{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,18]],"date-time":"2026-09-18T01:54:25Z","timestamp":1789696465660,"version":"4.0.1"},"reference-count":32,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2018,11,29]],"date-time":"2018-11-29T00:00:00Z","timestamp":1543449600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"The National Key Research and Development Program of China","award":["2017YFD0200506"],"award-info":[{"award-number":["2017YFD0200506"]}]},{"name":"The National Nature Science Foundation of China","award":["21867003"],"award-info":[{"award-number":["21867003"]}]},{"name":"the Special Fund for Outstanding Scientific, Technological Candidates of Guizhou Province","award":["2015035"],"award-info":[{"award-number":["2015035"]}]},{"name":"Major Program of Innovation Research Team of Educational Commission of Guizhou Province","award":["2016113"],"award-info":[{"award-number":["2016113"]}]},{"name":"Science and Technology Platform for Talent of Guizhou Province","award":["20165608"],"award-info":[{"award-number":["20165608"]}]},{"DOI":"10.13039\/501100018555","name":"Science and Technology Project of Guizhou Province","doi-asserted-by":"publisher","award":["20172956"],"award-info":[{"award-number":["20172956"]}],"id":[{"id":"10.13039\/501100018555","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5\u201327.3 \u03bcg\/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 \u03bcg\/mL) and Thiodiazole copper (41.1% \u03bcg\/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.<\/jats:p>","DOI":"10.3390\/molecules23123132","type":"journal-article","created":{"date-parts":[[2018,11,29]],"date-time":"2018-11-29T11:47:53Z","timestamp":1543492073000},"page":"3132","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":44,"title":["Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties"],"prefix":"10.3390","volume":"23","author":[{"given":"Xianghui","family":"Ruan","sequence":"first","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Cheng","family":"Zhang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Shichun","family":"Jiang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Tao","family":"Guo","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Rongjiao","family":"Xia","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ying","family":"Chen","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xu","family":"Tang","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Wei","family":"Xue","sequence":"additional","affiliation":[{"name":"Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Huaxi District, Guiyang 550025, China"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2018,11,29]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Song, B.A., Jin, L.H., Yang, S., and Bhadury, P.S. (2010). Environment-friendly antiviral agents for plants, Springer Publishing.","DOI":"10.1007\/978-3-642-03692-7"},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"299","DOI":"10.1007\/s11101-014-9367-z","article-title":"The pharmaceutical industry and natural products: Historical status and new trends","volume":"14","author":"David","year":"2014","journal-title":"Phytochem. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1046\/j.1365-3180.2000.00161.x","article-title":"Natural products as sources of herbicides: Current status and future trends","volume":"40","author":"Duke","year":"2000","journal-title":"Weed Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"4022","DOI":"10.1016\/j.bmc.2009.01.046","article-title":"Natural products in crop protection","volume":"17","author":"Dayan","year":"2009","journal-title":"Bioorg. Med. Chem."},{"key":"ref_5","first-page":"840","article-title":"Patent analysis: A look at the innovative nature of plant-based cosmetics","volume":"40","author":"Cesar","year":"2017","journal-title":"Quim. Nova"},{"key":"ref_6","unstructured":"Sarker, S.D., Latif, Z., and Gray, A.I. (1998). Natural Products Isolation, Springer Publishing."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Yu, L., Gan, X., Zhou, D., He, F., Zeng, S., and Hu, D. (2017). Synthesis and antiviral activity of novel 1,4-pentadien-3-one derivatives containing a 1,3,4-thiadiazole moiety. Molecules, 22.","DOI":"10.3390\/molecules22040658"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"396","DOI":"10.3109\/13880209.2010.519390","article-title":"Cytotoxicity, antiviral and antimicrobial activities of alkaloids, flavonoids, and phenolic acids","volume":"49","author":"Ozcelik","year":"2011","journal-title":"Pharm. Biol."},{"key":"ref_9","first-page":"19","article-title":"Preformulation studies of myricetin: A natural antioxidant flavonoid","volume":"69","author":"Yao","year":"2014","journal-title":"Die Pharmazie"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/S0306-3623(96)00421-1","article-title":"Biological effects of myricetin","volume":"29","author":"Ong","year":"1997","journal-title":"Gen. Pharmacol."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.foodchem.2010.03.088","article-title":"\u03b1-glucosidase and \u03b1-amylase inhibitory activities of guava leaves","volume":"123","author":"Wang","year":"2010","journal-title":"Food Chem."},{"key":"ref_12","first-page":"401","article-title":"Flavonoids from the seeds of hovenia acerba and their in vitro antiviral activity","volume":"6","author":"Song","year":"2016","journal-title":"J. Pharm. Biomed. Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"1569","DOI":"10.1016\/j.foodchem.2016.10.136","article-title":"Myricetin inhibits the generation of superoxide anion by reduced form of xanthine oxidase","volume":"221","author":"Zhang","year":"2017","journal-title":"Food Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1131","DOI":"10.1016\/j.biopha.2017.11.018","article-title":"Chemopreventive effect of myricetin, a natural occurring compound, on colonic chronic inflammation and inflammation-driven tumorigenesis in mice","volume":"97","author":"Zhang","year":"2018","journal-title":"Biomed. Pharmacother."