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      A Facile Synthesis of Deaza-Analogues of the Bisindole Marine Alkaloid Topsentin

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          Abstract

          A series of substituted ethyl 1-[( tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1 H-indol-3-yl)-4-[(1-methyl-1 H-indol-3-yl)carbonyl]-1 H-pyrrole-3-carboxylates were prepared in excellent yields (82-98%) by one-pot reactions between β-dicarbonyl compounds 12a– e and 1,2-diaza-1,3-diene (DD) 13. Derivatives 10a, c– e, deazaanalogues of the bis-indole alkaloid topsentin, screened by the National Cancer Institute (Bethesda, MD, USA) in the in vitro one dose primary anticancer assay against a panel of about 60 human tumor cell lines, showed no significant activity, with the exception of compound 9e, which showed moderate activity against the HOP-92 cell line of the non small cell lung cancer sub-panel and the SNB-75 cell line of the CNS sub-panel.

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          Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor cell lines.

          A. Monks, D Scudiero, P Skehan … (1991)
          We describe here the development and implementation of a pilot-scale, in vitro, anticancer drug screen utilizing a panel of 60 human tumor cell lines organized into subpanels representing leukemia, melanoma, and cancers of the lung, colon, kidney, ovary, and central nervous system. The ultimate goal of this disease-oriented screen is to facilitate the discovery of new compounds with potential cell line-specific and/or subpanel-specific antitumor activity. In the current screening protocol, each cell line is inoculated onto microtiter plates, then preincubated for 24-28 hours. Subsequently, test agents are added in five 10-fold dilutions and the culture is incubated for an additional 48 hours. For each test agent, a dose-response profile is generated. End-point determinations of the cell viability or cell growth are performed by in situ fixation of cells, followed by staining with a protein-binding dye, sulforhodamine B (SRB). The SRB binds to the basic amino acids of cellular macromolecules; the solubilized stain is measured spectrophotometrically to determine relative cell growth or viability in treated and untreated cells. Following the pilot screening studies, a screening rate of 400 compounds per week has been consistently achieved.
          Article 0 comments Cited 390 times – based on 0 reviews     Review now
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            Indole alkaloid marine natural products: An established source of cancer drug leads with considerable promise for the control of parasitic, neurological and other diseases

            Waseem Gul, Mark T. Hamann (2005)
            The marine environment produces natural products from a variety of structural classes exhibiting activity against numerous disease targets. Historically marine natural products have largely been explored as anticancer agents. The indole alkaloids are a class of marine natural products that show unique promise in the development of new drug leads. This report reviews the literature on indole alkaloids of marine origin and also highlights our own research. Specific biological activities of indole alkaloids presented here include: cytotoxicity, antiviral, antiparasitic, anti-inflammatory, serotonin antagonism, Ca-releasing, calmodulin antagonism, and other pharmacological activities.
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              Cytotoxic bisindole alkaloids from a marine sponge Spongosorites sp.

              Baoquan Bao, Chong-Kil Lee, Jongki Hong … (2005)
              Three new bisindole alkaloids of the hamacanthin class (1-3) and one new bisindole alkaloid of the topsentin class (6) were isolated along with known bisindole alkaloids (4, 5, 7-11) from the MeOH extract of a marine sponge Spongosorites sp. by bioactivity-guided fractionation. The planar structures were established on the basis of NMR, MS, and IR spectroscopic analyses. Configurations of compounds 1-4 were derived from 1H NMR data and optical rotation. Compounds 1, 4, 5, and 11 showed moderate to significant cytotoxicity against five human tumor cell lines, and compounds 1-5 showed weak antibacterial activity against clinically isolated methicillin-resistant strains.
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                Author and article information

                Journal
                Journal ID (nlm-ta): Molecules
                Journal ID (iso-abbrev): Molecules
                Journal ID (publisher-id): molecules
                Title: Molecules
                Publisher: MDPI
                ISSN (Electronic): 1420-3049
                Publication date (Electronic): 26 February 2013
                Publication date Collection: March 2013
                Volume: 18
                Issue: 3
                Pages: 2518-2527
                Affiliations
                [1 ]Dipartimento di Scienze e Tecnologie Biologiche Chimiche e Farmaceutiche, Università degli Studi di Palermo, Via Archirafi 32, 90123 Palermo, Italy
                [2 ]Dipartimento di Scienze Biomolecolari, Università degli Studi di Urbino “Carlo Bo”, Via I Maggetti 24, 61029 Urbino, Italy
                Author notes
                [* ] Authors to whom correspondence should be addressed; E-Mails: anna.carbone@ 123456unipa.it (A.C.); gianfranco.favi@ 123456uniurb.it (G.F.); Tel.: +39-091-23896826 (A.C.); Fax: +39-091-23860854 (A.C.); Tel.: +39-0722-303440 (G.F.).
                Article
                Publisher ID: molecules-18-02518
                DOI: 10.3390/molecules18032518
                PMC ID: 6269752
                PubMed ID: 23442928
                SO-VID: 1f8e41ed-f822-47df-808b-712b28ed112d
                Copyright statement: © 2013 by the authors; licensee MDPI, Basel, Switzerland.
                License:

                This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license ( http://creativecommons.org/licenses/by/3.0/).

                History
                Date received : 21 January 2013
                Date revision received : 31 January 2013
                Date accepted : 07 February 2013
                Categories
                Subject: Article

                Keywords: topsentin,bis-indole alkaloids,antitumor activity,ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1h-indol-3-yl)-4-[(1-methyl-1h-indol-3-yl)-carbonyl]-1h-pyrrole-3-carboxylates
                Data availability:
                Keywords: topsentin, bis-indole alkaloids, antitumor activity, ethyl 1-[(tert-butoxycarbonyl)amino]-2-methyl-5-(1-methyl-1h-indol-3-yl)-4-[(1-methyl-1h-indol-3-yl)-carbonyl]-1h-pyrrole-3-carboxylates

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