Hydrotrope assisted green synthesis of dicoumarols and in silico and in vitro antibacterial, antioxidant and xanthine oxidase inhibition studies

References

• Abu-Gharbieh, E., Shehab, N. G., Almasri, I. M., & Bustanji, Y. (2018). Antihyperuricemic and xanthine oxidase inhibitory activities of Tribulus arabicus and its isolated compound, ursolic acid: In vitro and in vivo investigation and docking simulations. PLoS One, 13(8), e0202572–12. https://doi.org/10.1371/journal.pone.0202572
   PubMed Web of Science ®Google Scholar
• Agarwal, D. K., Sethiya, A., Teli, P., Manhas, A., Soni, J., Sahiba, N., Jha, P. C., Agarwal, S., & Goyal, P. K. (2020). Click chemistry-inspired design, synthesis, and molecular docking studies of biscoumarin derivatives using carbon-based acid catalyst. Journal of Heterocyclic Chemistry. 57(9), 3294–3309. https://doi.org/10.1002/jhet.4045
   Web of Science ®Google Scholar
• Al-Amiery, A. A., Al-Majedy, Y. K., Kadhum, A. A. H., & Mohamad, A. B. (2015). Hydrogen peroxide scavenging activity of novel coumarins synthesized using different approaches. PLoS One, 10(7), e0132175–10. https://doi.org/10.1371/journal.pone.0132175
   PubMed Web of Science ®Google Scholar
• Amin, K. M., Abdel Gawad, N. M., Abdel Rahman, D. E., & El Ashry, M. K. (2014). New series of 6-substituted coumarin derivatives as effective factor Xa inhibitors: Synthesis, in vivo antithrombotic evaluation and molecular docking. Bioorganic Chemistry, 52, 31–43. https://doi.org/10.1016/j.bioorg.2013.11.002
   PubMed Web of Science ®Google Scholar
• Bensalah, D., Mnasri, A., Chakchouk-Mtibaa, A., Mansour, L., Mellouli, L., & Hamdi, N. (2020). Synthesis and antioxidant properties of some new thiazolyl coumarin derivatives. Green Chemistry Letters and Reviews. 13(2), 155–163. https://doi.org/10.1080/17518253.2020.1762935
   Web of Science ®Google Scholar
• BIOVIA. (2021). Dassault Systèmes, Discovery Studio Visualizer, R2 client, San Diego: Dassault Systèmes.
   Google Scholar
• Brahmachari, G., & Begam, S. (2019). Ceric ammonium nitrate (CAN): An efficient and eco-friendly catalyst for one-pot synthesis of diversely functionalized biscoumarins in aqueous medium under ambient conditions. ChemistrySelect, 4(19), 5415–5420. https://doi.org/10.1002/slct.201900961
   Web of Science ®Google Scholar
• Chen, Y., Zhang, W., Shi, Q., Hesek, D., Lee, M., Mobashery, S., & Shoichet, B. K. (2009). Crystal structures of penicillin-binding protein 6 from Escherichia coli. Journal of the American Chemical Society, 131(40), 14345–14354. https://doi.org/10.1021/ja903773f
   PubMed Web of Science ®Google Scholar
• Chohan, Z. H., Rauf, A., Naseer, M. M., Somra, M. A., & Supuran, C. T. (2006). Antibacterial, antifungal and cytotoxic properties of some sulfonamide-derived chromones. Journal of Enzyme Inhibition and Medicinal Chemistry, 21(2), 173–177. https://doi.org/10.1080/14756360500533059
   PubMed Web of Science ®Google Scholar
• Dawood, D. H., Batran, R. Z., Farghaly, T. A., Khedr, M. A., & Abdulla, M. (2015). New coumarin derivatives as potent selective COX-2 inhibitors: Synthesis, anti-inflammatory, QSAR, and molecular modeling studies. Archiv der Pharmazie, 348(12), 875–888. https://doi.org/10.1002/ardp.201500274
   PubMed Web of Science ®Google Scholar
• de Araújo, R., S. A., Guerra, F. Q. S., Lima, E., de, O., de Simone, C. A., Tavares, J. F., Scotti, L., Scotti, M. T., de Aquino, T. M., de Moura, R. O., Mendonça, F. J. B., & Barbosa-Filho, J. M. (2013). Synthesis, structure-activity relationships (SAR) and in silico studies of coumarin derivatives with antifungal activity. International Journal of Molecular Sciences, 14(1), 1293–1309. https://doi.org/10.3390/ijms14011293
