Molecular Diversity

, Volume 16, Issue 2, pp 251–260 | Cite as

Synthesis, structure, and biological activity of novel (oxdi/tri)azoles derivatives containing 1,2,3-thiadiazole or methyl moiety

Full-Length Paper
First Online:
Received:
Accepted:

Abstract

To develop novel inhibitors of ketol-acid reductoisomerase, a series of (oxdi/tri)azoles derivatives was synthesized and characterized by 1H  NMR, MS, elemental analyses, and crystallography. According to the biological activities of these compounds obtained both in vivo and in vitro, compound 4-cyclopropyl-3-((4-fluorobenzyl)thio)-5-methyl-4H-1,2,4-triazole showed excellent KARI inhibitory activity (100% at 100 μg mL −1  in vitro). In addition, most of the title compounds exhibited good herbicidal activity against Brassica campestris in vivo.

Keywords

1,2,4-Triazole 1,3,4-Oxidiazole Crystal structure Herbicidal activity KARI activity 
This is a preview of subscription content, log in to check access.

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Supplementary material

11030_2011_9352_MOESM1_ESM.doc (7.1 mb)
ESM 1 (DOC 7237 kb)

References

  1. 1.
    Chaleff RS, Mauvais CJ (1984) Acetolactate synthase is the site of action of two sulfonylurea herbicides in higher plants. Science 224: 1443–1445. doi: 10.1126/science.224.4656.1443 PubMedCrossRefGoogle Scholar
  2. 2.
    Shaner DL, Anderson PC, Stidham MA (1984) Imidazolinones. Potent inhibitors of acetohydroxy acid synthase. Plant Physiol 76: 545–546. doi: 10.1104/pp.76.2.545 PubMedCrossRefGoogle Scholar
  3. 3.
    Simon K (1983) Analytical investigation of the process for manufacturing 1,2,4-1H-triazole. Hung J Ind Chem 11: 291–299Google Scholar
  4. 4.
    Duggleby RG, Pang SS (2000) Acetohydroxyacid synthase. J Biochem Mol Biol 33: 1–36Google Scholar
  5. 5.
    Dumas R, Biou VF, Douce HR, Duggleby RG (2001) Enzymology, structure, and dynamics of acetohydroxy acid isomeroreductase. Acc Chem Res 34: 399–408. doi: 10.1021/ar000082w PubMedCrossRefGoogle Scholar
  6. 6.
    Dumas R, Butikofer MC, Job D, Douce R (1995) Evidence for two catalytically different magnesium-binding sites in acetohydroxy acid isomeroreductase by site-directed mutagenesis. Biochemistry 34: 6026–6036. doi: 10.1021/bi00018a004 PubMedCrossRefGoogle Scholar
  7. 7.
    Chunduru SK, Mrachko GT, Calvo KC (1989) Mechanism of ketol acid reductoisomerase. Steady-state analysis and metal ion requirement. Biochemistry 28: 486–493. doi: 10.1021/bi00428a012 PubMedCrossRefGoogle Scholar
  8. 8.
    Gerwick BC, Mireles LC, Eilers RJ (1993) Rapid diagnosis of ALS/AHAS-resistant weeds. Weed Technol 7: 519–524Google Scholar
  9. 9.
    Schulz A, Sponemann P, Kocher H, Wengenmayer F (1988) The herbicidally active experimental compound Hoe 704 is a potent inhibitor of the enzyme acetolactate reductoisomerase. FEBS Lett 238: 375–378. doi: 10.1016/0014-5793(88)80515-5 PubMedCrossRefGoogle Scholar
  10. 10.
    Aulabaugh A, Schloss JV (1990) Oxalyl hydroxamates as reaction-intermediate analogs for ketol-acid reductoisomerase. Biochemistry 29: 2824–2840. doi: 10.1021/bi00463a027 PubMedCrossRefGoogle Scholar
  11. 11.
    Lee YT, Ta HT, Duggleby RG (2005) Cyclopropane-1,1-dicarboxylate is a slow-, tight-binding inhibitor of rice ketol-acid reductoisomerase. Plant Sci 168: 1035–1040. doi: 10.1021/bi00428a012 CrossRefGoogle Scholar
  12. 12.
