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Short and Efficient Synthesis of Alkyl- and Aryl-Ortho-Hydroxy-Anilides and their Antibiotic Activity.

Krauß J, Plesch E, Clausen S, Bracher F - Sci Pharm (2014)

Bottom Line: An important step in the total synthesis of these antibiotics or their derivatives is the preparation of the o-hydroxy-anilide partial structure.The presented method allows the preparation of o-hydroxy-anilides and o-dihydroxy-anilides from 2-nitrophenol esters in a one-step synthesis without protecting the hydroxy group.Aryl- and alkyl-anilides were prepared following this method as simple analogues of platensimycin (A).

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.

ABSTRACT
Ortho-hydroxy-anilides are part of natural products like the new antibiotics platencin (A) and platensimycin (B). An important step in the total synthesis of these antibiotics or their derivatives is the preparation of the o-hydroxy-anilide partial structure. The presented method allows the preparation of o-hydroxy-anilides and o-dihydroxy-anilides from 2-nitrophenol esters in a one-step synthesis without protecting the hydroxy group. Aryl- and alkyl-anilides were prepared following this method as simple analogues of platensimycin (A). The resulting compounds were tested in an agar diffusion assay for their antibiotic potency.

No MeSH data available.


Schematic diagram showing the key interactions between platensimycin and the FabF enzyme [4]
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Figure 2: Schematic diagram showing the key interactions between platensimycin and the FabF enzyme [4]

Mentions: Platencin and platensimycin show a new mechanism of action by inhibiting the bacterial fatty acid synthesis. Bacterial fatty acid synthesis is carried out by fatty acid synthase (FAS II). Each step in this synthesis is encoded by separate proteins. A key step in the pathway is the condensation of the acyl-enzyme intermediate and malonyl-acyl carrier protein by catalysis of the FabF–enzyme towards the ß-ketoacyl-acyl carrier protein (elongation of the fatty acid chain). Both natural products inhibit the FabF-enzyme (Fig. 2) [1–4].


Short and Efficient Synthesis of Alkyl- and Aryl-Ortho-Hydroxy-Anilides and their Antibiotic Activity.

Krauß J, Plesch E, Clausen S, Bracher F - Sci Pharm (2014)

Schematic diagram showing the key interactions between platensimycin and the FabF enzyme [4]
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4318158&req=5

Figure 2: Schematic diagram showing the key interactions between platensimycin and the FabF enzyme [4]
Mentions: Platencin and platensimycin show a new mechanism of action by inhibiting the bacterial fatty acid synthesis. Bacterial fatty acid synthesis is carried out by fatty acid synthase (FAS II). Each step in this synthesis is encoded by separate proteins. A key step in the pathway is the condensation of the acyl-enzyme intermediate and malonyl-acyl carrier protein by catalysis of the FabF–enzyme towards the ß-ketoacyl-acyl carrier protein (elongation of the fatty acid chain). Both natural products inhibit the FabF-enzyme (Fig. 2) [1–4].

Bottom Line: An important step in the total synthesis of these antibiotics or their derivatives is the preparation of the o-hydroxy-anilide partial structure.The presented method allows the preparation of o-hydroxy-anilides and o-dihydroxy-anilides from 2-nitrophenol esters in a one-step synthesis without protecting the hydroxy group.Aryl- and alkyl-anilides were prepared following this method as simple analogues of platensimycin (A).

View Article: PubMed Central - PubMed

Affiliation: Department of Pharmacy - Center for Drug Research, Ludwig-Maximilian-University, Butenandtstr. 5-13, 81377 Munich, Germany.

ABSTRACT
Ortho-hydroxy-anilides are part of natural products like the new antibiotics platencin (A) and platensimycin (B). An important step in the total synthesis of these antibiotics or their derivatives is the preparation of the o-hydroxy-anilide partial structure. The presented method allows the preparation of o-hydroxy-anilides and o-dihydroxy-anilides from 2-nitrophenol esters in a one-step synthesis without protecting the hydroxy group. Aryl- and alkyl-anilides were prepared following this method as simple analogues of platensimycin (A). The resulting compounds were tested in an agar diffusion assay for their antibiotic potency.

No MeSH data available.