Article Sidebar

Download
PDF

Main Article Content

Abstract

In present work, a convenient method for the nucleophilic ring-opening of epoxides with secondary amine in presence of ethyl acetate as a polar aprotic solvent using catalytic amount of base is described. Present method is highly regioselective and furnishes the products in short time of period with excellent yield. The regioselectivity of this ring opening was confirmed using FT-IR, 1H NMR, 13C NMR, elemental analysis and mass spectral data. The antimicrobial screening of all these synthesized compounds was done against some bacterial and fungal strains in two polar solvents, DMSO and DMF using agar well diffusion method. These compounds showed good inhibition of bacterial strains and potent against fungal strains than standard drug.

Keywords

Benzohydrazides Regioselctivity Ring-opening Antimicrobial activity.

Article Details

License

Copyright (c) 2021 AJC

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite
H. Lalavani, N., A. Bhensdadia, K., & H. Baluja, S. (2021). Highly Regioselective Ring-Opening of Epoxides: Synthesis and Biological Evaluation as Potent Antimicrobial Agents. Asian Journal of Organic & Medicinal Chemistry, 6(3), 228–234. https://doi.org/10.14233/ajomc.2021.AJOMC-P341
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. F. Hakim and S.R. Salfidoer, Asian J. Chem., 33, 1757 (2021); https://doi.org/10.14233/ajchem.2021.23226
  2. S. Rollas and S.G. Küçükgüzel, Biological Activities of Hydrazone Derivatives, Molecules, 12, 1910 (2007); https://doi.org/10.3390/12081910
  3. P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera and R. Loddo, Synthesis and Antiproliferative Activity of Benzo[d]isothia-zole Hydrazones, Eur. J. Med. Chem., 41, 624 (2006); https://doi.org/10.1016/j.ejmech.2006.01.010
  4. R.M. Mohareb, K.A. El-Sharkawy and F.O. Al-Farouk, Synthesis, Cytotoxicity against Cancer and Normal Cell Lines of Novel Hydrazide–Hydrazone Derivatives bearing 5H-Chromen-5-one, Med. Chem. Res., 28, 1885 (2019); https://doi.org/10.1007/s00044-019-02421-6
  5. P. Kumar, B. Narasimhan, K. Ramasamy, V. Mani, R.K. Mishra and A.B.A. Majeed, Synthesis, Antimicrobial, Anticancer Evaluation and QSAR Studies of 2/3-Bromo-N¢-(substituted benzylidene/3-phenylallylidene)-benzohydrazides, Arab. J. Chem., 10, S3740 (2017); https://doi.org/10.1016/j.arabjc.2014.05.010
  6. A. Özdemir, G. Turan-Zitouni, Z.A. Kaplancikli and Y. Tunali, Synthesis and Biological Activities of New Hydrazide Derivatives, J. Enzyme Inhib. Med. Chem., 24, 825 (2009); https://doi.org/10.1080/14756360802399712
  7. M.A.A. Radwan, E.A. Ragab, N.M. Sabry and S.M. El-Shenawy, Synthesis and Biological Evaluation of New 3-Substituted Indole Derivatives as Potential Anti-inflammatory and Analgesic Agents, Bioorg. Med. Chem., 15, 3832 (2007); https://doi.org/10.1016/j.bmc.2007.03.024
  8. V. Sharma, E.K. Arora and S. Cardoza, 4-Hydroxy-benzoic acid (4-Diethylamino-2-hydroxy-benzylidene)hydrazide: DFT, Antioxidant, Spectroscopic and Nolecular Docking Studies with BSA, Luminescence, 31, 738 (2016); https://doi.org/10.1002/bio.3018
  9. P. Melnyk, V. Leroux, C. Sergheraert and P. Grellier, Design, Synthesis and in vitro Antimalarial Activity of an Acylhydrazone Library, Bioorg. Med. Chem. Lett., 16, 31 (2006); https://doi.org/10.1016/j.bmcl.2005.09.058
  10. S.K. Sridhar, S.N. Pandeya, J.P. Stables and A. Ramesh, Anticonvulsant Activity of Hydrazones, Schiff and Mannich Bases of Isatin Derivatives, Eur. J. Pharm. Sci., 16, 129 (2002); https://doi.org/10.1016/S0928-0987(02)00077-5
  11. A. Almasirad, M. Tajik, D. Bakhtiari, A. Shafiee, M. Abdollahi, M.J. Zamani, R. Khorasani and H. Esmaily, Synthesis and Analgesic Activity of N-Arylhydrazone Derivatives of Mefenamic Acid, J. Pharm. Pharm. Sci., 8, 419 (2005).
  12. W. Khalid, A. Badshah, A. Khan, H. Nadeem and S. Ahmed, Synthesis, Characterization, Molecular Docking Evaluation, Antiplatelet and Anticoagulant Actions of 1,2,4 Triazole Hydrazone and Sulphonamide Novel Derivatives, Chem. Cent. J., 12, 11 (2018); https://doi.org/10.1186/s13065-018-0378-5
  13. V. Velezheva, P. Brennan, P. Ivanov, A. Kornienko, S. Lyubimov, K. Kazarian, B. Nikonenko, K. Majorov and A. Apt, Synthesis and Antituberculosis Activity of Indole-Pyridine Derived Hydrazides, Hydrazide–Hydrazones and Thiosemicarbazones, Bioorg. Med. Chem. Lett., 26, 978 (2016); https://doi.org/10.1016/j.bmcl.2015.12.049
  14. M. Quiliano, A. Pabón, G. Ramirez-Calderon, C. Barea, E. Deharo, S. Galiano and I. Aldana, New Hydrazine and Hydrazide Quinoxaline 1,4-Di-N-Oxide Derivatives: In silico ADMET, Antiplasmodial and Antileishmanial Activity, Bioorg. Med. Chem. Lett., 27, 1820 (2017); https://doi.org/10.1016/j.bmcl.2017.02.049
  15. C.-H. Chao, Y.-J. Lin, J.-C. Cheng, H.-C. Huang, Y.-J. Yeh, T.-S. Wu, S.-Y. Hwang and Y.-C. Wu, Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester, Molecules, 21, 1239 (2016); https://doi.org/10.3390/molecules21091239
  16. S. Veeramanikandan and H.B. Sherine, Synthesis, Characterization and Biological Applications of Substituted Benzohydrazide Derivatives, Der Pharma Chem., 7, 70 (2015).
  17. R. Elancheran, K. Saravanan, B. Choudhury, S. Divakar, B. Das, M. Ramanathan, S. Kabilan, R. Devi and J. Kotoky, Design and Development of Oxobenzimidazoles as Novel Androgen Receptor Antagonists, Med. Chem. Res., 25, 539 (2016); https://doi.org/10.1007/s00044-016-1504-3