Design, synthesis and antifungal activities of novel pyrrole- and pyrazole-substituted coumarin derivatives

Molecular Diversity - Tập 23 - Trang 915-925 - 2019
Shu-Guang Zhang1, Chao-Gen Liang1, Yue-Qing Sun1, Peng Teng1, Jia-Qun Wang1, Wei-Hua Zhang1
1Jiangsu Key Laboratory of Pesticide, College of Sciences, Nanjing Agricultural University, Nanjing, People’s Republic of China

Tóm tắt

We synthesized a series of novel pyrrole- and pyrazole-substituted coumarin derivatives and evaluated their antifungal activity against six phytopathogenic fungi in vitro. The primary assay results demonstrated that some designed compounds displayed potent activities. Among them, compounds 5g, 6a, 6b, 6c, 6d and 6h exhibited more effective control than Osthole against Cucumber anthrax and Alternaria leaf spot. Furthermore, compound 5g displayed stronger antifungal activity against Rhizoctorzia solani (EC50 = 15.4 µg/mL) than positive control Osthole (EC50 = 67.2 µg/mL).

Tài liệu tham khảo

Hu YQ, Xu Z, Zhang S, Wu X, Ding JW, Lv ZS, Feng LS (2017) Recent development of coumarin-containing derivatives and their anti-tubercular activity. Eur J Med Chem 136:122–130. https://doi.org/10.1016/j.ejmech.2017.05.004 Emami S, Dadashpour S (2015) Current developments of coumarin-based anti-cancer agents in medicinal chemistry. Eur J Med Chem 102:611–630. https://doi.org/10.1016/j.ejmech.2015.08.033 Vogl S, Zehl M, Picker P, Urban E, Wawrosch C, Reznicek G, Saukel J, Kopp B (2011) Identification and quantification of coumarins in Peucedanum ostruthium (L.) Koch by HPLC-DAD and HPLC-DAD-MS. J Agric Food Chem 59:4371–4377. https://doi.org/10.1021/jf104772x lyer D, Patil UK (2014) Evaluation of antihyperlipidemic and antitumor activities of isolated coumarins from Salvadora indica. Pharm Biol 52:78–85. https://doi.org/10.3109/13880209.2013.815633 Shah MR, Shamim A, White LS, Bertino MF, Mesaik MA, Soomro S (2014) The anti-inflammatory properties of Au-scopoletin nanoconjugates. New J Chem 38:5566–5572. https://doi.org/10.1039/C4NJ00792A Liu W, Wu J, Wang SJ, Kong WS, Qin YH, Yang GY, Chen YK (2014) A new coumarin from roots and stems of flue-cured tobacco and its anti-tobacco mosaic virus activity. Asian J Chem 26:2820–2822. https://doi.org/10.14233/ajchem.2014.15807 Domagala A, Jarosz T, Lapkowski M (2015) Living on pyrrolic foundations-Advances in natural and artificial bioactive pyrrole derivatives. Eur J Med Chem 100:176–187. https://doi.org/10.1016/j.ejmech.2015.06.009 Gholap SS (2016) Pyrrole: an emerging scaffold for construction of valuable therapeutic agents. Eur J Med Chem 110:13–31. https://doi.org/10.1016/j.ejmech.2015.12.017 Ahmad S, Alam O, Javed Naim M, Shaquiquzzaman M, Mumtaz Alam M, Iqbal M (2018) Pyrrole: an insight into recent pharmacological advances with structure activity relationship. Eur J Med Chem 157:527–561. https://doi.org/10.1016/j.ejmech.2018.08.002 Küçükgüzel ŞG, Şenkardeş S (2015) Recent advances in bioactive pyrazoles. Eur J Med Chem 97:786–815. https://doi.org/10.1016/j.ejmech.2014.11.059 Khan MF, Alam MM, Verma G, Akhtar W, Akhter M, Shaquiquzzaman M (2016) The therapeutic voyage of pyrazole and its analogs: a review. Eur J Med Chem 120:170–201. https://doi.org/10.1016/j.ejmech.2016.04.077 Zhu XF, van Pée KH, Naismith JH (2010) The ternary complex of PrnB (the second enzyme in the pyrrolnitrin biosynthesis pathway), tryptophan, and cyanide yields new mechanistic insights into the indolamine dioxygenase superfamily. J Biol Chem 285:21126–21133. https://doi.org/10.1074/jbc.M110.120485 