Synthesis and Antiviral Activity Evaluation of Some Aminoadamantane Derivatives

Journal of Medicinal Chemistry
1994.0

Abstract

The synthesis of some spiro[cyclopropane-1,2'-adamantan]-2-amines and methanamines and some spiro[pyrrolidine-2,2'-adamantanes] is described. The title compounds were evaluated against a wide range of viruses (influenza A, influenza B, parainfluenza 3, RSV, HSV-1, TK- HSV-1, HSV-2, vaccinia, vesicular stomatitis, polio 1, coxsackie B4, sindbis, semliki forest, Reo 1, HIV-1, and HIV-2), and some of them (compounds 6b, 6c, 9a, 16a, 16b, and 17) inhibited the cytopathicity of influenza A virus at a concentration significantly lower than that of amantadine and also significantly lower than the concentrations at which they proved cytotoxic to the host cells. None of the new aminoadamantane derivatives was active against influenza B virus or any of the other viruses tested, which points to their specificity as anti-influenza A virus agents.

Knowledge Graph

Similar Paper

Synthesis and Antiviral Activity Evaluation of Some Aminoadamantane Derivatives
Journal of Medicinal Chemistry 1994.0
Synthesis and Antiviral Activity Evaluation of Some New Aminoadamantane Derivatives. 2
Journal of Medicinal Chemistry 1996.0
Novel 3-(2-Adamantyl)pyrrolidines with potent activity against influenza A virus—identification of aminoadamantane derivatives bearing two pharmacophoric amine groups
Bioorganic & Medicinal Chemistry Letters 2001.0
Design and synthesis of bioactive adamantane spiro heterocycles
Bioorganic & Medicinal Chemistry Letters 2007.0
Spiro[pyrrolidine-2,2′-adamantanes]: synthesis, anti-influenza virus activity and conformational properties
Bioorganic & Medicinal Chemistry Letters 2003.0
Synthesis of 2-(2-adamantyl)piperidines and structure anti-influenza virus a activity relationship study using a combination of NMR spectroscopy and molecular modeling
Bioorganic & Medicinal Chemistry Letters 1999.0
Design and synthesis of 1,2-annulated adamantane piperidines with anti-influenza virus activity
Bioorganic & Medicinal Chemistry 2009.0
Microwave assisted synthesis and anti-influenza virus activity of 1-adamantyl substituted N-(1-thia-4-azaspiro[4.5]decan-4-yl)carboxamide derivatives
Bioorganic & Medicinal Chemistry 2012.0
Synthesis and Anti-influenza A Virus Activity of 2,2-Dialkylamantadines and Related Compounds
ACS Medicinal Chemistry Letters 2012.0
Design and synthesis of bioactive adamantanaminoalcohols and adamantanamines
European Journal of Medicinal Chemistry 2010.0