New neplanocin analogs. 1. Synthesis of 6'-modified neplanocin A derivatives as broad-spectrum antiviral agents

Journal of Medicinal Chemistry
1992.0

Abstract

Novel neplanocin A analogues modified at the 6'-position, i.e., 6'-deoxy analogues (2, 3, 6, 9, 20), 6'-O-methylneplanocin A (15), and 6'-C-methylneplanocin A's (22a and 22b) have been synthesized and evaluated for their antiviral activity in a wide variety of DNA and RNA virus systems. These compounds showed an activity spectrum that conforms to that of S-adenosylhomocysteine hydrolase inhibitors. They were particularly active against pox- (vaccinia), paramyxo-(parainfluenza, measles, respiratory syncytial), arena- (Junin, Tacaribe), rhabdo- (vesicular stomatitis), reo-, and cytomegalovirus. In order of (increasing) antiviral activity, the compounds ranked as follows: 3 less than 15 approximately 20 less than 6 less than 9 approximately 2 less than 22a. Of the two diastereomeric forms of 22, only 22a was active; 22a surpassed neplanocin A both in antiviral potency and selectivity. Compound 22a appears to be a promising candidate drug for the treatment of pox-, paramyxo-, arena-, rhabdo-, reo-, and cytomegalovirus infections.

Knowledge Graph

Similar Paper

New neplanocin analogs. 1. Synthesis of 6'-modified neplanocin A derivatives as broad-spectrum antiviral agents
Journal of Medicinal Chemistry 1992.0
New Neplanocin Analogues. 6. Synthesis and Potent Antiviral Activity of 6‘-Homoneplanocin A
Journal of Medicinal Chemistry 1996.0
New Neplanocin Analogues. 7. Synthesis and Antiviral Activity of 2-Halo Derivatives of Neplanocin A
Journal of Medicinal Chemistry 1996.0
New neplanocin analogues. III. 6′R-configuration is essential for the antiviral activity of 6′-C-methyl-3-deazaneplanocin a's
Bioorganic & Medicinal Chemistry Letters 1994.0
The enantiomers of the 1′,6′-isomer of neplanocin A: Synthesis and antiviral properties
Bioorganic & Medicinal Chemistry 2014.0
Potential inhibitors of S-adenosylmethionine-dependent methyltransferases. 11. Molecular dissections of neplanocin A as potential inhibitors of S-adenosylhomocysteine hydrolase
Journal of Medicinal Chemistry 1988.0
Synthesis of 3-deazaneplanocin A, a powerful inhibitor of S-adenosylhomocysteine hydrolase with potent and selective in vitro and in vivo antiviral activities
Journal of Medicinal Chemistry 1989.0
An Epimer of 5'-Noraristeromycin and Its Antiviral Properties
Journal of Medicinal Chemistry 1994.0
Structure–Activity Relationships of Neplanocin A Analogues as S-Adenosylhomocysteine Hydrolase Inhibitors and Their Antiviral and Antitumor Activities
Journal of Medicinal Chemistry 2015.0
New Neplanocin Analogues. 12. Alternative Synthesis and Antimalarial Effect of (6‘R)-6‘-C-Methylneplanocin A, a Potent AdoHcy Hydrolase Inhibitor
Journal of Medicinal Chemistry 2002.0