Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives
- PMID: 26969844
- DOI: 10.1002/anie.201508227
Synthesis of Amaryllidaceae Constituents and Unnatural Derivatives
Abstract
This update covers the syntheses of Amaryllidaceae alkaloids since the publication of the last major review in 2008. A short summary of past syntheses and their step count is provided for the major constituents; pancratistatin, 7-deoxypancratistatin, narciclasine, lycoricidine, lycorine, and for other natural constituents, as well as for unnatural derivatives. Discussion of biological activities is provided for unnatural derivatives. Future prospects and further developments in this area are covered at the end of the review. The literature is covered to the end of August 2015.
Keywords: Amaryllidaceae alkaloids; anticancer drugs; biological activity; structure-activity relationship; total synthesis.
© 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
Similar articles
-
Total synthesis and biological evaluation of Amaryllidaceae alkaloids: narciclasine, ent-7-deoxypancratistatin, regioisomer of 7-deoxypancratistatin, 10b-epi-deoxypancratistatin, and truncated derivatives.J Org Chem. 2002 Dec 13;67(25):8726-43. doi: 10.1021/jo020129m. J Org Chem. 2002. PMID: 12467383
-
Chemoenzymatic approaches to lycorine-type Amaryllidaceae alkaloids: total syntheses of ent-lycoricidine, 3-epi-ent-lycoricidine, and 4-deoxy-3-epi-ent-lycoricidine.Org Lett. 2007 Aug 30;9(18):3683-5. doi: 10.1021/ol701552r. Epub 2007 Aug 8. Org Lett. 2007. PMID: 17685535
-
Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay(1a).J Org Chem. 2001 Apr 20;66(8):2583-7. doi: 10.1021/jo000710n. J Org Chem. 2001. PMID: 11304174
-
Chemical and Biological Aspects of Montanine-Type Alkaloids Isolated from Plants of the Amaryllidaceae Family.Molecules. 2020 May 16;25(10):2337. doi: 10.3390/molecules25102337. Molecules. 2020. PMID: 32429491 Free PMC article. Review.
-
Amaryllidaceae and Sceletium alkaloids.Nat Prod Rep. 2019 Oct 16;36(10):1462-1488. doi: 10.1039/c8np00055g. Nat Prod Rep. 2019. PMID: 30707215 Review.
Cited by
-
Potential Deoxycytidine Kinase Inhibitory Activity of Amaryllidaceae Alkaloids: An In Silico Approach.J Pharm Bioallied Sci. 2018 Jul-Sep;10(3):137-143. doi: 10.4103/jpbs.JPBS_44_18. J Pharm Bioallied Sci. 2018. PMID: 30237684 Free PMC article.
-
Unveiling the Anticancer Potential: Computational Exploration of Nitrogenated Derivatives of (+)-Pancratistatin as Topoisomerase I Inhibitors.Int J Mol Sci. 2024 Oct 7;25(19):10779. doi: 10.3390/ijms251910779. Int J Mol Sci. 2024. PMID: 39409108 Free PMC article.
-
Ru-NHC-Catalyzed Asymmetric, Complete Hydrogenation of Indoles and Benzofurans: One Catalyst with Dual Function.J Am Chem Soc. 2023 Jul 26;145(29):15695-15701. doi: 10.1021/jacs.3c04983. Epub 2023 Jul 12. J Am Chem Soc. 2023. PMID: 37435957 Free PMC article.
-
Enantioselective Synthesis of Isocarbostyril Alkaloids and Analogs Using Catalytic Dearomative Functionalization of Benzene.J Am Chem Soc. 2019 Jan 9;141(1):657-670. doi: 10.1021/jacs.8b12123. Epub 2018 Dec 20. J Am Chem Soc. 2019. PMID: 30520639 Free PMC article.
-
Asymmetric Entry into 10b-aza-Analogues of Amaryllidaceae Alkaloids Reveals a Pronounced Electronic Effect on Antiviral Activity.ACS Omega. 2018 Sep 30;3(9):11469-11476. doi: 10.1021/acsomega.8b01987. Epub 2018 Sep 20. ACS Omega. 2018. PMID: 30320263 Free PMC article.
Publication types
MeSH terms
Substances
LinkOut - more resources
Full Text Sources
Other Literature Sources
Miscellaneous