Total Synthesis and Synthetic Approaches towards Marine Bioactive Natural Products and Analogues

A special issue of Marine Drugs (ISSN 1660-3397). This special issue belongs to the section "Synthesis and Medicinal Chemistry of Marine Natural Products".

Deadline for manuscript submissions: 31 July 2024 | Viewed by 6340

Special Issue Editors

Department of Organic Chemistry, Faculty of Science, University of Málaga, 29071 Málaga, Spain
Interests: natural products; bioactive compounds; total synthesis; antitumor; antibiotics; cyclodepsipeptides; cyclopeptides
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Marine organisms have proven to be a rich and powerful source of bioactive natural products featuring diverse and complex molecular architectures and a broad array of biological activities. Since the importance and value of these natural products has become clear in biology and medicine, total synthesis is now essential for the development of such secondary metabolites, either as biological tools or as potential leads in medicine. The general problem that represents scarce and difficult-to-access marine natural products, as well as their structural determination, can be overcome via total synthesis. In addition, total synthesis and synthetic approaches, such as semisynthesis, allow access to analogues for structure–activity relationship (SAR) and drug discovery studies. Therefore, given the importance of this field, this Special Issue will cover total synthesis and the synthetic approaches to reflect the major role of this discipline and its implications in the development of bioactive compounds of marine origin.

Prof. Dr. Francisco Sarabia
Dr. Ivan Cheng-Sanchez
Guest Editors

Manuscript Submission Information

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Keywords

  • total synthesis
  • marine natural products
  • biological activity
  • synthetic approaches
  • semisynthesis
  • analogues
  • structure–activity relationships
  • structural determination

Published Papers (5 papers)

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Research

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12 pages, 1352 KiB  
Article
Semisynthesis and Cytotoxic Evaluation of an Ether Analogue Library Based on a Polyhalogenated Diphenyl Ether Scaffold Isolated from a Lamellodysidea Sponge
by Kelsey S. Ramage, Aaron Lock, Jonathan M. White, Merrick G. Ekins, Milton J. Kiefel, Vicky M. Avery and Rohan A. Davis
Mar. Drugs 2024, 22(1), 33; https://doi.org/10.3390/md22010033 - 03 Jan 2024
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Abstract
The known oxygenated polyhalogenated diphenyl ether, 2-(2′,4′-dibromophenoxy)-3,5-dibromophenol (1), with previously reported activity in multiple cytotoxicity assays was isolated from the sponge Lamellodysidea sp. and proved to be an amenable scaffold for semisynthetic library generation. The phenol group of 1 was targeted [...] Read more.
The known oxygenated polyhalogenated diphenyl ether, 2-(2′,4′-dibromophenoxy)-3,5-dibromophenol (1), with previously reported activity in multiple cytotoxicity assays was isolated from the sponge Lamellodysidea sp. and proved to be an amenable scaffold for semisynthetic library generation. The phenol group of 1 was targeted to generate 12 ether analogues in low-to-excellent yields, and the new library was fully characterized by NMR, UV, and MS analyses. The chemical structures for 2, 8, and 9 were additionally determined via single-crystal X-ray diffraction analysis. All natural and semisynthetic compounds were evaluated for their ability to inhibit the growth of DU145, LNCaP, MCF-7, and MDA-MB-231 cancer cell lines. Compound 3 was shown to have near-equivalent activity compared to scaffold 1 in two in vitro assays, and the activity of the compounds with an additional benzyl ring appeared to be reliant on the presence and position of additional halogens. Full article
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11 pages, 1124 KiB  
Article
Oxidative Cyclization at ortho-Position of Phenol: Improved Total Synthesis of 3-(Phenethylamino)demethyl(oxy)aaptamine
by Yuki Nakatani, Risa Kimura, Tomoyo Kimata and Naoyuki Kotoku
Mar. Drugs 2023, 21(5), 311; https://doi.org/10.3390/md21050311 - 19 May 2023
Viewed by 1198
Abstract
A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting [...] Read more.
A shorter synthesis of the demethyl(oxy)aaptamine skeleton was developed via oxidative intramolecular cyclization of 1-(2-azidoethyl)-6-methoxyisoquinolin-7-ol followed by dehydrogenation with a hypervalent iodine reagent. This is the first example of oxidative cyclization at the ortho-position of phenol that does not involve spiro-cyclization, resulting in the improved total synthesis of 3-(phenethylamino)demethyl(oxy)aaptamine, a potent anti-dormant mycobacterial agent. Full article
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Review

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18 pages, 10784 KiB  
Review
Dimeric (Poly)Hydroxynaphthazarins, Metabolites of Echinoderms and Lichens: The History of the Synthesis and Structure Elucidation
by Dmitry N. Pelageev, Ksenia L. Borisova and Victor Ph. Anufriev
Mar. Drugs 2023, 21(7), 407; https://doi.org/10.3390/md21070407 - 19 Jul 2023
Viewed by 785
Abstract
This review provides information on the synthesis and revision of the structures of natural dimeric (poly)hydroxynaphthazarins, metabolites of echinoderms and lichens, and on the refinement of the direction and mechanism of reactions in the synthesis of some of these compounds. Full article
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15 pages, 3683 KiB  
Review
An Overview of Aplysinopsins: Synthesis and Biological Activities
by Eslam R. El-Sawy and Gilbert Kirsch
Mar. Drugs 2023, 21(5), 268; https://doi.org/10.3390/md21050268 - 26 Apr 2023
Cited by 1 | Viewed by 1042
Abstract
Marine products are among the most promising sources of biologically active molecules. Aplysinopsins, tryptophan-derived marine natural products, were isolated from different natural marine sources including sponges, stony corals (hard corals) especially genus scleractinian, as well as sea anemone, in addition to one nudibranch. [...] Read more.
Marine products are among the most promising sources of biologically active molecules. Aplysinopsins, tryptophan-derived marine natural products, were isolated from different natural marine sources including sponges, stony corals (hard corals) especially genus scleractinian, as well as sea anemone, in addition to one nudibranch. Aplysinopsins were reported to be isolated from different marine organisms related to various geographic areas such as Pacific, Indonesia, Caribbean, and Mediterranean regions. This review gives an up-to-date overview of marine alkaloid aplysinopsins: their various sources, their synthesis, and the fact that many aplysinopsin derivatives are biologically active compounds. Full article
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Other

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17 pages, 2825 KiB  
Perspective
Marine Puupehenone and Puupehedione: Synthesis and Future Perspectives
by Antonio Rosales Martínez and Ignacio Rodríguez-García
Mar. Drugs 2023, 21(6), 322; https://doi.org/10.3390/md21060322 - 26 May 2023
Viewed by 1032
Abstract
Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to [...] Read more.
Puupehenone and puupehedione are natural products isolated from marine organisms. These compounds display a broad spectrum of biological activities, the in vitro antitubercular activity of puupehenone being a stand out, and are equipped with an interesting structural complexity. These products have served to stimulate the continual interest of the synthetic community. The first part of this article is a review of their total synthesis, using natural compounds which have the potential to be transformed into these marine compounds as starting materials; the synthetic routes employed to generate the basic skeleton; and the advances made to synthesize the pyran C ring with the required diastereoselectivity to obtain the natural products. Finally, this perspective shows a personal reflection of the authors on a possible unified and efficient retrosynthetic route that could allow easy access to these natural products, as well as their epimers at the C8 carbon and which could be used to address future biological issues in the production of pharmacologically active compounds. Full article
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