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"378","DOI":"10.1016\/j.biopha.2017.04.100","article-title":"Anti-cancer activity of myricetin against human papillary thyroid cancer cells involves mitochondrial dysfunction-mediated apoptosis","volume":"91","author":"Ha","year":"2017","journal-title":"Biomed. Pharmacother."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"10","DOI":"10.1016\/j.canlet.2017.04.014","article-title":"Myricetin suppresses invasion and promotes cell death in human placental choriocarcinoma cells through induction of oxidative stress","volume":"399","author":"Yang","year":"2017","journal-title":"Cancer Lett."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4974","DOI":"10.3892\/ol.2017.6031","article-title":"Myricetin induces apoptosis and enhances chemosensitivity in ovarian cancer cells","volume":"13","author":"Zheng","year":"2017","journal-title":"Oncol. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1186\/s13065-017-0336-7","article-title":"Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold","volume":"11","author":"Zhong","year":"2017","journal-title":"Chem. Cent. J."},{"key":"ref_19","first-page":"1197","article-title":"Syntheses and Bioactivities of Myricetin Derivatives Containing Piperazine Acidamide Moiety","volume":"39","author":"Ruan","year":"2018","journal-title":"Chem. J. Chin. Univ."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1016\/j.ejmech.2015.04.063","article-title":"Novel myricetin derivatives: Design, synthesis and anticancer activity","volume":"97","author":"Xue","year":"2015","journal-title":"Eur. J. Med. Chem."},{"key":"ref_21","first-page":"35","article-title":"Synthesis and antibacterial activities of myricetin derivatives containing acidamide moiety","volume":"38","author":"Xiao","year":"2017","journal-title":"Chem. J. Chin. Univ."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"285","DOI":"10.1016\/S0166-1280(01)00550-4","article-title":"A theoretical study on the aromaticity of thiadiazoles and related compounds","volume":"549","author":"Daniel","year":"2001","journal-title":"J. Mol. Struct. THEOCHEM"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"5572","DOI":"10.1021\/cr400131u","article-title":"1,3,4-thiadiazole: Synthesis, reactions, and applications in medicinal, agricultural, and materials chemistry","volume":"114","author":"Hu","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3370","DOI":"10.1016\/j.bmcl.2017.06.004","article-title":"Synthesis and biological evaluation of 5-fatty-acylamido-1,3,4-thiadiazole-2-thioglycosides","volume":"27","author":"Vudhgiri","year":"2017","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1036","DOI":"10.1021\/jf203772d","article-title":"Inhibition of tobacco bacterial wilt with sulfone derivatives containing an 1,3,4-oxadiazole moiety","volume":"60","author":"Xu","year":"2012","journal-title":"J. Agric. Food Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"9575","DOI":"10.1021\/jf403193q","article-title":"Synthesis and bioactivity evaluation of novel arylimines containing a 3-aminoethyl-2-((q-trifluoromethoxy) aniline)-4-(3H)-quinazolinone moiety","volume":"61","author":"Wang","year":"2013","journal-title":"J. Agric. Food Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"954","DOI":"10.1080\/10426507.2017.1295963","article-title":"Synthesis and antibacterial activity of novel phosphorylated flavonoid derivatives","volume":"192","author":"Huang","year":"2017","journal-title":"Phosphorus Sulfur Silicon Relat. Elem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"34005","DOI":"10.1039\/C7RA04819J","article-title":"Synthesis of novel 1,2,4-triazole derivatives containing the quinazolinylpiperidinyl moiety and N-(substituted phenyl)acetamide group as efficient bactericides against the phytopathogenic bacterium xanthomonas oryzae pv. Oryzae","volume":"7","author":"Yang","year":"2017","journal-title":"RSC Adv."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"948","DOI":"10.1016\/j.cclet.2016.01.051","article-title":"Synthesis and antiviral activities of novel 1,4-pentadien-3-one derivatives bearing an emodin moiety","volume":"27","author":"Wu","year":"2016","journal-title":"Chin. Chem. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"598","DOI":"10.1111\/j.1747-0285.2012.01433.x","article-title":"Design, Facile Synthesis, and Antibacterial Activity of Hybrid 1,3,4-thiadiazole-1,3,5-triazine Derivatives Tethered via-S-Bridge","volume":"80","author":"Dubey","year":"2012","journal-title":"Chem. Biol. Drug Des."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"817","DOI":"10.1016\/j.cclet.2012.04.005","article-title":"Synthesis and in vitro antitumor activity of 1,3,4-thiadiazole derivatives based on benzisoselenazolone","volume":"23","author":"Zhao","year":"2012","journal-title":"Chin. Chem. Lett."},{"key":"ref_32","unstructured":"Huang, S.Y., Li, X.W., Zhi, S., Wang, P.B., and Liu, D.K. (2013). Thiadiazole Derivatives. (CN 102276625B)."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/12\/3132\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T15:33:19Z","timestamp":1760196799000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/23\/12\/3132"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,29]]},"references-count":32,"journal-issue":{"issue":"12","published-online":{"date-parts":[[2018,12]]}},"alternative-id":["molecules23123132"],"URL":"https:\/\/doi.org\/10.3390\/molecules23123132","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,29]]}}}