Citation: Qi-Chun DING, Yi-Min CAI, Si-Lei WANG, Pei-Pao YAO, Ru-Ya YANG. Exploration of a Library of Triazolothiadiazines as Potent Plant Growth Promoters: Design, Synthesis, X-ray Diffraction Analysis and Bioactivity Studies[J]. Chinese Journal of Structural Chemistry, ;2021, 40(8): 1098-1106. doi: 10.14102/j.cnki.0254–5861.2011–3225 shu

Exploration of a Library of Triazolothiadiazines as Potent Plant Growth Promoters: Design, Synthesis, X-ray Diffraction Analysis and Bioactivity Studies

  • Corresponding author: Qi-Chun DING, 177426824@qq.com
  • Received Date: 9 April 2021
    Accepted Date: 25 June 2021

    Fund Project: the Education Research Project of Fujian Province, China JZ180850

Figures(4)

  • A series of novel 3-methyl-6-aryl-7-aroyl-6, 7-dihydro-5H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazines were designed, synthesized and tested for their antiproliferative activity against HepG2 cell lines in vitro by the standard SRB assay and plant growth regulation activities on wheat (amonocotyledon) and radish (adicotyledon). The results indicated all the title compounds exhibited a very weak antiproliferative activity against HepG2 cell lines in vitro unexpectedly, while showed potent plant growth-regulating activities on both wheat and radish. The crystal structure of trans-4d was obtained from X-ray diffraction: C18H13N4OSCl3, Mr = 439.75, monoclinic system, space group P21/n, a = 5.3224(7), b = 14.3578(18), c = 24.442(3) Å, β = 94.180(2)°, V = 1862.8(4) Å3, F(000) = 899, Z = 4, Dc = 1.5679 g/cm3, λ = 0.71073 Å, μ = 0.621 mm-1 and the final R = 0.0382 for 3274 unique reflections with 2851 observed ones (I > 2σ(I)).
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    1. [1]

      Gavara, L.; Verdirosa, F.; Legru, A.; Mercuri, P. S.; Nauton, L.; Sevaille, L.; Feller, G.; Berthomieu, D.; Sannio, F.; Marcoccia, F.; Tanfoni, S.; Luca, F. D.; Gresh, N.; Galleni, M.; Docquier, J. D.; Hernandez, J. F. 4-(N-Alkyl- and -acyl-amino)-1, 2, 4-triazole-3-thione analogs as metallo-β-lactamase inhibitors: impact of 4-linker on potency and spectrum of inhibition. Biomol. 2020, 10, 1094–1111.

    2. [2]

      Salah, K. B. H.; Maingot, M.; Blayo, A. L.; M'Kadmi, C.; Damian, M.; Mary, S.; Cantel, S.; Neasta, J.; Oiry, C.; Péraldi-Roux, S.; Fernandez, G.; Romero, G. G.; Perello, M.; Marie, J.; Banères, J. L.; Fehrentz, J. A.; Denoyelle, S. Development of non-peptidic inverse agonists of the ghrelin receptor (GHSR) based on the 1, 2, 4-triazole scaffold. J. Med. Chem. 2020, 63, 10796–10815.  doi: 10.1021/acs.jmedchem.9b02122

    3. [3]

      Pagniez, F.; Lebouvier, N.; Na, Y. M.; Ourliac-Garnier, I.; Picot, C.; Borgne, M. L.; Pape, P. L. Biological exploration of a novel 1, 2, 4-triazole-indole hybrid molecule as antifungal agent. J. Enzyme Inhib. Med. Chem. 2020, 35, 398–403.  doi: 10.1080/14756366.2019.1705292

    4. [4]

      Cheng, Y. N.; Jiang, Z. H.; Sun, L. S.; Su, Z. Y.; Zhang, M. M.; Li, H. L. Synthesis of 1, 2, 4-triazole benzoyl arylamine derivatives and their high antifungal activities. Eur. J. Med. Chem. 2020, 200, 112463–112473.  doi: 10.1016/j.ejmech.2020.112463

    5. [5]

      Shi, J.; Ding, M. H.; Luo, N.; Wan, S. R.; Li, P. J.; Li, J. H.; Bao, X. P. Design, synthesis, crystal structure, and antimicrobial evaluation of 6-fluoroquinazolinylpiperidinyl-containing 1, 2, 4-triazole mannich base derivatives against phytopathogenic bacteria and fungi. J. Agric. Food Chem. 2020, 68, 9613–9623.  doi: 10.1021/acs.jafc.0c01365

