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Title: Design and synthesis of bioactive 1,2-annulated adamantane derivatives. Author: Zoidis G, Tsotinis A, Kolocouris N, Kelly JM, Prathalingam SR, Naesens L, De Clercq E. Journal: Org Biomol Chem; 2008 Sep 07; 6(17):3177-85. PubMed ID: 18698478. Abstract: Adamantanopyrrolidines 8, 9 and 10, adamantanopyrrolidines 16 and 18, adamantanoxazolone 20, adamantanopyrazolone 23, adamantanopyrazolothione 24 and adamantanocyclopentanamine 32 were synthesized and tested for anti-influenza A virus and trypanocidal activity. The stereoelectronic requirements for optimal antiviral and trypanocidal potency were investigated. Pyrrolidine 16 proved to be the most active of the compounds tested against influenza A virus, being 4-fold more active than amantadine, equipotent to rimantadine and 19-fold more potent than ribavirin. Oxazolone 20 showed significant trypanocidal activity against bloodstream forms of the African trypanosome, Trypanosoma brucei, being approximately 3 times more potent than rimantadine and almost 50-fold more active than amantadine.[Abstract] [Full Text] [Related] [New Search]