Antitumor activity of the marine natural product dibromophakellstatin in vitro

Zöllinger, Michael; Kelter, Gerhard; Fiebig, Heinz‐Herbert; Lindel, Thomas

doi:10.1016/j.bmcl.2006.10.046

Cited by 44 publications

(25 citation statements)

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“…Cyclopropanation of the electron-rich C10-C10a double bond of dipyrrolopyrazinone 3 (Scheme 1) turned out to be surprisingly facile on reaction with 50 % NaOH/CHCl 3 in the presence of nBu 4 NBr [3]. Acyliminium ion formation and ring opening do not take place.…”

Section: Resultsmentioning

confidence: 96%

“…Tetracycle 4 structurally corresponds to the replacement of the imidazolidinone moiety of dibromophakellstatin (1) by a dichlorocyclopropane unit and was isolated in 85 % yield after 2 h. Reinvestigation revealed that side product 5 containing a ringexpanded pyridopyrazinone partial structure was also formed. The unprecedented structures of the protonpoor compounds 4 [3] and 5 could be secured by X-ray analyses [10]. If the reaction time was increased from 2 h to 12 h, the percentage of 5 rose Scheme 1.…”

Section: Resultsmentioning

confidence: 99%

“…Cyclopropanation of dipyrrolopyrazinone 3. Yields of 4 and 5 change to 35 % each after 12 h. Molecular structures of 4 [3] and 5 in the crystal (displacement ellipsoids at the 50 % probability level, hydrogen atoms omitted for clarity). from 10 % to 35 %.…”

Section: Resultsmentioning

confidence: 99%

“…Structural analogs of dibromophakellstatin (1) are interesting because of the antitumor activity of (−)-1 [2,3]. Structures [4] and total syntheses [5] of the pyrrole-imidazole alkaloids have been reviewed.…”

Section: Introductionmentioning

confidence: 99%

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Skeleton Diversity by Cyclopropanation of Tricyclic Acylenamines

Zöllinger

Mayer

Lindel

2009

Zeitschrift Für Naturforschung B

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Aiming at the structural diversification of phakellin-and isophakellin-type pyrrole-imidazole alkaloids on the skeleton level, the reaction of dipyrrolopyrazinones and pyrroloindolizines with dichlorocarbene was investigated. Conversions resulted in ring expansion affording novel chlorinated and brominated dipyrroloazepinones, pyridopyrroloazepinones, and dipyrrolopyrazinones. Structures of the tetracyclic products with hitherto unknown architectures have been secured by X-ray analyses.

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Section: Resultsmentioning

confidence: 96%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Skeleton Diversity by Cyclopropanation of Tricyclic Acylenamines

Zöllinger

Mayer

Lindel

2009

Zeitschrift Für Naturforschung B

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“…The ovarian cancer cell line OVXF 899L proved to be most sensitive (IC50 = 0.60 mol/L), followed by the glioblastoma cell line CNXF 498NL (0.93), the nonsmall lung cancer cell line LXF 529L (0.96 mol/L), and the uterine cancer cell line UXF 1138L (1.21 mol/L). The selectivity profile of rac-dibromophakellstatin may be indicative of a novel mechanism of action [54] . There are many other alkaloids which exert cytotoxic and potentially anticancerogenic activities, which have been identified in various species of marine sponges.…”

Section: Poriferamentioning

confidence: 99%

Bioactive substances with anti-neoplastic efficacy from marine invertebrates:PoriferaandCoelenterata

Šima

Větvička

2011

WJCO

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An ever increasing demand for new lead compounds in the pharmaceutical industry has led scientists to search for natural bioactive products. Based on this extensive research, marine invertebrates now represent a rich source of novel substances with significant antineoplastic activities. As the current approach of synthesizing new and chemically modifying old drugs seems to have slowed down, and the identification of new anticancer drugs is not too promising, a new approach is clearly needed. The objective of this review is to present up-to-date data on these newer compounds. Based on the data summarized in this short review, it is clear that marine invertebrates represent an extremely important source of compounds with potential anti-cancer effects. Considering that we tested only a tiny number of Porifera and Coelenterata , the best is yet to come.

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Porifera (Sponges)–2

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: Secondary Metabolites of Hadromerida and Chondrosida Perforating Power of Clionaidae lyso ‐Phospholipids and Sulfated Sphingosines of Spirastrella abata Brominated Acetylenic Derivatives of Diplastrella Cyclic Peroxides Terpenes Unconventional Sterols Macrolactones: Latrunculins and Spongistatins Atypical Glycosides of Latrunculia corticata Other Nitrogen‐Free Toxins Peptides and Depsipeptides Pyrrole Derivatives and other Nitrogen‐Containing Heterocycles Atypical Nucleosides Secondary Metabolites of Lithistida Particular Characteristics of Lithistid Sponges Unusual Halogenated Fatty Acids Nitrogen‐Containing Sesquiterpenes of Theonella Specific Glycolipids of Theonella swinhoei, Discodermia calyx and D. dissoluta Long‐Chain Polyacetylenic Derivatives of Theonella sp 3β‐Methoxysterols of Jereicopsis graphidiophora 4‐Methylene Sterols and Sterones of Theonella Macrolides Examples of Acetogenins: Discodermolide, Calyculins, and Onnamides Linear Amides and Peptides Mono‐ and Bicyclic Peptides Symbiotic Origin of Some Polypeptides Cyclic and Linear Depsipeptides Atypical Nitrogenous Derivatives Secondary Metabolites of Spirophorida Atypical Sterols of Cinachyra, Microscleroderma , and Scleritoderma Cinachyrolide A, Enigmazole A Microsclerodermins and Aciculitins Examples of Atypical Derivatives of Some Sponges of the Tetillidae Secondary Metabolites of Agelasida Sterols Diterpenes and Carotenoids Gracilioethers of Agelas gracilis Merosesquiterpenes and Nitrogen‐Containing Meroditerpenes Galactosylceramides and Glycolipids Oroidin and Related C 11 N 5 Bromopyrrole Alkaloids Oroidin Series Agelastatin A Series Other Series Pyrrole‐2‐carboxylic Acid Derivatives Other Examples of Nitrogen‐Containing Heterocycles Betaines Secondary Metabolites of Halichondrida A‐ nor ‐Steroids and Other Nonconventional Sterols Conventional Terpenes Nitrogen‐Containing Terpenes: Isonitriles and Related Derivatives Other Terpenes Long‐Chain Linear Polyamines and α,ω‐bis‐isothiocyanates Polyethers: Halichondrins, Okadaic, and Glycookadaic Acids Various Lipids Linear Peptides of the Genera Auletta and Cymbastela Depsipeptides and Cyclic Peptides Unusual Amino Acids and Betaines Pyrrole, Imidazole, Pyridine, Isoquinoline, and Indole Derivatives Pyrrole Derivatives Imidazole Derivatives Pyridine and Isoquinoline Derivatives Indole Derivatives Heterocycles Related to the Oroidin Family Atypical Halogenated and Sulfur‐Containing Derivatives

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Antitumor activity of the marine natural product dibromophakellstatin in vitro

Cited by 44 publications

References 11 publications

Skeleton Diversity by Cyclopropanation of Tricyclic Acylenamines

Skeleton Diversity by Cyclopropanation of Tricyclic Acylenamines

Bioactive substances with anti-neoplastic efficacy from marine invertebrates:PoriferaandCoelenterata

Porifera (Sponges)–2

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