18165-76-9Relevant academic research and scientific papers
Synthesis and biological activity of Δ-5,6-norcantharimides: importance of the 5,6-bridge
Thaqi, Ali,Scott, Janet L.,Gilbert, Jayne,Sakoff, Jennette A.,McCluskey, Adam
supporting information; experimental part, p. 1717 - 1723 (2010/07/02)
Cantharidin (1) and norcantharidin (2) are potent protein phosphatase 1 and 2A inhibitors that also display high levels of anticancer activity against a broad range of tumor cells lines. Surprisingly, Δ-5,6-ethyl norcantharidin (3, cis-tetrahydrofurano[3,4-c]furan-1,3-dione) displays neither phosphatase inhibition nor anticancer activity. This suggests that the 5,6-ethyl bridge is pivotal to both anti-cancer and protein phosphatase activity. Additionally bioisosteric replacement of the ethereal oxygen has no effect on biological activity nor does modification of the anhydride moiety. Unlike the parent norcantharidin, anhydride ring opening has no effect on either protein phosphatase inhibition or anti-cancer activity. Additionally, this work highlights the discovery of the octyl substituted, cis-5-benzyl-2-hexyltetrahydro-2H,3aH-pyrrolo[3,4-c]pyrrole-1,3-dione, 9p, and the octyl substituted, cis-octyltetrahydro-5H-furo[3,4-c]pyrrole-4,6-dione, 8p, as two new cytotoxic agents which are equipotent (9p) with, and more potent (8p) than norcantharidin. Crown Copyright
Synthesis of butenolides recently isolated from marine microorganisms
Karlsson, Staffan,Andersson, Fredrik,Breistein, Palle,Hedenstr?m, Erik
, p. 7878 - 7881 (2008/03/11)
The syntheses and 13C NMR analyses of four diastereomeric butenolides, two of which were recently isolated from the marine microorganisms Streptomycete B 5632 and Streptoverticillium luteoverticillatum 11014 are described. The two isolated butenolides were found to be one of the two diastereomers (4S,10R*,11R*)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (RRS-1 or SSS-1) and one of the two diastereomers (4S,10S*,11R*)-4,11-dihydroxy-10-methyl-dodec-2-en-1,4-olide (SRS-1 or RSS-1). An asymmetric 1,3-dipolar cycloaddition of a thiocarbonyl ylide with a dipolarophile attached to camphorsultam and a ring-opening of an enantiomerically pure vinyloxirane by lithiated dithiane served as key steps for the construction of the three stereogenic centres. Further elaborations including ring-closing metathesis and Mitsunobu inversion furnished the four diastereomeric butenolides.
Method of producing silylalkylthiols
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, (2008/06/13)
Silylalkylthiols are produced by reacting silylalkylsulfanylsilanes with water. The silylalkylsulfanylsilanes used as starting products can be produced by reacting bil-silylalkylpolysulfanes or bis-silylalkyldisulfanes with alkali metal and chlorosilanes.
Synthesis and Reactions of 3-Mercaptocyclobutanol and Derivatives. Preparation of a 2,4-Dithiabicycloheptane
Block, Eric,Laffitte, Jean-Alex,Eswarakrishnan, Venkatachalan
, p. 3428 - 3435 (2007/10/02)
Reaction of the lithio derivative of 2-tetrahydropyran (4) with epichlorohydrin gave both isomers of 3--3-(trimethylsilyl)-1-(trimethylsiloxy)cyclobutane (5).The latter compound upon treatment wi
GENERATION OF THIOALDEHYDES VIA FLUORIDE INDUCED ELIMINATION OF Α-SILYLDISULFIDES
Krafft, Grant A.,Meinke, Peter T.
, p. 1947 - 1950 (2007/10/02)
A mild, efficient and general method for the generation of reactive thioaldehydes from α-silyldisulfides is described.
