37516-12-4Relevant articles and documents
Substituted dienes prepared from betulinic acid – Synthesis, cytotoxicity, mechanism of action, and pharmacological parameters
Frydrych, Ivo,Urban, Milan,?arek, Jan,Benická, Sandra,D?ubák, Petr,Gurská, Soňa,Hajdúch, Marián,Kotulová, Jana,Li?ková, Barbora,Olejníková, Denisa,Pokorny, Jan
, (2021/07/28)
A set of new substituted dienes were synthesized from betulinic acid by its oxidation to 30-oxobetulinic acid followed by the Wittig reaction. Cytotoxicity of all compounds was tested in vitro in eight cancer cell lines and two noncancer fibroblasts. Almost all dienes were more cytotoxic than betulinic acid. Compounds 4.22, 4.30, 4.33, 4.39 had IC50 below 5 μmol/L; 4.22 and 4.39 were selected for studies of the mechanism of action. Cell cycle analysis revealed an increase in the number of apoptotic cells at 5 × IC50 concentration, where activation of irreversible changes leading to cell death can be expected. Both 4.22 and 4.39 led to the accumulation of cells in the G0/G1 phase with partial inhibition of DNA/RNA synthesis at 1 × IC50 and almost complete inhibition at 5 × IC50. Interestingly, compound 4.39 at 5 × IC50 caused the accumulation of cells in the S phase. Higher concentrations of tested drugs probably inhibit more off-targets than lower concentrations. Mechanisms disrupting cellular metabolism can induce the accumulation of cells in the S phase. Both compounds 4.22 and 4.39 trigger selective apoptosis in cancer cells via intrinsic pathway, which we have demonstrated by changes in the expression of the crucial apoptosis-related protein. Pharmacological parameters of derivative 4.22 were superior to 4.39, therefore 4.22 was the finally selected candidate for the development of anticancer drug.
One-pot synthesis of pentafluorophenyl or chlorotetrafluorophenyl halogenoallenes
Shen, Yanchang,Zhang, Zenghong
, p. 69 - 71 (2007/10/03)
The consecutive reaction of phosphonium salt (1) with n-butyllithium, hexafluorobenzene or chloropentafluorobezene, halogen acyl halide and triethylamine gives pentafluorophenyl or chlorotetrafluorophenyl halogenoallenes in 63-93% yields.
A Facile Synthesis of Perfluoro- and ω-Chloroperfluoro-1-pentafluorophenyl-1-alkynes
Shen, Yanchang,Qiu, Weiming
, p. 42 - 43 (2007/10/02)
Perfluoro-1-pentafluorophenyl-1-alkynes and the corresponding ω-chloroperfluoro compounds are conveniently prepared by the following two-step sequence: Reaction of methylenetriphenylphosphorane with hexafluorobenzene followed by C-acylation of the resulta
Ylide-Carbene Chemistry. Synthesis of 1,1-Difluoro-1-alkenes
Wheaton, Gregory A.,Burton, Donald J.
, p. 917 - 927 (2007/10/02)
The reaction between nonstabilized alkylidenetriphenylphosphoranes and chlorodifluoromethane has been found to be a useful alternative to the Wittig reaction for the synthesis of many difluoromethylene olefins.Both primary and secondary ylides which do not contain strongly electron-withdrawing substituents within the alkylidene portion of the ylide react with chlorodifluoromethane to give the corresponding difluoromethylene olefins in yields which are significantly better than those obtained by the Wittig reaction.The formation of triphenylphosphine oxide is avoided, and all phosphorus-containing moieties can be recovered and recycled.The reaction proceeds by initial dehydrochlorination of chlorodifluoromethane by the ylide to generate difluorocarbene.The intermediate difluorocarbene is then trapped by a second equivalent of the nucleophilic ylide.Mechanistic evidence indicates that either a zwitterionic intermediate or a three-membered cyclic phosphorane can account for the 1,1-difluoro-1-alkene products.The isolation of several 1-hydro-1-fluoro-1-alkene products such as FCH=CHPh, FHC=CPh2, and FHC=CHCH=CHPh after steam distillation of the reaction mixtures, however, can only be accounted for via a three-membered cyclic phosphorane.
Hochfluorierte Phosphor-Ylide und Phosphoniumsalze
Schmidbaur, Hubert,Zybill, Christian E.
, p. 3589 - 3598 (2007/10/02)
The (perfluoroalkyl)iodophosphanes n-C6F13PI2 and (n-C6F13)2PI, obtained from n-C6F13I and white phosphorus at 235 deg C under pressure, are converted into the chlorides n-C6F13PCl2 and (n-C6F13)2PCl with HgCl2.The chlorides are methylated with LiCH3 to f
