Bioorg Med Chem. 2010 Sep 1;18(17):6559-68. Epub 2010 Jun 22.

4''-O-(omega-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens.

Fajdetić A, Cipcić Paljetak H, Lazarevski G, Hutinec A, Alihodzić S, Derek M, Stimac V, Andreotti D, Sunjić V, Berge JM, Mutak S, Dumić M, Lociuro S, Holmes DJ, Marsić N, Eraković Haber V, Spaventi R.

Source

GlaxoSmithKline Research Centre Zagreb Ltd, Prilaz baruna Filipovića 29, HR-10000 Zagreb, Croatia. andrea.z.fajdetic@gsk.com

Abstract

Four macrolides-6-O-methyl-8a-aza-8a-homoerythromycin, clarithromycin, azithromycin and azithromycin 11,12-cyclic carbonate, have been selected for the construction of a series of new quinolone derivatives. The quinolone moiety is connected to the macrolide scaffold via a diaminoaklyl 4''-O-propionyl ester chain of varying length. At the terminus the linker is attached via one of the nitrogen atoms in the linker at C(6) or C(7) of the quinolone. Many of compounds described, particularly clarithromycin derivative 37, and azithromycin derivatives 48 and 55, exhibited excellent antibacterial activity against a wide range of clinically relevant macrolide-resistant organisms, with profiles superior to that of telithromycin, an enhanced spectrum ketolide.

PMID:: 20634078; [PubMed - indexed for MEDLINE]

MeSH Terms, Substances

MeSH Terms

Substances

LinkOut - more resources

Full Text Sources

Medical

Antibiotics - MedlinePlus Health Information

Molecular Biology Databases

ERYTHROMYCIN - HSDB

Supplemental Content

Save items

Related citations in PubMed

Novel 8a-aza-8a-homoerythromycin--4''-(3-substituted-amino)propionates with broad spectrum antibacterial activity. [Bioorg Med Chem Lett. 2010]
Novel 8a-aza-8a-homoerythromycin--4''-(3-substituted-amino)propionates with broad spectrum antibacterial activity.
Hutinec A, Derek M, Lazarevski G, Sunjić V, Paljetak HC, Alihodzić S, Eraković Haber V, Dumić M, Marsić N, Mutak S. Bioorg Med Chem Lett. 2010 Jun 1; 20(11):3244-9. Epub 2010 Apr 18.
Synthesis and antibacterial activity of isomeric 15-membered azalides. [J Antibiot (Tokyo). 2006]
Synthesis and antibacterial activity of isomeric 15-membered azalides.
Alihodzic S, Fajdetic A, Kobrehel G, Lazarevski G, Mutak S, Pavlovic D, Stimac V, Cipcic H, Kramaric MD, Erakovic V, et al. J Antibiot (Tokyo). 2006 Dec; 59(12):753-69.
Activities of two novel macrolides, GW 773546 and GW 708408, compared with those of telithromycin, erythromycin, azithromycin, and clarithromycin against Haemophilus influenzae. [Antimicrob Agents Chemother. 2...]
Activities of two novel macrolides, GW 773546 and GW 708408, compared with those of telithromycin, erythromycin, azithromycin, and clarithromycin against Haemophilus influenzae.
Kosowska K, Credito K, Pankuch GA, Hoellman D, Lin G, Clark C, Dewasse B, McGhee P, Jacobs MR, Appelbaum PC. Antimicrob Agents Chemother. 2004 Nov; 48(11):4113-9.
Review The ketolides: a critical review. [Drugs. 2002]
Review The ketolides: a critical review.
Zhanel GG, Walters M, Noreddin A, Vercaigne LM, Wierzbowski A, Embil JM, Gin AS, Douthwaite S, Hoban DJ. Drugs. 2002; 62(12):1771-804.
Review Azalides from azithromycin to new azalide derivatives. [J Antibiot (Tokyo). 2007]
Review Azalides from azithromycin to new azalide derivatives.
Mutak S. J Antibiot (Tokyo). 2007 Feb; 60(2):85-122.

See reviews... See all...

Related information

Related Citations
Calculated set of PubMed citations closely related to the selected article(s) retrieved using a word weight algorithm. Related articles are displayed in ranked order from most to least relevant, with the “linked from” citation displayed first.
BioAssay
PubChem BioAssay experiments on the biological activities of small molecules that cite the current articles. The depositors of BioAssay data provide these references.
Compound (MeSH Keyword)
PubChem chemical compound records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.
Substance (MeSH Keyword)
PubChem chemical substance (submitted) records that are classified under the same Medical Subject Headings (MeSH) controlled vocabulary as the current articles.

Recent activity

Clear Turn Off Turn On

4''-O-(omega-Quinolylamino-alkylamino)propionyl derivatives of selected macrolid...
4''-O-(omega-Quinolylamino-alkylamino)propionyl derivatives of selected macrolides with the activity against the key erythromycin resistant respiratory pathogens.
Bioorg Med Chem. 2010 Sep 1 ;18(17):6559-68. Epub 2010 Jun 22 .

PubMed
[Can breast cancer be prevented?].
[Can breast cancer be prevented?].
Tidsskr Nor Laegeforen. 1991 May 30 ;111(14):1745-8.

PubMed
What should be the principle imaging test in heart failure--CMR or echocardiogra...
What should be the principle imaging test in heart failure--CMR or echocardiography?
JACC Cardiovasc Imaging. 2010 Jul ;3(7):776-82.

PubMed
[Posttraumatic hypopituitarism].
[Posttraumatic hypopituitarism].
Tidsskr Nor Laegeforen. 1991 May 30 ;111(14):1718-20.

PubMed
Amplification of IGH/CCND1 fusion gene in a primary plasma cell leukemia case.
Amplification of IGH/CCND1 fusion gene in a primary plasma cell leukemia case.
Cancer Genet Cytogenet. 2010 Aug ;201(1):62-5.

PubMed

Your browsing activity is empty.

Activity recording is turned off.

Turn recording back on

PubMed

Result Filters

Display Settings:

Send to: