3-(Azolylmethyl)-1H-indoles as Selective P450 Aromatase Inhibitors

The synthesis of 1‐(halobenzyl) and 1‐tosyl‐3‐(1H‐imidazol‐1‐ylmethyl)‐1H‐indoles, 1‐(halobenzyl) and 1‐tosyl‐3‐(1H‐1, 2, 4‐triazol‐1‐ylmethyl)‐1H‐indoles and 1‐(halobenzyl)‐3‐(4H‐1, 2, 4‐triazol‐4‐ylmethyl)‐1H‐indoles is described. 3‐(Azolylmethyl)‐1H‐indoles were obtained in three steps from 1H‐in...

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Bibliographic Details
Published in:Pharmacy and Pharmacology Communications 1998-04, Vol.4 (4), p.211-218
Main Authors: Marchand, P., Borgne, M. Le, Duflos, M., Robert-Piessard, S., Baut, G. Le, Ahmadi, M., Hartmann, R. W., Palzer, M.
Format: Article
Language:English
Subjects:
Cancer
Chemical Sciences
Life Sciences
Medication
Medicinal Chemistry
Pharmaceutical sciences
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Summary:The synthesis of 1‐(halobenzyl) and 1‐tosyl‐3‐(1H‐imidazol‐1‐ylmethyl)‐1H‐indoles, 1‐(halobenzyl) and 1‐tosyl‐3‐(1H‐1, 2, 4‐triazol‐1‐ylmethyl)‐1H‐indoles and 1‐(halobenzyl)‐3‐(4H‐1, 2, 4‐triazol‐4‐ylmethyl)‐1H‐indoles is described. 3‐(Azolylmethyl)‐1H‐indoles were obtained in three steps from 1H‐indole‐3‐carbaldehyde (1) by benzylation or tosylation, reduction and azole moiety fixation. In an alternative method, the bromo intermediates issued from the corresponding alcohols were condensed with the azolium sodium salts. Inhibitory activity against P450arom and P45017α, and influence on retinoic acid metabolism were evaluated. Three imidazole compounds exhibited potent and selective aromatase inhibitory activity.
ISSN:1460-8081
2042-7158
DOI:10.1111/j.2042-7158.1998.tb00337.x