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KMID : 0043320190420090780
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Archives of Pharmacal Research
2019 Volume.42 No. 9 p.780 ~ p.789
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Synthesis and anti-HIV activity of l-2′,3′-Dideoxy-4′-selenonucleosides (l-4′-Se-ddNs)
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Yu Jin-Ha
Kim Gyu-Dong
Jarhad Dnyandev B.
Kim Hong-Rae
Jeong Lak-Shin
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Abstract
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Based on the potent anti-HIV activity of l-2′,3′-dideoxycytidine (l-ddC), l-2′,3′-dideoxy-4′-selenonucleosides (l-4′-Se-ddNs) have been synthesized from natural chiral template, l-glutamic acid, using Pummerer-type condensation as a key step. All synthesized compounds were assayed for anti-HIV-1 activity, but none of them did show any significant antiviral activity up to 100 μM, probably due to conformational differences between l-ddC and l-4′-Se-ddC, induced by the bulky selenium atom, which might play an important role in phosphorylation by cellular kinase.
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KEYWORD
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Antiviral, l-2′,3′-Dideoxy-4′-selenonucleosides, l-Nucleoside, Pummerer-type condensation, l-4′-Se-ddC
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