• Archives of Pharmacal Research
• /
• v.28 no.1
• /
• pp.16-21
• /
• 2005

We wanted to elucidate the reason why the trityloxymethyl substituent in $\gamma$-trityloxymethyl-$\gamma$­butyrolactone takes a sterically unfavorable specific conformation, and so we synthesized 5-trityloxymethyldihydrofuran-3-one, 3-(trityloxymethyl)-4-butanolide and 2-trityloxymethyl- tetrahy­drofuran and we then analyzed their conformation by $^{1}H-NMR$ analysis.

• Archives of Pharmacal Research
• /
• v.26 no.9
• /
• pp.679-685
• /
• 2003

A series of novel cyclopropyl nucleosides was synthesized using the highly stereoselective Simmons-Smith reaction starting from 1,2:5,6-di-Ο-isopropylidene-D-mannitol. The structural assignments of these nucleosides were determined by NMR studies and X-ray crystallography. All the synthesized nucleosides were assayed against several viruses.

• Archives of Pharmacal Research
• /
• v.23 no.6
• /
• pp.559-563
• /
• 2000

Novel exomethylene cyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate 5 was synthesized in 4 steps, from Feists acid 1 and was condensed with purine derivatives by the $S_N2$ type reaction to give some cyclopropyl nucleosides. The synthesized nucleosides did not showed any significant antiviral activity against HSV-1, HSV-2, HCMV, HIV-1, HIV-2, and HBV up to 100 $\mu\textrm{m}$.

• Biotechnology and Bioprocess Engineering:BBE
• /
• v.4 no.1
• /
• pp.17-20
• /
• 1999

Facile synthetic methods of 2',5'-dideoxy-, 2',3'-dideoxy- and 3'-deoxy-1, N6-ethenoadenosine nucleosides by either an enzymatic dideoxyribosyl transfer reaction or a simple chemical reaction were proposed. The synthesis products were isolated and purified by preparative HPLC and their structures were confirmed by 1H NMR (500 MHz) and FAB-MS including high resolution mass measurement. These modified nucleoside analogs have not been reported yet. Therefore, these modified nucleoside analogs are of potential value to be studied further for biological activity such as anticancer or antiviral.

• YAKHAK HOEJI
• /
• v.32 no.3
• /
• pp.177-181
• /
• 1988

Methyl 6-0-benzoyl-3-0-benzyl-2, 5-di-deoxy-2-fluoro-allofuranose (11) and 1, 2-0-di-acetyl-6-0-benzoyl-3, 5-di-deoxy-3-fluoro-glucofuranoes (22), sugar moieties of potential antiviral and/or anticancer chemotherapeutic nucleoside, were synthesized from D-glucose.

• YAKHAK HOEJI
• /
• v.47 no.6
• /
• pp.417-421
• /
• 2003

This paper describes a synthetic route to novel 2'-methyl and 4'-hydroxy carbocyclic nucleosides. The methyl group was successfully installed by carbonyl addition reaction of isopropenyl magnesium bromide followed by ring-closing metathesis and the hydroxy group was directly introduced from carbohydrate chiral template "D-lactose".ose".uot;.

• YAKHAK HOEJI
• /
• v.48 no.1
• /
• pp.88-92
• /
• 2004

In this study; a series of 2',4'-doubly branched carbocyclic nucleosides (8,9,10) were synthesized from simple acyclic ketone derivative as starting material. The installation of the 4'-quaternary carbon needed was carried out using a 〔3,3〕-sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2'-position was accomplished by Grig-nard reaction. Bis-vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst. Although all the synthesized compounds were assayed against several viruses, only cytosine analogue 9 showed weak antiviral viral activity (EC$_{50}$=45.4 $\mu$M) against CoxB3 virus.s.

• Bulletin of the Korean Chemical Society
• /
• v.25 no.12
• /
• pp.1812-1816
• /
• 2004

The stereoselective synthesis 4′,6′-dually branched carbocyclic nucleosides was accomplished in this study. The introduction of a methyl group in the 6′$({\alpha})$-position was accomplished by Felkin-Anh controlled alkylation. The construction of the required 4′$({\alpha})$-quaternary carbon was carried out using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited good antiviral activity against the HCMV.

• Bulletin of the Korean Chemical Society
• /
• v.29 no.9
• /
• pp.1723-1728
• /
• 2008

An efficient synthetic route for carbocyclic versions of stavudine analogues and their evaluation on antiviral activity are described. The construction of an ethynylated quaternary carbon at the 4'-position of carbocyclic nucleosides was accomplished using Claisen rearrangement of 11 and ring-closing metathesis (RCM) of dienyne 14 as key transformations. An antiviral evaluation of the synthesized compounds, 20, 21, 22, and 25 against HIV-1, HSV-1, HSV-2, and HCMV showed that only the guanine analogue 25 is moderately active against HIV-1 in the MT-4 cell line ($EC_{50}$ = 11.91 $\mu$mol).

• YAKHAK HOEJI
• /
• v.49 no.1
• /
• pp.20-24
• /
• 2005

The synthesis of 4',5'-doubly branched carbocyclic nucleosides was accomplished in this study. The selective methylation in the 5'-position was made by Felkin-Anh controlled Grignard addition. The construction of the required 4'-quaternary carbon was carried out by using a [3,3]-sigmatropic rearrangement. Bis-vinyl 6 was successfully cyclized using a Grubbs' catalyst II. The natural pyrimidine bases (cytosine, uracil, thymine) were efficiently coupled using a Pd(0) catalyst. When the synthesized compounds were examined for their activity against several viruses such as the HIV-1, HSV-1, HSV-2 and HCMV, the cytosine analogue 13 exhibited weak antiviral activity against the HCMV.