Author Type

Graduate Student

Date of Award

2007

Document Type

Dissertation

Publication Status

Version of Record

Submission Date

October 2026

Thesis/Dissertation Advisor [Chair]

Parkanyi, Cyril

Abstract

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.

Extent

155 p.

Comments

Includes bibliography.|Dissertation (Ph.D.)--Florida Atlantic University, 2007.|FAU Electronic Theses and Dissertations Collection|Charles E. Schmidt College of Science|Includes bibliography.

Identifier

FA00000886

Format

pdf

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