title: C-3 halo and 3-methyl substituted 5'-nor-3-deazaaristeromycins: synthesis and antiviral properties.
abstract: To expand on the antiviral properties of 5'-noraristeromycin, synthetic entry into 3-substituted 3-deaza-5'-noraristeromyin derivatives (i.e., bromo, 4; iodo, 5; chloro, 6; and, methyl, 7) has been accomplished from a common intermediate. An extensive antiviral analysis showed 7 to be basically inactive (except for weak effects against VSV) and there were no general trends among the halo compounds (except versus reovirus-1 and influenza B). Individually, compound 4 was most favorable towards HCMV, VZV, HBV, and VV; product 5 against HBV, VSV, VV, influenza B, HCMV, and measles; and, target 6 towards Punta Toro, VSV, measles, parainflucenza-3, influenza A (H5N1), and influenza B. The methyl target 7 was inactive in all viral assays.
authors.affiliation: Molette Laboratory for Drug Discovery, Department of Chemistry and Biochemistry, Auburn University, Auburn, AL 36849-5312, United States.
authors.forename: Chong
authors.initials: C
authors.lastname: Liu
authors.forename: Qi
authors.initials: Q
authors.lastname: Chen
authors.forename: Minmin
authors.initials: M
authors.lastname: Yang
authors.forename: Stewart W
authors.initials: SW
authors.lastname: Schneller
mesh_terms: D000225:Adenine / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000241:Adenosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D006801:Humans; D008958:Models, Molecular; D014777:Virus Diseases / Q000188:drug therapy; D014780:Viruses / Q000187:drug effects*
chemical_list: D000998:Antiviral Agents; C076829:5'-noraristeromycin; C055133:3-deazaadenine; D000225:Adenine; D000241:Adenosine