5042-08-0Relevant articles and documents
DNA binding property and antitumor evaluation of xanthone with dimethylamine side chain
Shen, Rui,Wang, Weihua,Yang, Gengliang
, p. 959 - 966 (2014)
In this work, a xanthone derivative was obtained by cationic modification of the free hydroxyl group of xanthone with dimethylamine group of high pKa value. The interactions of xanthones with DNA were investigated by spectroscopic methods, electrophoretic migration assay and polymerase chain reaction test. Results indicate that xanthones can intercalate into the DNA base pairs by the hydrophobic plane and the xanthone with dimethylamine side chain may also bind the DNA phosphate framework by the basic amine alkyl chain, thus showing a better DNA binding ability than the xanthone. Furthermore, inhibition on tumor cells (ECA109, SGC7901, GLC-82) proliferation of xanthones were evaluated by MTT method. Analysis results show that the xanthone with dimethylamine side chain exhibits more effective inhibition activity against three cancer cells than the xanthone. The effects on the inhibition of tumor cells in vitro agree with the studies of DNA binding. It means that the amine alkyl chain would play an important role in its antitumor activity and DNA binding property.
An efficient and convenient microwave-assisted chemical synthesis of (thio)xanthones with additional in vitro and in silico characterization
Verbanac, Donatella,Jain, Subhash C.,Jain, Nidhi,Chand, Mahesh,?ip?i? Paljetak, Hana,Matija?i?, Mario,Peri?, Mihaela,Stepani?, Vi?nja,Saso, Luciano
experimental part, p. 3180 - 3185 (2012/07/14)
Xanthones and their thio-derivatives are a class of pleiotropic compounds with various reported pharmacological and biological activities. Although these activities are mainly determined in laboratory conditions, the class itself has a great potential to be utilized as promising chemical scaffold for the synthesis of new drug candidates. One of the main obstacles in utilization of these compounds was related to the difficulties in their chemical synthesis. Most of the known methods require two steps, and are limited to specific reagents not applicable to a large number of starting materials. In this paper a new and improved method for chemical synthesis of xanthones is presented. By applying a new procedure, we have successfully obtained these compounds with the desired regioselectivity in a shorter reaction time (50 s) and with better yield (>80%). Finally, the preliminary in vitro screenings on different bacterial species and cytotoxicity assessment, as well as in silico activity evaluation were performed. The obtained results confirm potential pharmacological use of this class of molecules.
Excited-state intramolecular proton transfer in 2-(2′,6′-dihydroxyphenyl)benzoxazole: effect of dual hydrogen bonding on the optical properties
Chen, Wei-Hua,Pang, Yi
experimental part, p. 1914 - 1918 (2010/09/07)
2-(2′,6′-Dihydroxyphenyl)benzoxazole (DHBO) has been synthesized by using palladium-catalyzed oxidative cyclization. The compound utilizes both O-H···N and O-H···O bonds to ensure a coplanar structure between the benzoxazole and phenol fragments. Optical comparison with the parent compound 2-(2′-hydroxyphenyl)benzoxazole (HBO) reveals that the dual hydrogen bonding in DHBO plays an essential role in raising the desirable keto emission for ESIPT and tuning the polarity sensitivity toward the molecular environment. DHBO also exhibits a higher quantum yield (φ{symbol}fl = 0.108 in methanol) than HBO (φ{symbol}fl = 0.0025) in the same solvent.
