Publication details
GLYOXYL ANALOGS OF INDOLE PHYTOALEXINS: SYNTHESIS AND ANTICANCER ACTIVITY
| Authors | |
|---|---|
| Year of publication | 2010 |
| Type | Article in Periodical |
| Magazine / Source | Collection of Czechoslovak Chemical Communications |
| MU Faculty or unit | |
| Citation | |
| Field | Organic chemistry |
| Keywords | Heterocycles; Indoles; Natural products; Phytoalexins; Glyoxylindoles; |
| Description | Glyoxyl analogs of indole phytoalexins brassinin, 1-methoxybrassinin, brassitin, 1-methoxybrassitin and 1-methoxybrassenin B were prepared, using (1H-indol-3-yl)-, (1-methoxyindol- 3-yl)- and [1-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl)indol-3-yl]glyoxyl chlorides as starting compounds. Synthesized products were examined for their antiproliferative activity against human cancer cell lines Jurkat (T-cell acute lymphoblastic leukemia), MCF-7 (breast adenocarcinoma, estrogen receptor-positive), MDA-MB-231 (breast adenocarcinoma, estrogen receptor-negative), HeLa (cervical adenocarcinoma), CCRF-CEM cell line (T-cell acute lymphoblastic leukemia) and A-549 cell line (lung adenocarcinoma), and their activity compared with natural phytoalexins and corresponding (1H-indol-3-yl)acetic acid derivatives. The highest potency with IC50 3.3-66.1 mímol l-1 was found for glyoxyl analogs of 1-methoxybrassenin B. |