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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.


Structure of platencin (A) and platensimycin (B)
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Figure 1: Structure of platencin (A) and platensimycin (B)

Mentions: The 3-amino-2,4-dihydroxybenzoic acid core is an essential part of the new antibiotic drugs platencin (A) and platensimycin (B) [Figure 1], which show a high activity against Gram-positive bacteria, especially methicillin-resistant Staphylococcus aureus (MRSA) or vancomycin-resistant enterococci (VRE). Platencin (A) shows MIC values against MRSA of about 0.1 μg/mL and platensimycin (B) 0.2–0.4 μg/mL against MRSA and 0.4–0.8 μg/mL against VRE. Furthermore, platensimycin (B) shows low toxicity against mammalian cells (IC50 > 1000 μg/mL in HeLa cells).


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)

Structure of platencin (A) and platensimycin (B)
© Copyright Policy - open-access
Related In: Results  -  Collection

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

Figure 1: Structure of platencin (A) and platensimycin (B)
Mentions: The 3-amino-2,4-dihydroxybenzoic acid core is an essential part of the new antibiotic drugs platencin (A) and platensimycin (B) [Figure 1], which show a high activity against Gram-positive bacteria, especially methicillin-resistant Staphylococcus aureus (MRSA) or vancomycin-resistant enterococci (VRE). Platencin (A) shows MIC values against MRSA of about 0.1 μg/mL and platensimycin (B) 0.2–0.4 μg/mL against MRSA and 0.4–0.8 μg/mL against VRE. Furthermore, platensimycin (B) shows low toxicity against mammalian cells (IC50 > 1000 μg/mL in HeLa cells).

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.