Considering that high levels of nitric oxide(NO) exert anti-cancer effect and the derivatives of oleanolic acid(OA) have shown potent anti-cancer activity, new O^2-vinyl diazeniumdiolate-based NO releasing derivatives...Considering that high levels of nitric oxide(NO) exert anti-cancer effect and the derivatives of oleanolic acid(OA) have shown potent anti-cancer activity, new O^2-vinyl diazeniumdiolate-based NO releasing derivatives(5a–l, 11a–l) of OA were designed, synthesized, and biologically evaluated in the present study. These derivatives could release different amounts of NO in liver cells. Among them, 5d, 5i, 5j, 11g, 11h, and 11j released more NO in SMMC-7721 cells and displayed stronger proliferative inhibition against SMMC-7721 and Hep G2 cells than OA and other tested compounds. The most active compound 5j showed almost 20-fold better solubility than OA in aqueous solution, released larger amounts of NO in liver cancer cells than that in normal ones, and exhibited potent anti-hepatocellular carcinoma activity but little effect on the normal liver cells. The inhibitory activity against the cancer cells was significantly diminished upon addition of an NO scavenger, suggesting that NO may contribute, at least in part, to the activity of 5j.展开更多
Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules.Due to the low...Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules.Due to the low reactivities of trifluoromethylthiolating reagents,these transformations often require activation through an exogenous Lewis/Br0nsted acid.We report herein the quantification of the activation capabilities of Lewis/Br0nsted acids for trifluoromethylthiolating reagents through computing the differenee in trifluoromethylthio cation donor ability(Tt+DA)between the"activated"and"unactivated"reagent.A moderate correlation is found to exist between the activation capability and Lewis acidity.展开更多
基金supported by grants from the National Natural Science Foundation of China(Nos.81273378 and 21372261)
文摘Considering that high levels of nitric oxide(NO) exert anti-cancer effect and the derivatives of oleanolic acid(OA) have shown potent anti-cancer activity, new O^2-vinyl diazeniumdiolate-based NO releasing derivatives(5a–l, 11a–l) of OA were designed, synthesized, and biologically evaluated in the present study. These derivatives could release different amounts of NO in liver cells. Among them, 5d, 5i, 5j, 11g, 11h, and 11j released more NO in SMMC-7721 cells and displayed stronger proliferative inhibition against SMMC-7721 and Hep G2 cells than OA and other tested compounds. The most active compound 5j showed almost 20-fold better solubility than OA in aqueous solution, released larger amounts of NO in liver cancer cells than that in normal ones, and exhibited potent anti-hepatocellular carcinoma activity but little effect on the normal liver cells. The inhibitory activity against the cancer cells was significantly diminished upon addition of an NO scavenger, suggesting that NO may contribute, at least in part, to the activity of 5j.
基金the National Natural Science Foundation of China(Grant Nos.21772098 and 21933004)the Fun dame ntal Research Funds for the Central Un iversities.
文摘Summary of main observation and conclusion Electrophilic trifluoromethylthiolation has emerged as an important and efficient methodology for installing the SCF3 moiety onto an array of organic molecules.Due to the low reactivities of trifluoromethylthiolating reagents,these transformations often require activation through an exogenous Lewis/Br0nsted acid.We report herein the quantification of the activation capabilities of Lewis/Br0nsted acids for trifluoromethylthiolating reagents through computing the differenee in trifluoromethylthio cation donor ability(Tt+DA)between the"activated"and"unactivated"reagent.A moderate correlation is found to exist between the activation capability and Lewis acidity.