    Halgand F, Vives F, Dumas R, Biou V, Andersen J, Andrieu JP, Cantegril R, Gagnon J, Douce R, Forest E, Job D (1998) Kinetic and mass spectrometric analyses of the interactions between plant acetohydroxy acid isomeroreductase and thiadiazole derivatives. Biochemistry 37: 4773–4781. doi: 10.1021/bi9721389 PubMedCrossRefGoogle Scholar
  13. 13.
    Liu XH, Chen PQ, Wang BL, Li YH, Wang SH, Li ZM (2007) Synthesis bioactivity theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropane carboxamide as ketol-acid reductoisomerase inhibitor. Bioorg Med Chem Lett 17: 3784–3788. doi: 10.1016/j.bmcl.2007.04.003 PubMedCrossRefGoogle Scholar
  14. 14.
    Liu XH, Chen PQ, He FQ, Li YH, Wang SH, Li ZM (2007) Structure bioactivity and theoretical study of 1-cyano-N-p-tolylcyclo-propanecarboxamide. Struct Chem 5: 563–568. doi: 10.1007/s11224-007-9175-9 CrossRefGoogle Scholar
  15. 15.
    Liu XH, Zhang CY, Guo WC, Li YH, Chen PQ, Wang T, Dong WL, Sun HW, Li ZM (2009) Synthesis bioactivity and SAR study of N′-(5-substituted-1,3,4-thiadiazol-2-yl) - N-cyclopropyformyl-thiourea as ketol-acid reductoisomerase inhibitor. J Enzyme Inhib Med Chem 24: 545–552. doi: 10.1080/14756360802234943 PubMedCrossRefGoogle Scholar
  16. 16.
    Liu XH, Chen PQ, Wang BL, Dong WL, Li YH, Xie XQ, Li ZM (2010) High throughput receptor based virtual screening under ZINC-Database, synthesis and biological evaluation of ketol-acid reductoisomerase inhibitors. Chem Biol Drug Des 75: 228–232. doi: 10.1111/j.1747-0285.2009.00924.x PubMedCrossRefGoogle Scholar
  17. 17.
    Wang BL, Shi YX, Ma Y, Liu XH, Li YH, Song HB, Li BJ, Li ZM (2010) Synthesis and biological activity of some novel trifluoromethyl-substituted 1,2,4-triazole and bis(1,2,4-triazole) mannich bases containing piperazine rings. J Agric Food Chem 58: 5515–5522. doi: 10.1021/jf100300a PubMedCrossRefGoogle Scholar
  18. 18.
    Li ZG, Wang QM, Huang JM (2001) Preparetion of organic intermediates, 2nd ed. Chemical Industry Press, Beijing, 96–97Google Scholar
  19. 19.
    Dong WL, Liu ZX, Liu XH, Li ZM, Zhao WG (2010) Synthesis and antiviral activity of new acrylamide derivatives containing 1,2,3-thiadiazole as inhibitors of hepatitis B virus replication. Eur J Med Chem 45: 1919–1926. doi: 10.1016/j.ejmech.2010.01.032 PubMedCrossRefGoogle Scholar
  20. 20.
    Liu XH, Pan L, Tan CX, Weng JQ, Wang BL, Li ZM (2011) Synthesis, crystal structure, bioactivity and DFT calculation of new oxime ester derivatives containing cyclopropane moiety. Pestic Biochem Physiol. doi: 10.1016/j.pestbp.2011.08.006
  21. 21.
    Liu XH, Weng JQ, Tan CX, Pan L, Wang BL, Li ZM (2011) Synthesis, biological activities and DFT calculation of α-aminophosphonate containing cyclopropane moiety. Asian J Chem 23: 4031–4036Google Scholar
  22. 22.
    Laemmli UK (1970) Cleavage of structural proteins during the assembly of the head of bacteriophage T4. Nature 227: 680–685. doi: 10.1038/227680a0 PubMedCrossRefGoogle Scholar
  23. 23.
    Smith PK, Krohn RI, Hermanson GT, Mallia AK, Gartner FH, Provenzano MD, Fujimoto EK, Goeke NM, Olson BJ, Klenk DC (1985) Measurement of protein using bicinchoninic acid. Anal Biochem 150: 76–85. doi: 10.1016/0003-2697(85)90442-7 PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Xing-Hai Liu
    • 1
  • Li Pan
    • 2
  • Jian-Quan Weng
    • 1
  • Cheng-Xia Tan
    • 1
  • Yong-Hong Li
    • 2
  • Bao-Lei Wang
    • 2
  • Zheng-Ming Li
    • 2
  1. 1.College of Chemical Engineering & Materials SciencesZhejiang University of TechnologyHangzhouChina
  2. 2.State-Key Laboratory of Elemento-Organic ChemistryNankai UniversityTianjinChina

Personalised recommendations