   PubMed Web of Science ®Google Scholar
• El-Desoky, E. S. I., Keshk, E. M., El-Sawi, A. A., Abozeid, M. A., Abouzeid, L. A., & Abdel-Rahman, A. R. H. (2018). Synthesis, biological evaluation and in silico molecular docking of novel 1-hydroxy-naphthyl substituted heterocycles. Saudi Pharmaceutical Journal : SPJ : The Official Publication of the Saudi Pharmaceutical Society, 26(6), 852–859. https://doi.org/10.1016/j.jsps.2018.03.013
   PubMed Web of Science ®Google Scholar
• Elsenety, M. M., Elsayed, B. A., Ibrahem, I. A., & Bedair, M. A. (2020). Photophysical, DFT and molecular docking studies of Sm(III) and Eu(III) complexes of newly synthesized coumarin ligand. Inorganic Chemistry Communications, 121(September), 108213. https://doi.org/10.1016/j.inoche.2020.108213
   Google Scholar
• Elshikh, M., Ahmed, S., Funston, S., Dunlop, P., Mcgaw, M., Marchant, R., & Banat, I. M. (2016). Resazurin-based 96-well plate microdilution method for the determination of minimum inhibitory concentration of biosurfactants. Biotechnology Letters, 38, 1015–1019. https://doi.org/10.1007/s10529-016-2079-2
   PubMed Web of Science ®Google Scholar
• Faisal, M., Larik, F. A., & Saeed, A. (2019). A highly promising approach for the one-pot synthesis of biscoumarins using HY zeolite as recyclable and green catalyst. Journal of Porous Materials, 26(2), 455–466. https://doi.org/10.1007/s10934-018-0625-0
   Web of Science ®Google Scholar
• Fatima, I., Zafar, H., Khan, K. M., Saad, S. M., Javaid, S., Perveen, S., & Choudhary, M. I. (2018). Synthesis, molecular docking and xanthine oxidase inhibitory activity of 5-aryl-1H-tetrazoles. Bioorganic Chemistry, 79(May), 201–211. https://doi.org/10.1016/j.bioorg.2018.04.021
   PubMedGoogle Scholar
• Fu, Y., Lu, Z., Fang, K., He, X., Huang, H., & Hu, Y. (2019). Promiscuous enzyme-catalyzed cascade reaction in water: Synthesis of dicoumarol derivatives. Bioorganic & Medicinal Chemistry Letters, 29(10), 1236–1240. https://doi.org/10.1016/j.bmcl.2019.03.007
   PubMed Web of Science ®Google Scholar
• Gorai, S., Junghare, V., Kundu, K., Gharui, S., Kumar, M., Patro, B. S., Nayak, S. K., Hazra, S., & Mula, S. (2022). Synthesis of dihydrobenzofuro[3,2-b]Chromenes as potential 3CLpro inhibitors of SARS-CoV-2: A molecular docking and molecular dynamics study. ChemMedChem, 17(8), 1–12. https://doi.org/10.1002/cmdc.202100782
   Web of Science ®Google Scholar
• Heaslet, H., Harris, M., Fahnoe, K., Sarver, R., Putz, H., Chang, J., Subramanyam, C., Barreiro, G., & Miller, J. R. (2009). Structural comparison of chromosomal and exogenous dihydrofolate reductase from Staphylococcus aureus in complex with the potent inhibitor trimethoprim. Proteins, 76(3), 706–717. https://doi.org/10.1002/prot.22383
   PubMed Web of Science ®Google Scholar
• Kadhum, A. A. H., Al-Amiery, A. A., Musa, A. Y., & Mohamad, A. B. (2011). The antioxidant activity of new coumarin derivatives. International Journal of Molecular Sciences, 12(9), 5747–5761. https://doi.org/10.3390/ijms12095747
   PubMed Web of Science ®Google Scholar
• Kamble, S. B., Kumbhar, A. S., Jadhav, S. N., & Salunkhe, R. S. (2014). Microwave assisted attractive and rapid process for synthesis of octahydroquinazolinone in aqueous hydrotropic solutions. Procedia Materials Science, 6, 1850–1856. https://doi.org/10.1016/j.mspro.2014.07.215
   Google Scholar
• Kamble, S., Rashinkar, G., Kumbhar, A., & Salunkhe, R. (2012). Hydrotrope induced catalysis in water: A clean and green approach for the synthesis of medicinally relevant Bis-(Indolyl) methanes and 2-aryl benzimidazoles. Synthetic Communications, 42(5), 756–766. https://doi.org/10.1080/00397911.2010.530730
