• Archives of Pharmacal Research
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• v.29 no.6
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• pp.464-468
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• 2006

Novel phenyl branched apiosyl nucleosides were synthesized in this study. The introduction of phenyl group in the 4'-position was accomplished by a [3,3]-sigmatropic rearrangement. Apiosyl sugar moiety was constructed by sequential ozonolysis and reductions. The natural bases (cytosine and adenine) were efficiently coupled with an apiosyl sugar by classical glycosyl condensation procedure (persilyated base and TMSOTf). The antiviral activities of the synthesized compounds were evaluated against the HIV-1, HSV-1, HSV-2 and HCMV.

• Proceedings of the PSK Conference
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• 2002.10a
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• pp.363.2-363.2
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• 2002

A number of 2',3'-deoxynucleosides have been discovered to possess significant antiviral activity against HIV-1 and other viruses. Since it has been suggested that proper conformation of the dideoxynucleosides in terms of ring puckering of the five-membered sugar moiety is required for them to exhibit antiviral activity a number of nucleoside analogues to fix sugar-ring puckering have been synthesize and evaluated for antiviral activity. (omitted)

• Korean Journal of Microbiology
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• v.29 no.1
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• pp.25-33
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• 1991

Antiviral activities of papaverine and nucleoside analogs, 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine (DHPG) and acyclovir, against human cytomegalovirus (HCMV) infection were compared in vitro. Papaverine and DHPG were effective in reducing infectious HCMV yields with $ED_{50}{\s}$ (effective dose 50: the concentraion at which 50% of virus yields was obtained) of approximately 1.02 and $0.45{\mu}{\M}$, respectively; while acyclovir was less effective with an $ED_{50}$ of about $10.4{\mu}{\M}$The relative cytotoxicity of these drugs was evaluated under the same conditions used to measure infectious HCMV yields. Papaverine and DHPG demonstrated little cellular toxicity as measured by their effect on the viability of confluent cells at concentrations in the range of those demonstrating potent inhibition of HCMV replication. Similarly, protein synthesis was largely unaffected by these drugs in stationary mock-infected cells as measured by the incorporation of isotopically labelled amino acids. In contrast, cellular DNA synthesis was invariably reduced in the presence of either drug. HCMV-specific DNA synthesis was also strongly inhibited by papaverine and DHPG.

• YAKHAK HOEJI
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• v.56 no.4
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• pp.230-235
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• 2012

Synthesis of novel cyclopropyl pyrimidine and purine nucleoside derivatives 2~8 with ${\alpha}$-configuration was successfully accomplished using an epoxide-ring opening reaction, lactonization, a hydroboration-oxidation reaction and a Mitsunobu reaction as the key steps. Antiviral activities against HSV-1 and -2, HIV-1 and -2, coxsackie B1and B3 viruses and poliovirus were assayed. Three compounds 4, 7 and 8 exhibit cytotoxicity-derived antiviral activity only in HIV-1 and -2.

• Bulletin of the Korean Chemical Society
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• v.26 no.10
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• pp.1520-1524
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• 2005

This paper describes the racemic and stereoselective synthetic route for a novel 4'$\alpha$-phenyl and 6'$\alpha$-methyl doubly branched carbocyclic nucleosides from an acyclic 2-hydroxy acetophenone. The installation of phenyl group at the 4'-position of carbocyclic nucleoside was successfully accomplished via a sequential [3,3]-sigmatropic rearrangement. The stereoselective introduction of a methyl group in the 6'$\alpha$-position was accomplished by Felkin-Anh controlled alkylation. Bis-vinyl 11 compound was successfully cyclized using a Grubbs’ catalyst II to desired carbocycles. The natural bases (adenine and cytosine) were efficiently coupled using a Pd(0) catalyst. Although all the synthesized compounds were examined for their activity against several viruses such as HIV-1, HSV-1, HSV-2 and HCMV, only cytosine analogues 17 exhibited weak antiviral activity against HCMV.

• Bulletin of the Korean Chemical Society
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• v.33 no.8
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• pp.2574-2580
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• 2012

The discovery that threosyl phosphonate nucleoside (PMDTA, $EC_{50}=2.53{\mu}M$) is a potent anti-HIV agent has led to the synthesis and biological evaluation of 5'-deoxy versions of threosyl phosphonate nucleosides. In the present study, (E)-3'-phosphonoalkenyl and 3'-phosphonoalkyl nucleoside analogues 13, 16, 20 and 23 were synthesized from acetol and tested for anti-HIV activity and cytotoxicity. The adenine analogue 16 was found to exhibit moderate in vitro anti-HIV-1 activity ($EC_{50}=22.2{\mu}M$).

• Bulletin of the Korean Chemical Society
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• v.31 no.9
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• pp.2514-2518
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• 2010

A very simple synthetic route of a novel SATE prodrug type of 6'-fluoro-6'-methyl-5'-noradeonosine carbocyclic nucleoside phosphonic acid is described. The key fluorinated alcohol intermediate 7 was prepared from the epoxide intermediate 6a via selective ring-opening of epoxide. Coupling of 7 with $N^6$-bis-Boc-adenine under a Mitsunobu reaction followed by phosphonation and deprotection afforded the carbocyclic phosphonic acid. The chemical stability of the bis(SATE) derivative 13 was measured at neutral (pH 7.2) and slightly acidic (Milli-Q water, pH 5.5) pH. The antiviral activity test of the SATE prodrug 13 and its parent nucleoside phosphonic acid 11 were evaluated against HIV-1.

• Bulletin of the Korean Chemical Society
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• v.35 no.12
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• pp.3502-3508
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• 2014

The first synthetic route to 5'-norcarbocyclic C-nucleoside [7-oxa-7,9-dideazadenosine (furo[3,2-d]pyrimidine) and 9-deazaadenosine (pyrrolo[3,2-d]pyrimidine)] phosphonic acids from commercially available 1,3-dihydroxy cyclopentane was described. The key C-C bond formation from sugar to base precursor was performed using Knoevenagel-type condensation from a ketone derivative. Synthesized C-nucleoside phosphonic acids were tested for anti-HIV activity as well as anti-leukemic activity. Compound 26 showed significant anti-leukemic activity.

• Bulletin of the Korean Chemical Society
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• v.26 no.11
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• pp.1767-1770
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• 2005

Novel 1',4'-dimethyl branched carbocyclic nucleosides were synthesized from acetol. The 4'-methyl group was installed via a Claisen rearrangement reaction, and the carbonyl addition of methylmagnesium bromide was used to introduce the 1'-methyl group. The coupling of nucleosidic bases and desilylation was used to produce a series of novel nucleosides.

• Proceedings of the PSK Conference
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• 2003.04a
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• pp.237.3-238
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• 2003

Carbonucleosides has extensively been studied as a promising anti-viral agents having chemical and metabolical stability. As yet there are no rules relating the structures of carbocyclic nucleosides to their therapeutic activity. although trends among certain kinds of structure have been tentatively put forward. In our research program for discovery of anti-viral drugs, the novel cyclobutyl nucleosides can be expected to be potential antiviral drugs as analogues of cyclobut-A, anti-HBV agent. (omitted)