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Page 1
Biological activities of pyridoacridines.
Marshall KM, Barrows LR. Marshall KM, et al. Nat Prod Rep. 2004 Dec;21(6):731-51. doi: 10.1039/b401662a. Epub 2004 Oct 29. Nat Prod Rep. 2004. PMID: 15565252 Review.
This review summarizes recent progress in structure activity relationships for analogues of amphimedine 2 and ascididemin 3 classes of pyridoacridines and correlates reported molecular mechanisms of action with biological activities....
This review summarizes recent progress in structure activity relationships for analogues of amphimedine 2 and ascididemin 3 classes o …
A mini review on pyridoacridines: Prospective lead compounds in medicinal chemistry.
Sharma V, Sharma PC, Kumar V. Sharma V, et al. J Adv Res. 2015 Jan;6(1):63-71. doi: 10.1016/j.jare.2014.11.002. Epub 2014 Nov 15. J Adv Res. 2015. PMID: 25685544 Free PMC article. Review.
Pyridoacridine is such a moiety which forms the basic structure of numerous medicinally important natural products such as, but not limited to, amphimedine, ascididemin, eilatin, and sampangine. Interestingly, synthetic analogues of natural pyridoacridine exhibit diverse p …
Pyridoacridine is such a moiety which forms the basic structure of numerous medicinally important natural products such as, but not limited …
Bioinspired Syntheses of the Pyridoacridine Marine Alkaloids Demethyldeoxyamphimedine, Deoxyamphimedine, and Amphimedine.
Khalil IM, Barker D, Copp BR. Khalil IM, et al. J Org Chem. 2016 Jan 4;81(1):282-9. doi: 10.1021/acs.joc.5b02312. Epub 2015 Dec 17. J Org Chem. 2016. PMID: 26642369
Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxyamphimedine and …
Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave amphimedine in 8 steps from tryptamine with an overall yield …
Oxidative Cyclization of Kynuramine and Ynones Enabling Collective Syntheses of Pyridoacridine Alkaloids.
Jiang D, Wang S. Jiang D, et al. J Org Chem. 2021 Nov 5;86(21):15532-15543. doi: 10.1021/acs.joc.1c02009. Epub 2021 Oct 14. J Org Chem. 2021. PMID: 34648288
By combining with an intramolecular acylation and the chemoselective late-stage functionalization of pyridine rings, different approaches with 4-10 steps have been designed to accomplish the synthesis of alkaloids demethyldeoxyamphimedine (1), amphimedine (2), meridine (3) …
By combining with an intramolecular acylation and the chemoselective late-stage functionalization of pyridine rings, different approaches wi …
Synthesis and cytotoxic evaluation of analogues of the marine pyridoacridine amphimedine.
Brahic C, Darro F, Belloir M, Bastide J, Kiss R, Delfourne E. Brahic C, et al. Bioorg Med Chem. 2002 Sep;10(9):2845-53. doi: 10.1016/s0968-0896(02)00148-7. Bioorg Med Chem. 2002. PMID: 12110304
4-Substituted-7H-pyrido-[4,3,2-de][1,8] or [1,9]-phenanthroline-7-ones and 9-methyl-1,4-diazanaphtacene-3,10-dione, analogues of the marine pyridoacridine amphimedine were synthesised from isoquinoline-5,8-dione. The first compounds were obtained starting from a Diels-Alde …
4-Substituted-7H-pyrido-[4,3,2-de][1,8] or [1,9]-phenanthroline-7-ones and 9-methyl-1,4-diazanaphtacene-3,10-dione, analogues of the marine …
Structures and cytotoxic properties of sponge-derived bisannulated acridines.
Thale Z, Johnson T, Tenney K, Wenzel PJ, Lobkovsky E, Clardy J, Media J, Pietraszkiewicz H, Valeriote FA, Crews P. Thale Z, et al. J Org Chem. 2002 Dec 27;67(26):9384-91. doi: 10.1021/jo026459o. J Org Chem. 2002. PMID: 12492342
A disk diffusion soft agar assay, using a panel of five cancer cell lines (solid tumors and leukemias) and two normal cells, was used to evaluate the differential cytotoxicity (solid tumor selectivity) of the sponge semipure extracts and selected compounds including amphimedin
A disk diffusion soft agar assay, using a panel of five cancer cell lines (solid tumors and leukemias) and two normal cells, was used to eva …
Evaluation of pyridoacridine alkaloids in a zebrafish phenotypic assay.
Wei X, Bugni TS, Harper MK, Sandoval IT, Manos EJ, Swift J, Van Wagoner RM, Jones DA, Ireland CM. Wei X, et al. Mar Drugs. 2010 Jun 2;8(6):1769-78. doi: 10.3390/md8061769. Mar Drugs. 2010. PMID: 20631869 Free PMC article.
Three new minor components, the pyridoacridine alkaloids 1-hydroxy-deoxyamphimedine (1), 3-hydroxy-deoxyamphimedine (2), debromopetrosamine (3), and three known compounds, amphimedine (4), neoamphimedine (5) and deoxyamphimedine (6), have been isolated from the sponge Xest …
Three new minor components, the pyridoacridine alkaloids 1-hydroxy-deoxyamphimedine (1), 3-hydroxy-deoxyamphimedine (2), debromopetrosamine …
The anti-neoplastic and novel topoisomerase II-mediated cytotoxicity of neoamphimedine, a marine pyridoacridine.
Marshall KM, Matsumoto SS, Holden JA, Concepción GP, Tasdemir D, Ireland CM, Barrows LR. Marshall KM, et al. Biochem Pharmacol. 2003 Aug 1;66(3):447-58. doi: 10.1016/s0006-2952(03)00209-0. Biochem Pharmacol. 2003. PMID: 12907244
Here we report the novel top2 activity of neoamphimedine, an isomer of the marine pyridoacridine amphimedine. Neoamphimedine was cytotoxic in yeast and mammalian cell lines. ...Neoamphimedine was as effective as etoposide in mice bearing KB tumors and as effective as 9-ami …
Here we report the novel top2 activity of neoamphimedine, an isomer of the marine pyridoacridine amphimedine. Neoamphimedine was cyto …
Deoxyamphimedine, a pyridoacridine alkaloid, damages DNA via the production of reactive oxygen species.
Marshall KM, Andjelic CD, Tasdemir D, Concepción GP, Ireland CM, Barrows LR. Marshall KM, et al. Mar Drugs. 2009 May 25;7(2):196-209. doi: 10.3390/md7020196. Mar Drugs. 2009. PMID: 19597581 Free PMC article.
Here we demonstrate that while structurally similar to neoamphimedine and amphimedine, the biological activity of deoxyamphimedine differs greatly. ...
Here we demonstrate that while structurally similar to neoamphimedine and amphimedine, the biological activity of deoxyamphimedine di …