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Synthesis and biological evaluation of ferrocene-containing bioorganometallics inspired by the antibiotic platensimycin lead structure


Patra, M; Gasser, G; Wenzel, M; Merz, K; Bandow, J E; Metzler-Nolte, N (2010). Synthesis and biological evaluation of ferrocene-containing bioorganometallics inspired by the antibiotic platensimycin lead structure. Organometallics, 29(19):4312-4319.

Abstract

The recent discovery of the natural product platensimycin (1) as a new antibiotic lead structure has triggered the synthesis of numerous organic derivatives for structure-activity relationships (SAR) in order to improve the poor in vivo efficacy of 1. The synthesis, characterization, and biological evaluation of the first four ferrocene-containing bioorganometallic compounds based on the platensimycin lead structure are reported herein, namely 3-(4,4-diferrocenoylpentanamido)-2,4-dihydroxybenzoic acid (2), 3-(4,4-diferrocenoylbutanamido)-2,4-dihydroxybenzoic acid (3), 3-{4-(acetylferrocenoyl)butanamido}-2,4-dihydroxybenzoic acid (4), and 3-(4-ferrocenoylbutanamido)-2,4-dihydroxybenzoic acid (5). All new compounds were unambiguously characterized by all common analytical methods, including H-1 and C-13 NMR, mass spectrometry, IR spectroscopy, and elemental analysis. Furthermore, the single-crystal X-ray structures of methyl 4,4-diferrocenoylbutanoate (9), methyl 4,4-diferrocenoylpentanoate (10), 4,4-diferrocenoylpentanoic acid (14), 4,4-diferrocenoylbutanoic acid (15), and 4-(acetylferrocenoyl)butanoic acid (16) were also determined. Among 2-5 and their intermediate carboxylic acids tested, only 3 was found to inhibit selectively the growth of S. aureus Mu50 strain (VISA) at a minimum inhibitory concentration (MIC) value of 128 mu g/mL.

The recent discovery of the natural product platensimycin (1) as a new antibiotic lead structure has triggered the synthesis of numerous organic derivatives for structure-activity relationships (SAR) in order to improve the poor in vivo efficacy of 1. The synthesis, characterization, and biological evaluation of the first four ferrocene-containing bioorganometallic compounds based on the platensimycin lead structure are reported herein, namely 3-(4,4-diferrocenoylpentanamido)-2,4-dihydroxybenzoic acid (2), 3-(4,4-diferrocenoylbutanamido)-2,4-dihydroxybenzoic acid (3), 3-{4-(acetylferrocenoyl)butanamido}-2,4-dihydroxybenzoic acid (4), and 3-(4-ferrocenoylbutanamido)-2,4-dihydroxybenzoic acid (5). All new compounds were unambiguously characterized by all common analytical methods, including H-1 and C-13 NMR, mass spectrometry, IR spectroscopy, and elemental analysis. Furthermore, the single-crystal X-ray structures of methyl 4,4-diferrocenoylbutanoate (9), methyl 4,4-diferrocenoylpentanoate (10), 4,4-diferrocenoylpentanoic acid (14), 4,4-diferrocenoylbutanoic acid (15), and 4-(acetylferrocenoyl)butanoic acid (16) were also determined. Among 2-5 and their intermediate carboxylic acids tested, only 3 was found to inhibit selectively the growth of S. aureus Mu50 strain (VISA) at a minimum inhibitory concentration (MIC) value of 128 mu g/mL.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:October 2010
Deposited On:03 Mar 2011 15:42
Last Modified:05 Apr 2016 14:52
Publisher:American Chemical Society
ISSN:0276-7333
Publisher DOI:https://doi.org/10.1021/om100614c
Other Identification Number:ISI:000282303300015
Permanent URL: https://doi.org/10.5167/uzh-47372

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