Main Article Content
Abstract
A substituted pyrimidine derivatives were synthesized from chalcone of 3-acetyl-2,5-dimethyl thiophene with corresponding active aldehyde in microwave oven. The newly synthesized compounds were characterized by TLC, IR, 1H NMR, 13C NMR spectral analysis. Pyrimidine derivative were screened for their antibacterial activity in vitro by the disk diffusion assay against two Gram-positive and two Gram-negative bacteria and then the minimum inhibitory concentration (MIC) was carried with the reference of standard drugs amoxicillin, ampicillin and ciprofloxacin. The pyrimidine derivatives shows better inhibiting action against both types of bacteria (Gram-positive and Gram-negative) compared to amoxicillin, ampicillin and ciprofloxacin standard drugs.
Keywords
Article Details
References
- T.A. Naik, and K.H. Chikhalia, Studies on Synthesis of Pyrimidine Derivatives and their Pharmacological Evaluation, E-J. Chem., 4, 60 (2007); https://doi.org/10.1155/2007/507590
- M.S. Mohamed, S.M. Awad and A.I. Sayed, Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents, Molecules, 15, 1882 (2010); https://doi.org/10.3390/molecules15031882
- Y.K. Gupta, V. Gupta and S. Singh, Synthesis, Characterization and Antimicrobial Activity of Pyrimidine based Derivatives, J. Pharm. Res., 7, 491 (2013); https://doi.org/10.1016/j.jopr.2013.05.020
- P. Sharma, N. Rane and V.K. Gurram, Synthesis and QSAR Studies of Pyrimido[4,5-d]pyrimidine-2,5-dione Derivatives as Potential Antimicrobial Agents, Bioorg. Med. Chem. Lett., 14, 4185 (2004); https://doi.org/10.1016/j.bmcl.2004.06.014
- S.M. Sondhi, N. Singh, M. Johar and A. Kumar, Synthesis, Anti-inflammatory and Analgesic Activities Evaluation of Some Mono, Bi and Tricyclic Pyrimidine Derivatives, Bioorg. Med. Chem., 13, 6158 (2005); https://doi.org/10.1016/j.bmc.2005.06.063
- K.M. Amin, M.M. Hanna, H.E. Abo-Youssef and R.F. George, Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents, Eur. J. Med. Chem., 15, 1882 (2009). https://doi.org/10.3390/molecules15031882
- N. Ingarsal, G. Saravanan, P. Amutha and S. Nagarajan, Synthesis, in vitro Antibacterial and Antifungal Evaluations of 2-Amino-4-(1-naphthyl)-6-arylpyrimidines, Eur. J. Med. Chem., 42, 517 (2007); https://doi.org/10.1016/j.ejmech.2006.09.012
- X.L. Zhao, Y.F. Zhao, S.C. Guo, H.S. Song, D. Wang and P. Gong, Synthesis and Anti-tumor Activities of Novel [1,2,4]triazolo[1,5-a]-pyrimidines, Molecules, 12, 1136 (2007); https://doi.org/10.3390/12051136
- K. Singh and T. Kaur, Pyrimidine-based Antimalarials: Design Strategies and Antiplasmodial Effects, MedChemComm, 7, 749 (2016); https://doi.org/10.1039/c6md00084c
- S.A.-M. Abdel-Aziz, M.A. Hussein and I.T. Abdel-Raheem, Design, Synthesis and Antidiabetic Activity of Some New 4-amino (or 6-Oxo)-2-methyl/Benzylthio (or Substituted Amino)pyrimidine Derivatives, Bull. Pharm. Sci., Assiut Univ., 34, 149 (2011).
- M. Dumbare, L. Kawale, V. Nade and R. Deshmukh, Thiazolidine-2,4-diones: An Update Review of Antidiabetic Agents, Int. Res. J. Pharm., 8, 12 (2017); https://doi.org/10.7897/2230-8407.0812245
- V.B. Arunlal, K. Byju, K. Vandana, C.R. Biju and G. Babu, Synthesis and Screening of 4,6-Disubstituted Pyrimidine Derivatives as Anti-bacterial Agents, Int. J. Innov. Pharm. Sci. Res., 3, 302 (2015).
- N.E.A. Abd El-Sattar, E.H.K. Badawy and M.S.A. Abdel-Mottaleb, Synthesis of Some Pyrimidine, Pyrazole and Pyridine Derivatives and their Reactivity Descriptors, J. Chem., 2018, 8795061 (2018); https://doi.org/10.1155/2018/8795061
- S.A. Khan, A.M. Asiri, K.A. Alamry, S.A. El-daly and M.A.M. Zayed, Eco-friendly Synthesis and in vitro Antibacterial Activities of Some Novel Chalcones, Russ. J. Bioorg. Chem., 39, 312 (2013); https://doi.org/10.1134/S1068162013030072
- E.H.A. El-All, N.A. Osman, A.M. El-Mahmoudy and A.N. Hassan, Synthesis of New Pyrimidine Derivatives and Evaluation of their Anti-cancer and Antimicrobial Activities, Asian J. Pharm. Clin. Res., 9, 306 (2016).