    6. [6]

      Stingaci, E.; Zveaghinteva, M.; Pogrebnoia, S.; Lupascu, L.; Valica, V.; Uncu, L.; Smetanscaia, A.; Drumea, M.; Petrou, A.; Ciric, A.; Glamoclija, J.; Sokovic, M.; Kravtsov, V.; Geronikaki, A.; Macaev, F. New vinyl-1, 2, 4-triazole derivatives as antimicrobial agents: synthesis, biological evaluation and molecular docking studies. Bioorg. Med. Chem. Lett. 2020, 30, 127368–127374.  doi: 10.1016/j.bmcl.2020.127368

    7. [7]

      Ma, W. F.; Chen, P.; Huo, X. S.; Ma, Y. F.; Li, Y. H.; Diao, P. C.; Yang, F.; Zheng, S. Q.; Hu, M. J.; You, W. W.; Zhao, P. L. Development of triazolothiadiazine derivatives as highly potent tubulin polymerization inhibitors: structure-activity relationship, in vitro and in vivo study. Eur. J. Med. Chem. 2020, 208, 112847–112861.  doi: 10.1016/j.ejmech.2020.112847

    8. [8]

      Li, Z. Q.; Bai, X. G.; Deng, Q.; Zhang, G. N.; Zhou, L.; Liu, Y. S.; Wang, J. X.; Wang, Y. C. Preliminary SAR and biological evaluation of antitubercular triazolothiadiazine derivatives against drug-susceptible and drugresistant Mtb strains. Bioorg. Med. Chem. 2017, 25, 213–220.  doi: 10.1016/j.bmc.2016.10.027

    9. [9]

      Winton, V. J.; Aldrich, C.; Kiessling, L. L. Carboxylate surrogates enhance the antimycobacterial activity of UDP-galactopyranose mutase probes. ACS Infect. Dis. 2016, 2, 538–543.  doi: 10.1021/acsinfecdis.6b00021

    10. [10]

      Khan, I.; Bakht, S. M.; Ibrar, A.; Abbas, S.; Hameed, S.; White, J. M.; Rana, U. A.; Zaib, S.; Shahid, M.; Iqbal, J. Exploration of a library of triazolothiadiazole and triazolothiadiazine compounds as a highly potent and selective family of cholinesterase and monoamine oxidase inhibitors: design, synthesis, X-ray diffraction analysis and molecular docking studies. RSC Adv. 2015, 5, 21249–21267.  doi: 10.1039/C5RA00906E

    11. [11]

      Alafeefy, A. M.; Abdel-Aziz, H. A.; Vullo, D.; Al-Tamimi, A. M. S.; Awaad, A. S.; Mohamed, M. A.; Capasso, C.; Supuran, C. T. Inhibition of human carbonic anhydrase isozymes I, II, IX and XII with a new series of sulfonamides incorporating aroylhydrazone-, [1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazinyl- or 2-(cyanophenylmethylene)-1, 3, 4-thiadiazol-3(2H)-yl moieties. J. Enzyme Inhib. Med. Chem. 2015, 30, 52–56.  doi: 10.3109/14756366.2013.877897

    12. [12]

      Zhang, B.; Li, Y. H.; Liu, Y.; Chen, Y. R.; Pan, E. S.; You, W. W.; Zhao, P. L. Design, synthesis and biological evaluation of novel 1, 2, 4-triazolo[3, 4-b][1, 3, 4] thiadiazines bearing furan and thiophene nucleus. Eur. J. Med. Chem. 2015, 103, 335–342.  doi: 10.1016/j.ejmech.2015.08.053

    13. [13]

      Ding, Q. C.; Zou, Y. H.; Li, Q. L.; Huang, J. J.; Zhang, L. X.; Yin, H. Y. Synthesis, crystal structure and biological activities of phenyl(6-phenyl-3-p-tolyl-6, 7-dihydro-5H-[1, 2, 4]triazolo[3, 4-b][1, 3, 4]thiadiazin-7-yl)methanone. Chin. J. Struct. Chem. 2020, 39, 1531–1538.

