Synthetic Approaches to the  Lamellarins—A Comprehensive Review

Imbri, Dennis; Tauber, Johannes; Opatz, Till

doi:10.3390/md12126142

Cited by 85 publications

(60 citation statements)

References 93 publications

(72 reference statements)

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“…These data highlight that peptides can be considered as a valuable scaffold to reverse MDR. From our understanding the total synthesis of compound 94 has not yet been reported.…”

Section: Kendarimidementioning

confidence: 99%

“…The subsequent hydrogenolysis afforded lamellarin 41 (Scheme 7c) [108]. In 2012, Vazquez et al used the Paal-Knorr pyrrole synthesis to synthesize 41 in 25% yield in seven steps, and 43 in 28% yield in six steps [94].…”

Section: Lamellarins and Derivativesmentioning

confidence: 99%

“…Another synthetic model compound (N- From our understanding the total synthesis of compound 94 has not yet been reported. L-pyroMeGlu-L-Phe-OEt is the moiety that was synthetized as a model compound to represent pyroMeGlu of 94 as described in Scheme 18a [198].…”

Section: Kendarimidementioning

confidence: 99%

“…Lamellarins are a group of polycyclic pyrrole-containing alkaloids possessing a common 14-phenyl-6H-[1]-benzopyrano[4′,3′,3,5]pyrrolo-[2,1-α]isoquinoline ring system [94]. Lamellarins …”

Section: Lamellarins and Derivativesmentioning

confidence: 99%

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Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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Multidrug resistance (MDR) to anticancer drugs is a serious health problem that in many cases leads to cancer treatment failure. The ATP binding cassette (ABC) transporter P-glycoprotein (P-gp), which leads to premature efflux of drugs from cancer cells, is often responsible for MDR. On the other hand, a strategy to search for modulators from natural products to overcome MDR had been in place during the last decades. However, Nature limits the amount of some natural products, which has led to the development of synthetic strategies to increase their availability. This review summarizes the research findings on marine natural products and derivatives, mainly alkaloids, polyoxygenated sterols, polyketides, terpenoids, diketopiperazines, and peptides, with P-gp inhibitory activity highlighting the established structure-activity relationships. The synthetic pathways for the total synthesis of the most promising members and analogs are also presented. It is expected that the data gathered during the last decades concerning their synthesis and MDR-inhibiting activities will help medicinal chemists develop potential drug candidates using marine natural products as models which can deliver new ABC transporter inhibitor scaffolds.

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“…These data highlight that peptides can be considered as a valuable scaffold to reverse MDR. From our understanding the total synthesis of compound 94 has not yet been reported.…”

Section: Kendarimidementioning

confidence: 99%

Section: Lamellarins and Derivativesmentioning

confidence: 99%

Section: Kendarimidementioning

confidence: 99%

Section: Lamellarins and Derivativesmentioning

confidence: 99%

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Marine Natural Products as Models to Circumvent Multidrug Resistance

et al. 2016

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“…Since the first report, more than 50 lamellarins have been found mainly in Didemnum spp. ascidians as well as in various sponges . Of all the lamellarins identified up to date, lamellarin D ( 76 ; Fig.…”

Section: Mollusk‐derived Anticancer Agentsmentioning

confidence: 99%

Marine Mollusk‐Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance

Ciavatta

Lefranc

Carbone

et al. 2016

Medicinal Research Reviews

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The chemical investigation of marine mollusks has led to the isolation of a wide variety of bioactive metabolites, which evolved in marine organisms as favorable adaptations to survive in different environments. Most of them are derived from food sources, but they can be also biosynthesized de novo by the mollusks themselves, or produced by symbionts. Consequently, the isolated compounds cannot be strictly considered as “chemotaxonomic markers” for the different molluscan species. However, the chemical investigation of this phylum has provided many compounds of interest as potential anticancer drugs that assume particular importance in the light of the growing literature on cancer biology and chemotherapy. The current review highlights the diversity of chemical structures, mechanisms of action, and, most importantly, the potential of mollusk‐derived metabolites as anticancer agents, including those biosynthesized by mollusks and those of dietary origin. After the discussion of dolastatins and kahalalides, compounds previously studied in clinical trials, the review covers potentially promising anticancer agents, which are grouped based on their structural type and include terpenes, steroids, peptides, polyketides and nitrogen‐containing compounds. The “promise” of a mollusk‐derived natural product as an anticancer agent is evaluated on the basis of its ability to target biological characteristics of cancer cells responsible for poor treatment outcomes. These characteristics include high antiproliferative potency against cancer cells in vitro, preferential inhibition of the proliferation of cancer cells over normal ones, mechanism of action via nonapoptotic signaling pathways, circumvention of multidrug resistance phenotype, and high activity in vivo, among others. The review also includes sections on the targeted delivery of mollusk‐derived anticancer agents and solutions to their procurement in quantity.

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Four‐Component Construction of Coumarin‐Fused Pyrrolo[2,1‐a]isoquinoline: Expedient Synthesis of Lamellarins and Their Regioselective Demethylation

et al. 2021

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Construction of the coumarin-fused pyrrolo[2,1a]isolquinoline skeleton was realized through a four-component reaction between isoquinoline, ethyl bromoacetate, ohydroxybenzaldehyde and nitromethane. This methodology was further extended to the synthesis of lamellarin D trimethyl ether and a formal synthesis of lamellarin D. The controlled demethylation of lamellarin D trimethyl ether yielded dihydroxy and tetrahydroxy lamellarin analogues regioselectively.

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Synthetic Approaches to the Lamellarins—A Comprehensive Review

Cited by 85 publications

References 93 publications

Marine Natural Products as Models to Circumvent Multidrug Resistance

Marine Natural Products as Models to Circumvent Multidrug Resistance

Marine Mollusk‐Derived Agents with Antiproliferative Activity as Promising Anticancer Agents to Overcome Chemotherapy Resistance

Four‐Component Construction of Coumarin‐Fused Pyrrolo[2,1‐a]isoquinoline: Expedient Synthesis of Lamellarins and Their Regioselective Demethylation

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