119136-14-0Relevant academic research and scientific papers
Design, synthesis and biological evaluation of dimethyl cardamonin (DMC) derivatives as P-glycoprotein-mediated multidrug resistance reversal agents
Liu, Jianwen,Ma, Lei,Shi, Ximeng,Yin, Huanhuan,Zhao, Yuyu,Zhou, Licheng
, p. 1270 - 1282 (2020/10/06)
Background: P-glycoprotein (P-gp) has been regarded as an important factor in the multidrug resistance (MDR) of tumor cells within the last decade, which can be solved by inhibiting P-gp to reverse MDR. Thus, it is an effective strategy to develop inhibitor of P-gp. Objective: In this study, the synthesis of a series of derivatives had been carried out by bioisosterism design on the basis of Dimethyl Cardamonin (DMC). Subsequently, we evaluated their reversal activities as potential P-glycoprotein (P-gp)-mediated Multidrug Resistance (MDR) agents. Methods: Dimethyl cardamonin derivatives were synthesized from acetophenones and the corresponding benzaldehydes in the presence of 40% KOH by Claisen-Schmidt reaction. Their cytotoxicity and reversal activities in vitro were assessed with MTT. Moreover, the compound B4 was evaluated by Doxorubicin (DOX) accumulation, Western blot and wound-healing assays deeply. Results and Discussion: The results showed that compounds B2, B4 and B6 had the potency of MDR reversers with little intrinsic cytotoxicity. Meanwhile, these compounds also demonstrated the capability to inhibit MCF-7 and MCF-7/DOX cells migration. Besides, the most compound B4 was selected for further study, which promoted the accumulation of DOX in MCF-7/DOX cells and inhibited the expressionof P-gp at protein levels. Conclusion: The above findings may provide new insights for the research and development of P-gp-mediated MDR reversal agents.
Synthesis of Pyranoisoflavones from Pyronochalcones: Synthesis of Elongatin and Its Angular Isomer
Tsukayama, Masao,Kawamura, Yasuhiko,Tamaki, Hiroto,Kubo, Tomoya,Horie, Tokunaru
, p. 826 - 832 (2007/10/02)
Elongatin (4',5-dihydroxy-2',5'-dimethoxy-2'',2''-dimethylpyranoisoflavone) was synthesized by an oxidative rearrangement of the corresponding pyronochalcone with thallium(III) nitrate and a regioselective reduction of 7-(4-benzoyloxy-2,5-dimethoxyphenyl)-2,3-dihydro-2,2-dimethyl-5-tosyloxy-4H,6H-benzodipyran-4,6-dione with sodium borohydride-palladium chloride, followed by dehydration of the resultant alcohol and hydrolysis.Its angular isomer (4',5-dihydroxy-2',5'-dimethoxy-2'',2''-dimethylpyranoisoflavone) was also synthesized from the corresponding pyronochalcone in a similar manner.
