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Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e][1,3]oxazine derivatives

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Abstract

The synthesis of novel coumarin[8,7-e][1,3]oxazine derivatives through a microwave-assisted three-component one-pot Mannich reaction is described in this study. All the target compounds were evaluated in vitro for their antifungal activity against Botrytis cinerea, Colletotrichum capsici, Alternaria solani, Gibberella zeae, Rhizoctonia solani, and Alternaria mali. The preliminary bioassays showed that 5e, 5m, and 5s exhibited good antifungal activity and the most active compound was 5m with an \(\hbox {EC}_{50}\) value as low as 2.1 nM against Botrytis cinerea.

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References

  1. Thakur A, Singla R, Jaitak V (2015) Coumarins as anticancer agents: a review on synthetic strategies, mechanism of action and SAR studies. Eur J Med Chem 101:476–495. doi:10.1016/j.ejmech.2015.07.010

    Article  CAS  PubMed  Google Scholar 

  2. Riveiro ME, De Kimpe N, Moglioni A, Vazquez R, Monczor F, Shayo C (2010) Coumarins: old compounds with novel promising therapeutic perspectives. Curr Med Chem 17:1325–1338. doi:10.2174/092986710790936284

    Article  CAS  PubMed  Google Scholar 

  3. Curini M, Cravotto G, Epifano F, Giannone G (2006) Chemistry and biological activity of natural and synthetic prenyloxycoumarins. Curr Med Chem 13:199–222. doi:10.2174/092986706775197890

    Article  CAS  PubMed  Google Scholar 

  4. Holbrook AM, Pereira JA, Labiris R, McDonald H, Douketis JD, Crowther M (2005) Systematic overview of warfarin and its drug and food interactions. Arch Intern Med 165:1095–1106. doi:10.1001/archinte.165.10.1095

    Article  CAS  PubMed  Google Scholar 

  5. Cesar JM, Garcia-Avello A, Navarro JL, Herraez MV (2004) Aging and oral anticoagulant therapy using acenocoumarol. Blood Coagul Fibrin 15:673–676. doi:10.1097/00001721-200412000-00007

    Article  CAS  Google Scholar 

  6. Ufer M (2005) Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet 44:1227–1246. doi:10.2165/00003088-200544120-00003

    Article  CAS  PubMed  Google Scholar 

  7. Vogl S, Zehl M, Picker P, Urban E, Wawrosch C, Reznicek G (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. doi:10.1021/jf104772x

    Article  CAS  PubMed  Google Scholar 

  8. Wei Y, Zhang T, Ito Y (2004) Preparative isolation of osthol and xanthotoxol from Common Cnidium Fruit (Chinese traditional herb) using stepwise elution by high-speed counter-current chromatography. J Chromatogr A 1033:373–377. doi:10.1016/j.chroma.2004.01.058

    Article  CAS  PubMed  Google Scholar 

  9. Shi Z, Wang F, Zhou W, Zhang P, Fan YJ (2007) Application of osthol induces a resistance response against powdery mildew in pumpkin leaves. Int J Mol Sci 8:1001–1012

    Article  PubMed Central  Google Scholar 

  10. Guan A, Liu C, Yang X, Dekeyser M (2014) Application of the intermediate derivatization approach in agrochemical discovery. Chem Rev 114:7079–7107. doi:10.1021/cr4005605

    Article  CAS  PubMed  Google Scholar 

  11. Guan AY, Liu CL, Li M, Zhang H, Li ZN, Li ZM (2011) Design, synthesis and structure-activity relationship of novel coumarin derivatives. Pest Manag Sci 67:647–655. doi:10.1002/ps.2103

    Article  CAS  PubMed  Google Scholar 

  12. Liu C, Guan A, Yang J, Chai B, Li M, Li H (2015) Efficient approach to discover novel agrochemical candidates: intermediate derivatization method. J Agric Food Chem. doi:10.1021/jf5054707

  13. Yan H, Yin W, Liu P, Liu J, Hu MC, Zhang W (2014) Palladium-catalyzed synthesis of 6-allylcoumarins using organotin reagents as multicoupling organometallic nucleophiles. Appl Organomet Chem 28:747–749. doi:10.1002/aoc.3188

    Article  CAS  Google Scholar 

  14. Zhang R, Xu Z, Yin W, Liu P, Zhang W (2014) Microwave-assisted synthesis and antifungal activities of polysubstituted Furo[3,2-c]chromen-4-ones and7,8,9,10-tetrahydro-6H-benzofuro[3,2-c]chromen-6-ones. Synthetic Commun 44:3257–3263. doi:10.1080/00397911.2014.935436

    Article  CAS  Google Scholar 

  15. Yin Q, Yan H, Zhang Y, Wang Y, Zhang G, He Y, Zhang W (2013) Palladium-catalyzed synthesis of 8-allyl or 8-prenylcoumarins by using organotin reagents as multicoupling nucleophiles. Appl Organomet Chem 27:85–88. doi:10.1002/aoc.2944

    Article  CAS  Google Scholar 

  16. Mathew BP, Kumar A, Sharma S, Shukla PK, Nath M (2010) An eco-friendly synthesis and antimicrobial activities of dihydro-2H-benzo- and naphtho-1,3-oxazine derivatives. Eur J Med Chem 45:1502–1507. doi:10.1016/j.ejmech.2009.12.058

