Publication Cover
Natural Product Research
Formerly Natural Product Letters
Volume 35, 2021 - Issue 23
355
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Total synthesis of (-)-2-methoxy-2-butenolide-3-cinnamate and its antimicrobial potentials

, , , , , , & show all
Pages 5177-5182 | Received 31 Mar 2020, Accepted 23 Jun 2020, Published online: 09 Jul 2020

References

  • Boukouvalas J, Loach RP. 2008. General, regiodefined access to alpha-substituted butenolides through metal-halogen exchange of 3-bromo-2-silyloxyfurans. Efficient synthesis of an anti-inflammatory gorgonian lipid. J Org Chem. 73(20):8109–8112.
  • Bourdreux Y, Bodio E, Willis C, Billaud C, Le Gall T, Mioskowski C. 2008. Synthesis of vulpinic and pulvinic acids from tetronic acid. Tetrahedron. 64(37):8930–8937.
  • Clark B, Capon RJ, Lacey E, Tennant S, Gill JH, Bulheller B, Bringmann G. 2005. Gymnoascolides A-C: aromatic butenolides from an Australian isolate of the soil ascomycete Gymnoascus reessii. J Nat Prod. 68(8):1226–1230.
  • Chen Y, Tsao K, De Francesco É, Keillor JW. 2015. Ring substituent effects on the thiol addition and hydrolysis reactions of N-arylmaleimides. J Org Chem. 80(24):12182–12192.
  • El-Kashef DH, Daletos G, Plenker M, Hartmann R, Mándi A, Kurtán T, Weber H, Lin W, Ancheeva E, Proksch P. 2019. Polyketides and a dihydroquinolone alkaloid from a marine-derived strain of the fungus Metarhizium marquandii. J Nat Prod. 82(9):2460–2469.
  • Elkhayat ES, Ibrahim SRM, Mohamed GA, Ross SA. 2016. Terrenolide S, a new antileishmanialbutenolide from the endophytic fungus Aspergillus terreus. Nat Pro Res. 30(7):814–820.
  • Gamard P, Sauriol F, Benhamou N, Bélanger RR, Paulitz TC. 1997. Novel butyrolactones with antifungal activity produced by Pseudomonas aureofaciens strain 63-28. J Antibiot. 50(9):742–749.
  • Husain A, Alam MM, Shaharyar M, Lal S. 2010. Antimicrobial activities of some synthetic butenolides and their pyrrolone derivatives. J Enzyme Inhib Med Chem. 25(1):54–61.
  • Janecki T. 2014. Natural lactones and lactams: synthesis, occurrence and biological activity, first edition. Edited by Wiley-VCH Verlag GmbH & Co. KGaA. Published 2014 by Wiley-VCH Verlag GmbH & Co. KGaA.
  • Mao B, Fañanás-Mastral M, Feringa BL. 2017. Catalytic asymmetric synthesis of butenolides and butyrolactones. Chem Rev. 117(15):10502–10566.
  • Mori N, Nishiuma K, Sugiyama T, Hayashi H, Akiyama K. 2016. Carlactone-type strigolactones and their synthetic analogues as inducers of hyphal branching in arbuscular mycorrhizal fungi. Phytochemistry. 130:90–98.
  • Murray EJ, Crowley RC, Truman A, Clarke SR, Cottam JA, Jadhav GP, Steele VR, O’Shea P, Lindholm C, Cockayne A, et al. 2014. Targeting staphylococcus aureus quorum sensing with nonpeptidic small molecule inhibitors. J Med Chem. 57(6):2813–2819.
  • Parvatkar RR, D’Souza C, Tripathi A, Naik CG. 2009. Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus. Phytochemistry. 70(1):128–132.
  • Patt WC, Edmunds JJ, Repine JT, Berryman KA, Reisdorph BR, Lee C, Plummer MS, Shahripour A, Haleen SJ, Keiser JA, et al. 1997. Structure-activity relationships in a series of orally active gamma-hydroxy butenolide endothelin antagonists . J Med Chem. 40(7):1063–1074.
  • Roggo BE, Petersen F, Delmendo R, Jenny HB, Peter HH, Roesel J. 1994. 3-Alkanoyl-5-hydroxymethyl tetronic acid homologues and resistomycin: new inhibitors of HIV-1 protease. I. Fermentation, isolation and biological activity. J Antibiot. 47(2):136–142.
  • Schobert R, Schlenk A. 2008. Tetramic and tetronic acids: an update on new derivatives and biological aspects. Bioorg Med Chem. 16(8):4203–4221.
  • Said MS, Chinchansure AA, Nawale L, Durge A, Wadhwani A, Kulkarni SS, Sarkar D, Joshi SP. 2015. A new butenolide cinnamate and other biological active chemical constituents from Polygonum glabrum. Nat Prod Res. 29(22):2080–2086.
  • Sanchez E, Artuso E, Lombardi C, Visentin I, Lace B, Saeed W, Lolli ML, Kobauri P, Ali Z, Spyrakis F, Cubas P, et al. 2018. Structure-activity relationships of strigolactones via a novel, quantitative in planta bioassay. J Exp Bot. 69(9):2333–2343.
  • Wang XJ, Xu HW, Guo LL, Zheng JX, Xu B, Guo X, Zheng CX, Liu HM. 2011. Synthesis and in vitro antitumor activity of new butenolide-containing dithiocarbamates. Bioorg Med Chem Lett. 21(10):3074–3077.
  • Willis C, Bodio E, Bourdreux Y, Billaud C, Gall TL, Mioskowski C. 2007. Flexible synthesis of vulpinic acid from tetronic acid. Tetrahedron Lett. 48(37):6421–6424.
  • Zhang CL, Chatterjee SS, Stein U, Heinemann U. 1992. Comparison of the effects of losigamone and its isomers on maximal electroshock induced convulsions in mice and on three different patterns of low magnesium induced epileptiform activity in slices of the rat temporal cortex. Naunyn Schmiedebergs Arch Pharmacol. 345(1):85–92.
  • Zhao J-H, Wang Z-C, Ji M-H, Cheng J-L, Zhu G-N, Yu C-M. 2012. Synthesis and bioactivity evaluation of novel spiromesifen derivatives. Pest Manag Sci. 68(1):10–15.
  • Zografos AL, Georgiadis D. 2006. Synthetic strategies towards naturally occurring tetronic acids. Synthesis. 2006(19):3157–3188.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.