150
Views
0
CrossRef citations to date
0
Altmetric
Research Articles

Synthesis and antibacterial and antifungal activities of novel thiochroman-4-one derivatives incorporating oxime ether and 1,3,4-oxadiazole thioether moieties

, , &
Pages 1063-1068 | Received 06 Jan 2022, Accepted 19 Mar 2022, Published online: 11 May 2022

References

  • Mann, R. S.; Kaufman, P. E. Natural Product Pesticides: Their Development, Delivery and Use against Insect Vectors. Mini-Rev. Org. Chem. 2012, 9, 185–202. DOI: 10.2174/157019312800604733.
  • Dias, D. A.; Urban, S.; Roessner, U. A Historical Overview of Natural Products in Drug Discovery. Metabolites 2012, 2, 303–336. DOI: 10.3390/metabo2020303.
  • Copping, L. G.; Duke, S. O. Natural Products That Have Been Used Commercially as Crop Protection Agents. Pest Manag. Sci. 2007, 63, 524–554. DOI: 10.1002/ps.137817487882.
  • Ujváry, I. Natural Product Pesticides. In Encyclopedia of Agrochemicals; Plimmer J.R., Ed.; Wiley: Hoboken, NJ, 2003; vol. 3, pp 1090–1104.
  • Lin, Y.; He, Z.; Rosskopf, E. N.; Conn, K. L.; Powell, C. A.; Lazarovits, G. A Nylon Membrane Bag Assay for Determination of the Effect of Chemicals on Soilborne Plant Pathogens in Soil. Plant Dis. 2010, 94, 201–206. DOI: 10.1094/PDIS-94-2-020130754264.
  • Saengchantara, S. T.; Wallace, T. W. Chromanols, Chromanones, and Chromones. Nat. Prod. Rep. 1986, 3, 465–475. DOI: 10.1039/np9860300465.
  • Wang, A. L.; Zhou, W. C.; Wang, R. R.; Zhang, Y. W.; Zhou, W. M. Synthesis and Antifungal Activity of 3-Substituted-Benzylidene-6,7-Methylenedioxy-4-Chromanone. Chin. J. Pest. Sci. 2013, 15, 622–628.
  • Suresh, L.; Kumar, P. S. V.; Poornachandra, Y.; Kumar, C. G.; Babu, N. J.; Chandramouli, G. V. P. An Expeditious Four-Component Domino Protocol for the Synthesis of Novel Thiazolo[3,2-a]Thiochromeno[4,3-d]Pyrimidine Derivatives as Antibacterial and Antibiofilm Agents. Bioorg. Med. Chem. 2016, 24, 3808–3817. DOI: 10.1016/j.bmc.2016.06.025.
  • Chouchène, N.; Toumi, A.; Boudriga, S.; Edziri, H.; Sobeh, M.; Abdelfattah, M. A.; Askri, M.; Knorr, M.; Strohmann, C.; Brieger, L.; Soldera, A. Antimicrobial Activity and DFT Studies of a Novel Set of Spiropyrrolidines Tethered with Thiochroman-4-One/Chroman-4-One Scaffolds. Molecules 2022, 27, 582. DOI: 10.3390/molecules27030582.
  • Sun, X. Y.; Feng, J. J.; Li, S. B.; Feng, S. R.; Liu, Z. M.; Song, Y. L.; Qiao, X. Q. Design, Synthesis, and Antifungal Activity of Novel Thiochromanone Derivatives Containing 1,3,4-Oxadiazole Skeleton. Chin. J. Org. Chem. 2019, 39, 1037–1043. DOI: 10.6023/cjoc201808016.
  • Xu, H.; Hu, Y. K.; Guo, M. B.; Huang, A. S.; Su, X.; Guo, C. Design, Synthesis and Antifungal Activity of Novel Selenochroman-4-One Derivatives. Chem. Pap. 2017, 71, 2455–2463. DOI: 10.1007/s11696-017-0239-z.
