ArticleThe Journal of antibiotics2013
Syntheses and evaluation of macrocyclic engelhardione analogs as antitubercular and antibacterial agents.
Article in The Journal of antibiotics, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
What it found
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The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.
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Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
8 citing papers in PubMed.
- Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles.Molecules (Basel, Switzerland) · 2022Review
- Direct Synthesis of Polyaromatic Cyclophanes Containing Bis-Methylene-InterruptedInternational journal of molecular sciences · 2021Article
- Recent Studies on Cyclic 1,7-Diarylheptanoids: Their Isolation, Structures, Biological Activities, and Chemical Synthesis.Molecules (Basel, Switzerland) · 2018Review
- Limonoids Containing a C₁⁻Marine drugs · 2018Article
- Synthesis and antibacterial evaluation of macrocyclic diarylheptanoid derivatives.Bioorganic & medicinal chemistry letters · 2016Article
- Synthesis and antibacterial evaluation of anziaic acid and analogues as topoisomerase I inhibitors.MedChemComm · 2013Article
- Macrocyclic drugs and synthetic methodologies toward macrocycles.Molecules (Basel, Switzerland) · 2013Review
- RECENT SYNTHETIC DEVELOPMENTS AND APPLICATIONS OF THE ULLMANN REACTION. A REVIEW.Organic preparations and procedures international · 2013Article
Corrections and comments
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Authors and funding
9 authors.
Funding
Abstract
The natural product engelhardione is an underexplored chemotype for developing novel treatments for bacterial infections; we therefore explored this natural product scaffold for chemical diversification and structure-activity relationship studies. Macrocyclic engelhardione and structural regioisomers were synthesized using a series of aldol condensations and selective hydrogenations to generate the 1,7-diarylheptan-3-one derivatives, followed by microwave-assisted intramolecular Ullmann coupling to afford a series of macrocyclic diaryl ether analogs. An extended macrocyclic chemical library was then produced by oxime formation, reductive amination and O-alkylation. Antibacterial evaluation revealed that the reductive amination derivatives 7b and 7d showed moderate activities (minimum inhibitory concentrations: 12.5-25 μg ml(-1)) against Mycobacterium tuberculosis and Gram-positive pathogens, as well as anti-Gram-negative activity against an efflux impaired Escherichia coli strain. These results provide validated leads for further optimization and development.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.