Marine pyridoacridine alkaloids

Molinski, T. F. 1993. Marine pyridoacridines alkaloids Structure, synthesis, an biological chemistry. Chemical Reviews, 93 1825-1838. 

Molinski, T. F., Marine pyridoacridine alkaloids structure, synthesis, and biological chemistry, Chem. Rev., 93, 1825, 1993. 

Porphobilinogen and Studies of Its Biosynthesis, ft. Neier. Synthesis and Cycloaddition Reactions of Iso-Condensed Heteroaromatic Pyrroles, C. K. Sha. Azacyclopentadienyl Metal Compounds Historical Background and Recent Advances, C. Janiak and N. Kuhn. Recent Developments in the Synthesis of Marine Pyridoacridine Alkaloids, A. M. Echavar-ren. Alkaloid Synthesis Using 1-Acylpyridinium Salts as Intermediates, D. L. Comins and S. P. Joseph. Index. S S... 

Structure, synthesis, and biochemistry of marine pyridoacridine alkaloids 93CRV1825. 

Delfourne E, Bastide J. Marine pyridoacridine alkaloids and synthetic analogues as antitumor agents. Med. Res. Rev. 2003 23 234-252. 

Marine Pyridoacridine Alkaloids Structure, Synthesis, and Biological Chemistry, Molinski T. F. Chem. Rev. 1993, 93, 1825... 

Delfoume, E., Darro, R, Bontemps-Subielos, N., Decaestecker, Ch., Bastide, J., Fryd-man. A., Kiss, R. (2001). Synthesis and Characterization of the Antitumor Activities of Analogues of Meridine, a Marine Pyridoacridine Alkaloid, J. Med. Chem., 44. 3275-3282. 

A. Plodek, S. Raeder, F. Bracher, A novel approach to ring A analogues of the marine pyridoacridine alkaloid ascididemin. Tetrahedron 69 (2013) 9857-9864. 

Molmski, T.E. (1993) Marine pyridoacridine alkaloids structure, synthesis, and biological chemistry. Chem. Rev., 93,1825-1838. Monniot, F. (1978) Connaissances actuelles sur les ions metalliques chez les asddies, in Les metaux era milieu marin, phosphore et derives phosphores, vol. 2, Actualite de Biochimie Marine, Editions du CNRS, Paris, pp. 185-194. 

Echavarren, A.M. (1996) Recent developments in the synthesis of marine pyridoacridine alkaloids. Adv. Nitrt pn Heterocyd., 2, 211-250. 

Legentil, L., Bastide, J., and DeUbume, E. (2003) Total synthesis of the marine pyridoacridine alkaloid sebastianine A. Tetrahedron Lett., 44, 2473-2475. 

Ciufolini, MA. Shm, Y.-C. Bishop, M.J. (1995) A unified strategy for the synthesis of sulfur-containing pyridoacridine alkaloids antitumor agents of marine origin. J. Am. Chem. Soc., 117,12460-9. 

Ding, Q. Z., Chichak, K., and Lown, J. W., Pyrroloquinoline and pyridoacridine alkaloids from marine sources, Curr. Med. Chem., 6, 1, 1999. 

Alkaloids related to pyridoacridines are known also from sponges and tunicates. Discorhabdin C (79), which is the first marine pyrroloquinoline alkaloid, was isolated from the sponge Latmnculia cf. bocagei. More than 20 alkaloids of this class are known at moment (30). Additional examples of this family are batzelline A (80) from a deep-sea sponge of the genus Batzella and wakayin (81) from an ascidian Clavelina sp. 

The Japp-Klingemann reaction was the key step during the first synthesis of the pentacyclic pyridoacridine marine cytotoxic alkaloid amoamine A by E. Delfoume et a P The diazonium salt was added to a vigorously stirred solution of ethyl-2-methyl-3-oxobutyrate in ethanol containing KOH, NaOAc and water. The resulting hydrazone was exposed to polyphosphoric acid to form the indole ring. 

Pyridoacridines are characterized by an 1 lH-pyrido-4,3,2-acridine moiety and have only been reported to occur in marine organisms [86]. Marine invertebrates, such as sponges and tunicates, are often brightly coloured due to the presence of pyridoacridine alkaloids. The colours exhibited by the pyridoacridines may vary according to differences in pH. This physico-chemical property is related to the two basic nitrogens in the aromatic ring systems. These alkaloids exhibit a variety of biological activities, e.g. cytotoxicity [86], inhibition of topoisomerase II [87], anti-HIV activity [88], release of Ca2+ [89], and intercalation of DNA [90]. 

J. (1992) Pyridoacridine alkaloids from deep-water marine sponges of the family Pachastrellidae structure revision of dercitin and related compounds and correlation with the kuanomamines. J. Org. Chem. 57, 1523—1526. 

The known tetracyclic pyridoacridine alkaloids from marine sources are dominated by those isolated from tunicates. All reported tetracyclic pyridoacridine alkaloids to date have oxygen functionality at C8, and the alkaloids can readily be divided into a group that has a carbonyl group at... 

Nordercitin, Dercitamine, Dercitamide, and Cyclodercitin. A series of three pyridoacridine alkaloids related to the shermilamines were reported by Gunawardana et al. (1989). In assigning the structures of nordercitin (R = NMe2) dercitamine (R = NHMe), and dercitamide (R = NHCOEt) (33), isolated from two deep-water marine sponges of the family Pachastrellidae, the authors used a combination of COLOC and HMBC spectra. The report did not compare results of the two experiments nor unfortunately did it... 

Aoki, S., Wei, H., Matsui, K., Rachmat, R and Kobayashi, M. (2003) Pyridoacridine alkaloids inducing neuronal differentiation in a neuroblastoma cell line, from marine sponge Biemna Jbrtis. Bioorg. Med. Chem. Lett., 11, 1969-1973. 

Barnes, E.C., Said, NA.B.M., Williams, E.D., and Hooper, J.NA. (2010) Ecionines A and B, two new cytotoxic pyridoacridine alkaloids from the Australian marine sponge Edonemia geodides. Tetrahedron, 66, 283-287. 

Agrawal, M. and Bowden, B.F. (2007) Nordehydrocyclodercitin, a hexacyclic pyridoacridine alkaloid from the marine ascidian, Aplidium sp. Nat. Prod. Res., 21, 782-786. 

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