Unusual Sulfamate Indoles and a Novel Indolo[3,2-a]carbazole from Ancorina sp

Four new indoles, ancorinolates A−C and bis-ancorinolate B, which contain sulfamate and sulfate groups, were isolated from the aqueous extract of the sponge Ancorina sp. In addition, ancorinazole, an indolo[3,2-a]carbazole also possessing sulfamate and sulfate groups, was isolated from two separate...

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Bibliographic Details
Published in:Journal of organic chemistry 2002-09, Vol.67 (19), p.6671-6677
Main Authors: Meragelman, Karina M, West, Lyndon M, Northcote, Peter T, Pannell, Lewis K, McKee, Tawnya C, Boyd, Michael R
Format: Article
Language:English
Subjects:
Acetylation
Animals
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
Biological and medical sciences
Chromatography, High Pressure Liquid
General pharmacology
Hydrolysis
Indoles - chemistry
Indoles - isolation & purification
Indoles - pharmacology
Mass Spectrometry
Medical sciences
Molecular Structure
New Zealand
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Porifera - chemistry
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Summary:Four new indoles, ancorinolates A−C and bis-ancorinolate B, which contain sulfamate and sulfate groups, were isolated from the aqueous extract of the sponge Ancorina sp. In addition, ancorinazole, an indolo[3,2-a]carbazole also possessing sulfamate and sulfate groups, was isolated from two separate New Zealand collections of Ancorina sp. Ancorinazole is the first indolo[3,2-a]carbazole described as a natural product. Ancorinolates A (1) and C (3) showed weak HIV-inhibitory activity in the XTT-based, anticytopathicity assay.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo020120k