Synthesis, molecular properties prediction and anticancer, antioxidant evaluation of new edaravone derivatives

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• 作者：Naveen Polkam^a ; Venkat Ragavan Ramaswamy^b ; Parsharamulu Rayam^a ; Tejeswara Rao Allaka^a ; Hasitha Shilpa Anantaraju^c ; Sriram Dharmarajan^c ; Yogeeswari Perumal^c ; Durgaiah Gandamalla^d ; Narsimha Reddy Yellu^d ; Sridhar Balasubramanian^e ; Jaya Shree Anireddy^a ; ^{jayashreeanireddy@gmail.com" class="auth_mail" title="E-mail the corresponding author}
• 关键词：Anticancer activity ; Antioxidant activity ; Crystallography ; Edaravone ; Lipinski&rsquo ; s rule of five
• 刊名：Bioorganic & Medicinal Chemistry Letters
• 出版年：2016
• 出版时间：15 May 2016
• 年：2016
• 卷：26
• 期：10
• 页码：2562-2568
• 全文大小：884 K

文摘

A series of new edaravone derivatives class="boldFont">3–class="boldFont">7 have been synthesized, characterised using various spectroscopic techniques and screened for their in vitro anti-cancer, antioxidant activities. Structure of class="boldFont">5d was further substantiated through single crystal X-ray diffraction. Among the tested, class="boldFont">5l exhibited pronounced activity against PC3 cancer cells. Compounds class="boldFont">5i, class="boldFont">5l, class="boldFont">7c showed potent activity against A549 cancer cells. Products class="boldFont">5k, class="boldFont">6, class="boldFont">7c demonstrated good antioxidant activity with MIC values of 18.60, 16.27, 16.07 μg/mL respectively. Further the reported analogues were also tested on normal HEK293T cells and displayed low to good safer profiles. Derivatives class="boldFont">5l and class="boldFont">7c have come out to be safer potent anticancer, antioxidant agents. Additionally, the target products were subjected to their molecular properties prediction and drug likeness by employing Molinspiration and Osiris property explorer toolkits. None of them violated Lipinski’s boundaries classifying the title compounds as potential anticancer and antioxidant agents.