   Web of Science ®Google Scholar
• Kandaswamy, N., & Raveendiran, N. (2015). Synthesis, characterization, in vitro antimicrobial and anticancer evaluation of random copolyesters bearing biscoumarin units in the main chains. Research on Chemical Intermediates, 41(10), 7189–7206. https://doi.org/10.1007/s11164-014-1806-3
   Web of Science ®Google Scholar
• Kapoor, N., & Saxena, S. (2016). Xanthine oxidase inhibitory and antioxidant potential of Indian Muscodor species. 3 Biotech, 6(2), 1–6. https://doi.org/10.1007/s13205-016-0569-5
   PubMedGoogle Scholar
• Karmakar, B., Nayak, A., & Banerji, J. (2012). Sulfated titania catalyzed water mediated efficient synthesis of dicoumarols - A green approach. Tetrahedron Letters, 53(33), 4343–4346. https://doi.org/10.1016/j.tetlet.2012.06.024
   Web of Science ®Google Scholar
• Kasperkiewicz, K., Ponczek, M. B., Owczarek, J., Guga, P., & Budzisz, E. (2020). Antagonists of vitamin K-popular coumarin drugs and new synthetic and natural coumarin derivatives. Molecules, 25(6), 1465–1424. https://doi.org/10.3390/molecules25061465
   PubMed Web of Science ®Google Scholar
• Keri, R. S., Budagumpi, S., Pai, R. K., & Balakrishna, R. G. (2014). Chromones as a privileged scaffold in drug discovery: A review. European Journal of Medicinal Chemistry, 78, 340–374. https://doi.org/10.1016/j.ejmech.2014.03.047
   PubMed Web of Science ®Google Scholar
• Khan, K. M., Iqbal, S., Lodhi, M. A., Maharvi, G. M., Ullah, Zia., Choudhary, M. I., Rahman, Atta-ur., & Perveen, S. (2004). Biscoumarin: New class of urease inhibitors; economical synthesis and activity. Bioorganic & Medicinal Chemistry, 12(8), 1963–1968. https://doi.org/10.1016/j.bmc.2004.01.010
   PubMed Web of Science ®Google Scholar
• Kishida, H., Unzai, S., Roper, D. I., Lloyd, A., Park, S. Y., & Tame, J. R. H. (2006). Crystal structure of penicillin binding protein 4 (DacB) from Escherichia coli, both in the native form and covalently linked to various antibiotics. Biochemistry, 45(3), 783–792. https://doi.org/10.1021/bi051533t
   PubMed Web of Science ®Google Scholar
• Kumbhar, A., Kanase, D., Mohite, S., Salunkhe, R., & Lohar, T. (2021). Bronsted acid hydrotrope combined catalysis in water: A green approach for the synthesis of indoloquinoxalines and bis-tetronic acids. Research on Chemical Intermediates, 47(6), 2263–2278. https://doi.org/10.1007/s11164-021-04430-w
   Web of Science ®Google Scholar
• Li, Y., Cao, T. T., Guo, S., Zhong, Q., Li, C. H., Li, Y., Dong, L., Zheng, S., Wang, G., & Yin, S. F. (2016). Discovery of novel allopurinol derivatives with anticancer activity and attenuated xanthine oxidase inhibition. Molecules, 21(6), 771. https://doi.org/10.3390/molecules21060771
   PubMed Web of Science ®Google Scholar
• Lončarić, M., Gašo-Sokač, D., Jokić, S., & Molnar, M. (2020). Recent advances in the synthesis of coumarin derivatives from different starting materials. Biomolecules, 10(1), 151. https://doi.org/10.3390/biom10010151
   PubMed Web of Science ®Google Scholar
• Mahmoodi, N. O., Jalalifard, Z., & Fathanbari, G. P. (2020). Green synthesis of bis-coumarin derivatives using Fe(SD)3 as a catalyst and investigation of their biological activities. Journal of the Chinese Chemical Society, 67(1), 172–182. https://doi.org/10.1002/jccs.201800444
   Web of Science ®Google Scholar
• Mali, G., Shaikh, B. A., Garg, S., Kumar, A., Bhattacharyya, S., Erande, R. D., & Chate, A. V. (2021). Design, synthesis, and biological evaluation of densely substituted Dihydropyrano[2,3-c]Pyrazoles via a taurine-catalyzed green multicomponent approach. ACS Omega, 6(45), 30734–30742. https://doi.org/10.1021/acsomega.1c04773
