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An enantiospecific synthesis of 3-deaza-5'-noraristeromycin as its dihydrochloride ((-)-6) has been accomplished in six steps beginning with the reaction of (+)-(1R,4S)-4-hydroxy-2-cyclopenten-1-yl acetate with 4-chloro-1H-imidazo[4,5-c]pyridine. The preparation of 7-deaza-5'-noraristeromycin ((-)-7) was described previously. Compounds (-)-6 and (-)-7 were evaluated for antiviral activity against a large number of viruses. Compound (-)-6 produced an antiviral activity pattern similar to 5'-noraristeromycin but was less potent. Compound (-)-6 inhibited CEM cell proliferation at a 50% inhibitory concentration of 27 micrograms/mL but proved not inhibitory to HEL cell proliferation and not toxic to E6SM, HeLa, Vero, and MDCK cells at concentrations up to 200 micrograms/mL. While (-)-6 showed inhibition of S-adenosyl-L-homocysteine (AdoHcy) hydrolase, it was less inhibitory than 5'-noraristeromycin. Compound (-)-7 displayed no antiviral properties or inhibitory effects toward AdoHcy hydrolase.
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
July 2003,
Bioorganic & medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
February 1997,
Journal of medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
June 1998,
Bioorganic & medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
February 1997,
Journal of medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
July 2006,
Bioorganic & medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
December 2014,
Bioorganic & medicinal chemistry,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
August 1997,
Antimicrobial agents and chemotherapy,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
August 2020,
Molecules (Basel, Switzerland),
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
February 2016,
Bioorganic & medicinal chemistry letters,
S M Siddiqi, and
X Chen, and
J Rao, and
S W Schneller, and
S Ikeda, and
R Snoeck, and
G Andrei, and
J Balzarini, and
E De Clercq
May 2005,
Organic & biomolecular chemistry,
