Biological Evaluation and Molecular Docking Study of Euparin and Its Maleic Anhydride and Semicarbazide Derivatives

References

• G. Eren, S. Unlü, M. T. Nuñez, L. Labeaga, F. Ledo, A. Entrena, E. Banoğlu, G. Costantino, and M. F. Sahin, “Synthesis, Biological Evaluation, and Docking Studies of Novel Heterocyclic Diaryl Compounds as Selective COX-2 Inhibitors,” Bioorganic & Medicinal Chemistry 18, no. 17 (2010): 6367–76.
   PubMed Web of Science ®Google Scholar
• B. M. K. Khandapu, L. R. Bhavanam, N. Polam, and H. B. Bollikolla, “A Simplified Synthetic Route and Study of Cytotoxicity of Ethyl 2-(4-Fluorophenyl)-5-Hydroxy-6-Nitrobenzofuran-3-Carboxylate and Its Methyl Derivative,” Organic Communications 11, no. 1 (2018): 62–7.
   Web of Science ®Google Scholar
• K. M. Dawood, “Benzofuran Derivatives: A Patent Review,” Expert Opinion on Therapeutic Patents 23, no. 9 (2013): 1133–56.
   PubMed Web of Science ®Google Scholar
• G. W. Gribble, “Furans and Benzofurans, Metalation of Azoles and Related Five-Membered Ring Heterocycles,” Springer 29 (2012): 47–76.
   Google Scholar
• H. Khanam, “Bioactive Benzofuran Derivatives: A Review,” European Journal of Medicinal Chemistry 97 (2015): 483–504.
   PubMed Web of Science ®Google Scholar
• G. Zheng, S. Luo, S. Li, J. Hua, W. Li, and S. Li, “Specialized Metabolites from Ageratina Adenophora and Their Inhibitory Activities against Pathogenic Fungi,” Phytochemistry 148 (2018): 57–62.
   PubMed Web of Science ®Google Scholar
• R. Kenchappa, Y. D. Bodke, S. K. Peethambar, S. Telkar, and V. K. Bhovi, “Synthesis of β-Amino Carbonyl Derivatives of Coumarin and Benzofuran and Evaluation of Their Biological Activity,” Medicinal Chemistry Research 22, no. 10 (2013): 4787–97.
   Web of Science ®Google Scholar
• A. Soleimani, J. Asadi, F. Rostami-Charati, and R. Gharaei, “High Cytotoxicity and Apoptotic Effects of Natural Bioactive Benzofuran Derivative on the MCF-7 Breast Cancer Cell Line,” Combinatorial Chemistry & High Throughput Screening 18, no. 5 (2015): 505–13.
   PubMed Web of Science ®Google Scholar
• Q. Liu, L. Shen, T. T. Wang, C. J. Chen, W. Y. Qi, and K. Gao, “Novel Modified Furanoeremophilane-Type Sesquiterpenes and Benzofuran Derivatives from Ligularia Veitchiana,” Food Chemistry 122, no. 1 (2010): 55–9.
   Web of Science ®Google Scholar
• Z. Zoofishan, J. Hohmann, and A. Hunyadi, “Phenolic Antioxidants of Morus Nigra Roots, and Antitumor Potential of Morusin,” Phytochemistry Reviews 17, no. 5 (2018): 1031–45.
   Web of Science ®Google Scholar
• S. Boonyaketgoson, V. Rukachaisirikul, S. Phongpaichit, and K. Trisuwan, “Cytotoxic Arylbenzofuran and Stilbene Derivatives from the Twigs of Artocarpus Heterophyllus,” Tetrahedron Letters 58, no. no. 16 (2017): 1585–9.
   Web of Science ®Google Scholar
• M. Sasadhar, and D. Das, “Chemical Derivatization of Natural Products: Semisynthesis and Pharmacological aspects- A Decade Update,” Tetrahedron 78 (2021): 131801.
   Web of Science ®Google Scholar
• X. Chen, Y. Zheng, and Y. Shen, “Natural Products with Maleic Anhydride Structure:  Nonadrides, Tautomycin, Chaetomellic Anhydride, and Other compounds,” Chemical Reviews 107, no. 5 (2007): 1777–830.
   PubMed Web of Science ®Google Scholar
• H. Rajak, B. S. Thakur, A. Singh, K. Raghuvanshi, A. K. Sah, R. Veerasamy, P. Ch. Sharma, R. S. Pawar, and M. D. Kharya, “Novel Limonene and Citral Based 2,5-Disubstituted-1,3,4-Oxadiazoles: A Natural Product Coupled Approach to Semicarbazones for Antiepileptic Activity,” Bioorganic & Medicinal Chemistry Letters 23, no. 3 (2013): 864–8.
   PubMed Web of Science ®Google Scholar
• F. Khaleghi, L. B. Din, F. R. Charati, W. A. Yaacob, M. A. Khalilzadeh, B. Skelton, and M. Makha, “A New Bioactive Compound from the Roots of Petasites Hybridus,” Phytochemistry Letters 4, no. 3 (2011): 254–8.