   PubMed Web of Science ®Google Scholar
• Malik, N., Dhiman, P., & Khatkar, A. (2019). In silico design and synthesis of targeted rutin derivatives as xanthine oxidase inhibitors. BMC Chemistry, 13(3), 1–13. https://doi.org/10.1186/s13065-019-0585-8
   PubMedGoogle Scholar
• Mathavan, S., Kannan, K., & Yamajala, R. B. R. D. (2019). Thiamine hydrochloride as a recyclable organocatalyst for the synthesis of Bis(Indolyl)Methanes, Tris(Indolyl)Methanes, 3,3-Di(Indol-3-Yl)Indolin-2-Ones and biscoumarins. Organic & Biomolecular Chemistry, 17(44), 9620–9626. https://doi.org/10.1039/c9ob02090j
   PubMed Web of Science ®Google Scholar
• Mishra, R., Jana, A., Panday, A. K., & Choudhury, L. H. (2018). Synthesis of fused pyrroles containing 4-hydroxycoumarins by regioselective metal-free multicomponent reactions. Organic & Biomolecular Chemistry, 16(17), 3289–3302. https://doi.org/10.1039/c8ob00161h
   PubMed Web of Science ®Google Scholar
• Mishra, S., Pandey, A., & Manvati, S. (2020). Coumarin: An emerging antiviral agent. Heliyon, 6(1), e03217. https://doi.org/10.1016/j.heliyon.2020.e03217
   PubMed Web of Science ®Google Scholar
• Morris, G. M.,Huey, R.,Lindstrom, W.,Sanner, M. F.,Belew, R. K.,Goodsell, D. S., &Olson, A. J. (2009). AutoDock4 and AutoDockTools4: Automated docking with selective receptor flexibility. Journal of Computational Chemistry, 30(16), 2785–2791. https://doi.org/10.1002/jcc.21256
   PubMed Web of Science ®Google Scholar
• Mutai, P., Breuzard, G., Pagano, A., Allegro, D., Peyrot, V., & Chibale, K. (2017). Synthesis and biological evaluation of 4 aryl coumarin analogues as tubulin-targeting antitumor agents. Bioorganic & Medicinal Chemistry, 25(5), 1652–1665. https://doi.org/10.1016/j.bmc.2017.01.035
   PubMed Web of Science ®Google Scholar
• Nolan, K. A., Doncaster, J. R., Dunstan, M. S., Scott, K. A., Frenkel, A. D., Siegel, D., Ross, D., Barnes, J., Levy, C., Leys, D., Whitehead, R. C., Stratford, I. J., & Bryce, R. A. (2009). Synthesis and biological evaluation of coumarin-based inhibitors of NAD(P)H: Quinone oxidoreductase-1 (NQO1). Journal of Medicinal Chemistry, 52(22), 7142–7156. https://doi.org/10.1021/jm9011609
   PubMed Web of Science ®Google Scholar
• Obi, J., & Ezenwa, T. (2018). Synthesis of analogues of dicoumarol and their biological evaluation. International Journal of Chemistry, 10(3), 1. https://doi.org/10.5539/ijc.v10n3p1
   Google Scholar
• Olyaei, A., Dortaj, E., Khoeiniha, R., & Rajabi, F. (2018). One-pot synthesis of novel 3-(Aryl(Heteroaryl amino)methyl)-2H-chromen-2-one derivatives. Journal of Heterocyclic Chemistry, 55(12), 2971–2976. https://doi.org/10.1002/jhet.3379
   Web of Science ®Google Scholar
• Olyaei, A., Moghadam, H. R., & Sadeghpour, M. (2020). Catalyst-free one-pot synthesis of a new class of 2H-Furo[3,2-c]chromene-2,4(3H)-dione and aryl amino-bis(coumarin)methane derivatives on water. Journal of Heterocyclic Chemistry, 57(8), 3029–3036. https://doi.org/10.1002/jhet.4007
   Web of Science ®Google Scholar
• Owis, A. I., El-Hawary, M., S., El Amir, D., Aly, O. M., Abdel Mohsen, U. R., & Kamel, M. S. (2020). Molecular docking reveals the potential of Salvadora Persica flavonoids to inhibit COVID-19 virus main protease. RSC Advances, 10(33), 19570–19575. https://doi.org/10.1039/d0ra03582c
   PubMed Web of Science ®Google Scholar
• Pancholi, K., Borisagar, M., & Karia, D. (2016). Research article evaluation of 4-hydroxy-coumarin derivatives as antimicrobial agents. Journal of Chemical and Pharmaceutical Research, 8(9), 85–88.
