Chapter 21
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Synthesis of Novel gem-Difluorinatedcyclopropane Hybrids: Applications for Material and Medicinal Sciences Toshiyuki Itoh Department of Materials Science, Faculty of Engineering, Tottori University, 4-101 Koyama Minami, Tottori 680-8552, Japan
Recent developments in application of gem -difluorocyclopropane derivatives are reviewed. They are useful tool for various types of biologically active compounds, for unique polymers, and liquid crystal compounds. Further, the results of interesting DNA cleavage property for 9anthracenecarboxylic acid substituted gem-difluorocyclopropane derivatives that we recently discovered are reported.
Introduction The cyclopropyl group is a structural element present in a wide range of naturally occurring biologically active compounds found in both plants and microorganisms (1). Since substitution of two fluorine atoms on the cyclopropane ring is expected to alter both chemical reactivity and biological activity due to the strong electron-withdrawing nature of fluorine, gemdifluorocyclopropanes are expected to display unique biological and physical properties and a great deal of attention has been paid to the chemistry and unique properties of gem-difluorocyclopropanes (2-5). We review here the chemistry of gem-difluorocyclopropanes that have unique biological activities or physical properties. In particular, we report the results of our attempt to use gem-difluorocyclopropane derivatives as novel DNA cleavage agents. 352
© 2007 American Chemical Society
In Current Fluoroorganic Chemistry; Soloshonok, V., et al.; ACS Symposium Series; American Chemical Society: Washington, DC, 2007.
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Boilogicall active gem-difluorocyclopropanes Numerous types of gem-difluorocyclopropanes have been synthesized, however, examples of biologically active compounds are not so many (6-14). Examples of biologically active gem-difluorocyclopropanes are shown in Figure 1.
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