Synthesis and herbicidal evaluation of N-cinnamoyl-N-substituted hydroxylamine and its derivatives
DOI:
https://doi.org/10.18011/bioeng.2025.v19.1282Keywords:
Cinnamo hydroxamic acid, NMR spectroscopy, Raphanus sativus, Herbicidal activity, Pendimethalin, PASS studiesAbstract
The group of cinnamon and hydroxylamine produces significant results in the field of agriculture. So, the combination of both groups in the compound performs effective results in numerous fields of the medicinal and chemical industry. Still, this type of moiety combination is not used in the agricultural field as an herbicide. The cost-effective plant that grows alongside crops develops resistance to current herbicides. To effectively combat undesirable herbs, new or modified groupings are needed. To investigate the prospect of discovering a new class of herbicide, the current work aims to synthesize derivatives of cinnamon hydroxamic acid and screen them for herbicidal activity. A cinnamo hydroxamic acid derivative was synthesized by a reaction of substituted cinnamic acids and hydroxylamine derivatives, and the final product was characterized by FTIR, 1H NMR, and 13C NMR spectroscopy. The final product was tested for herbicidal activity against Radish (Raphanus sativus) seeds at 50, 100 and 200 ppm concentrations and compared with standard pendimethalin. Amongst the tested compounds, 3-nitro cinnamo hydroxamic acid (A2), o-tolyl-(3-bromo) cinnamo hydroxamic acid (B1) and 2-bromo-(4-chloro) cinnamo hydroxamic acid) (C1) exhibited activity at par with standard pendimethalin at a concentration of 200 ppm and In silico PASS studies also showed that it has excellent herbicidal properties.
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References
Agrawal, Y. K., & Tandon, S. G. (1971). N-Arylhydroxamic acids. Journal of Chemical & Engineering Data, 16(4), 495–496. https://doi.org/10.1021/je60051a004.
Arnold, M., Brown, D. A., Deeg, O., Errington, W., Haase, W., Herlihy, K., Kemp, T. J., Nimir, H., & Werner, R. (1998). Hydroxamate-bridged dinuclear nickel complexes as models for urease inhibition. Inorganic Chemistry, 37(12), 2920–2925. https://doi.org/10.1021/ic9711628.
Arya, S., Mahawer, S. K., Karakoti, H., Kumar, R., Prakash, O., Kumar, S., Latwal, M., Panday, G., Srivastava, R. M., De Oliveira, M. S., & Rawat, D. S. (2023). Study of the variability of the chemical profile, and biological activity approaches of Hedychium coronarium J. Koenig essential oil from different habitats of Uttarakhand, India. Journal of Food Quality, 2023(1), 7335134. https://doi.org/10.1155/2023/7335134.
Asadi, G. S., Abdizadeh, R., & Abdizadeh, T. (2023). Investigation of a set of flavonoid compounds as Helicobacter pylori urease inhibitors: Insights from in silico studies. Journal of Biomolecular Structure and Dynamics, 15(1), 1–23. https://doi.org/10.1080/07391102.2023.2295973.
Botos, I., Scapozza, L., Zhang, D., Liotta, L. A., & Meyer, E. F. (1996). Batimastat, a potent matrix metalloproteinase inhibitor, exhibits an unexpected mode of binding. Proceedings of the National Academy of Sciences, 93(7), 2749–2754. https://doi.org/10.1073/pnas.93.7.2749.
Brown, D. A., Cuffe, L. P., Fitzpatrick, N. J., & Ryan, Á. T. (2004). A DFT study of model complexes of zinc hydrolases and their inhibition by hydroxamic acids. Inorganic Chemistry, 43(1), 297–302. https://doi.org/10.1021/ic034432x.
Chan, R. I., San, R. H., & Stich, H. F. (1986). Mechanism of inhibition of N-methyl-N'-nitro-N-nitrosoguanidine-induced mutagenesis by phenolic compounds. Cancer letters, 31(1), 27–34. https://doi.org/10.1016/0304-3835(86)90163-1.