   Google Scholar
• Pancu, D. F., Scurtu, A., Macasoi, I. G., Marti, D., Mioc, M., Soica, C., Coricovac, D., Horhat, D., Poenaru, M., & Dehelean, C. (2021). Antibiotics: Conventional therapy and natural compounds with antibacterial activity-a pharmaco-toxicological screening. Antibiotics, 10(4), 401. https://doi.org/10.3390/antibiotics10040401
   Google Scholar
• Patil, A., Mane, A., Kamat, S., Lohar, T., & Salunkhe, R. (2019). Aqueous hydrotropic solution: Green reaction medium for synthesis of pyridopyrimidine carbonitrile and spiro-oxindole dihydroquinazolinone derivatives. Research on Chemical Intermediates, 45(6), 3441–3452. https://doi.org/10.1007/s11164-019-03801-8
   Web of Science ®Google Scholar
• Prabhakar, M. (2013). EDTA-catalyzed fast and efficient eco-friendly synthesis of dicoumarol derivatives in water. Journal of Chemical and Pharmaceutical Research, 5(5), 89–93.
   Google Scholar
• Rousta, A. M., Mirahmadi, S. M., Shahmohammadi, A., Ramzi, S., Baluchnejadmojarad, T., & Roghani, M. (2020). S-allyl cysteine, an active ingredient of garlic, attenuates acute liver dysfunction induced by lipopolysaccharide/d-galactosamine in mouse: underlying mechanisms. Journal of Biochemical and Molecular Toxicology, 34(9), e22518. https://doi.org/10.1002/jbt.22518
   PubMed Web of Science ®Google Scholar
• Sarker, S. D., Nahar, L., & Kumarasamy, Y. (2007). Microtitre plate-based antibacterial assay incorporating resazurin as an indicator of cell growth, and its application in the in vitro antibacterial screening of phytochemicals. Methods (San Diego, Calif.), 42(4), 321–324. https://doi.org/10.1016/j.ymeth.2007.01.006
   PubMed Web of Science ®Google Scholar
• Sethiya, A., Teli, P., Manhas, A., Agarwal, D., Soni, J., Sahiba, N., Jha, P., & Agarwal, S. (2020). Carbon-SO3H: An efficient catalyst for the synthesis of biscoumarin under ambient reaction conditions and their in silico studies. Synthetic Communications. 50(16), 2440–2460. https://doi.org/10.1080/00397911.2020.1780613
   Web of Science ®Google Scholar
• Shahzad, S., Qadir, M. A., Ahmed, M., Ahmad, S., Khan, M. J., Gulzar, A., & Muddassar, M. (2020). Folic acid-sulfonamide conjugates as antibacterial agents: Design, synthesis and molecular docking studies. RSC Advances, 10(70), 42983–42992. https://doi.org/10.1039/d0ra09051d
   PubMed Web of Science ®Google Scholar
• Simijonović, D., Vlachou, E. E., Petrović, Z. D., Hadjipavlou-Litina, D. J., Litinas, Κ. E., Stanković, N., Mihović, N., & Mladenović, M. P. (2018). Dicoumarol derivatives: Green synthesis and molecular modelling studies of their anti-LOX activity. Bioorganic Chemistry, 80, 741–752. https://doi.org/10.1016/j.bioorg.2018.07.021
   PubMed Web of Science ®Google Scholar
• Singhal, S., Khanna, P., & Khanna, L. (2019). Synthesis, DFT studies, molecular docking, antimicrobial screening and UV fluorescence studies on Ct-DNA for novel Schiff bases of 2-(1-Aminobenzyl) benzimidazole. Heliyon, 5(10), e02596. https://doi.org/10.1016/j.heliyon.2019.e02596
   PubMed Web of Science ®Google Scholar
• Singhal, S., Khanna, P., & Khanna, L. (2021). Synthesis, comparative in vitro antibacterial, antioxidant and UV Fluorescence studies of bis indole schiff bases and molecular docking with Ct-DNA and SARS-CoV-2 Mpro. Luminescence : The Journal of Biological and Chemical Luminescence, 36(6), 1531–1543. https://doi.org/10.1002/bio.4098
