Previously, the natural£]-carboline metabolites as potent antitumor and antival agents have spurred a great interest on the synthetic and pharmacological studies of£]-carboline derivatives. Herein, a simple synthetic method by the application of Pictet-Spengler reaction and DDQ oxidation allowed the preparation of 1-substituted£]-carboline derivatives. Compounds 88-91 were synthesized from tryptamine and N-substituted-3-carbazole carboxaldehyde via Pictet-Spengler cyclization. Then, oxidation of compounds 88-91 by DDQ provided compounds 92-95. Their structures were determined by spectroscopic methods. Biological screening revealed that compounds 88 and 93 possessed in vitro cytotoxicties against two tumor cell lines (KB, Hepa), respectively. The ED50 value of compound 88 showed cytotoxicities against Hepa (Human hepatoma) tumor cell lines were 1.12 £gg/ml. The ED50 value of compound 93 showed cytotoxicities against KB (Human oral epidermoid carcinoma) tumor cell lines were 0.48 £gg/ml.
On the other hand, the marine sponge Cacospongia sp. was collected along seashore area of Lan-Yu in Taiwan. Fractionation of the MeOH/CHCl3 extract by using silica gel column chromatography yielded a dauble bond isomer fasciculatin (97). The structure of 97 was identified by UV¡BIR¡BMS¡B1D and 2D NMR.
| Identifer | oai:union.ndltd.org:NSYSU/oai:NSYSU:etd-0208101-153402 |
| Date | 08 February 2001 |
| Creators | Lin, Chun-Ling |
| Contributors | Jeh-Jeng Wang, Chun-Nan Lin, Ya-Ching Shen |
| 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-0208101-153402 |
| Rights | not_available, Copyright information available at source archive |
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