Volume 32, Issue 45
Heterocyclic Compounds
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ChemInform Abstract: Novel 3-(2-Adamantyl)pyrrolidines with Potent Activity Against Influenza A Virus — Identification of Aminoadamantane Derivatives Bearing Two Pharmacophoric Amine Groups.

George Stamatiou

George Stamatiou

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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Antonios Kolocouris

Antonios Kolocouris

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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Nicolas Kolocouris

Nicolas Kolocouris

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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George Fytas

George Fytas

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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George B. Foscolos

George B. Foscolos

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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Johan Neyts

Johan Neyts

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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Erik De Clercq

Erik De Clercq

Dep. Pharm., Div. Pharm. Chem., Univ. Athens, GR-15771 Athens, Greece

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First published: 23 May 2010

Abstract

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ChemInform Abstract

In order to examine the stereoelectronic requirements of aminoadamantanes for optimal antiinfluenza A activity, the adamantylpyrrolidines (VIII) and (XIV) are synthesized. Pyrrolidines (VIIIb)—(VIIId) and (XIV) are found to be active against H2N2 and H3N2 strains of influenza virus A. Surprisingly, the lactam amine precursors (VIIb) and (VIIc) of the potent diamine analogues (VIIIb) and (VIIIc) are also active. In addition, a conformational analysis of parent pyrrolidine (XIV) is carried out.

chemical structure image

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