Anti-Metastatic Propensity of Biscoumarin Scaffold Synthesized Under Catalyst Free Aqueous Phase Microwave Irradiation

Abstract

An environmentally benign, catalyst free, aqueous phase, microwave assisted method for the synthesis of biscoumarin derivatives using 4-hydroxycoumarin and different aldehydes is reported. The comparative investigation of the same synthetic methodology under conventional refluxing, domestic and scientific programmable microwave synthesizer has been attempted for the purpose of comparing the reaction performance in terms of % yield, reaction time, reproducibility and reaction control. In addition to the increased yields and attenuated reaction times for biscoumarin synthesis, the difficulty of reaction control and result reproducibility usually encountered with domestic microwave ovens have been addressed through an optimized synthetic methodology using microwave synthesizer. Screening bioactive compounds for their propensity towards inhibition of cancer metastasis is a must step in advancement of cancer chemotherapy. The synthesized biscoumarin scaffold was investigated for inhibitory metastatic activity against human lung carcinoma cell line, A549 through in vitro wound healing and invasion assays. The biscoumarin scaffold was found to possess an effective anti-proliferative activity. It was also found to be efficient in ablating the migration and invasiveness of these cells under in vitro conditions.

Antituberculosis Propensity of Synthetic Biscoumarin Derivatives: An In Silico and In Vitro Approach

“…Mass Spectra were obtained on Waters Micromass Q-Tof Micro instrument. A programmable microwave synthesizer (Anton Paar mono wave 300) was used for microwave-assisted synthesis [26]. Perfit melting point apparatus was used to take the melting points in open capillaries.…”

Green Chemistry Approach to the Synthesis of Biscoumarins from 4-Hydroxycoumarin

“…Biscoumarins are commonly prepared through Knovenagel reactions of 4-hydroxycoumarin with different aldehydes (Scheme S1), utilizing a wide range of different catalysts, solvents, and reaction conditions, all resulting in different reaction times and different yields. [23] So far, biscoumarins were synthesized using ultrasound irradiation, [25,26] microwave irradiation, [27,28] different thermal conditions (reflux, heating, room temperature), [2,29,30,31] using catalysts such as: solid catalysts, [32] ionic liquids. [33] nanoparticles, [34] phasetransfer catalysts, [35] Lewis acids, [30,36] heteropoly acids, [37] and nanocomposites.…”

Synthesis, Antiaggregatory and Anticoagulant Activity of Dimedonylchromenones

“…Большой интерес к таким системам связан с широким распространением их в живой природе, например, хроменоновый гетерофрагмент встречается в структуре витамина Е. Также они отличаются высокой химической активностью. Соединения, содержащие хроменоновое ядро, проявляют множество различных, полезных для человека свойств, так, для них выявлена возможность ингибирования ВИЧ-интегразы [1][2][3], многочисленные исследования показывают, что хроменоны проявляют противоопухолевую [4][5][6] и антиоксидантную активность [7]. Моди-фикация структуры хроменона позволит получить ранее неизвестные соединения, которые потенциально могут проявлять широкий спектр активности.…”