35 Crystal Structure of a Cis and Trans Isomers of An Indenone Heterocycle Podophyllotoxin Derivative

Wednesday, November 4, 2009
Ballroom A+B (Camino Real Hotel)
Paul Tongwa , Department of Chemistry, New Mexico Highlands University, Las Vegas, NM
Dr Tatiana Timofeeva , Department of Chemistry, New Mexico Highlands University, Las Vegas, NM
Nikolai Evdokimov , Department of Chemistry, New Mexico Institute of mining and technology
Igor Margedov , New Mexico Institute of mining and technology
Dr Alexander Kornienko , Department of Chemistry, New Mexico Institute of mining and technology

Trans- indenone

Cis- indenone

                                                                                                                     

                    

                                                          

           

Heterocycles fused with an indenone ring system represent important biological and medicinal scaffolds. Podophyllotoxins have been extensively used as a lead agent in the development of new anticancer drugs. A novel multi-step synthesis involving a reaction of 3,4-dihydronaphthalen-1(2H)-one and 3,5-dibromobenzaldehyde as starting materials yielded the trans and cis analogue in a 1.6:1 ratio. Reaction products from multi-step synthesis were crystallized from the solvent, CHCl3. The cis-isomer crystallizes in a centro-symmetric triclinic space group of P-1, Z = 2, with two independent molecules in the unit cell with dissimilar geometries, while the trans-isomer crystallizes in an acentric space group P212121, Z = 4. NMR and IR- spectroscopy do not determine the structure of compounds with a 100% certainty. Only X-Ray diffraction could accurately characterize, determine and confirm the structure of these compounds. Results of testing of cytotoxicity against cancer cells of these and similar materials are ongoing.

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