SELECTED ASPECTS OF BIOLOGICAL ACTIVITY OF 5-HYDROXYCOUMARIN DERIVATIVES
DOI:
https://doi.org/10.56782/pps.47Abstract
Coumarin and its derivatives constitute an important research topic in medicinal chemistry. A review of the latest scientific literature indicates that in addition to anticancer, antibacterial, antifungal and anti-inflammatory activities, these compounds have also anticoagulant and antioxidant effects. In this paper, a review of literature reports is presented on the activity of 5-hydroxycoumarin derivatives as a valuable, but still inadequately explored, source of lead structures in the search for new therapeutic substances.
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Najmanova I., Dosedel M., Hrdina R., Cardiovascular Effects of Coumarins Besides their Antioxidant Activity, Current Topics in Medicinal Chemistry, 2015, 15, 830-849. DOI: https://doi.org/10.2174/1568026615666150220112437
Ostrowska K., Grzeszczuk D., Maciejewska D., Synthesis and biological screening of a new series of 5-[4-(4-aryl-1-piperazinyl) butoxy]coumarins, Monatshefte fur Chemie, 2016, 147, 1615-1627. DOI: https://doi.org/10.1007/s00706-016-1725-7
Chukwujekwu J.C., De Kock C.A., Smith P.J., Antiplasmodial and Antibacterial Activity of Compounds Isolated from Ormocarpum trichocarpum, Planta Medica, 2012, 78, 1857-1860. DOI: https://doi.org/10.1055/s-0032-1315386
Joshi B.S., Kamat V.N., Govindachari T.R., Isolation and structure of surangin A and surangin B, two new coumarins from Mammea longifolia (wight), Tetrahedron, 1969, 25, 1453-1458. DOI: https://doi.org/10.1016/S0040-4020(01)82716-2
Ngo N.T.N, Nguyen V.T., Vo H.V., Cytotoxic Coumarins from the Bark of Mammea siamensis, Chemical and Pharmaceutical Bulletin, 2010, 58(11), 1487-1491. DOI: https://doi.org/10.1248/cpb.58.1487
Lee K.H., Chai H.B., Tamez P.A., Biologically active alkylated coumarins from Kayea assamica, Phytochemistry, 2003, 64, 535-541. DOI: https://doi.org/10.1016/S0031-9422(03)00243-7
Mao W., Wang T., Zeng H., Synthesis and evaluation of novel substituted 5-hydroxycoumarin and pyranocoumarin derivatives exhibiting significant antiproliferative activity against breast cancer cell lines, Bioorganic & Medicinal Chemistry Letters, 2009, 19, 4570-4573. DOI: https://doi.org/10.1016/j.bmcl.2009.06.098
Tomida I., Pertwee R.G., Azura-Blanco A., Cannabinoids and glaucoma, British Journal of Ophthalmology, 2004, 88(5), 708-713. DOI: https://doi.org/10.1136/bjo.2003.032250
Buchwald A., Derendorf J., Nagaraja W., Soft cannabinoid analogues as potential anti-glaucoma agents, Pharmazie, 2002, 57(2), 108-114.