  • Steiner, G.; Schmidt, T.; Kordes, M.; Von Deyn, W.; Hofmann, M.; Baumann, E.; Puhl, M.; Heffernan, G.; Culbertson, D. L.; Treacy, M. F. PCT Int. Appl. WO. 2004080170, 2004.
  • Ichiro, N.; Mitsuru, S.; Masashi, S.; Kazuyoshi, K. PCT Int. Appl. WO. 199401431, 1994.
  • Yu, L.; Chi, J. Y.; Xiao, L. L.; Li, J.; Tang, Z. F.; Tan, S. M.; Li, P. Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation. Molecules 2021, 26, 2925. DOI: 10.3390/molecules26102925.
  • Chi, J. Y.; Yu, L.; Li, P.; Xiao, L. L.; Tang, Z. F.; Li, J.; Tan, S. M.; Wang, X.; Chen, M. H. Design, Synthesis, and Antibacterial Activity of Novel Thiochromanone Derivatives Containing an Acylhydrazone Moiety. Phosphorus Sulfur 2021, 197, 13–17. DOI: 10.1080/10426507.2021.1986501.
  • Xiao, L. L.; Yu, L.; Li, P.; Chi, J. Y.; Tang, Z. F.; Li, J.; Tan, S. M.; Wang, X. D. Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety. Molecules 2021, 26, 4391. DOI: 10.3390/molecules26154391.
  • Yu, L.; Xiao, L. L.; Chi, J. Y.; Tang, Z. F.; Li, J.; Tan, S. M.; Li, P. Design, Synthesis, and Bioactivity Evaluation of Novel Thiochromanone Derivatives Containing an Oxime or Oxime Ether Moiety. J. Heterocyclic Chem. 2021, 58, 2124–2131. DOI: 10.1002/jhet.4338.
  • Wang, X. B.; Zhong, X. M.; Zhu, X. S.; Wang, H.; Li, Q.; Zhang, J. P.; Ruan, X. H.; Xue, W. Synthesis and Antibacterial Activity of Oxime Ester Derivatives Containing 1, 2, 4-Triazole or 1, 3, 4-Oxadiazole Moiety. Chem. Pap. 2017, 71, 1953–1960. DOI: 10.1007/s11696-017-0189-5.
  • Chen, M. H.; Chen, L. J.; Zhu, X. S.; Wang, X. B.; Li, Q.; Zhang, J. P.; Lu, D. W.; Xue, W. Synthesis and Biological Activities of Cyclanone O-(2-(3-Aryl-4-Amino-4H-1,2,4-Triazol-3-yl)Thio)Acetyl)Oxime Derivatives. Phosphorus Sulfur 2017, 192, 1259–1263. DOI: 10.1080/10426507.2017.1315419.
  • Xia, R. J.; Guo, T.; Chen, M.; Su, S. J.; He, J.; Tang, X.; Jiang, S. C.; Xue, W. Synthesis, Antiviral and Antibacterial Activities and Action Mechanism of Penta-1,4-Dien-3-One Oxime Ether Derivatives Containing a Quinoxaline Moiety. New J. Chem. 2019, 43, 16461–16467. DOI: 10.1039/C9NJ03019K.
  • Liu, S.; Niu, L. Z.; Shi, Y. H.; Wan, F. X.; Jiang, L. Design, Synthesis and Antifungal Activity of Novel 1-(Adamantan-1-yl) Ethanone Oxime Esters. LDDD. 2020, 17, 526–532. DOI: 10.2174/1570180816666190329225307.
  • Bian, Q.; Zhao, R. Q.; Peng, X. J.; Gao, L. J.; Zhou, G. N.; Yu, S. J.; Zhao, W. G. Design, Synthesis, and Fungicidal Activities of Novel Piperidyl Thiazole Derivatives Containing Oxime Ether or Oxime Ester Moieties. J. Agric. Food Chem. 2021, 69, 3848–3858. DOI: 10.1021/acs.jafc.0c07581.
