• Bulletin of the Korean Chemical Society
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• 제24권9호
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• pp.1284-1288
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• 2003

A very short and concise synthetic route for a novel acyclic version of d4T is described. The required quaternary carbon was successfully installed using a [3,3]-sigmatropic rearrangement. The condensation of the mesylates 16-18 with an adenine base under standard nucleophilic substitution conditions ($K_2CO_3$, 18-Crown- 6, DMF) in addition to deblocking afforded the target acyclic nucleosides 22-24. In addition, the antiviral evaluations against various viruses were performed.

• Bulletin of the Korean Chemical Society
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• 제9권5호
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• pp.295-298
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• 1988

Acyclic nucleosides, 1-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-2-thiopyrimidine, 9-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-6-amino -2-thiopurine, 1-(2-acetoxyethoxymethyl)-2-thiopyrimidine, and 9-[[1,3-bis(benzyloxy)-2-propoxy]methyl]-6-amino -2-thiopurine have been synthesized by coupling pyrimidine and purine bases with acyclic acetates using a new coupling reagent of lithium bromide in the presence of trifluoro acetic acid in acetonitrile.

• Archives of Pharmacal Research
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• 제26권12호
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• pp.1109-1116
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• 2003

A series of 3'- and 4'-branched carbocyclic nucleosides 25, 26, 27, 28, 29 and 30 were synthesized starting from simple acyclic ketone derivatives. The construction of the required quaternary carbon was made using a [3,3]-sigmatropic rearrangement. In addition, the installation of a methyl group in the 3'-position was accomplished using a Horner-Wadsworth-Emmons (HWE) reaction with triethyl 2-phosphonopropionate. Bis-vinyl was successfully cyclized using a Grubbs' catalyst (Ⅱ). Natural bases (adenine, cytosine, uracil) were efficiently coupled with the use of a Pd(0) catalyst.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.2
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• pp.346.2-346.2
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• 2002

Recently, several branched-nucleosides have been synthesized and evaluated as potent antitumor or antiviral agents. Among them, 4'${\alpha}$--C-ethenyl and 4'${\alpha}$-C-ethynyl nucleosides which having an additional double or triple bond at 4'-position were reported to be as potent antiviral and anlitumor activities. Encouraged by these interesting structures and antiviral activities, it was determined to synthesize novel classes of nucleosides comprising branched carbocyclic nucleosides with an additional aryl group at 4'${\alpha}$-position using versatile reiterative three-step sequences from simple acyclic precursor '2-hydroxyacetophenone. Our efforts toward the synthesis of novel nucleosides analogues are reported herein.

• 대한약학회:학술대회논문집
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• 대한약학회 2002년도 Proceedings of the Convention of the Pharmaceutical Society of Korea Vol.1
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• pp.184.2-184.2
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• 2002

• 대한약학회:학술대회논문집
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• 대한약학회 2001년도 Proceedings of International Convention of the Pharmaceutical Society of Korea
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• pp.131.1-131.1
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• 2001

• 약학회지
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• 제33권6호
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• pp.361-364
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• 1989

The Synthesis of acyclic derivatives of ribavirin (2'-azido and halo seco derivatives) for the development of new antiviral agents is described. These acyclic nucleosides are synthesized from ribavirin by the method of ring opening reaction of sugar moietry.

• Archives of Pharmacal Research
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• 제17권6호
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• pp.480-482
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• 1994

A number of 5-substituted pyrimidine acyclic nucleosides were synthesized and tested for invitor cytotoxicity against four cell lines (j-82 cell, p-388 cell, FM-3A cell and U-938 cell lines). Synthesis of 1-cyanomethyl-5-substituted pyrimidines (1a-e) and 1-(4-cyanobutyl)-5-substituted pyrimidines (2a-e) was acomplished from the series of alkylation reactions ofl 5-substituted uracils with the corresponding chloacetonitrile and 5-chlorovaleronitile in DMSO under $50^{\circ}C$ temperature. These 5-substituted pyrimidine acylic nucleosides (1a-e and 2a-e) exhibited moderate to significant acitivity aginst four cell lines.

• 약학회지
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• 제48권1호
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• pp.88-92
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• 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
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• 제26권10호
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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.