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Keywords = 5-iodoindole

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10 pages, 1156 KB  
Article
Concise Syntheses of Marine (Bis)indole Alkaloids Meridianin C, D, F, and G and Scalaridine A via One-Pot Masuda Borylation-Suzuki Coupling Sequence
by Marco Kruppa, Gereon A. Sommer and Thomas J. J. Müller
Molecules 2022, 27(7), 2233; https://doi.org/10.3390/molecules27072233 - 30 Mar 2022
Cited by 19 | Viewed by 3909
Abstract
N-Protected 3-iodoindoles were reacted with (di)azine halides in a sequentially Pd-catalyzed one-pot fashion, i.e., by Masuda borylation–Suzuki coupling (MBSC) sequence. This methodology was successfully applied to the concise syntheses of marine indole alkaloids meridianin C, D, F, and G, as well as [...] Read more.
N-Protected 3-iodoindoles were reacted with (di)azine halides in a sequentially Pd-catalyzed one-pot fashion, i.e., by Masuda borylation–Suzuki coupling (MBSC) sequence. This methodology was successfully applied to the concise syntheses of marine indole alkaloids meridianin C, D, F, and G, as well as to the bisindole alkaloid scalaridine A, which were obtained in moderate to excellent yield. Full article
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13 pages, 3283 KB  
Article
Rapid Killing and Biofilm Inhibition of Multidrug-Resistant Acinetobacter baumannii Strains and Other Microbes by Iodoindoles
by Chaitany Jayprakash Raorane, Jin-Hyung Lee and Jintae Lee
Biomolecules 2020, 10(8), 1186; https://doi.org/10.3390/biom10081186 - 14 Aug 2020
Cited by 42 | Viewed by 6830
Abstract
Multi-drug resistant Acinetobacter baumannii is well-known for its rapid acclimatization in hospital environments. The ability of the bacterium to endure desiccation and starvation on dry surfaces for up to a month results in outbreaks of health care-associated infections. Previously, indole and its derivatives [...] Read more.
Multi-drug resistant Acinetobacter baumannii is well-known for its rapid acclimatization in hospital environments. The ability of the bacterium to endure desiccation and starvation on dry surfaces for up to a month results in outbreaks of health care-associated infections. Previously, indole and its derivatives were shown to inhibit other persistent bacteria. We found that among 16 halogenated indoles, 5-iodoindole swiftly inhibited A. baumannii growth, constrained biofilm formation and motility, and killed the bacterium as effectively as commercial antibiotics such as ciprofloxacin, colistin, and gentamicin. 5-Iodoindole treatment was found to induce reactive oxygen species, resulting in loss of plasma membrane integrity and cell shrinkage. In addition, 5-iodoindole rapidly killed three Escherichia coli strains, Staphylococcus aureus, and the fungus Candida albicans, but did not inhibit the growth of Pseudomonas aeruginosa. This study indicates the mechanism responsible for the activities of 5-iodoindole warrants additional study to further characterize its bactericidal effects on antibiotic-resistant A. baumannii and other microbes. Full article
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6 pages, 665 KB  
Short Note
7-Iodo-1H-indole-3-carbonitrile
by Rosanna Meine, Hannes Falke, Jana Kötz, Sandra I. Schweda and Conrad Kunick
Molbank 2015, 2015(4), M869; https://doi.org/10.3390/M869 - 23 Oct 2015
Cited by 1 | Viewed by 4597
Abstract
The title compound was prepared by a Friedel–Crafts acylation-oxime synthesis-decarboxylation/dehydration sequence starting from commercially available 7-iodoindole with 2-(7-iodo-1H-indol-3-yl)-2-oxoacetic acid as isolated intermediate. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR, EI-MS), and [...] Read more.
The title compound was prepared by a Friedel–Crafts acylation-oxime synthesis-decarboxylation/dehydration sequence starting from commercially available 7-iodoindole with 2-(7-iodo-1H-indol-3-yl)-2-oxoacetic acid as isolated intermediate. The structural identity of the title compound was proven by elemental analysis and spectroscopic methods (IR, NMR, EI-MS), and purity was assessed by two independent HPLC methods. Full article
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