  • Bai, H.; Liu, X. L.; Chenzhang, P. F.; Xiao, Y. M.; Fu, B.; Qin, Z. H. Design, Synthesis and Fungicidal Activity of New 1, 2, 4-Triazole Derivatives Containing Oxime Ether and Phenoxyl Pyridinyl Moiety. Molecules 2020, 25, 5852. DOI: 10.3390/molecules25245852.
  • Chen, L. J.; Wang, X. B.; Tang, X.; Xia, R. J.; Guo, T.; Zhang, C.; Li, X. Y.; Xue, W. Design, Synthesis, Antiviral Bioactivities and Interaction Mechanisms of Penta-1,4-Diene-3-One Oxime Ether Derivatives Containing a Quinazolin-4(3H)-One Scaffold. BMC Chem. 2019, 13, 24. DOI: 10.1186/s13065-019-0547-1.
  • Xu, X. J.; Cai, X. H.; Wang, B.; Min, W.; Wang, Q.; Lai, C.; Hu, H.; Xu, D. F. Synthesis and Herbicidal Activities of Novel Substituted Acetophenone Oxime Esters of Pyrithiobac. ChemistrySelect 2020, 5, 69–74. DOI: 10.1002/slct.201903927.
  • Sun, G. S.; Xu, X.; Jin, S. H.; Lin, L.; Zhang, J. J. Ovicidal and Insecticidal Activities of Pyriproxyfen Derivatives with an Oxime Ester Group. Molecules 2017, 22, 958. DOI: 10.3390/molecules22060958.
  • Li, P.; Hu, D. Y.; Xie, D. D.; Chen, J. X.; Jin, L. H.; Song, B. A. Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents. J. Agric. Food Chem. 2018, 66, 3093–3100. DOI: 10.1021/acs.jafc.7b0606129502398.
  • Li, P.; Tian, P. Y.; Chen, Y. Z.; Song, X. P.; Xue, W.; Jin, L. H.; Hu, D. Y.; Yang, S.; Song, B. A. Novel Bisthioether Derivatives Containing a 1,3,4-Oxadiazole Moiety: design, Synthesis, Antibacterial and Nematocidal Activities. Pest Manag. Sci. 2018, 74, 844–852. DOI: 10.1002/ps.476229024290.
  • Zhang, M.-Z.; Mulholland, N.; Beattie, D.; Irwin, D.; Gu, Y.-C.; Chen, Q.; Yang, G.-F.; Clough, J. Synthesis and Antifungal Activity of 3-(1,3,4-Oxadiazol-5-yl)-Indoles and 3-(1,3,4-Oxadiazol-5-yl)Methyl-Indoles. Eur. J. Med. Chem. 2013, 63, 22–32. DOI: 10.1016/j.ejmech.2013.01.03823454531.
  • Xu, W. M.; Li, S. Z.; He, M.; Yang, S.; Li, X. Y.; Li, P. Synthesis and Bioactivities of Novel Thioether/Sulfone Derivatives Containing 1,2,3-Thiadiazole and 1,3,4-Oxadiazole/Thiadiazole Moiety. Bioorg. Med. Chem. Lett. 2013, 23, 5821–5824. DOI: 10.1016/j.bmcl.2013.08.10724070781.
  • Gan, X. H.; Hu, D. Y.; Chen, Z.; Wang, Y. J.; Song, B. A. Synthesis and Antiviral Evaluation of Novel 1,3,4-Oxadiazole/Thiadiazole-Chalcone Conjugates. Bioorg. Med. Chem. Lett. 2017, 27, 4298–4301. DOI: 10.1016/j.bmcl.2017.08.03828838690.