Green K., Symonds C., Oliver N.W., Intraocular pressure following systemic administration of cannabinoids, Current Eye Research, 1982, 2, 247-253. DOI: https://doi.org/10.3109/02713688209011626
Mukherjee S.,Adams M., Whiteaker K., Daza A., Kage K., Cassar S., Meyer M., Yao B.B., Species comparison and pharmacological characterization of rat and human CB2 cannabinoid receptors, Europen Journal of Pharmacology, 2004, 505, 1-9. DOI: https://doi.org/10.1016/j.ejphar.2004.09.058
Mingna S., Jinfeng H., Xiuyun S., Coumarin derivatives protect against ischemic brain injury in rats, European Journal of Medicinal Chemistry, 2013, 67, 39-53. DOI: https://doi.org/10.1016/j.ejmech.2013.04.015
Al-Soud Y.A., Al-Masoudi I.A., Saeed B., Synthesis of New 1H-1,2,4-Triazolylcoumarins and Their Antitumor and Anti-HIV Activities, Chemistry of Heterocyclic Compounds, 2006, 42(5), 583-590. DOI: https://doi.org/10.1007/s10593-006-0130-2
Nishioka H., Uesugi K., Ueda N., Synthesis and Anti-human Immunodeficiency Virus Activity of the Skeleton Isomers of 3’,4’-Di-(O)-(-)-camphanoyl-(+)-khellactone, Chemical and Pharmaceutical Bulletin, 2011, 59(8), 1075-1076. DOI: https://doi.org/10.1248/cpb.59.1075
Edenharder R., Tang X., Inhibition of the Mutagenicity of 2-Nitrofluorene, 3-Nitrofluoranthene and 1-Nitropyrene by Flavonoids, Coumarins, Quinones and Other Phenolic Compounds, Food and Chemical Toxicology, 1997, 35, 357-372. DOI: https://doi.org/10.1016/S0278-6915(97)00125-7
Danielson P.B., The cytochrome P450 superfamily: biochemistry, evolution and drug metabolism in humans, Current Drug Metabolism, 2002, 3(6), 561–97. DOI: https://doi.org/10.2174/1389200023337054
Brunton L.L., Lazo J.S., Parker K.L., Farmakologia Goodmana & Gilmana, wyd. Czelej, Lublin 2007, wydanie I, tom 1, 78.
Brunton L.L., Lazo J.S., Parker K.L., Farmakologia Goodmana & Gilmana, wyd. Czelej, Lublin 2007, wydanie I, tom 1, 79.
Oda K., Yamaguchi Y., Yoshimura T., Synthetic Models Related to Furanocoumarin–CYP3A4 Interactions. Comparison of Furanocoumarin, Coumarin, and Benzofuran Dimers as Potent Inhibitors of CYP3A4 Activity, Chemical and Pharmaceutical Bulletin, 2007, 55(9), 1419-1421. DOI: https://doi.org/10.1248/cpb.55.1419
Yamaguchi Y., Akimoto I., Motegi K., Synthetic Models Related to Methoxalen and Menthofuran–Cytochrome P450 (CYP) 2A6 Interactions. Benzofuran and Coumarin Derivatives as Potent and Selective Inhibitors of CYP2A6, Chemical and Pharmaceutical Bulletin, 2013, 61(10), 997-1001. DOI: https://doi.org/10.1248/cpb.c12-00872
Akopyan G., Bonavida B., Understanding tobacco smoke carcinogen NNK and lung tumorigenesis, International Journal of Oncology, 2006, 29(4), 745–752. DOI: https://doi.org/10.3892/ijo.29.4.745
Li G., Wang D.M., Sun M.N., Discovery and Optimization of Novel 3-Piperazinylcoumarin Antagonist of Chemokine-like Factor 1 with Oral Antiasthma Activity in Mice, Journal of Medicinal Chemistry, 2010, 53, 1741-1754. DOI: https://doi.org/10.1021/jm901652p
The National Center for Biotechnology Information, CKLF chemokine like factor, https://www.ncbi.nlm.nih.gov/gene?Db = gene&Cmd = ShowDetailView&TermTo Search = 51192 (dostęp 11.12.2016).
Kuhn H., Banthiya S., van Leyen K., Mammalian lipoxygenases and their biological relevance, Biochimica Et Biophysica Acta, 2015, 1851(4), 308-330. DOI: https://doi.org/10.1016/j.bbalip.2014.10.002
Kenyon V., Chorny I., Carvajal W.J., Novel Human Lipoxygenase Inhibitors Discovered Using Virtual Screening with Homology Models, Journal of Medicinal Chemistry, 2006, 49, 1356-1363. DOI: https://doi.org/10.1021/jm050639j
Iranshahi M., Jabbari A.,Orafaie A., Synthesis and SAR studies of mono O-prenylated coumarins as potent 15-lipoxygenase inhibitors, European Journal of Medicinal Chemistry, 2012, 57, 134-142. DOI: https://doi.org/10.1016/j.ejmech.2012.09.006
Grzeszczuk D., Nowe pochodne 5-[4-(4-arylopiperazyn-1-ylo)-butoksy]kumaryny – synteza i wstępna ocena aktywności biologicznej in vitro, Praca magisterska wykonana w Zakładzie Chemii Organicznej Wydziału Farmaceutycznego Warszawskiego Uniwersytetu Medycznego, Warszawa 2017.
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