   Web of Science ®Google Scholar
• A. M. do Nascimento, M. J. Salvador, R. C. Candido, I. Y. Ito, and D. C. R. de Oliveira, “Antimicrobial Activity of Extracts and Some Compounds from Calea Platylepis,” Fitoterapia 75, no. 5 (2004): 514–9.
   PubMed Web of Science ®Google Scholar
• J. H. Ke, L. S. Zhang, S. X. Chen, S. N. Shen, T. Zhang, C. X. Zhou, J. X. Mo, L. G. Lin, and L. S. Gan, “Benzofurans from Eupatorium Chinense Enhance Insulin-Stimulated Glucose Uptake in C2C12 Myotubes and Suppress Inflammatory Response in RAW264.7 Macrophages,” Fitoterapia 134 (2019): 346–54.
   PubMed Web of Science ®Google Scholar
• H. Sajjadi‐Ghotbabadi, S. Javanshir, and F. Rostami‐Charati, “Synthesis, Characterization, and Antioxidant Evaluations of New 2‐Oxochromene and Benzofuran Derivatives Catalyzed by KF/CP,” Journal of Heterocyclic Chemistry 54, no. 2 (2017): 979–85.
   Web of Science ®Google Scholar
• E. Ezzatzadeh, and Z. Hossaini, “Green Synthesis and Antioxidant Activity of Novel Series of Benzofurans from Euparin Extracted of Petasites Hybridus,” Natural Product Research 33, no. 11 (2019): 1617–23.
   PubMed Web of Science ®Google Scholar
• B. Kamthong, and A. Robertson, “196. Furano-Compomds. Part III. Euparin,” Journal of the Chemical Society 196 (1939): 925–30.
   Google Scholar
• W. J. Davidson, and J. A. Elix, “Annelated Furans. IV. Diels-Alder Synthesis of Dibenzofurans,” Australian Journal of Chemistry 23, no. 10 (1970): 2119–31.
   Web of Science ®Google Scholar
• M. Masubuchi, K. Kawasaki, H. Ebiike, Y. Ikeda, S. Tsujii, S. Sogabe, T. Fujii, K. Sakata, Y. Shiratori, Y. Aoki, et al. “Design and Synthesis of Novel Benzofurans as a New Class of Antifungal Agents Targeting Fungal N-Myristoyltransferase Part 1,” Bioorganic & Medicinal Chemistry Letters 11, no. 14 (2001): 1833–7.
   PubMed Web of Science ®Google Scholar
• H. Ebiike, M. Masubuchi, P. L. Kawasaki, K. I. Kawasaki, K. Morikami, S. Sogabe, M. Hayase, T. Fujii, K. Sakata, H. Shindoh, et al. “Design and Synthesis of Novel Benzofurans as a New Class of Antifungal Agents Targeting Fungal N-Myristoyltransferase Part 2,” Bioorganic & Medicinal Chemistry Letters 12, no. 4 (2002): 607–10.
   PubMed Web of Science ®Google Scholar
• K. Kawasaki, M. Masubuchi, K. Morikami, S. Sogabe, T. Aoyama, H. Ebiike, S. Niizuma, M. Hayase, T. Fujii, K. Sakata, et al. “Design and Synthesis of Novel Benzofurans as a New Class of Antifungal Agents Targeting Fungal N-Myristoyltransferase Part 3,” Bioorganic & Medicinal Chemistry Letters 13, no. 1 (2003): 87–91.
   PubMed Web of Science ®Google Scholar
• N. H. Georgopapadakou, “Antifungals Targeted to Protein Modification: Focus on Protein N-Myristoyltransferase,” Expert Opinion on Investigational Drugs 11, no. 8 (2002): 1117–25.
   PubMed Web of Science ®Google Scholar
• C. Sheng, J. Zhu, W. Zhang, M. Zhang, H. Ji, Y. Song, H. Xu, J. Yao, Z. Miao, Y. Zhou, et al. “3D-QSAR and Molecular Docking Studies on Benzothiazole Derivatives as Candida albicans N-Myristoyltransferase Inhibitors,” European Journal of Medicinal Chemistry 42, no. 4 (2007): 477–86.
   PubMed Web of Science ®Google Scholar
• Z. Ghanbarimasir, A. Bekhradnia, K. Morteza-Semnani, A. Rafiei, N. Razzaghi-Asl, and M. Kardan, “Design, Synthesis, Biological Assessment and Molecular Docking Studies of New 2-Aminoimidazole-Quinoxaline Hybrids as Potential Anticancer Agents,” Spectrochimica Acta Part A, Molecular and Biomolecular Spectroscopy 194 (2018): 21–35.
   PubMed Web of Science ®Google Scholar
• M. Pfaller, and D. Diekema, “Progress in Antifungal Susceptibility Testing of Candida Spp. by Use of Clinical and Laboratory Standards Institute Broth Microdilution methods, 2010 to 2012,” Journal of Clinical Microbiology 50, no. 9 (2012): 2846–56. 10.1128/JCM.00937-12.
