Marine indole alkaloids containing an 1-(indol-3-yl)ethane-1,2-diamine fragment (Review)

Голанцов, Никита Е.; Festa, Alexey А.; Карчава, А. В.; Yurovskaya, M. A.

doi:10.1007/s10593-013-1238-9

Cited by 22 publications

(18 citation statements)

References 75 publications

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“…(Okinawa), although the exact positioning of the alkyne functionalities is uncertain and hence the compounds are likely a mixture of related congeners. 674 High-level DFT calculations helped conrm the unusually deshielded 13 C chemical shis found in trikentramides A-D 649-652, isolated using an NMR-guided approach from Trikentrion abelliforme (East Point Bommies, Northern Territory, Australia). 675 The synthesis of igzamide (Plocamissa igzo) 676 was achieved.…”

Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2015

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This review covers the literature published in 2013 for marine natural products (MNPs), with 982 citations (644 for the period January to December 2013) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1163 for 2013), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that lead to the revision of structures or stereochemistries, have been included.

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Section: Spongesmentioning

confidence: 99%

Marine natural products

et al. 2015

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“…It is obvious that compounds 7-9 possess a non-NRPS origin of this metabolite. [18] Compound 10, a manzamine alkaloid, was isolated from an Okinawan Amphimedon sp. marine sponge.…”

Section: Indole Alkaloidsmentioning

confidence: 99%

Recent Advances on Marine Alkaloids from Sponges

Bian

Wang

Zhou

et al. 2020

Chemistry & Biodiversity

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Alkaloids from marine secondary metabolites have received extensive attention from pharmacists in recent years. Miscellaneous alkaloids derived from marine sponges possessed various pharmacological activities including cytotoxicity, antimicrobial, antioxidant, and so on. Herein, we summarized 149 marine alkaloids from sponges based on their structures and bioactivities reported from 2015 to 2020 and analyzed the production environment of marine sponges with rich alkaloids. Moreover, we discussed biosynthesis routes of pyrrole and guanidine alkaloids from marine sponges Agelas and Monanchora. This article will be beneficial for future research on drugs from marine natural products.

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“…1 A whole series of alkaloids containing the (indol-3-yl)ethane-1,2-diamine moiety in their structures and their aromatized derivatives were isolated from deep-water sponges in the last 30 years. 2 In particular, spongotines ( 1 ) and topsentins ( 2 ) contain two indoles connected through imidazoline or imidazole linker. Two indole substituents in the structures of hamacanthins ( 3 ) and dragmacidins ( 4 ) are bonded to dihydropyrazinone and piperazine rings, respectively (Figure 1 ).…”

mentioning

confidence: 99%

“…Total syntheses of many of the natural products from this group have been reported; 2 5 6 however, no synthesis of topsentin C has been reported. Compounds exhibiting antibacterial, cytotoxic, antiviral, and fungicidal properties were discovered among these alkaloids and their synthetic analogues.…”

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Revision of the Structure and Total Synthesis of Topsentin C

et al. 2017

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An efficient synthetic approach to access (indol-3-yl)ethane-1,2-diamines with a protecting group at the indole N atom from readily available 3-(2-nitrovinyl)indoles is reported. This approach includes solvent-free conjugate addition of O -pivaloylhydroxylamines to 1-Boc-3-(2-nitrovinyl)indoles followed by mild reduction of the adducts. The obtained (indol-3-yl)ethane-1,2-diamines are convenient synthetic precursors for several classes of marine alkaloids. The first total synthesis of racemic topsentin C, a secondary metabolite from Hexadella sp., based on this approach is reported. The initially proposed structure for topsentin C has been revised.

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Marine indole alkaloids containing an 1-(indol-3-yl)ethane-1,2-diamine fragment (Review)

Cited by 22 publications

References 75 publications

Marine natural products

Marine natural products

Recent Advances on Marine Alkaloids from Sponges

Revision of the Structure and Total Synthesis of Topsentin C

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