Combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death
| Title | Combined experimental and density functional theory study on the Pd-mediated cycloisomerization of o-alkynylnitrobenzenes - synthesis of isatogens and their evaluation as modulators of ROS-mediated cell death |
| Publication Type | Journal Article |
| Year of Publication | 2010 |
| Authors | Ramana, CV, Patel, P, Vanka, K, Miao, B, Degterev, A |
| Journal | European Journal of Organic Chemistry |
| Issue | 31 |
| Pagination | 5955-5966 |
| Date Published | NOV |
| ISSN | 1434-193X |
| Keywords | Anthranil, cyclization, Density functional calculations, isatogens, Nitro-alkyne cycloisomerization, Palladium |
| Abstract | Highly selective cycloisomerization of o-alkynylnitrobenzenes, leading to isatogens, has been achieved by employment of a Pd-II complex. This reaction is very general and functional-group-tolerant. The possible mechanism of this reaction was investigated with the help of DFT calculations. Three possible pathways - namely, the addition of the nitro group either in (i) 5-exo-dig or (ii) 6-endo-dig mode and (iii) halopalladation - and subsequent intramolecular events have been considered and studied in detail. These investigations revealed that pathway (i) is the favored route to isatogen formation. A preliminary screening of the available isatogens reveals the 2-alkylisatogens to be novel ROS scavengers capable of inhibiting cellular necroptosis. |
| DOI | 10.1002/ejoc.201000769 |
| Type of Journal (Indian or Foreign) | Foreign |
| Impact Factor (IF) | 3.206 |