title: Photoactivated [3+2] addition of 6,7-seco-angustilobine B to fullerene [C60].
abstract: A synthesis of a new alkaloid-fullerene conjugate (1) is reported. The reaction was carried out by photoinduced [3+2] cycloaddition of the Alstonia indole alkaloid, 6,7-seco-angustilobine B (2), to fullerene[C60] (3) under aerobic conditions. The major monoaddition photoadduct (1) was characterized unambiguously by UV, IR, MALDI-TOFMS and NMR experiments. A mechanism highlighted by sequential photoinduced electron transfer andradical recombination pathways is also proposed. No significant enhancement in inhibition against M. tuberculosis H37Rv was observed for 1 compared with its parent compounds 2 and 3.
authors: Organic Synthesis and Phytochemistry Laboratory, Research Center for the Natural and Applied Sciences, University of Santo Tomas, Espana, Manila 1015, Philippines. allanpatrick_m@yahoo.com
authors: Allan Patrick G
authors: AP
authors: Macabeo
authors: Dietmar
authors: D
authors: Gehle
authors: Karsten
authors: K
authors: Krohn
authors: Scott G
authors: SG
authors: Franzblau
authors: Alicia M
authors: AM
authors: Aguinaldo
mesh_terms: D037741:Fullerenes / Q000737:chemistry*; D026121:Indole Alkaloids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010777:Photochemistry / Q000379:methods*; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
chemical_list: D037741:Fullerenes; D026121:Indole Alkaloids