CHED 868 |
Synthesis and Bergman cyclization of a meso-tethered porphyrenediyne
| John D. Spence and Amanda E. Hargrove. Department of Chemistry, Trinity University, One Trinity Place, San Antonio, TX 78212-7200 |
The natural enediyne antitumor antibiotics employ Bergman cyclizations to abstract hydrogen atoms from DNA leading to strand scission and cell death. We have developed an enediyne pro-drug that contains a porphyrin macrocycle that can ultimately be used to impart tumor cell selectivity and DNA binding properties to the pro-drug. The porphyrin is conjugated to the enediyne alkyne and therefore provides the opportunity to explore photochemical activation based upon absorption of the porphyrin chromophore. A model porphyrenediyne, 3, has been prepared via coupling of arenediyne 1 with meso-iodoporphyrin 2. The synthesis of porphyrenediyne 3 and studies directed towards the thermal and photochemical Bergman cyclization will be presented. |
| |
|
|