    14. [14]

      Salam, H. A. A. E.; Yakout, E. S. M. A.; Nawwar, G. A. M.; El-Hashash, M. A.; Mossa, A. T. H. Synthesis of some new 1, 2, 4-triazoles containing olyl moiety and evaluation of their antimicrobial and antioxidant activities. Monatsh. Chem. 2017, 148, 291–304.  doi: 10.1007/s00706-016-1751-5

    15. [15]

      Ahmad, A.; Varshney, H.; Rauf, A.; Sherwani, A.; Owais, M. Synthesis and anticancer activity of long chain substituted 1, 3, 4-oxadiazol-2-thione, 1, 2, 4-triazol-3-thione and 1, 2, 4-triazolo[3, 4-b]-1, 3, 4-thiadiazine derivatives. Arab. J. Chem. 2014, 10, S3347–S3357.

    16. [16]

      Dabholkar, V. V.; Patil, S. R.; Pandey, R. V. Dimethylformamide catalyzed synthesis of novel heterocycles—their characterization and antimicrobial evaluation. J. Heterocyclic Chem. 2013, 50, 403–407.  doi: 10.1002/jhet.1073

    17. [17]

      Olson, M. E.; Li, M.; Harris, R. S.; Harki, D. A. Small-molecule APOBEC3G DNA cytosine deaminase inhibitors based on a 4-amino-1, 2, 4-triazole-3-thiol scaffold. ChemMedChem. 2013, 8, 112–117.  doi: 10.1002/cmdc.201200411

    18. [18]

      Bakavoli, M.; Seyedi, S. M.; Shiri, A.; Saberi, S.; Gholami, M.; Sadeghian, H. Synthesis of new derivatives of pyrimido[5, 4-e] [1, 2, 4] triazolo-[3, 4-b][1, 3, 4] thiadiazine and their enzyme inhibitory activity assessment on soybean 15-lipoxygenase. J. Chem. Res. 2013, 37, 48–50.  doi: 10.3184/174751912X13549029453945

    19. [19]

      Pundeer, R.; Kiran, V.; Prakash, R.; Sushma; Bhatia, S. C.; Sharma, C.; Aneja, K. R. α, α-Dibromoacetophenones mediated synthesis of some new 7H-7-alkoxy-3-alkyl/phenyl-6-aryl-s-triazolo[3, 4-b][1, 3, 4] thiadiazines and their antimicrobial evaluation. Med. Chem. Res. 2012, 21, 4043–4052.  doi: 10.1007/s00044-011-9945-1

    20. [20]

      Iradyan, M. A.; Iradyan, N. S.; Paronikyan, R. V.; Stepanyan, G. M. Synthesis and biological activity of substituted 6-alkyl(6H)-3-phenyl-1, 2, 4-triazolo[3, 4-b]-1, 3, 4-thiadiazines. Pharm. Chem. J. 2010, 44, 413–417.  doi: 10.1007/s11094-010-0479-5

    21. [21]

      Bourhis, L. J.; Dolomanov, O. V.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. The anatomy of a comprehensive constrained, restrained refinement program for the modern computing environment – Olex2 dissected. Acta Cryst. 2015, A71, 59–75.

    22. [22]

      Zhou, S. N.; Zhang, L. X.; Wu, X. H.; Tian, Y. J.; Liu, L. Q.; Pan, B.; Luo, Y. F.; Shi, M. R. Synthesis and plant growth regulating effects of novel 6-aryl-3-(5-hydroxypentyl)-7-1, 2, 4-trazole[3, 4-b][1, 3, 4]thiadiazines. Chin. J. Synth. Chem. 2019, 27, 19–24.
       

    23. [23]

      Ding, Q. C.; Zhang, L. X.; Zhang, H. L. Synthesis and biological activities of some novel triazolothiadiazines and Schiff bases derived from 4-amino-3-(4-hydroxyphenyl)-1H-1, 2, 4-triazole-5(4H)-thione. Phosphorus, Sulfur Silicon Relat. Elem. 2010, 185, 567–572.  doi: 10.1080/10426500902848393

    24. [24]

      Zhou, S. N.; Zhang, L. X.; Jin, J. Y.; Zhang, A. J.; Lei, X. X.; Lin, J. S.; He, J. W.; Zhang, H. L. Synthesis and biological activities of some novel triazolothiadiazines and Schiff bases derived from 1, 2, 4-triazole. Phosphorus, Sulfur Silicon Relat. Elem. 2007, 182, 419–432.  doi: 10.1080/10426500600976884

    25. [25]

      Jin, J. Y.; Zhang, L. X.; Chen, X. X.; Zhang, A. J.; Zhang, H. L. Syntheses and biological activities of 6-aryl-3-(3-hydroxy-propyl)-7H-1, 2, 4-triazolo[3, 4-b][1, 3, 4]thiadiazines. Molecules 2007, 12, 297–303.  doi: 10.3390/12030297

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