    Article  CAS  PubMed  Google Scholar 

  17. Kategaonkar AH, Sonar SS, Pokalwar RU, Kategaonkar AH, Shingate BB, Shingare MS (2010) An efficient synthesis of 3,4-Dihydro-3-substituted-2H-naphtho[2,1-e][1,3]oxazine derivatives catalyzed by zirconyl(IV) chloride and evaluation of its biological activities. Bull Korean Chem Soc 31:1657–1660. doi:10.5012/bkcs.2010.31.6.1657

    Article  CAS  Google Scholar 

  18. Velikorodov AV, Kovalev VB, Degtyarev OV, Titova OL (2011) Synthesis and antifungal activity of some carbamate-containing azaheterocycles. Pharm Chem J 44:536–539. doi:10.1007/s11094-011-0513-2

    Article  CAS  Google Scholar 

  19. Sindhu TJ, Arikkatt SD, Vincent G, Chanran M, Bhat AR, Krishnakumar K (2013) Biological activities of oxazine and its derivatives: a review. Int J Pharma Sci Res 4:134–143

    Article  CAS  Google Scholar 

  20. Kontogiorgis C, Hadjipavlou-Litina DJ (2005) Synthesis and antiinflammatory activity of coumarin derivatives. J Med Chem 48:6400–6408. doi:10.1021/jm0580149

    Article  CAS  PubMed  Google Scholar 

  21. Jogi PS, Meshram JS, Sheikh J (2013) Design, Synthesis and evaluation of antimicrobial activity of novel oxazine derivatives using Betti’s protocol. Lett Drug Des Discov 10:283–288. doi:10.2174/1570180811310030013

    CAS  Google Scholar 

  22. Meyerhoefer TJ, Kershaw S, Caliendo N, Eltayeb S, Hanawa-Romero E, Bykovskaya P, Huang V, Marzabadi CH, De Castro M (2015) A practical synthesis of various 2-deoxy-N-glycosides by using D-glucal. Eur J Org Chem 2015:2457–2462. doi:10.1002/ejoc.201500001

    Article  CAS  Google Scholar 

  23. Mostafavi H, Najjar R, Maskani E (2013) Synthesis and characterization of novel 7-hydroxycoumarin derivatives. Chem Nat Compd 49:423–425. doi:10.1007/s10600-013-0628-7

    Article  CAS  Google Scholar 

  24. Nagorichna IV, Garazd MM, Garazd YL, Khilya VP (2007) Modified coumarins. 26. Synthesis of angular dihydrooxazinocoumarins from 3-hydroxydibenzo[b, d]pyran-6-one. Chem Nat Compd 43:15–18. doi:10.1007/s10600-007-0054-9

    Article  CAS  Google Scholar 

  25. Sharma GVM, Reddy JJ, Lakshmi PS, Krishna PR (2005) An efficient ZrCl\(_{4}\) catalyzed one-pot solvent free protocol for the synthesis of 4-substituted coumarins. Tetrahedron Lett 46:6119–6121. doi:10.1016/j.tetlet.2005.06.166

  26. Xu C, Hou Y, Wang J, Yang G, Liang X, Zhou M (2014) Activity of a novel strobilurin fungicide benzothiostrobin against Sclerotinia sclerotiorum. Pestic Biochem Physiol 115:32–38. doi:10.1016/j.pestbp.2014.08.001

    Article  CAS  PubMed  Google Scholar 

  27. Xie SS, Wang X, Jiang N, Yu W, Wang KD, Lan JS et al (2015) Multi-target tacrine-coumarin hybrids: cholinesterase and monoamine oxidase B inhibition properties against Alzheimer’s disease. Eur J Med Chem 95:153–165. doi:10.1016/j.ejmech.2015.03.040

  28. Ji Q, Ge Z, Ge Z, Chen K, Wu H, Liu X et al (2016) Synthesis and biological evaluation of novel phosphoramidate derivatives of coumarin as chitin synthase inhibitors and antifungal agents. Eur J Med Chem 108:166–176. doi:10.1016/j.ejmech.2015.11.027

    Article  CAS  PubMed  Google Scholar 

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Acknowledgments

The authors are grateful to the National Natural Science Foundation of China (No. 21272116) and the “Fundamental Research Funds for the Central Universities” (KYZ201426). We also thank Dr. John Clough from Syngenta Jealott’s Hill International Research Centre (UK) for suggestion and manuscript revision.

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Authors and Affiliations

  1. Jiangsu Key Laboratory of Pesticide Science, College of Sciences, Nanjing Agricultural University, Nanjing, 210095, People’s Republic of China

    Ming-Zhi Zhang, Rong-Rong Zhang, Wen-Zheng Yin, Xiang Yu, Ya-Ling Zhang, Pin Liu & Wei-Hua Zhang

  2. Syngenta Jealott’s Hill International Research Centre, Bracknell, Berkshire, RG42 6EY, UK

    Yu-Cheng Gu

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  1. Ming-Zhi Zhang
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Correspondence to Wei-Hua Zhang.

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Zhang, MZ., Zhang, RR., Yin, WZ. et al. Microwave-assisted Synthesis and antifungal activity of coumarin[8,7-e][1,3]oxazine derivatives. Mol Divers 20, 611–618 (2016). https://doi.org/10.1007/s11030-016-9662-2

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  • DOI: https://doi.org/10.1007/s11030-016-9662-2

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