Synthesis and characterization of the 7-(4-aminomethyl-1H-1,2,3-triazol-1-yl) analogue of kabiramide C.
The 7-(4-aminomethyl-1H-1,2,3-triazol-1-yl) analogue of kabiramide C (5) was synthesized by using the Mitsunobu reaction and 1,3-dipolar cycloaddition. This compound and the intermediate compounds 2 and 4 were shown to bind tightly to G-actin in a 1:1 complex and exhibited the same degree of cytotoxicity as 1. Compound 5 serves as a key intermediate for the synthesis of actin-directed optical probes and drugs.
Petchprayoon
Chutima
C
Bioactive Marine Natural Products Chemistry Research Unit (BMNCU), Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand.
Suwanborirux
Khanit
K
Miller
Reagan
R
Sakata
Tomoyo
T
Marriott
Gerard
G
D000199:Actins / Q000378:metabolism; D000818:Animals; D006367:HeLa Cells; D006801:Humans; D015394:Molecular Structure; D010080:Oxazoles / Q000138:chemical synthesis* / Q000737:chemistry*; D011161:Porifera / Q000737:chemistry; D011817:Rabbits; D013785:Thailand; D014230:Triazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology
D000199:Actins; D010080:Oxazoles; D014230:Triazoles; C489776:kabiramide C