1221741-75-8Relevant academic research and scientific papers
Synthesis of skeletal analogues of saxitoxin derivatives and evaluation of their inhibitory activity on sodium ion channels NaV1.4 and Na V1.5
Shinohara, Ryoko,Akimoto, Takafumi,Iwamoto, Osamu,Hirokawa, Takatsugu,Yotsu-Yamashita, Mari,Yamaoka, Kaoru,Nagasawa, Kazuo
experimental part, p. 12144 - 12152 (2011/11/14)
Skeletal analogues of saxitoxin (STX) that possess a fused-type tricyclic ring system, designated FD-STX, were synthesized as candidate sodium ion channel modulators. Three kinds of FD-STX derivatives 4 a-c with different substitution at C13 were synthesized, and their inhibitory activity on sodium ion channels was examined by means of cell-based assay. (-)-FD-STX (4 a) and (-)-FD-dcSTX (4 b), which showed moderate inhibitory activity, were further evaluated by the use of the patch-clamp method in cells that expressed NaV1.4 (a tetrodotoxin-sensitive sodium channel subtype) and NaV1.5 (a tetrodotoxin-resistant sodium channel subtype). These compounds showed moderate inhibitory activity towards NaV1.4, and weaker inhibitory activity towards NaV1.5. Uniquely, however, the inhibition of Na V1.5 by (-)-FD-dcSTX (4 b) was "irreversible".
Total synthesis of (+)-decarbamoylsaxitoxin and (+)-gonyautoxin 3
Iwamoto, Osamu,Nagasawa, Kazuo
supporting information; experimental part, p. 2150 - 2153 (2010/08/05)
Figure presented Facile construction of the complex saxitoxin (STX) skeleton is carried out by using a novel, conformationally controlled, guanidine cyclization process that relies on the use of neighboring group participation. The utility of this methodology is verified by its employment in syntheses of both natural and unnatural STX derivatives.