   PubMed Web of Science ®Google Scholar
• Smelcerovic, Z., Veljkovic, A., Kocic, G., Yancheva, D., Petronijevic, Z., Anderluh, M., & Smelcerovic, A. (2015). Xanthine oxidase inhibitory properties and anti-inflammatory activity of 2-amino-5-alkylidene-thiazol-4-ones. Chemico-Biological Interactions, 229(January), 73–81. https://doi.org/10.1016/j.cbi.2015.01.022
   PubMedGoogle Scholar
• Srivastava, P., Vyas, V. K., Variya, B., Patel, P., Qureshi, G., & Ghate, M. (2016). Synthesis, anti-inflammatory, analgesic, 5-lipoxygenase (5-LOX) inhibition activities, and molecular docking study of 7-substituted coumarin derivatives. Bioorganic Chemistry, 67, 130–138. https://doi.org/10.1016/j.bioorg.2016.06.004
   PubMed Web of Science ®Google Scholar
• Van Der Spoel, D.,Lindahl, E.,Hess, B.,Groenhof, G.,Mark, A. E., &Berendsen, H. J. C. (2005). GROMACS: fast, flexible, and free. Journal of Computational Chemistry, 26(16), 1701–1718. https://doi.org/10.1002/jcc.20291
   PubMed Web of Science ®Google Scholar
• Wang, S. F., Yin, Y., Wu, X., Qiao, F., Sha, S., Lv, P. C., Zhao, J., & Zhu, H. L. (2014). Synthesis, molecular docking and biological evaluation of coumarin derivatives containing piperazine skeleton as potential antibacterial agents. Bioorganic & Medicinal Chemistry, 22(21), 5727–5737. https://doi.org/10.1016/j.bmc.2014.09.048
   PubMed Web of Science ®Google Scholar
• Wright, D. L., & Anderson, A. C. (2011). Antifolate agents: A patent review (2006-2010). Expert Opinion on Therapeutic Patents, 21(9), 1293–1308. https://doi.org/10.1517/13543776.2011.587804
   PubMed Web of Science ®Google Scholar
• Xu, G. D., & Huang, Z. Z. (2018). A Rh(III)-catalyzed cascade C-H functionalization/cyclization reaction of salicylaldehydes with diazomalonates for the synthesis of 4-hydroxycoumarin derivatives. New Journal of Chemistry, 42(22), 18358–18362. https://doi.org/10.1039/C8NJ04576C
   Web of Science ®Google Scholar
• Yaqoob, S., Hameed, A., Ahmed, M., Imran, M., Qadir, M. A., Ramzan, M., Yousaf, N., Iqbal, J., & Muddassar, M. (2022). Antiurease screening of alkyl chain-linked thiourea derivatives: In vitro biological activities, molecular docking, and dynamic simulations studies. RSC Advances, 12(10), 6292–6302. https://doi.org/10.1039/d1ra08694d
   PubMed Web of Science ®Google Scholar
• Zajączkowski, S., Ziółkowski, W., Badtke, P., Zajączkowski, M. A., Flis, D. J., Figarski, A., Bylańska, M. S., & Wierzba, T. H. (2018). Promising effects of xanthine oxidase inhibition by allopurinol on autonomic heart regulation estimated by heart rate variability (HRV) analysis in rats exposed to hypoxia and hyperoxia. PLoS One, 13(2), e0192781. https://doi.org/10.1371/journal.pone.0192781
   PubMed Web of Science ®Google Scholar
• Zengin Kurt, B., Sonmez, F., Ozturk, D., Akdemir, A., Angeli, A., & Supuran, C. T. (2019). Synthesis of coumarin-sulfonamide derivatives and determination of their cytotoxicity, carbonic anhydrase inhibitory and molecular docking studies. European Journal of Medicinal Chemistry, 183, 111702. https://doi.org/10.1016/j.ejmech.2019.111702
   PubMed Web of Science ®Google Scholar