Main Article Content
Abstract
A series of tetracyclic thiazepine based pyrazoles (6a-j) have been synthesized and evaluated for antibacterial and antifungal activities. The newly synthesized compounds have been characterized by IR, 1H & 13C NMR, mass and elemental analyses. Compounds 6b (2-OCH3) and 6c (4-OCH3) have shown promising antibacterial, and 6g (3-NO2), 6f (2-NO2) and 6d (3,4-diOCH3) exhibited excellent an antifungal activity against standard drugs.
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References
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References
A.K. Singh, Synthesis and Antimicrobial Activity of Azepine Analogue of Lignan, J. Nep. Chem. Soc., 29, 44 (2013); https://doi.org/10.3126/jncs.v29i0.9236
N.A. El-Sayed, F.M. Awadallah, N.A. Ibrahim and M.T. El-Saadi, Synthesis, Anti-inflammatory and Ulcerogenicity Studies of Some Substituted Pyrimido[1,6-a]azepine Derivatives, Eur. J. Med. Chem., 45, 3147 (2010); https://doi.org/10.1016/j.ejmech.2010.04.005
W.B. Zhang, R.B. Han, W. Zhang, R.S. Jiang and F.Y. Piao, Synthesis and Anticonvulsant Activity of 8-Alkoxy-5,6-dihydro-4H-benzo[f]-[1,2,4]triazolo[4,3-a]azepine Derivatives, Med. Chem. Res., 21, 2587 (2012); https://doi.org/10.1007/s00044-011-9771-5
H. Turner, Spiroindolone NITD609 is a Novel Antimalarial Drug that Targets the P-type ATPase PfATP4, Future Med. Chem., 8, 227 (2016); https://doi.org/10.4155/fmc.15.177
A.K. Ghosh and D.D. Anderson, Tetrahydrofuran, Tetrahydropyran, Triazoles and Related Heterocyclic Derivatives as HIV-Protease Inhibitors, Future Med. Chem., 3, 1181 (2011); https://doi.org/10.4155/fmc.11.68
X. Pan, L. Tao, M. Ji, X. Chen and Z. Liu, Synthesis and SAR of Novel Capsazepine Analogs with Significant Anti-cancer Effects in Multiple Cancer Types, Bioorg. Med. Chem. Lett., 28, 866 (2018); https://doi.org/10.1016/j.bmcl.2018.02.004
J. De La Chapa, M. Valdez, F. Ruiz III, K. Gonzales, W. Mitchell, S.F. McHardy, M. Hart, S.R. Polusani and C.B. Gonzales, Bioorg. Med. Chem., 27, 208 (2019); https://doi.org/10.1016/j.bmc.2018.11.040
N. Kaur, N. Ahlawat, P. Bhardwaj, Y. Verma, P. Grewal and N.K. Jangid, Synthesis of Five-Membered N-Heterocycles using Rh Based Metal Catalysts, Synth. Commun., 50, 137 (2020); https://doi.org/10.1080/00397911.2019.1689271
U. Sharma, G.E. Cozier, E.D. Sturrock and K.R. Acharya, Molecular Basis for Omapatrilat and Sampatrilat Binding to Neprilysin-Implications for Dual Inhibitor Design with Angiotensin-Converting Enzyme, J. Med. Chem., 63, 5488 (2020); https://doi.org/10.1021/acs.jmedchem.0c00441
S. Kiyonaka, K. Kato, M. Nishida, K. Mio, T. Numaga, Y. Sawaguchi, T. Yoshida, M. Wakamori, E. Mori, T. Numata, M. Ishii, H. Takemoto, A. Ojida, K. Watanabe, A. Uemura, H. Kurose, T. Morii, T. Kobayashi, Y. Sato, C. Sato, I. Hamachi and Y. Mori, Selective and Direct Inhibition of TRPC3 Channels Underlies Biological Activities of a Pyrazole Compound, Proc. Natl. Acad. Sci. USA, 106, 5400 (2009); https://doi.org/10.1073/pnas.0808793106
