@article{3e5ea99c79e8423198804fb2af86dec4,
title = "Chemoenzymatic synthesis of amaryllidaceae constituents and biological evaluation of their C-1 analogues. the next generation synthesis of 7-deoxypancratistatin and trans -dihydrolycoricidine: Journal of Organic Chemistry",
abstract = "An efficient synthesis of C-1 derivatives of 7-deoxypancratistatin is reported. The key steps include the following: selective opening of an epoxide with aluminum acetylide in the presence of an aziridine; solid-state silica-gel-catalyzed opening of an aziridine; and oxidative cleavage of a phenanthrene core and its recyclization to phenanthridone to provide the key C-1 aldehyde 22. The conversion of this aldehyde to C-1 acetoxymethyl and C-1 hydroxymethyl derivatives is described along with the evaluation of their biological activity against several cancer cell lines and in an apoptosis study. The C-1 acetoxymethyl derivative has shown promising activity comparable to that of the natural product. In addition, a total synthesis of trans-dihydrolycoricidine and a formal total synthesis of 7-deoxypancratistatin are reported from aldehyde 22. Detailed experimental and spectral data are provided for all new compounds.",
keywords = "Aldehydes, Amaryllidaceae Alkaloids, Antineoplastic Agents, Phytogenic, Apoptosis, Aziridines, Catalysis, Cell Line, Tumor, Cyclization, Drug Screening Assays, Antitumor, Epoxy Compounds, Humans, Isoquinolines, Molecular Structure, Oxidation-Reduction, Phenanthrenes, Stereoisomerism, Structure-Activity Relationship, Cell culture, Cell death, Gels, Methanol, Silica, Synthesis (chemical), ((1,2,3,4,4a,11b) 2,3,4 trihydroxy 6 oxo 1,2,3,4,4a,5,6,11b octahydro [1,3]dioxolo[4,5 j]phenanthridin 1 yl)methyl acetate, (1,2,3,4,4a,11b) 2,3,4 trihydroxy 1 (hydroxymethyl) 1,2,3,4,4a,5 hexahydro [1,3]dioxolo[4,5 j]phenanthridin 6(11bH) one, 7 deoxypancratistatin, aldehyde, Amaryllidaceae alkaloid, aziridine, epoxide, phenanthrene, silica gel, trans dihydrolycoricidine, unclassified drug, Acetylides, Amaryllidaceae, Biological activities, Biological evaluation, Cancer cell lines, Chemo-enzymatic synthesis, Efficient synthesis, Natural products, Oxidative cleavages, Spectral data, Total synthesis, animal cell, apoptosis, article, biological activity, cancer cell culture, catalysis, controlled study, cyclization, enzyme synthesis, human, human cell, mouse, nonhuman, oxidation, pharmacophore, solid state, Ionic liquids, Aldehydes/chemistry, Amaryllidaceae Alkaloids/chemical synthesis, Isoquinolines/chemical synthesis, Antineoplastic Agents, Phytogenic/chemical synthesis, Epoxy Compounds/chemistry, Aziridines/chemistry, Apoptosis/drug effects, Phenanthrenes/chemistry",
author = "J. Collins and U. Rinner and M. Moser and T. Hudlicky and I. Ghiviriga and A.E. Romero and A. Kornienko and D. Ma and C. Griffin and S. Pandey",
note = "Export Date: 13 June 2023; Cited By: 57; Correspondence Address: T. Hudlicky; Chemistry Department and Centre for Biotechnology, Brock University, St. Catharines, ON L2S 3A1, 500 Glenridge Avenue, Canada; email:
[email protected]; CODEN: JOCEA",
year = "2010",
month = apr,
day = "7",
doi = "10.1021/jo1003136",
language = "English",
volume = "75",
pages = "3069--3084",
journal = "J. Org. Chem.",
issn = "1520-6904",
number = "9",
}
