Main Article Content
Abstract
Some novel derivatives of 2,2′-(4,4′-(((4-(3-oxomorpholino)phenyl)-azanediyl)-bis(methylene))bis(1H-1,2,3-triazole-4,1-diyl))bis(N-(4-phenyl-pyrimidin-2-yl)acetamide) have been synthesized from 4-(4-aminophenyl)morpholin-3-one molecule by multistep process. The structures of all the synthesized compounds were established by different spectroscopic techniques such as 1H NMR, infrared and mass. The antimicrobial activity of these pyrimidine-triazole derivatives were also investigated against selected bacterial and fungal strains in two different organic solvents (N,N-dimethyl formamide and dimethyl sulphoxide).
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References
- N. Kerru, L. Gummidi, S. Maddila, K. Gangu and S.B. Jonnalagadda, A Review on Recent Advances in Nitrogen-Containing Molecules and their Biological Applications, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
- T. Qadir, A. Amin, P.K. Sharma, I. Jeelani and H. Abe, A Review on Medicinally Important Heterocyclic Compounds, The Open Med. Chem. J., 16, 1 (2022); https://doi.org/10.2174/18741045-v16-e2202280
- M.M. Heravi and V. Zadsirjan, Prescribed Drugs containing Nitrogen Heterocycles: An Overview, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
- F. Gao, T. Wang, J. Xiao and G. Huang, Antibacterial Activity Study of 1,2,4-Triazole Derivatives, Eur. J. Med. Chem., 173, 274 (2019); https://doi.org/10.1016/j.ejmech.2019.04.043
- M. Ellouz, N.K. Sebbar, I. Fichtali, Y. Ouzidan, Z. Mennane, R. Charof, J.T. Mague, M. Urrutigoïty and E.M. Essassi, Synthesis and Anti-bacterial Activity of New 1,2,3-Triazolylmethyl-2H-1,4-benzothiazin-3(4H)-one Derivatives, Chem. Cent. J., 12, 123 (2018); https://doi.org/10.1186/s13065-018-0494-2
- T. Ni, L. Pang, Z. Cai, F. Xie, Z. Ding, Y. Hao, R. Li, S. Yu, X. Chai, T. Wang and Y. Jin Design, Synthesis, and in vitro Antifungal Evaluation of Novel Triazole Derivatives bearing Alkynyl Side Chains, J. Saudi Chem. Soc., 23, 576 (2019); https://doi.org/10.1016/j.jscs.2018.10.003
- Z. Rezaei, S. K. K. Pakshir, Z. Hossaini, F. Amiri and E. Assadpour, Design, Synthesis, and Antifungal Activity of Triazole and Benzotriazole Derivatives, Eur. J. Med. Chem., 44, 3064 (2009); https://doi.org/10.1016/j.ejmech.2008.07.012
- X.M. Chu, C. Wang, W.L. Wang, L.L. Liang, W. Liu, K.K. Gong and K.L. Sun, Triazole derivatives and their antiplasmodial and antimalarial activities. Eur. J. Med. Chem., 166, 206 (2019); https://doi.org/10.1016/j.ejmech.2019.01.047
- H.H. Klnfe and Y.H. Belay, Synthesis and Biological Evaluation of Novel Thiosemicarbazone–Triazole Hybrid Compounds Antimalarial Agents, S. Afr. J. Chem., 66, 130 (2013).
- G.V. Suresh Kumar, Y. Rajendraprasad, B.P. Mallikarjuna, S.M. Chandrashekar and C. Kistayya, Synthesis of Some Novel 2-Substituted-5-[isopropylthiazole] Cubbed 1,2,4-Triazole and 1,3,4-Oxadiazoles as Potential Antimicrobial and Antitubercular Agents, Eur. J. Med. Chem., 45, 2063 (2010); https://doi.org/10.1016/j.ejmech.2010.01.045
- R.S. Upadhayaya, G.M. Kulkarni, N.R. Vasireddy, J.K. Vandavasi, S.S. Dixit, V. Sharma and J. Chattopadhyaya, Design, Synthesis and Biological Evaluation of Novel Triazole, Urea and Thiourea Derivatives of Quinoline against Mycobacterium tuberculosis, Bioorg. Med. Chem., 17, 4681 (2009); https://doi.org/10.1016/j.bmc.2009.04.069
- G.R. Jadhav, M.U. Shaikh, R.P. Kale, M.R. Shiradkar and C.H. Gill, SAR Study of Clubbed [1,2,4]-Triazolyl with Fluorobenzimidazoles as Antimicrobial and Antituberculosis Agents, Eur. J. Med. Chem., 44, 2930 (2009); https://doi.org/10.1016/j.ejmech.2008.12.001
- A.H. Banday, S.A. Shameem, B.D. Gupta and H.M.S. Kumar, D-ring Substituted 1,2,3-Triazolyl 20-Keto Pregnenanes as Potential Anticancer Agents: Synthesis and Biological Evaluation, Steroids, 75, 801 (2010); https://doi.org/10.1016/j.steroids.2010.02.015
- D.A. Ibrahim, Synthesis and Biological Evaluation of 3,6-Disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives as a Novel Class of Potential Anti-tumor Agents, Eur. J. Med. Chem., 44, 2776 (2009); https://doi.org/10.1016/j.ejmech.2009.01.003
- H. Yuksek, S. Kolayli, M. Kucuk, M.O. Yuksek, Ocak, S. Ummuhan, S. Esra, E. Sivrikaya and M. Ocak, Synthesis and Antioxidant Activities of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Indian J. Chem., 45B, 715 (2006).