  • Garuti, L.; Roberti, M.; Clercq, E. D. Synthesis and Antiviral/Antiproliferative Activity of Some N-Sulphonylbenzimidazoles. Bioorg. Med. Chem. Lett. 2002, 12, 2707–2710. DOI: 10.1016/S0960-894X. (02)00535-8
  • Cao, S.; Qian, X. H.; Song, G. H.; Huang, Q. C. Syntheses and Insecticidal Activity of New 2-(5-(Trifluoromethyl)Pyridyloxymethyl)-1,3,4-Oxadiazoles. J. Fluorine Chem 2002, 117, 63–66. DOI: 10.1016/S0022-1139(02)00172-0.
  • Mohan, T. P.; Vishalakshi, B.; Bhat, K. S.; Rao, K. S.; Kendappa, G. N. Synthesis and Insecticidal Activity of Some 1,3,4-Oxadiazole Derivatives Containing Phenoxyfluorophenyl Group. Indian J. Chem. 2004, 43, 1798–1801.
  • Tajik, H.; Dadras, A. Synthesis and Herbicidal Activity of Novel 5-Chloro-3-Fluoro-2-Phenoxypyridines with a 1,3,4-Oxadiazole Ring. J. Pestic. Sci. 2011, 36, 27–32. DOI: 10.1584/jpestics.G10-62.
  • Liu, Z. M.; Yang, G. F.; Qin, X. H. Syntheses and Biological Activities of Novel Diheterocyclic Compounds Containing 1,2,4-Triazolo[1,5-a]Pyrimidine and 1,3,4-Oxadiazole. J. Chem. Technol. Biotechnol. 2001, 76, 1154–1158. DOI: 10.1002/jctb.500.
  • Harri, T.; Niko, M. Luminescent Lanthanide Chelates Having Three Chromophores and Ligands for the Chelates and Their Use. PCT 2013026790, 2013.
  • Shi, J.; Luo, N.; Ding, M. H.; Bao, X. P. Synthesis, in Vitro Antibacterial and Antifungal Evaluation of Novel 1,3,4-Oxadiazole Thioether Derivatives Bearing the 6-Fluoroquinazolinylpiperidinyl Moiety. Chin. Chem. Lett. 2020, 31, 434–438. DOI: 10.1016/j.cclet.2019.06.037.
  • Zou, X. Z.; Zhang, J. A.; Zhang, L. J.; Liu, Y. J.; Li, N.; Li, Y.; Wei, S. C.; Pan, M. Crystal Structures and Biological Activities of a Symmetrical Quinoline Thioether Ligand and Its Transition Metal Complexes. Inorg. Chem. Commun. 2015, 54, 21–24. DOI: 10.1016/j.inoche.2015.01.029.
  • Shrestha, S. K.; Fosso, M. Y.; Green, K. D.; Tsodikova, S. G. Amphiphilic Tobramycin Analogues as Antibacterial and Antifungal Agents. Antimicrob. Agents Chemother. 2015, 59, 4861–4869. DOI: 10.1128/AAC.00229-1526033722.
  • Komazin-Meredith, G.; Chou, S. W.; Prichard, M. N.; Hartline, C. B.; Cardinale, S. C.; Comeau, K.; Williams, J. D.; Khan, A. R.; Peet, N. P.; Bowlin, T. L. Human Cytomegalovirus UL97 Kinase is Involved in the Mechanism of Action of Methylenecyclopropane Analogs with 6-Ether and -Thioether Substitutions. Antimicrob. Agents Chemother. 2014, 58, 274–278. DOI: 10.1128/AAC.01726-1324145545.
  • Schaad, N. W.; Wang, Z. K.; Di, M.; McBeath, J.; Peterson, G. L.; Bonde, M. R. An Improved Infiltration Technique to Test the Pathogenicity of Xanthomonas oryzae pv. oryzae in Rice Seedlings. Seed Sci. Technol 1996, 24, 449–456.
  • Chattapadhyay, T. K.; Dureja, P. Antifungal Activity of 4-Methyl-6-Alkyl-2H-Pyran-2-Ones. J. Agric. Food Chem. 2006, 54, 2129–2133. DOI: 10.1021/jf052792s.

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.