Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds
Oleg S Radchenko
1
,
Vyacheslav L Novikov
1
,
Richard H. Willis
2
,
Peter T. Murphy
2
,
George B. Elyakov
1
Publication type: Journal Article
Publication date: 1997-05-01
scimago Q3
wos Q3
SJR: 0.334
CiteScore: 3.2
Impact factor: 1.5
ISSN: 00404039, 18733581
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
Polycarpine 1 , a highly cytotoxic marine natural product, has been synthesized in three steps from p-methoxyphenacyl bromide 4 in 57% overall yield. The key reaction for construction of the symmetrically substituted disulfide linkage of polycarpine is the treatment of 2-amino-4-(4-methoxyphenyl)-1-methylimidazole 17 with S2Cl2 in acetic acid. In a similar way ten related compounds, including three thiazole analogues, have been prepared. Most of them exhibit high cytotoxic activities against an array of human cancer cell lines.
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Total citations:
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Citations from 2025:
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GOST
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Radchenko O. S. et al. Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds // Tetrahedron Letters. 1997. Vol. 38. No. 20. pp. 3581-3584.
GOST all authors (up to 50)
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Radchenko O. S., Novikov V. L., Willis R. H., Murphy P. T., Elyakov G. B. Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds // Tetrahedron Letters. 1997. Vol. 38. No. 20. pp. 3581-3584.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1016/S0040-4039(97)00668-0
UR - https://doi.org/10.1016/S0040-4039(97)00668-0
TI - Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds
T2 - Tetrahedron Letters
AU - Radchenko, Oleg S
AU - Novikov, Vyacheslav L
AU - Willis, Richard H.
AU - Murphy, Peter T.
AU - Elyakov, George B.
PY - 1997
DA - 1997/05/01
PB - Elsevier
SP - 3581-3584
IS - 20
VL - 38
SN - 0040-4039
SN - 1873-3581
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{1997_Radchenko,
author = {Oleg S Radchenko and Vyacheslav L Novikov and Richard H. Willis and Peter T. Murphy and George B. Elyakov},
title = {Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds},
journal = {Tetrahedron Letters},
year = {1997},
volume = {38},
publisher = {Elsevier},
month = {may},
url = {https://doi.org/10.1016/S0040-4039(97)00668-0},
number = {20},
pages = {3581--3584},
doi = {10.1016/S0040-4039(97)00668-0}
}
Cite this
MLA
Copy
Radchenko, Oleg S., et al. “Synthesis of polycarpine, a cytotoxic sulfur-containing alkaloid from the ascidian Polycarpa aurata, and related compounds.” Tetrahedron Letters, vol. 38, no. 20, May. 1997, pp. 3581-3584. https://doi.org/10.1016/S0040-4039(97)00668-0.