- S. Hussain, J. Sharma and M. Amir, Synthesis and Antimicrobial Activities of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives of 5-Amino-2-Hydroxybenzoic Acid, E-J. Chem., 5, 963 (2008); https://doi.org/10.1155/2008/924734
- Y.G. Sameliuk, F.A. Zedan and M. Tetyana, 1,2,4-Triazole Derivatives in Medicine and Pharmacy and Application Prospects, Ankara Üniv. Eczacilik Fakul. Derg., 45, 598 (2021); https://doi.org/10.33483/jfpau.885888
- K.N. Mohana, B.N. Prasanna Kumar and L. Mallesha, Synthesis and Biological Activity of Some Pyrimidine Derivatives, Drug Inven. Today, 5, 216 (2013); https://doi.org/10.1016/j.dit.2013.08.004
- S.B. Patil, Biological and Medicinal Significance of Pyrimidines: A Review, Int. J. Pharm. Sci. Res., 9, 44 (2018); https://doi.org/10.13040/IJPSR.0975-8232.9(1).44-52
- V. Sharma, N. Chitranshi and A.K. Agarwal, Significance and Biological Importance of Pyrimidine in the Microbial World, Int. J. Med. Chem., 2014, 202784 (2014); https://doi.org/10.1155/2014/202784
- R. Sahu, S. Kumar, R.P. Aharwal and S.S. Sandhu, Antibacterial Activity of Isolated Endophytic Fungi from Rauvolfia serpentina (L.) benth. ex kurz, Int. J. Pharm. Pharm. Sci., 8, 38 (2016); https://doi.org/10.22159/ijpps.2016v8i11.9733
- A.A.M. El-Reedy and N.K. Soliman, Synthesis, Biological Activity and Molecular Modeling Study of Novel 1,2,4-Triazolo[4,3-b][1,2,4,5]-tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines, Sci. Rep., 10, 6137 (2020); https://doi.org/10.1038/s41598-020-62977-x
References
N. Kerru, L. Gummidi, S. Maddila, K. Gangu and S.B. Jonnalagadda, A Review on Recent Advances in Nitrogen-Containing Molecules and their Biological Applications, Molecules, 25, 1909 (2020); https://doi.org/10.3390/molecules25081909
T. Qadir, A. Amin, P.K. Sharma, I. Jeelani and H. Abe, A Review on Medicinally Important Heterocyclic Compounds, The Open Med. Chem. J., 16, 1 (2022); https://doi.org/10.2174/18741045-v16-e2202280
M.M. Heravi and V. Zadsirjan, Prescribed Drugs containing Nitrogen Heterocycles: An Overview, RSC Adv., 10, 44247 (2020); https://doi.org/10.1039/D0RA09198G
F. Gao, T. Wang, J. Xiao and G. Huang, Antibacterial Activity Study of 1,2,4-Triazole Derivatives, Eur. J. Med. Chem., 173, 274 (2019); https://doi.org/10.1016/j.ejmech.2019.04.043
M. Ellouz, N.K. Sebbar, I. Fichtali, Y. Ouzidan, Z. Mennane, R. Charof, J.T. Mague, M. Urrutigoïty and E.M. Essassi, Synthesis and Anti-bacterial Activity of New 1,2,3-Triazolylmethyl-2H-1,4-benzothiazin-3(4H)-one Derivatives, Chem. Cent. J., 12, 123 (2018); https://doi.org/10.1186/s13065-018-0494-2
T. Ni, L. Pang, Z. Cai, F. Xie, Z. Ding, Y. Hao, R. Li, S. Yu, X. Chai, T. Wang and Y. Jin Design, Synthesis, and in vitro Antifungal Evaluation of Novel Triazole Derivatives bearing Alkynyl Side Chains, J. Saudi Chem. Soc., 23, 576 (2019); https://doi.org/10.1016/j.jscs.2018.10.003
Z. Rezaei, S. K. K. Pakshir, Z. Hossaini, F. Amiri and E. Assadpour, Design, Synthesis, and Antifungal Activity of Triazole and Benzotriazole Derivatives, Eur. J. Med. Chem., 44, 3064 (2009); https://doi.org/10.1016/j.ejmech.2008.07.012
X.M. Chu, C. Wang, W.L. Wang, L.L. Liang, W. Liu, K.K. Gong and K.L. Sun, Triazole derivatives and their antiplasmodial and antimalarial activities. Eur. J. Med. Chem., 166, 206 (2019); https://doi.org/10.1016/j.ejmech.2019.01.047
H.H. Klnfe and Y.H. Belay, Synthesis and Biological Evaluation of Novel Thiosemicarbazone–Triazole Hybrid Compounds Antimalarial Agents, S. Afr. J. Chem., 66, 130 (2013).
