Marine natural products which contain a £]- carboline skeleton are widely distributed in marine invertebrates. The discovery of natural £]- carboline metabolites as potent antitumor and antival agents has stimulated a great interest on the synthetic and pharmatological studies of£]- carboline derivatives. Herein, the preparation, charactrization and biolgical evaluation of 1-substituted 1,2,3,4-tetrahydro-£]- carboline and 3,4-dihydro-£]- carboline derivatives are reported. A facile synthetic method by the application of Pictet-Sengler reaction and DDQ oxidation allowed the preparation of compounds 63-72. Compounds 63-67 were synthesized from tryptamine and N-substituted-3-carbazole carboxaldehyde via Pictet-Spengler cyclization. Subsequent oxidation of compounds 63-67 by DDQ furnished compounds 68-72. The structures of compounds 63-67 were determined by several spectroscopic methods. A series of 1-substituted-1,2,3,4-tetrahydro-£]- carboline (63-67) and 3,4-dihydro-£]- carboline derivatives (68-72) have been evaluated to possess cytotoxicity against human tumor cells including KB16, DLD and NCI cell lines.
On the other hand, chromatographic separation of acetone extract of Formosan grogonian coral Isis hippuris (collected in Gree island) has led to the isolation of four marine steroids namely hippurin-1 (74), 22-epi-hippurin-1 (80), 2-deacetylhippurin-1 (82) and 2-deacetyl-22-epi-hippurin-1 (83), as well as a new compound 4-hydroxy-5-(p-hydroxy phenyl)-pentane-2, 5-dione (86). The structures of all above compounds were established on the basis of spectral analysis. Biological studies revealed that compounds 74, 80, 82, 83 exhibited potent cytotoxicity against NUGC tumor cells, but compound 86 was inactive.
| Identifer | oai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0130101-172741 |
| Date | 30 January 2001 |
| Creators | Chang, Yao-To |
| Contributors | Ya-Ching Shen, none, none |
| Publisher | NSYSU |
| Source Sets | NSYSU Electronic Thesis and Dissertation Archive |
| Language | Cholon |
| Detected Language | English |
| Type | text |
| Format | application/pdf |
| Source | http://etd.lib.nsysu.edu.tw/ETD-db/ETD-search/view_etd?URN=etd-0130101-172741 |
| Rights | not_available, Copyright information available at source archive |
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