Serveur d'exploration Chloroquine

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New Manzamine Alkaloids with Potent Activity against Infectious Diseases

Identifieur interne : 002266 ( Main/Exploration ); précédent : 002265; suivant : 002267

New Manzamine Alkaloids with Potent Activity against Infectious Diseases

Auteurs : K. A. El Sayed [États-Unis] ; M. Kelly [États-Unis] ; U. A. K. Kara [États-Unis] ; K. K. H. Ang [États-Unis] ; I. Katsuyama [États-Unis] ; D. C. Dunbar [États-Unis] ; A. A. Khan [États-Unis] ; M. T. Hamann [États-Unis]

Source :

RBID : ISTEX:AAE58B1F3B604C75CD681D30CAC02F7E15341B9C

Abstract

The isolation of the new enantiomers of 8-hydroxymanzamine A (1), manzamine F (2), along with the unprecedented manzamine dimer, neo-kauluamine from an undescribed genus of Indo-Pacific sponge (family Petrosiidae, order Haplosclerida) is reported. The relative stereochemistry of neo-kauluamine was established through detailed analysis of NOE-correlations combined with molecular modeling. The significance of the manzamines as in vivo antimalarial agents with superior activity to the clinically used drugs artemisinin and chloroquine is discussed along with the activity in vitro against the AIDS-opportunistic infectious diseases tuberculosis and toxoplasmosis. Reexamination of the sponges identified as Prianos, and Pachypellina, in earlier publications has confirmed that these are members of the same genus as the sponge described here, but differ at the species level.

Url:
DOI: 10.1021/ja002073o


Affiliations:


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<div type="abstract">The isolation of the new enantiomers of 8-hydroxymanzamine A (1), manzamine F (2), along with the unprecedented manzamine dimer, neo-kauluamine from an undescribed genus of Indo-Pacific sponge (family Petrosiidae, order Haplosclerida) is reported. The relative stereochemistry of neo-kauluamine was established through detailed analysis of NOE-correlations combined with molecular modeling. The significance of the manzamines as in vivo antimalarial agents with superior activity to the clinically used drugs artemisinin and chloroquine is discussed along with the activity in vitro against the AIDS-opportunistic infectious diseases tuberculosis and toxoplasmosis. Reexamination of the sponges identified as Prianos, and Pachypellina, in earlier publications has confirmed that these are members of the same genus as the sponge described here, but differ at the species level.</div>
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