

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The main achievements in the development of methods for the design of semisynthetic antibiotics of a new generation belonging to the group of polycyclic glycopeptides directed against infections caused by multidrug-resistant bacteria and dangerous human and animal viruses are reviewed. The review is focused on the results obtained at the Gauze Institute in the area of chemical modification of natural antibiotics (eremomycin, vancomycin, teicoplanin, etc.) directed toward modification of their antibacterial and/or antiviral activity. A special emphasis is placed on the study of the mechanisms of action of these antibiotics, which could be the basis of a rational approach to their chemical modification involving the transformation of the inner binding pocket and the peripheral regions of the molecules that participate in the formation of their complexes with targets. The recently discovered antiviral activity of modified glycopeptides antibiotics is also discussed. A possibility of obtaining new highly active anti-HIV-1 and anti-HIV-2 preparations on the basis of hydrophobic derivatives of the aglycones of glycopeptide antibiotics was demonstrated. New semisynthetic derivatives of antibiotics that exhibit a high antibacterial activity in vivo, have good pharmacological characteristics, and are promising for practical use are described.

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Section: Mementioning

confidence: 99%

Structure-activity relationships in a series of semisynthetic polycyclic glycopeptide antibiotics

Olsuf'eva

Preobrazhenskaya

2006

Russ J Bioorg Chem

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Novel hydroxyamides and amides containing d -glucopyranose or d -fructose units: Biological assays in MCF-7 and MDST8 cell lines

Carreiro

Costa

Cordeiro

et al. 2016

Bioorganic & Medicinal Chemistry Letters

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a b s t r a c tA novel library of 15 compounds, hydroxyamides and amides containing a b-D-glucopyranose (D-Gluc) or a b-D-fructose (D-Fruc) units was designed and synthesized for antiproliferative assays in breast (MCF-7) and colon (MDST8) cancer cell lines. Twelve of them were hydroxyamides and were successfully synthesized from b-D-glucuronic acid (D-GluA). Six of these hydroxyamides which were acetylated hydroxy-b-Dglucopyranuronamide 2a-2f (1st Family) and the other six were their respective isomers, that is, hydroxy-b-D-fructuronamide 3a-3f (2nd Family), obtained by acid-base catalyzed isomerization. These compounds have the general structure, D-GlucAC@ONHACHRA(CH 2 ) n AOH and D-FrucAC@ONHACHRA (CH 2 ) n AOH, where R = an aromatic, alkyl or a hydrogen substituent, with n = 0 or 1. Eight of these contained a chiral aminoalcohol group. Three compounds were amides containing a D-glucopyranose unit (3rd Family). SAR studies were conducted with these compounds. Antiproliferative studies showed that compound 4a, the bromo-amide containing the b-D-glucopyranose ring, potently inhibits the proliferation of the MDST8 cells. Five compounds (2e, 2f, 3d, 3e, and 3f) were shown to potently selectively inhibit the proliferation of the MCF-7 cells. Compound 4b was the only one showing inhibition in both cell lines. In general, the more active compounds were the amides and hydroxyamides containing the b-D-fructose moiety, and containing an alkyl group or hydrogen. Half-inhibitory concentrations (IC 50 ) of between 0.01 and 10 lM, were observed.

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Reductive alkylation of the glycopeptide antibiotic eremomycin and its derivatives

Cited by 2 publications

References 2 publications

Structure-activity relationships in a series of semisynthetic polycyclic glycopeptide antibiotics

Structure-activity relationships in a series of semisynthetic polycyclic glycopeptide antibiotics

Novel hydroxyamides and amides containing d -glucopyranose or d -fructose units: Biological assays in MCF-7 and MDST8 cell lines

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