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Molecular design and synthesis of po...

Guenther, Sven Marco.

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Molecular design and synthesis of potential antiviral isonucleosides.

Record Type:	Electronic resources : Monograph/item
Title/Author:	Molecular design and synthesis of potential antiviral isonucleosides./
Author:	Guenther, Sven Marco.
Description:	246 p.
Notes:	Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1734.
Contained By:	Dissertation Abstracts International64-04B.
Subject:	Chemistry, Organic. -
Online resource:	http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3087635

Molecular design and synthesis of potential antiviral isonucleosides.
Guenther, Sven Marco.

Molecular design and synthesis of potential antiviral isonucleosides. - 246 p.

Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1734.

Thesis (Ph.D.)--The University of Iowa, 2003.

The wide and ongoing distribution of numerous infectious diseases among the human population, caused by viruses such as HSV, HIV, HBV, VZV, and many others, necessitates the continued search for new drugs with improved activity, toxicity, and resistance profiles.Subjects--Topical Terms:

516206
Chemistry, Organic.

Molecular design and synthesis of potential antiviral isonucleosides.
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035 $a (UnM)AAI3087635
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100 1 $a Guenther, Sven Marco. $3 1948131
245 1 0 $a Molecular design and synthesis of potential antiviral isonucleosides.
300 $a 246 p.
500 $a Source: Dissertation Abstracts International, Volume: 64-04, Section: B, page: 1734.
500 $a Supervisor: Vasu Nair.
502 $a Thesis (Ph.D.)--The University of Iowa, 2003.
520 $a The wide and ongoing distribution of numerous infectious diseases among the human population, caused by viruses such as HSV, HIV, HBV, VZV, and many others, necessitates the continued search for new drugs with improved activity, toxicity, and resistance profiles.
520 $a Among potential drug candidates, isonucleosides have been the subject of extensive investigations in the research program of our group. In one of these isomeric nucleoside analogs the glycosidic bond is transposed from the natural position. This structural modification has been shown to impart remarkable enzymatic stability to this class of compounds.
520 $a (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU) displays potent activity against HSV-1, HSV-2, and VZV. One major drawback of many 5-substituted 2'-deoxyuridine derivatives, including BVDU, is their susceptibility for cleavage by thymidine phosphorylase and uridine phosphorylase. This process significantly reduces their antiviral potential.
520 $a On the basis of molecular docking experiments with HSV-1 thymidine kinase, BVisoDDU, a novel isomeric analog of BVDU, and a series of other 5-substituted (S,S)-isodideoxyuridines and (SS)-isodeoxyuridines were designed and synthesized. Enzyme assays demonstrated that these compounds are completely resistant toward degradation by pyrimidine nucleoside phosphorylases. BVisoDDU exhibited pronounced and very specific activity against three different strains of HSV-1.
520 $a Adenosine deaminase (ADA) plays an important role in the de novo biosynthesis of purine nucleotides and in the purine salvage pathway. Inhibition of this enzyme affects the regulation of extracellular adenosine levels, which has a broad range of pathological consequences. ADA inhibitors have expressed immunosuppressive and antileukemic properties, and have been shown to enhance the potency of biologically active nucleoside analogs by preventing their deamination.
520 $a Motivated by the large array of applications for ADA inhibitors, ( S,S)-2',3'-isodideoxycoformycin (IsoDDCF), a novel isomeric analog of the potent ADA inhibitor 2' -deoxycoformycin (pentostatin), was designed and a synthetic scheme was developed. Although the total synthesis of IsoDDCF was ultimately unsuccessful due to failed sugar-base coupling attempts, a new isomeric analog of the IMPDH inhibitors ribavirin and mizoribine was obtained by following modifications of the original scheme.
590 $a School code: 0096.
650 4 $a Chemistry, Organic. $3 516206
650 4 $a Chemistry, Pharmaceutical. $3 550957
650 4 $a Health Sciences, Pharmacology. $3 1017717
690 $a 0490
690 $a 0491
690 $a 0419
710 2 0 $a The University of Iowa. $3 1017439
773 0 $t Dissertation Abstracts International $g 64-04B.
790 1 0 $a Nair, Vasu, $e advisor
790 $a 0096
791 $a Ph.D.
792 $a 2003
856 4 0 $u http://pqdd.sinica.edu.tw/twdaoapp/servlet/advanced?query=3087635