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>Synthesis of Novel AZA-Analogues of Tiazofurin with 2-5,5-bis(Hydroxymethyl)Pyrrolidin-2-yl Framework as Sugar Mimic
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Synthesis of Novel AZA-Analogues of Tiazofurin with 2-5,5-bis(Hydroxymethyl)Pyrrolidin-2-yl Framework as Sugar Mimic
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机译:以2- 5,5-双(羟甲基)吡咯烷基-2-基骨架为糖模拟物合成新颖的偶氮呋喃AZA类似物
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摘要
The novel aza-analogues of tiazofurin (TZF) with 2-[5,5-bis(hydroxymethyl)pyrrolidin-2-yl] moiety, as sugar mimic, were synthesized from O,O-cyclohexylidene derivative of 4,4-bis(hydroxymethyl)-4-nitrobutanal in multi-gram scale. The synthetic route consisted of three stages: (i) the synthesis of corresponding derivative of 5,5-bis(hydroxymethyl)pyrrolidine-2-carbonitrile, (ii) the construction of ethyl thiazole-2-carboxylate part by the conversion of the pyrrolidine-2-carbonitrile into the N-trifluoroacetyl derivative followed by cyclocondensation with L-cysteine ethyl ester and then by dehydrogenation, and (iii) the final transformation of the ethyl thiazole-4-carboxylate into the aza-analogues of TZF. The TZF aza-analogues were evaluated for their antiviral activities in cell-culture-based assays.
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