期刊
BIOORGANIC & MEDICINAL CHEMISTRY
卷 21, 期 21, 页码 6623-6633出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmc.2013.08.020
关键词
Cyclobrassinin; Phytoalexins; Indoles; Antiproliferative activity; Spirocyclization
资金
- Slovak Grant Agency for Science [1/0954/12, 1/0406/10]
- State NMR Programme [2003SP200280203, VVGS-2013-96]
An effective synthesis of analogs of the indole phytoalexin cyclobrassinin with NR1R2 group instead of SCH3 was developed starting from indole-3-carboxaldehyde. The target compounds were prepared by spirocyclization of 1-Boc-thioureas with the formation of isolable spiroindoline intermediates, followed by the trifluoroacetic acid-induced cascade reaction consisting of methanol elimination, deprotection and rearrangement of the iminium ion. The structures of novel products were elucided by the H-1 and C-13 NMR spectroscopy, including HMBC, HSQC, COSY, NOESY and DEPT measurements. Several newly synthesized compounds demonstrated significant antiproliferative/cytotoxic activity against human leukemia and solid tumor cell lines, as well as remarkable selectivity of these effects against cancer cells relative to the non-malignant HUVEC cells. (C) 2013 Elsevier Ltd. All rights reserved.
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