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.
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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.
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.