• Journal of Integrative Natural Science
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• v.8 no.3
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• pp.153-163
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• 2015

Racemic synthesis of novel 5',5'-difluoro-2'-methyl-apiose nucleoside phosphonic acid analogs was achieved as potent antiviral agents. Phosphonation was performed by direct displacement of triflate intermediate with diethyl (lithiodifluoromethyl) phosphonate to give the corresponding (${\alpha},{\alpha}$-difluoroalkyl) phosphonate. Condensation successfully proceeded from a glycosyl donor with persilylated bases to yield the nucleoside phosphonate analogs. Deprotection of diethyl phosphonates provided the target nucleoside analogs. An antiviral evaluation of the synthesized compounds against various viruses such as HIV, HSV-1, HSV-2 and HCMV revealed that the pyrimidine analogs (cytosine, uracil, and thymine) have weak anti-HIV or HCMV activity.

• Archives of Pharmacal Research
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• v.26 no.11
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• pp.887-891
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• 2003

Novel trans-2,2-dimethylcyclopropyl nucleosides were synthesized as potential antiviral agents. The key intermediate, 3, was synthesized via five steps from ethyl chrysanthemate and condensed with purine bases using the Mitsunobu reaction to give six cyclopropyl nucleosides. These synthesized nucleosides did not show any significant antiviral activity against HSV-1, HSV-2, EMCV, Cox B3, or VSV, at concentrations up to 100 $\mu M$.

• Proceedings of the PSK Conference
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• 2003.10b
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• pp.181.2-181.2
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• 2003

Inosine monophosphate dehydrogenase(IMPDH) catalyzes the $NAD^+$-dependent oxidation of IMP to XMP, the rate limiting step in the de novo biosynthesis of guanine nucleotide. Its critical role at the metabolic branch point in purine nucleotide biosynthesis makes it a useful target in the development of drugs for antiviral and anticancer chemotherapy and in immunosupressant area. Several compound with antiviral activity have been found to be inhibitors of IMPDH. For example, ribavirin, a competitive inhibitor of IMPDH, has broad spectrum antiviral activities against DNA and RNA viruses. (omitted)

• 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)

• Archives of Pharmacal Research
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• v.26 no.12
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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.

• Journal of Pharmaceutical Investigation
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• v.20 no.4
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• pp.205-208
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• 1990

1-Dodecylazacycloheptan-2-one (Azone) is a new agent that enhances the percutaneous penetration of a number of different chemicals. BVDU and FEAU were evaluated for their potential efficacy in the treatment of cutaneous herpes simplex virus infections by in vitro studies through hairless mouse skin. This study demonstrates the value of penetration enhancing agent (Azone) and the need for a predictable evaluations in the development of topical antiviral agents.

• Pediatric Gastroenterology, Hepatology & Nutrition
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• v.15 no.2
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• pp.63-73
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• 2012

Development of antiviral resistance to lamivudine is the most important factor for the treatment failure. It is necessary to establish proper guidelines to overcome drug resistance for children with chronic hepatitis B. Primary treatment with lamivudine should be considered if patients are in immune-clearance phase and have persistently elevated ALT levels more than twice the upper limit of normal value. Before initiating the therapy, careful consideration of the patient's status is required to exclude abnormal liver function tests due to other causes. The treatment option should be carefully decided to suppress the viral replication effectively. To obtain good compliance, clinicians should educate patients and their parents. Appropriate monitoring for virologic breakthrough and genotypic resistance is important in deciding to change the treatment plan. Sequential monotherapy should be avoided and a combination of drugs in other categories is recommended. New antiviral agents, such as entecavir and tenofovir, which have high potency and high genetic barrier, are soon expected to be available for use with children.

• Bulletin of the Korean Chemical Society
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• v.26 no.9
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• pp.1366-1368
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• 2005

The first synthesis of a 4'-branched carbocyclic C-nucleoside 11 was achieved via the key intermediate 6, which was prepared using Knovenagel type condensation from ketone derivative 4.

• Archives of Pharmacal Research
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• v.28 no.10
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• pp.1105-1110
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• 2005

Novel anomeric branched carbocyclic nucleosides were synthesized from 1,3-dihydroxy acetone. 4'-Hydroxymethyl was installed by [3,3]-sigmatropic rearrangement reaction and 1'-methyl group was introduced by carbonyl addition of methylmagnesium bromide. The coupling of nucleosidic bases and desilylation afforded a series of novel nucleosides. The synthesized compounds $16{\~}19$ were evaluated for their antiviral activity against HIV-1, HSV-1, HSV-2, and EMCV. Compounds 16 and 19 exhibit toxicity non-related to any anti-HIV-1 activity.

• Bulletin of the Korean Chemical Society
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• v.24 no.9
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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.