原创力文档synthesis and neuroprotective action of optically pure neoechinulin a and its analogs合成和神经保护作用的光学纯neoechinulin及其类似物.pdfVIP
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synthesis and neuroprotective action of optically pure neoechinulin a and its analogs合成和神经保护作用的光学纯neoechinulin及其类似物
Pharmaceuticals 2010, 3, 1063-1069; doi:10.3390/ph3041063
OPEN ACCESS
pharmaceuticals
ISSN 1424-8247
/journal/pharmaceuticals
Article
Synthesis and Neuroprotective Action of Optically Pure
Neoechinulin A and Its Analogs
Toshiaki Aoki 1,2, Kensuke Ohnishi 1,2, Masaaki Kimoto 3, Satoshi Fujieda 3, Kouji Kuramochi 2,3,
Toshifumi Takeuchi 3, Atsuo Nakazaki 1, Nobuo Watanabe 3, Fumio Sugawara 2,3, Takao Arai 3
and Susumu Kobayashi 1,2,*
1 Faculty of Pharmaceutical Sciences, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba,
278-8510, Japan
2 Genome and Drug Discovery Center, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba,
278-8510, Japan
3 Department of Applied Biological Science, Tokyo University of Science, 2641 Yamazaki, Noda,
Chiba, 278-8510, Japan
* Author to whom correspondence should be addressed; E-Mail: kobayash@rs.noda.tus.ac.jp; Tel
Fax: +8-147-121-3671.
Received: 21 December 2009; in revised form: 5 January 2010 / Accepted: 29 March 2010 /
Published: 31 March 2010
Abstract: We 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 t
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