- S.A. Khan and A.M. Asiri, Green synthesis, Characterization and Biological Evaluation of Novel Chalcones as Antibacterial Agents, Arab. J. Chem., 10(Suppl. 2), S2890 (2017); https://doi.org/10.1016/j.arabjc.2013.11.018
- M. Amerikova, I.P. El-Tibi, V. Maslarska and S. Bozhanov and K. Tachkov, Antimicrobial Activity, Mechanism of Action and Methods for Stabilization of Defensins as New Therapeutic Agents, Biotechnol. Biotechnol. Equip., 33, 671 (2019); https://doi.org/10.1080/13102818.2019.1611385
- B. Jat, S. Santra and P.K. Santra, Synthesis and Evaluation of Anti-microbial Activity of Pyrimidine Derivatives, Asian J. Pharm. Clin. Res., 12, 156 (2019); https://doi.org/10.22159/ajpcr.2019.v12i5.30919
- V. Sharma, N. Chitranshi, and A.K. Agarwal, Significance and Biol-ogical Importance of Pyrimidine in the Microbial World, Int. J. Med. Chem., 2014, 202784 (2014); https://doi.org/10.1155/2014/202784
- M. Balouiri, M. Sadiki and S.K. Ibnsouda, Methods for in vitro Evaluating Antimicrobial Activity: A Review, J. Pharm. Anal., 6, 71 (2016); https://doi.org/10.1016/j.jpha.2015.11.005
- A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Antibiotic Susceptibility Testing by a Standardized Single Disk Method, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
- B. Andrews, K. Komathi, and S. Mohan, Synthesis and Comparing the Antibacterial Activities of Pyrimidine Derivatives, J. Chem. Sci., 129, 335 (2017); https://doi.org/10.1007/s12039-017-1228-z
- A. Solankee, K. Patel, and R. Patel, A Facile Synthesis and Studies of Some New Chalcones and their Derivatives Based on Heterocyclic Ring, E-J. Chem., 9, 1897 (2012); https://doi.org/10.1155/2012/638452
- N. Kaur and D. Kishore, Application of Chalcones in Heterocycles Synthesis: Synthesis of 2-(isoxazolo, Pyrazolo and Pyrimido) Substituted Analogues of 1,4-benzodiazepin-5-carboxamides Linked through an Oxyphenyl Bridge, J. Chem. Sci., 125, 555 (2013).
References
T.A. Naik, and K.H. Chikhalia, Studies on Synthesis of Pyrimidine Derivatives and their Pharmacological Evaluation, E-J. Chem., 4, 60 (2007); https://doi.org/10.1155/2007/507590
M.S. Mohamed, S.M. Awad and A.I. Sayed, Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents, Molecules, 15, 1882 (2010); https://doi.org/10.3390/molecules15031882
Y.K. Gupta, V. Gupta and S. Singh, Synthesis, Characterization and Antimicrobial Activity of Pyrimidine based Derivatives, J. Pharm. Res., 7, 491 (2013); https://doi.org/10.1016/j.jopr.2013.05.020
P. Sharma, N. Rane and V.K. Gurram, Synthesis and QSAR Studies of Pyrimido[4,5-d]pyrimidine-2,5-dione Derivatives as Potential Antimicrobial Agents, Bioorg. Med. Chem. Lett., 14, 4185 (2004); https://doi.org/10.1016/j.bmcl.2004.06.014
S.M. Sondhi, N. Singh, M. Johar and A. Kumar, Synthesis, Anti-inflammatory and Analgesic Activities Evaluation of Some Mono, Bi and Tricyclic Pyrimidine Derivatives, Bioorg. Med. Chem., 13, 6158 (2005); https://doi.org/10.1016/j.bmc.2005.06.063
K.M. Amin, M.M. Hanna, H.E. Abo-Youssef and R.F. George, Synthesis of Certain Pyrimidine Derivatives as Antimicrobial Agents and Anti-Inflammatory Agents, Eur. J. Med. Chem., 15, 1882 (2009). https://doi.org/10.3390/molecules15031882
N. Ingarsal, G. Saravanan, P. Amutha and S. Nagarajan, Synthesis, in vitro Antibacterial and Antifungal Evaluations of 2-Amino-4-(1-naphthyl)-6-arylpyrimidines, Eur. J. Med. Chem., 42, 517 (2007); https://doi.org/10.1016/j.ejmech.2006.09.012
X.L. Zhao, Y.F. Zhao, S.C. Guo, H.S. Song, D. Wang and P. Gong, Synthesis and Anti-tumor Activities of Novel [1,2,4]triazolo[1,5-a]-pyrimidines, Molecules, 12, 1136 (2007); https://doi.org/10.3390/12051136
K. Singh and T. Kaur, Pyrimidine-based Antimalarials: Design Strategies and Antiplasmodial Effects, MedChemComm, 7, 749 (2016); https://doi.org/10.1039/c6md00084c
S.A.-M. Abdel-Aziz, M.A. Hussein and I.T. Abdel-Raheem, Design, Synthesis and Antidiabetic Activity of Some New 4-amino (or 6-Oxo)-2-methyl/Benzylthio (or Substituted Amino)pyrimidine Derivatives, Bull. Pharm. Sci., Assiut Univ., 34, 149 (2011).
