concise syntheses of trifluoromethylated cyclic and acyclic analogues of cadpr简洁的合成cadpr trifluoromethylated循环和非循环的类似物.pdfVIP

Molecules 2010, 15, 8689-8701; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Concise Syntheses of Trifluoromethylated Cyclic and Acyclic Analogues of cADPR Xiangchen Huang, Min Dong, Jian Liu, Kehui Zhang, Zhenjun Yang, Liangren Zhang * and Lihe Zhang State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China * Author to whom correspondence should be addressed; E-Mail: liangren@; Tel.: +86 10 Fax: +86 10 Received: 6 November 2010; in revised form: 17 November 2010/ Accepted: 22 November 2010 / Published: 30 November 2010 Abstract: A novel trifluoromethylated analogue of cADPR, 8-CF -cIDPDE (5) was 3 1 9 designed and synthesized via construction of N ,N -disubstituted hypoxanthine, trifluoromethylation and intramolecular condensation. A series of acyclic analogues of cADPR were also designed and synthesized. These compounds could be useful molecules for studying the structure-activity relationship of cADPR analogues and exploring the cADPR/RyR Ca2+ signalling system. Keywords: cADPR analogue; acyclic cADPR analogue; trifluoromethylation; synthesis 1. Introduction Cyclic adenosine diphosphate ribose (cADPR, 1, Figure 1), isolated from sea urchin eggs [1], is