Cheng, M., De, B., Pikul, S., Almstead, N. G., Natchus, M. G., Anastasio, M. V., McPhail, S. J., Snider, C. E., Taiwo, Y. O., Chen, L., & Dunaway, C. M. (2000). Design and synthesis of piperazine-based matrix metalloproteinase inhibitors. Journal of Medicinal Chemistry, 43(3), 369–380. https://doi.org/10.1021/jm990366q.
Coutts, R. T., Hubbard, J. W., Midha, K. K., & Prasad, K. (1971). Synthesis and properties of some hypotensive N-alkylaminopropionic esters and N,N-dialkylaminopropionic esters and their hydroxamic acids. Journal of Pharmaceutical Sciences, 60(1), 28–33. https://doi.org/10.1002/jps.2600600103.
Falkenberg, K. J., & Johnstone, R. W. (2014). Histone deacetylases and their inhibitors in cancer, neurological diseases and immune disorders. Nature Reviews Drug Discovery, 13(9), 673–691. https://doi.org/10.1038/nrd4360.
Finnin, M. S., Donigian, J. R., Cohen, A., Richon, V. M., Rifkind, R. A., Marks, P. A., Breslow, R., & Pavletich, N. P. (1999). Structures of a histone deacetylase homologue bound to the TSA and SAHA inhibitors. Nature, 401(6749), 188–193. https://doi.org/10.1038/43710.
Goel, R. K., Singh, D., Lagunin, A., & Poroikov, V. (2011). PASS-assisted exploration of new therapeutic potential of natural products. Medicinal Chemistry Research, 20(9), 1509–1514. https://doi.org/10.1007/s00044-010-9398-y.
Indiani, C., Santoni, E., Becucci, M., Boffi, A., Fukuyama, K., & Smulevich, G. (2003). New insight into the peroxidase-hydroxamic acid interaction revealed by the combination of spectroscopic and crystallographic studies. Biochemistry, 42(47), 14066–14074. https://doi.org/10.1021/bi035290l.
Köster, W. (2001). ABC transporter-mediated uptake of iron, siderophores, heme and vitamin B12. Research in Microbiology, 152(3–4), 291–301. https://doi.org/10.1016/S0923-2508(01)01200-1.
Kumar, A., Masroor, S., Khan, M. E., Ali, S. K., Khamaj, A., & Zakri, W. (2025). Eco-friendly synthesis of benzoxazole substituted chromene containing benzene sulfonamide derivatives: antibacterial activity and molecular docking. Journal of Molecular Structure, 1348. https://doi.org/10.1016/j.molstruc.2025.143429.
Kumar, A., Masroor, S., Kaya, S., Katin, K. P., Berisha, A., Khan, M. E., ... & Zakri, W. (2025). Synthesis of sustainable heterocyclic aryl sulfonamide derivatives: computational studies, molecular docking, and antibacterial assessment. Macromolecular Research, 33(3), 331-344. https://doi.org/10.1007/s13233-024-00335-w.
McGill, A. D., Zhang, W., Wittbrodt, J., Wang, J., Schlegel, H. B., & Wang, P. G. (2000). para-Substituted N-nitroso-N-oxybenzenamine ammonium salts: a new class of redox-sensitive nitric oxide releasing compounds. Bioorg Med Chem, 8(2), 405-412. https://doi.org/10.1016/s0968-0896(99)00300-4.
Miller, M. J. (1986). Hydroxamate approach to the synthesis of β-lactam antibiotics. Accounts of Chemical Research, 19(2), 49–56. https://doi.org/10.1021/ar00122a004.
Miller, M. J. (1989). Syntheses and therapeutic potential of hydroxamic acid based siderophores and analogs. Chemical Reviews, 89(7), 1563–1579. https://doi.org/10.1021/cr00097a011.
Priyadarshini, U., & Tandon, S. G. (1967). Preparation and properties of some N-aryl hydroxyamic acids. Journal of Chemical & Engineering Data, 12(1), 143–144. https://doi.org/10.1021/je60032a046.
Rajput, S. K., Patel, A., & Bapat, K. N. (2016). Spectrophotometric determination of vanadium (V) using N-methyl cinnamohydroxamic acid as reagent. Chemical and Materials Research, 8(7), 8–12.