G.V. Suresh Kumar, Y. Rajendraprasad, B.P. Mallikarjuna, S.M. Chandrashekar and C. Kistayya, Synthesis of Some Novel 2-Substituted-5-[isopropylthiazole] Cubbed 1,2,4-Triazole and 1,3,4-Oxadiazoles as Potential Antimicrobial and Antitubercular Agents, Eur. J. Med. Chem., 45, 2063 (2010); https://doi.org/10.1016/j.ejmech.2010.01.045
R.S. Upadhayaya, G.M. Kulkarni, N.R. Vasireddy, J.K. Vandavasi, S.S. Dixit, V. Sharma and J. Chattopadhyaya, Design, Synthesis and Biological Evaluation of Novel Triazole, Urea and Thiourea Derivatives of Quinoline against Mycobacterium tuberculosis, Bioorg. Med. Chem., 17, 4681 (2009); https://doi.org/10.1016/j.bmc.2009.04.069
G.R. Jadhav, M.U. Shaikh, R.P. Kale, M.R. Shiradkar and C.H. Gill, SAR Study of Clubbed [1,2,4]-Triazolyl with Fluorobenzimidazoles as Antimicrobial and Antituberculosis Agents, Eur. J. Med. Chem., 44, 2930 (2009); https://doi.org/10.1016/j.ejmech.2008.12.001
A.H. Banday, S.A. Shameem, B.D. Gupta and H.M.S. Kumar, D-ring Substituted 1,2,3-Triazolyl 20-Keto Pregnenanes as Potential Anticancer Agents: Synthesis and Biological Evaluation, Steroids, 75, 801 (2010); https://doi.org/10.1016/j.steroids.2010.02.015
D.A. Ibrahim, Synthesis and Biological Evaluation of 3,6-Disubstituted [1,2,4]triazolo[3,4-b][1,3,4]thiadiazole Derivatives as a Novel Class of Potential Anti-tumor Agents, Eur. J. Med. Chem., 44, 2776 (2009); https://doi.org/10.1016/j.ejmech.2009.01.003
H. Yuksek, S. Kolayli, M. Kucuk, M.O. Yuksek, Ocak, S. Ummuhan, S. Esra, E. Sivrikaya and M. Ocak, Synthesis and Antioxidant Activities of Some 4-Benzylidenamino-4,5-dihydro-1H-1,2,4-triazol-5-one Derivatives, Indian J. Chem., 45B, 715 (2006).
S. Hussain, J. Sharma and M. Amir, Synthesis and Antimicrobial Activities of 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives of 5-Amino-2-Hydroxybenzoic Acid, E-J. Chem., 5, 963 (2008); https://doi.org/10.1155/2008/924734
Y.G. Sameliuk, F.A. Zedan and M. Tetyana, 1,2,4-Triazole Derivatives in Medicine and Pharmacy and Application Prospects, Ankara Üniv. Eczacilik Fakul. Derg., 45, 598 (2021); https://doi.org/10.33483/jfpau.885888
K.N. Mohana, B.N. Prasanna Kumar and L. Mallesha, Synthesis and Biological Activity of Some Pyrimidine Derivatives, Drug Inven. Today, 5, 216 (2013); https://doi.org/10.1016/j.dit.2013.08.004
S.B. Patil, Biological and Medicinal Significance of Pyrimidines: A Review, Int. J. Pharm. Sci. Res., 9, 44 (2018); https://doi.org/10.13040/IJPSR.0975-8232.9(1).44-52
V. Sharma, N. Chitranshi and A.K. Agarwal, Significance and Biological Importance of Pyrimidine in the Microbial World, Int. J. Med. Chem., 2014, 202784 (2014); https://doi.org/10.1155/2014/202784
R. Sahu, S. Kumar, R.P. Aharwal and S.S. Sandhu, Antibacterial Activity of Isolated Endophytic Fungi from Rauvolfia serpentina (L.) benth. ex kurz, Int. J. Pharm. Pharm. Sci., 8, 38 (2016); https://doi.org/10.22159/ijpps.2016v8i11.9733
A.A.M. El-Reedy and N.K. Soliman, Synthesis, Biological Activity and Molecular Modeling Study of Novel 1,2,4-Triazolo[4,3-b][1,2,4,5]-tetrazines and 1,2,4-triazolo[4,3-b][1,2,4]triazines, Sci. Rep., 10, 6137 (2020); https://doi.org/10.1038/s41598-020-62977-x