   PubMed Web of Science ®Google Scholar
• J. Hudzicki, “Kirby-Bauer Disk Diffusion Susceptibility Test Protocol,” http://www.asmscience.org/content/education/protocol/protocol.3189 (accessed November 21, 2018).
   Google Scholar
• L. Ghasempour, S. Asghari, M. Tajbakhsh, and M. Mohseni, “One-Pot Synthesis of New Hydantoin (Thiohydantoin) Derivatives and Evaluation of Their Antibacterial and Antioxidant Activities,” Journal of Heterocyclic Chemistry 57, no. 12 (2020): 4136–48.
   Web of Science ®Google Scholar
• N. Gholami, R. A. Cohan, A. Razavi, R. Bigdeli, A. Dashbolaghi, and V. Asgary, “Cytotoxic and Apoptotic Properties of a Novel Nano-toxin Formulation Based on Biologically Synthesized Silver Nanoparticle Loaded with Recombinant Truncated Pseudomonas Exotoxin A,” Journal of Cellular Physiology 235, no. 4 (2020): 3711–20.
   PubMed Web of Science ®Google Scholar
• G. A. Fisher, and B. I. Sikic, “Clinical Studies with Modulators of Multidrug Resistance,” Hematology/Oncology Clinics of North America 9, no. 2 (1995): 363–82.
   PubMed Web of Science ®Google Scholar
• M. Azizi, H. Ghourchian, F. Yazdian, F. Dashtestani, and H. AlizadehZeinabad, “Cytotoxic Effect of Albumin Coated Copper Nanoparticle on Human Breast Cancer Cells of MDA-MB 231,” PLoS One 12, no. 11 (2017): e0188639.
   PubMed Web of Science ®Google Scholar
• R. A. Weinberg, C. A. McWherter, S. K. Freeman, D. C. Wood, J. I. Gordon, and S. C. Lee, “Genetic Studies Reveal That myristoylCoA: Protein N-myristoyltransferase is an Essential Enzyme in Candida albicans,” Molecular Microbiology 16, no. 2 (1995): 241–50.
   PubMed Web of Science ®Google Scholar
• P. M. G. Swamy, Y. R. Prasad, H. M. Ashvini, D. Giles, B. V. Shashidhar, and Y. S. Agasimundin, “Synthesis, Anticancer and Molecular Docking Studies of Benzofuran Derivatives,” Medicinal Chemistry Research 24, no. 9 (2015): 3437–52.
   Web of Science ®Google Scholar
• Z. Liang, H. Xu, Y. Tian, M. Guo, X. Su, and C. Guo, “Design, Synthesis and Antifungal Activity of Novel Benzofuran-Triazole Hybrids,” Molecules 21, no. 6 (2016): 732.
   PubMed Web of Science ®Google Scholar
• S. Sogabe, M. Masubuchi, K. Sakata, T. A. Fukami, K. Morikami, Y. Shiratori, H. Ebiike, K. Kawasaki, Y. Aoki, N. Shimma, et al. “Crystal Structures of Candida albicans N-Myristoyltransferase with Two Distinct Inhibitors,” Chemistry & Biology 9, no. 10 (2002): 1119–28.
   PubMedGoogle Scholar
• H. Xu, Z. Hou, Z. Liang, M. B. Guo, X. Su, and C. Guo, “Design, Synthesis and Antifungal Activity of Benzofuran and Its Analogues,” Chinese Journal of Chemistry 37, no. 12 (2019): 1245–50.
   Web of Science ®Google Scholar
• C. Sheng, H. Xu, W. Wang, Y. Cao, G. Dong, S. Wang, X. Che, H. Ji, Z. Miao, J. Yao, et al. “Design, Synthesis and Antifungal Activity of Isosteric Analogues of Benzoheterocyclic N-Myristoyltransferase Inhibitors,” European Journal of Medicinal Chemistry 45, no. 9 (2010): 3531–40.
   PubMed Web of Science ®Google Scholar
• V. N. Telvekar, H. S. Kundaikar, K. N. Patel, and H. K. Chaudhari, “3‐D QSAR and Molecular Docking Studies on Aryl Benzofuran‐2‐yl Ketoxime Derivatives as Candida albicans N‐Myristoyl Transferase Inhibitors,” QSAR & Combinatorial Science 27, no. 10 (2008): 1193–203.
   Google Scholar
• P. Proksch, M. Proksch, G. H. N. Towers, and E. Rodriguez, “Phototoxic and Insecticidal Activities of Chromens and Benzofurans from Encelia,” Journal of Natural Products 46, no. 3 (1983): 331–4.
   Web of Science ®Google Scholar
• W. J. Wang, L. Wang, X. J. Huang, R. W. Jiang, X. L. Yang, D. M. Zhang, W. M. Chen, B. Q. Tang, Y. Wang, X. Q. Zhang, et al. “Two Pairs of New Benzofuran Enantiomers with Unusual Skeletons from Eupatorium Chinense,” Tetrahedron Letters 54, no. 26 (2013): 3321–4.
   Web of Science ®Google Scholar