M. Dumbare, L. Kawale, V. Nade and R. Deshmukh, Thiazolidine-2,4-diones: An Update Review of Antidiabetic Agents, Int. Res. J. Pharm., 8, 12 (2017); https://doi.org/10.7897/2230-8407.0812245
V.B. Arunlal, K. Byju, K. Vandana, C.R. Biju and G. Babu, Synthesis and Screening of 4,6-Disubstituted Pyrimidine Derivatives as Anti-bacterial Agents, Int. J. Innov. Pharm. Sci. Res., 3, 302 (2015).
N.E.A. Abd El-Sattar, E.H.K. Badawy and M.S.A. Abdel-Mottaleb, Synthesis of Some Pyrimidine, Pyrazole and Pyridine Derivatives and their Reactivity Descriptors, J. Chem., 2018, 8795061 (2018); https://doi.org/10.1155/2018/8795061
S.A. Khan, A.M. Asiri, K.A. Alamry, S.A. El-daly and M.A.M. Zayed, Eco-friendly Synthesis and in vitro Antibacterial Activities of Some Novel Chalcones, Russ. J. Bioorg. Chem., 39, 312 (2013); https://doi.org/10.1134/S1068162013030072
E.H.A. El-All, N.A. Osman, A.M. El-Mahmoudy and A.N. Hassan, Synthesis of New Pyrimidine Derivatives and Evaluation of their Anti-cancer and Antimicrobial Activities, Asian J. Pharm. Clin. Res., 9, 306 (2016).
S.A. Khan and A.M. Asiri, Green synthesis, Characterization and Biological Evaluation of Novel Chalcones as Antibacterial Agents, Arab. J. Chem., 10(Suppl. 2), S2890 (2017); https://doi.org/10.1016/j.arabjc.2013.11.018
M. Amerikova, I.P. El-Tibi, V. Maslarska and S. Bozhanov and K. Tachkov, Antimicrobial Activity, Mechanism of Action and Methods for Stabilization of Defensins as New Therapeutic Agents, Biotechnol. Biotechnol. Equip., 33, 671 (2019); https://doi.org/10.1080/13102818.2019.1611385
B. Jat, S. Santra and P.K. Santra, Synthesis and Evaluation of Anti-microbial Activity of Pyrimidine Derivatives, Asian J. Pharm. Clin. Res., 12, 156 (2019); https://doi.org/10.22159/ajpcr.2019.v12i5.30919
V. Sharma, N. Chitranshi, and A.K. Agarwal, Significance and Biol-ogical Importance of Pyrimidine in the Microbial World, Int. J. Med. Chem., 2014, 202784 (2014); https://doi.org/10.1155/2014/202784
M. Balouiri, M. Sadiki and S.K. Ibnsouda, Methods for in vitro Evaluating Antimicrobial Activity: A Review, J. Pharm. Anal., 6, 71 (2016); https://doi.org/10.1016/j.jpha.2015.11.005
A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Antibiotic Susceptibility Testing by a Standardized Single Disk Method, Am. J. Clin. Pathol., 45, 493 (1966); https://doi.org/10.1093/ajcp/45.4_ts.493
B. Andrews, K. Komathi, and S. Mohan, Synthesis and Comparing the Antibacterial Activities of Pyrimidine Derivatives, J. Chem. Sci., 129, 335 (2017); https://doi.org/10.1007/s12039-017-1228-z
A. Solankee, K. Patel, and R. Patel, A Facile Synthesis and Studies of Some New Chalcones and their Derivatives Based on Heterocyclic Ring, E-J. Chem., 9, 1897 (2012); https://doi.org/10.1155/2012/638452
N. Kaur and D. Kishore, Application of Chalcones in Heterocycles Synthesis: Synthesis of 2-(isoxazolo, Pyrazolo and Pyrimido) Substituted Analogues of 1,4-benzodiazepin-5-carboxamides Linked through an Oxyphenyl Bridge, J. Chem. Sci., 125, 555 (2013).