- freely available
Synthesis and Neuroprotective Action of Optically Pure Neoechinulin A and Its Analogs
AbstractWe developed an efficient, stereoselective synthetic method for the diketopiperazine moiety of neoechinulin A and its derivatives. The intramolecular cyclization at 80 ºC proceeded with minimal racemization of the stereogenic center at C-12 on neoechinulin A, even though the cyclization at 110 ºC caused partial racemization. In contrast with these results, the cyclization on diketopiperazine of 8,9-dihydroneoechinulin A derivatives did not cause epimerization of the stereogenic centers, even at 110 °C. We examined the structure-activity relationships for the cytoprotective activity against cytotoxicity induced by 3-morpholinosydnonimine (SIN-1) in nerve growth factor (NGF)-differentiated PC12 cells. The C-8/C-9 double bond, but not the stereogenic center derived from alanine, was found to play a key role in the cytoprotective activity.
Share & Cite This Article
Aoki, T.; Ohnishi, K.; Kimoto, M.; Fujieda, S.; Kuramochi, K.; Takeuchi, T.; Nakazaki, A.; Watanabe, N.; Sugawara, F.; Arai, T.; Kobayashi, S. Synthesis and Neuroprotective Action of Optically Pure Neoechinulin A and Its Analogs. Pharmaceuticals 2010, 3, 1063-1069.View more citation formats
Aoki T, Ohnishi K, Kimoto M, Fujieda S, Kuramochi K, Takeuchi T, Nakazaki A, Watanabe N, Sugawara F, Arai T, Kobayashi S. Synthesis and Neuroprotective Action of Optically Pure Neoechinulin A and Its Analogs. Pharmaceuticals. 2010; 3(4):1063-1069.Chicago/Turabian Style
Aoki, Toshiaki; Ohnishi, Kensuke; Kimoto, Masaaki; Fujieda, Satoshi; Kuramochi, Kouji; Takeuchi, Toshifumi; Nakazaki, Atsuo; Watanabe, Nobuo; Sugawara, Fumio; Arai, Takao; Kobayashi, Susumu. 2010. "Synthesis and Neuroprotective Action of Optically Pure Neoechinulin A and Its Analogs." Pharmaceuticals 3, no. 4: 1063-1069.
Notes: Multiple requests from the same IP address are counted as one view.