Main Article Content
Abstract
The conventional method used for β-blocker synthesis was 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 obtain 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 purity of the synthesized compounds was confirmed by melting point and thin layer chromatography. The synthesized compounds were analyzed by 1H NMR and FTIR spectroscopy to determine their structure. These compounds were 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 fungi R. solani and A. niger. Antibacterial activity was also determined against Bacillus species by zone of inhibition method. Compounds 5 and 7a-i were also evaluated for its herbicide activity.
Keywords
Article Details
This work is licensed under a Creative Commons Attribution 4.0 International License.
References
- G. Bhandari, An Overview of Agrochemicals and Their Effects on Environment in Nepal, Appl. Ecol. Environ. Sci., 2, 66 (2014).
- F.P. Carvalho, Pesticides, Environment and Food Safety, Food Energy Secur., 6, 48 (2017); https://doi.org/10.1002/fes3.108
- M. Decker, A. Konig, E. Glusa and J. Lehmann, Synthesis and Vasorelaxant Properties of Hybrid Molecules Out of NO-Donors and The β-receptor Blocking Drug Propranolol, Bioorg. Med. Chem. Lett., 14, 4995 (2004); https://doi.org/10.1016/j.bmcl.2004.07.014
- 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
- H. Eshghi and H.P. Yazdi, A Facile Synthesis of (S)–(-)–Propranolol, J. Sci., Islamic Republic of Iran, 14, 17 (2003).
- 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
- 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).
- R. Inkum, A. Teerawntgulrag, P. Puangsombat and R. Nuansri, Bioconversion of Biomass Residue from the Cultivation of Pea Sprouts on Spent Pleurotus sajor-caju Compost employing Lumbricus rubellus, Maejo Int. J. Sci., 6, 372 (2012).
- 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
- 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
- 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).
- 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., 42, 1609 (1994); https://doi.org/10.1248/cpb.42.1609
- 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-substitutedphenyl)hydrazone], Der Pharm. Lett., 2, 211 (2010).
- H.H. Thornberg, A Paper Disc Plate Method for the Quantitative Evaluation of Fungicides and Bactericides, Phytopathology, 44, 419 (1959).
- J. Tuite, Plant Pathological Methods. In: Fungi Bacteria, Burgess Publishing Company: Minneapolis, Minnesota, USA, p. 239 (1969).
- 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
References
G. Bhandari, An Overview of Agrochemicals and Their Effects on Environment in Nepal, Appl. Ecol. Environ. Sci., 2, 66 (2014).
F.P. Carvalho, Pesticides, Environment and Food Safety, Food Energy Secur., 6, 48 (2017); https://doi.org/10.1002/fes3.108
M. Decker, A. Konig, E. Glusa and J. Lehmann, Synthesis and Vasorelaxant Properties of Hybrid Molecules Out of NO-Donors and The β-receptor Blocking Drug Propranolol, Bioorg. Med. Chem. Lett., 14, 4995 (2004); https://doi.org/10.1016/j.bmcl.2004.07.014
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
H. Eshghi and H.P. Yazdi, A Facile Synthesis of (S)–(-)–Propranolol, J. Sci., Islamic Republic of Iran, 14, 17 (2003).
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
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).
R. Inkum, A. Teerawntgulrag, P. Puangsombat and R. Nuansri, Bioconversion of Biomass Residue from the Cultivation of Pea Sprouts on Spent Pleurotus sajor-caju Compost employing Lumbricus rubellus, Maejo Int. J. Sci., 6, 372 (2012).
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
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
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).
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., 42, 1609 (1994); https://doi.org/10.1248/cpb.42.1609
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-substitutedphenyl)hydrazone], Der Pharm. Lett., 2, 211 (2010).
H.H. Thornberg, A Paper Disc Plate Method for the Quantitative Evaluation of Fungicides and Bactericides, Phytopathology, 44, 419 (1959).
J. Tuite, Plant Pathological Methods. In: Fungi Bacteria, Burgess Publishing Company: Minneapolis, Minnesota, USA, p. 239 (1969).
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