Santos AFLOM, Ribeiro da Silva MAV (2010) Experimental and computational thermochemistry of 1-phenylpyrrole and 1-(4-methylphenyl)pyrrole. J Chem Thermodynamics 42:734–741. https://doi.org/10.1016/j.jct.2010.01.009 Bennett JW, Bentley R (2000) Seeing red: the story of prodigiosin. Adv Appl Microbiol 47:1–32. https://doi.org/10.1016/S0065-2164(00)47000-0 Williamson NR, Flineran PC, Leeper FJ, Salmond GPC (2006) The biosynthesis and regulation of bacterial prodiginines. Nat Rev Microbiol 4:887–899. https://doi.org/10.1038/nrmicro1531 Williamson NR, Fineran PC, Gristwood T, Chawrai SR, Leeper FJ, Salmond GPC (2007) Anticancer and immunosuppressive properties of bacterial prodiginines. Future Microbiol 2:605–618. https://doi.org/10.2217/17460913.2.6.605 Hassan GS, Abou-Seri SM, Kamel G, Ali MM (2014) Celecoxib analogs bearing benzofuran moiety as cyclooxygenase-2 inhibitors: design, synthesis and evaluation as potential anti-inflammatory agents. Eur J Med Chem 76:482–493. https://doi.org/10.1016/j.ejmech.2014.02.033 Sun HY, Ji FQ (2012) A molecular dynamics investigation on crizotinib resistance mechanism of C1156Y mutation in ALK. Biochem Biophys Res Comm 423:319–324. https://doi.org/10.1016/j.bbrc.2012.05.120 Brune K (1997) The early history of non-opioid analgesics. Acute Pain 1:33–40. https://doi.org/10.1016/S1366-0071(97)80033-2 Zhang MZ, Zhang RR, Yin WZ, Yu X, Zhang YL, Liu P, Gu YC, Zhang WH (2016) Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e] [1, 3]oxazine derivatives. Mol Divers 20:611–618. https://doi.org/10.1007/s11030-016-9662-2 Zhang RR, Liu J, Zhang Y, Hou MQ, Zhang MZ, Zhou F, Zhang WH (2016) Microwave-assisted synthesis and antifungal activity of novel coumarin derivatives: pyrano[3,2-c]chromene-2,5-diones. Eur J Med Chem 116:76–83. https://doi.org/10.1016/j.ejmech.2016.03.069 Zhang MZ, Zhang RR, Wang JQ, Yu X, Zhang YL, Wang QQ, Zhang WH (2016) Microwave-assisted synthesis and antifungal activity of novel fused Osthole derivatives. Eur J Med Chem 124:10–16. https://doi.org/10.1016/j.ejmech.2016.08.012 Zhang MZ, Zhang Y, Wang JQ, Zhang WH (2016) Design, synthesis and antifungal activity of coumarin ring-opening derivatives. Molecules 21:1387. https://doi.org/10.3390/molecules21101387 Yu X, Wen Y, Liang CG, Liu J, Ding YB, Zhang WH (2017) Design, synthesis and antifungal activity of psoralen derivatives. Molecules 22:1672. https://doi.org/10.3390/molecules22101672 Yu X, Teng P, Zhang YL, Xu ZJ, Zhang MZ, Zhang WH (2018) Design, synthesis and antifungal activity evaluation of coumarin-3-carboxamide derivatives. Fitoterapia 127:387–395. https://doi.org/10.1016/j.fitote.2018.03.013 Huang M, Xie SS, Jiang N, Lan JS, Kong LY, Wang XB (2015) Multifunctional coumarin derivatives: monoamine oxidase B (MAO-B) inhibition, anti-β-amyloid (Aβ) aggregation and metal chelation properties against Alzheimer’s disease. Bioorg Med Chem Lett 25:508–513. https://doi.org/10.1016/j.bmcl.2014.12.034 Kathuria A, Priya N, Chand K, Singh P, Gupta A, Jalal S, Gupta S, Raj HG, Sharma SK (2012) Substrate specificity of acetoxy derivatives of coumarins and quinolones towards calreticulin mediated transacetylation: investigations on antiplatelet function. Bioorg Med Chem 20:1624–1638. https://doi.org/10.1016/j.bmc.2011.11.016 Liu YF, Chen ZY, Ng TB, Zhang J, Zhou MG, Song FP, Lu F, Liu YZ (2007) Bacisubin, an antifungal protein with ribonuclease and hemagglutinating activities from Bacillus subtilis strain B-916. Peptides 28:553–559. https://doi.org/10.1016/j.peptides.2006.10.009