Total synthesis and cytotoxicity of Leucetta alkaloids.
The total synthesis of a number of representative natural products isolated from Leucetta and Clathrina sponges containing a polysubstituted 2-aminoimidazole are described. These syntheses take advantage of the site specific metallation reactions of 4,5-diiodoimidazoles resulting in the syntheses of three different classes of Leucetta derived natural products. The cytotoxicities of these natural products, along with several precursors in MCF7 cells were determined through an MTT growth assay. For comparative purposes a series of naphthimidazole-containing family members are included.
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Panduka B
PB
Koswatta
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Sabha
S
Kasiri
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Jayanta K
JK
Das
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Arunoday
A
Bhan
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Heather M
HM
Lima
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Beatriz
B
Garcia-Barboza
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Nicole N
NN
Khatibi
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Muhammed
M
Yousufuddin
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA.
Subhrangsu S
SS
Mandal
Department of Chemistry and Biochemistry, University of Texas at Arlington, Arlington, TX 76019-0065, USA. Electronic address: lovely@uta.edu.
Carl J
CJ
Lovely
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D000818:Animals; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006801:Humans; D061986:MCF-7 Cells; D011161:Porifera; D013057:Spectrum Analysis / Q000379:methods; D013329:Structure-Activity Relationship
D000470:Alkaloids; D001688:Biological Products
2-Aminoimidazole; Heterocycles; Metallation; Naphthimidazole; Reduction