6933-17-1Relevant 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.
Synthesis of three new donor- acceptor [4] dendralenes
Talpur, Mir Munsif Ali,Pirzada, Tajnees,Skabara, Peter,Westgate, Thomas,Shah, Mohammad Raza
, p. 1219 - 1225 (2013/09/23)
Three new donor - acceptor [4] dendralene compounds have been synthesized. Wittig reaction was used for the preparation of first two compounds and third one by Knoevehagel condensation. Their mass was calculated by APCI mass spectra which are in good agre
P-nitrobenzyl triphenyl phosphonium ylide as new initiator in polymerization of ethylacrylate
Prajapati, Kiran,Varshney, Anuradha
, p. 2361 - 2368 (2012/02/01)
1,2-Dipolar compound containing phosphorus ylide (p-NBTPY) initiated radical polymerization of ethylacrylate in dioxane yielding syndiotactic polyethylacrylate, as evidenced by FTIR and 1H NMR. It was investigated dilatometrically at 65 ± 0.1 °C for 1 h under nitrogen atmosphere. The kinetic expression is Rp ∞ [I]0.4 [M] 1.2. The system follows non-ideal kinetics because of primary radical termination. The activation energy and kp 2/kt were calculated as 53 kJ/mol and 0.15×10-2 mol L-1 s-1, respectively. Thermal properties of polymer have been established with the help of DSC and TGA technique. The polymer has been characterized by MALDI-TOF. The absence of phosphorus in polymer matrix is confirmed from the scanning electron microscopy. The initiation is brought about by phenyl radical as evidenced from six hyperfine lines in electron spin resonance spectrum.
