Article Sidebar

Download
PDF

Main Article Content

Abstract

Herein, the conventional method used for β-blocker synthesis is initiated by refluxing biphenyl-2-ol (1) with an epoxy ring (2) in the presence of K2CO3 to obtain 2-[(biphenyl-2-yloxy)methyl]oxirane (3). Compound (3) was then reacted with 99% isopropylamine (4) and various substituted phenols (6a-i) to form 1-(biphenyl-2-yloxy)-3-(propan-2-ylamino)propan-2-ol (5) and 1-(2,6-dimethyl-/4-methoxy-/4-chloro-3-hydroxy-/2,6-dimethoxy-/3,4-dimethyl-/4-amine-/4-bromo/3,4-dinitro-/2,4-dihydroxyphenoxy)-3-(biphenyl-2-yloxy)-propan-2-ols (7a-i), respectively. The synthesized compounds were analyzed by 1H NMR and FTIR spectroscopy to determine their structure and also evaluated for their antifungal activity against Rhizoctonia solani and Aspergillus niger using the food poison technique. From the activity data, it was found that compound 1-(biphenyl-2-yloxy)-3-(propan-2-ylamino)-propan-2-ol (5) was most active against both the fungi Rhizoctonia solani and Aspergillus niger. The antibacterial activity was also determined against Bacillus species by zone of inhibition method. The compounds (5, 7a-i) were also evaluated for its herbicidal activity.

Keywords

Propranolol β-Blockers Antifungal activity Herbicidal activity Antibacterial activity.

Article Details

License

Copyright (c) 2022 Asian Journal of Organic & Medicinal Chemistry

Creative Commons License

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

How to Cite
Sihag, S., Devi, P., Singh, R., & Singh, S. (2022). Synthesis, Characterization and Bioactivity of Propranolol and it’s Derivatives. Asian Journal of Organic & Medicinal Chemistry, 7(1), 92–98. https://doi.org/10.14233/ajomc.2022.AJOMC-P368
Download Citation
Endnote/Zotero/Mendeley (RIS)
BibTeX

References

  1. K.K. Sivakumar, A. Rajasekaran, I. Ponnilavarasan, A. Somasundaram and S. Kamalaveni, Synthesis and Evaluation of Antimicrobial and Analgesic Activity of Some (4Z)-3-Methyl-1-[(2-oxo-2H-chromen-4-yl)carbonyl]-1H-pyrazole-4,5-dione 4-[(4-substituted phenyl)- hydrazone], Der Pharm. Lett., 2, 211 (2010).
  2. T. Seki, T. Takezaki, R. Ohuchi, H. Ohuyabu, T. Ishimori and K. Yasuda, Studies on Agents with Vasodilator and ß-Blocking Activities. I, Chem. Pharm. Bull. (Tokyo), 42, 1609 (1994); https://doi.org/10.1248/cpb.42.1609
  3. S.M. Abdel Wahab, H.A. Almetaher, H. Fayad and E.A. Elhalaby, Oral versus Topical Propranolol for Management of Superficial Infantile Hemangiomas: A Comparative Study, Ann. Pediatr. Surg., 13, 1 (2017); https://doi.org/10.1097/01.XPS.0000482654.21247.63
  4. G. Bhandari, An Overview of Agrochemicals and their Effects on the Environment in Nepal, Appl. Ecol. Environ. Sci., 2, 66 (2014); https://doi.org/10.5958/2230-732X.2017.00083.3
  5. F.P. Carvalho, Pesticides, Environment, and Food Safety, Food Energy Secur., 6, 48 (2017); https://doi.org/10.1002/fes3.108
  6. M.S. Saini, A. Kumar, J. Dwivedi and R. Singh, A Review: Biological Significances of Heterocyclic Compounds, Int. J. Pharm. Sci. Res., 4, 66 (2013).
  7. M. Decker, A. Konig, E. Glusa and J. Lehmann, Synthesis and Vasorelaxant Properties of Hybrid Molecules out of NO-Donors and the b-Receptor Blocking Drug Propranolol, Bioorg. Med. Chem. Lett., 14, 4995 (2004); https://doi.org/10.1016/j.bmcl.2004.07.014
  8. M. Gao, M. Wang, K.D. Miller and Q.H. Zheng, Synthesis and Preliminary in vitro Biological Evaluation of New Carbon-11-Labeled Celecoxib Derivatives as Candidate PET Tracers for Imaging of COX-2 Expression in Cancer, Eur. J. Med. Chem., 46, 4760 (2011); https://doi.org/10.1016/j.ejmech.2011.05.024
  9. H.H. Thornberg, Phytopathology, 44, 419 (1959).
  10. R.K. Grover and J.D. Moore, Toximetric Studies of Fungicides against the Brown Rot Organisms, Sclerotinia fructicola and S. laxa, Phytopathology, 52, 876 (1962).
  11. J. Tuite, Plant Pathological Methods. Fungi Bacteria, Burgess Publishing Company: Minneapolis, Minnesota. USA, pp 239 (1969).
  12. F.M. Lagos, C. Del Campo, E.F. Llama and J.V. Sinisterra, New Yeast Strains for Enantioselective Production of Halohydrin Precursor of (S)-Propranolol, Enzyme Microb. Technol., 30, 895 (2002); https://doi.org/10.1016/S0141-0229(02)00023-6
  13. R. Inkum, A. Teerawntgulrag, P. Puangsombat and R. Nuansri, An Alternative Synthesis of (+)-Propranolol and (+)-Atenolol, Maejo Int. J. Sci., 6, 372 (2012).
  14. A. Kamal, M. Sandbhor and A.A. Shaik, Chemoenzymatic Synthesis of (S) and (R)-Propranolol and Sotalol Employing One-Pot Lipase Resolution Protocol, Bioorg. Med. Chem. Lett., 14, 4581 (2004); https://doi.org/10.1016/j.bmcl.2004.05.084
  15. H. Eshghi and H.P. Yazdi, A Facile Synthesis of (S)-(-)-Propranolol, J. Sci, I.R. Iran, 14, 17 (2003).
  16. L.S. Engel, H. Checkoway, M.C. Keifer, N.S. Seixas, W.T. Longstreth Jr., K.C. Scott, K. Hudnell, W.K. Anger and R. Camiciolni, Parkinsonism and Occupational Exposure to Pesticides, Occup. Environ. Med., 58, 582 (2001); https://doi.org/10.1136/oem.58.9.582