730964-35-9Relevant academic research and scientific papers
Biakamides A-D, Unique Polyketides from a Marine Sponge, Act as Selective Growth Inhibitors of Tumor Cells Adapted to Nutrient Starvation
Kotoku, Naoyuki,Ishida, Ryosuke,Matsumoto, Hirokazu,Arai, Masayoshi,Toda, Kazunari,Setiawan, Andi,Muraoka, Osamu,Kobayashi, Motomasa
, p. 1705 - 1718 (2017)
Biakamides A-D, novel unusually unique polyketides, were isolated from an Indonesian marine sponge (Petrosaspongia sp.) with a constructed bioassay using PANC-1 human pancreatic cancer cells. Through detailed analyses of the one- and two-dimensional NMR spectra of biakamides, planar chemical structures possessing a terminal thiazole, two N-methyl amides, a chloromethylene, and a substituted butyryl moiety were obtained. After elucidation of the configuration of the secondary alcohol moiety in biakamides A and B, the absolute stereostructures of the two secondary methyl groups in biakamides A-D were determined by the asymmetric total syntheses of all possible stereoisomers from the optically pure monoprotected 2,4-dimethyl-1,5-diol. Biakamides A-D showed selective antiproliferative activities against PANC-1 cells cultured under glucose-deficient conditions in a concentration-dependent manner. The primary mode of action of biakamides was found to be inhibition of complex I in the mitochondrial electron transport chain.
Unexpected stereochemical tolerance for the biological activity of tyroscherin
Tae, Hyun Seop,Hines, John,Schneekloth, Ashley R.,Crews, Craig M.
, p. 1708 - 1713 (2011/04/22)
Here we describe the concise syntheses of the 15 diastereomers and key analogs of the natural product tyroscherin. While systematic analysis of the analogs clearly demonstrated that the hydrocarbon tail is important for biological activity, structure-activity relationship studies of the complete tyroscherin diastereoarray revealed a surprisingly expansive stereochemical tolerance for the cytotoxic activity. Our results represent a departure from the tenet that biological activity is constrained to a narrow pharmacophore, and highlight the recently emerging appreciation for stereochemical flexibility in defining the essential structural elements of biologically active small molecules.
α,ω-functionalized 2,4-dimethylpentane dyads and 2,4,6-trimethylheptane triads through asymmetric hydrogenation
Zhou, Jianguang,Burgess, Kevin
, p. 1129 - 1131 (2008/03/14)
A match made in heaven: All the possible stereoisomers of α,ω-functionalized 2,4-dimethylpentane dyad and 2,4,6-tri- methylheptane triad chirons (see picture; A and B, respectively; FG = functional group, PG = protecting group) can be reached by using a c
An efficient and general method for the synthesis of α,ω- difunctional reduced polypropionates by Zr-catalyzed asymmetric carboalumination: Synthesis of the scyphostatin side chain
Tan, Ze,Negishi, Ei-Ichi
, p. 2911 - 2914 (2007/10/03)
A decrease in the number of linear synthetic steps and an increase in efficiency have been realized in the synthesis of the side chain of scyphostatin. An efficient and selective synthesis of α,ω- difunctional reduced polypropionates from methyl 3-hydroxy-2-methylpropionate through the use of a Zr-catalyzed asymmetric carboalumination has been developed (see scheme, TBS = tert-butyldimethylsilyl).