Rajput, S. K. ., Patel, A., & Bapat, K. N. (2017). Synthesis and Characterization of N-Methyl and N-Benzyl Cinnamohydroxamic Acids. Asian Journal of Chemistry, 29(4), 885–887. https://doi.org/10.14233/ajchem.2017.20348.
Rodrigues, G. C., Feijo, D. F., Bozza, M. T., Pan, P., Vullo, D., Parkkila, S., Supuran, C. T., Capasso, C., Aguiar, A. P., & Vermelho, A. B. (2014). Design, synthesis, and evaluation of hydroxamic acid derivatives as promising agents for the management of Chagas disease. Journal of Medicinal Chemistry, 57(2), 298–308. https://doi.org/10.1021/jm400902y.
Sahu, A., & Devkota, A. (2013). Allelopathic effects of aqueous extract of leaves of Mikania micrantha HBK on seed germination and seedling growth of Oryza sativa L. and Raphanus sativus L. Scientific World, 11(11), 90–93. https://doi.org/10.3126/sw.v11i11.8559.
Sani, M., Belotti, D., Giavazzi, R., Panzeri, W., Volonterio, A., & Zanda, M. (2004). Synthesis and evaluation of stereopure α-trifluoromethyl-malic hydroxamates as inhibitors of matrix metalloproteinases. Tetrahedron Letters, 45(8), 1611–1615. https://doi.org/10.1016/j.tetlet.2003.12.131.
Shao, J., Zhou, B., Chu, B., & Yen, Y. (2006). Ribonucleotide reductase inhibitors and future drug design. Current Cancer Drug Targets, 6(5), 409–431. https://doi.org/10.2174/156800906777723949.
Syed, Z., Sonu, K., Dongre, A., Sharma, G., & Sogani, M. (2020). A review on hydroxamic acids: Widespectrum chemotherapeutic agents. International Journal of Biology and Biomedicine, 14, 75–88. https://doi.org/10.46300/91011.2020.14.12.
Takeuchi, H., Tateiwa, J. I., Hata, S., Tsutsumi, K., & Osaki, Y. (2003). Selective aromatic N-substitution with N-(4-tolyl) hydroxylamine by addition of polar aprotic or diethereal solvent. European Journal of Organic Chemistry, 2003(20), 3920–3922. https://doi.org/10.1002/ejoc.200200576.
Tsuji, N., Kobayashi, M., Nagashima, K., Wakisaka, Y., & Koizumi, K. (1976). A new antifungal antibiotic, trichostatin. Journal of Antibiotics, 29(1), 1–6. https://doi.org/10.7164/antibiotics.29.1.
Ung, S., Falguières, A., Guy, A., & Ferroud, C. (2005). Ultrasonically activated reduction of substituted nitrobenzenes to corresponding N-arylhydroxylamines. Tetrahedron Letters, 46(35), 5913–5917. https://doi.org/10.1016/j.tetlet.2005.06.126.
Verstraete, W., & Alexander, M. (1973). Heterotrophic nitrification in samples of natural ecosystems. Environmental Science & Technology, 7(1), 39-42. https://doi.org/10.1021/es60073a007.
Vishnoi, S., Agrawal, V., & Kasana, V. K. (2009). Synthesis and structure–activity relationships of substituted cinnamic acids and amide analogues: A new class of herbicides. Journal of Agricultural and Food Chemistry, 57(8), 3261–3265. https://doi.org/10.1021/jf8034385.
Weber, G. (1983). Biochemical strategy of cancer cells and the design of chemotherapy: G. H. A. Clowes Memorial Lecture. Cancer Research, 43(8), 3466–3492
Wu, K., Chen, X., Chen, X., Zhang, S., Xu, Y., Xia, B., & Ma, S. (2021). Suberoylanilide hydroxamic acid enhances the radiosensitivity of lung cancer cells through acetylated wild-type and mutant p53-dependent modulation of mitochondrial apoptosis. Journal of International Medical Research, 49(2), 0300060520981545. https://doi.org/10.1177/0300060520981545.
Yadav, J. S., Reddy, B. V., & Sreedhar, P. (2003). Three-component one-pot synthesis of α-hydroxylamino phosphonates using ionic liquids. Advanced Synthesis & Catalysis, 345(5), 564–567. https://doi.org/10.1002/adsc.200202209.
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