Antiviral and antitumor structure-activity relationship studies on tetracyclic eudistomines
| Autor: | Van Maarseveen Jh, Jan Balzarini, Hans W. Scheeren, Chris G. Kruse, P. H. H. Hermkens, De Clercq E |
|---|---|
| Rok vydání: | 1992 |
| Předmět: |
Stereochemistry
T-Lymphocytes Substituent Antineoplastic Agents Antiviral Agents Mice Structure-Activity Relationship chemistry.chemical_compound Drug Discovery Tumor Cells Cultured Animals Humans Simplexvirus Structure–activity relationship Urochordata Leukemia L1210 Indole test Pictet–Spengler reaction Molecular Structure Leukemia P388 HIV Biological activity Condensation reaction In vitro chemistry Molecular Medicine Derivative (chemistry) Carbolines |
| Zdroj: | Journal of Medicinal Chemistry. 35:3223-3230 |
| ISSN: | 1520-4804 0022-2623 |
| Popis: | The in vitro antiviral and antitumor activities of (-)-debromoeudistomin K (1a) and 10 structural analogues (1b-1j and 11) were evaluated. The synthesis was accomplished with an intramolecular Pictet-Spengler condensation reaction as the key step. This examination revealed some structural and stereochemical features that are important for both the antiviral and antitumor activities. The most striking points for activity are the necessity to have the correct natural stereochemistry at both C(1) and C(13b) and the presence of the C(1)-NH2 substituent. As was revealed before with naturally isolated eudistomins a substituent in the indole ring greatly influences the biological activity. The 5-OMe derivative 1h shows high potency in both antiviral and antitumor models. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|