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Synthesis and In Vitro Evaluation of Some Novel Nucleoside analogs and DNA lntercalators as Potential Anticancer or Antiviral Agents
| Title: | Synthesis and In Vitro Evaluation of Some Novel Nucleoside analogs and DNA lntercalators as Potential Anticancer or Antiviral Agents. |
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| Name(s): |
Zhao, Yuxiang Florida Atlantic University, Degree grantor Parkanyi, Cyril, Thesis advisor Charles E. Schmidt College of Science Department of Chemistry and Biochemistry |
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| Type of Resource: | text | |
| Genre: | Electronic Thesis Or Dissertation | |
| Date Created: | 2007 | |
| Date Issued: | 2007 | |
| Publisher: | Florida Atlantic University | |
| Place of Publication: | Boca Raton, Fla. | |
| Physical Form: | application/pdf | |
| Extent: | 155 p. | |
| Language(s): | English | |
| Summary: | Thiadiazoles can be considered as analogs of pyrimidines because of the well known analogy between a -CH=CH- group in benzenoid hydrocarbons and bivalent sulfur, -S-, in aromatic heterocycles. Therefore, 5-amino-2H-1 ,2,4-thiadiazole-3-one and 5-amino-3H-1 ,3,4-thiadiazole-2-one are the analogs of cytosine. In our first project, the preparation of six thiadiazole nucleoside analogs is reported: 5-diacetylamino-1 ,2,4- thiadiazol-3-one (1), 5-amino-2-(tetrahydrofuran-2-yl)-1 ,2,4-thiadiazol-3-one (2), 5- amino-3-((2' -hydroxyethoxy)methyl)-1 ,3,4-thiadiazol-2-one (3), 5-amino-3-( 4' -hydroxy- 2' -hydroxyrnethyl-butyl)-1 ,3,4-thiadiazole-2-thione ( 4), (R)-5-am ino-3-(2' ,3' - dihydroxypropyl)-1 ,3,4-thiadiazole-2-thione (5), and (S)-5-amino-3-(2' ,3 ' - dihydroxypropyl )-1 ,3,4-thiadiazole-2-thione (6). (R)-5-amino-3-(2' ,3' -dihydroxypropyl)-1,3,4-thiadiazole-2-thione (5) and (S)-5-amino-3-(2' ,3' -dihydroxypropyl)-1 ,3,4- thiadiazole-2-thione (6) are stereoisomers. Their racemic mixture 7 was also prepared and tested. The synthesis, characterization, and properties of these new synthesized thiadiazole derivatives are discussed. A dimerization of 5-amino-3H-1 ,3 ,4-thiadiazole-2- thione (18) to produce di-(5-amino-1 ,3,4-thiadiazol-2-yl) disulfide (23) by sodium nitrite with either acetic acid or stannic chloride is also reported. Preliminary results indicate that 3 and 23 possess antimicrobial activity. In the second project, the synthesis of three series of bis-aminochloropyrimidine derivatives with different types of linkers as potential DNA intercalators is described. The first series are aminochloropyrimidines bridged by polyrnethylene chain linkers with various lengths. The second series are bridged by polyether linkers to lower the lipophilicity. The third series are bridged by linkers containing benzene rings to limit the flexibility. The spectral data and other physical properties of the new compounds are discussed. The preliminary screening results indicate that many new synthesized bisintercalators are biologically active. The relationship between bioactivity and structure is discussed as well. | |
| Identifier: | FA00000886 (IID) | |
| Degree granted: | Dissertation (Ph.D.)--Florida Atlantic University, 2007. | |
| Collection: | FAU Electronic Theses and Dissertations Collection | |
| Note(s): |
Includes bibliography. Charles E. Schmidt College of Science |
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| Subject(s): |
Biopharmaceutics Antineoplastic agents--Pharmacodynamics Nucleosides--Metabolism Pharmaceutical chemistry Antiviral agents--Synthesis |
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| Held by: | Florida Atlantic University Libraries | |
| Persistent Link to This Record: | http://purl.flvc.org/fau/fd/FA00000886 | |
| Sublocation: | Digital Library | |
| Use and Reproduction: | Copyright © is held by the author with permission granted to Florida Atlantic University to digitize, archive and distribute this item for non-profit research and educational purposes. Any reuse of this item in excess of fair use or other copyright exemptions requires permission of the copyright holder. | |
| Use and Reproduction: | http://rightsstatements.org/vocab/InC/1.0/ | |
| Host Institution: | FAU | |
| Is Part of Series: | Florida Atlantic University Digital Library Collections. |