M. Song, B. Liu, S. Yu, S. He, Y. Liang, S. Li, Q. Chen and X. Deng, New Hydrazone Derivatives of Pyrazole-4-carboxaldehydes Exhibited Anti-inflammatory Properties, Lett. Drug Des. Discov., 17, 502 (2020); https://doi.org/10.2174/1570180816666190731113441
Z. Yang, P. Li and X. Gan, Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity, Molecules, 23, 1798 (2018); https://doi.org/10.3390/molecules23071798
V. Alagarsamy and G. Saravanan, Synthesis and Anticonvulsant Activity of Novel Quinazolin-4(3H)-one Derived Pyrazole Analogs, Med. Chem. Res., 22, 1711 (2013); https://doi.org/10.1007/s00044-012-0169-9
S.A. Galal, A.S. Abdelsamie, S.A. Shouman, Y.M. Attia, H.I. Ali, A. Tabll, R. El-Shenawy, Y.S. El Abd, M.M. Ali, A.E. Mahmoud, A.H. Abdel-Halim, A.A. Fyiad, A.S. Girgis and H.I. El-Diwani, Part I: Design, Synthesis and Biological Evaluation of Novel Pyrazole-Benzimidazole Conjugates as Checkpoint Kinase 2 (Chk2) Inhibitors with Studying their Activities alone and in Combination with Genotoxic Drugs, Eur. J. Med. Chem., 134, 392 (2017); https://doi.org/10.1016/j.ejmech.2017.03.090
A. Messore, A. Corona, V.N. Madia, F. Saccoliti, V. Tudino, A. De Leo, L. Scipione, D. De Vita, G. Amendola, S. Di Maro, E. Novellino, S. Cosconati, M. Métifiot, M.-L. Andreola, P. Valenti, F. Esposito, N. Grandi, E. Tramontano, R. Costi and R. Di Santo, Pyrrolyl Pyrazoles as Non-Diketo Acid Inhibitors of the HIV-1 Ribonuclease H Function of Reverse Transcriptase, ACS Med. Chem. Lett., 11, 798 (2020); https://doi.org/10.1021/acsmedchemlett.9b00617
K.M. Pandya, A.H. Patel and P.S. Desai, Development of Antimicrobial, Antimalarial and Antitubercular Compounds Based on a Quinoline-Pyrazole Clubbed Scaffold Derived via Doebner Reaction, Chem. Afr., 3, 89 (2020); https://doi.org/10.1007/s42250-019-00096-5
A. Titi, M. Messali, B.A. Alqurashy, R. Touzani, T. Shiga, H. Oshio, M. Fettouhi, M. Rajabi, F.A. Almalki and T. Ben Hadda, Synthesis, Characterization, X-Ray Crystal Study and Bioctivities of Pyrazole Derivatives: Identification of Antitumor, Antifungal and Antibacterial Pharmacophore Sites, J. Mol. Struct., 1205, 127625 (2020); https://doi.org/10.1016/j.molstruc.2019.127625
W.A. Fadaly, Y.A. Elshaier, E.H. Hassanein and K.R. Abdellatif, New 1,2,4-Triazole/Pyrazole Hybrids Linked to Oxime Moiety as Nitric Oxide Donor Celecoxib Analogs: Synthesis, Cyclooxygenase Inhibition Anti-Inflammatory, Ulcerogenicity, Anti-proliferative Activities, Apoptosis, Molecular Modeling and Nitric Oxide Release Studies, Bioorg. Chem., 98, 103752 (2020); https://doi.org/10.1016/j.bioorg.2020.103752
K.R. Abdellatif, W.A. Fadaly, Y.A. Elshaier, W.A. Ali and G.M. Kamel, Non-Acidic 1,3,4-Trisubstituted-Pyrazole Derivatives as Lonazolac Analogs with Promising COX-2 Selectivity, Anti-inflammatory Activity and Gastric Safety Profile, Bioorg. Chem., 77, 568 (2018); https://doi.org/10.1016/j.bioorg.2018.02.018
J.B. Hirani, M.K. Pandya and S.B. Koradiya, Synthesis of Diverse Fused Tetracyclic Thiazepine-Chalcone Derivatives by Claisen-Schmidt Condensation Reaction and their Antimicrobial Activity, Asian J. Chem., 32, 2860 (2020: https://doi.org/10.14233/ajchem.2020.22867
A.L. Banty, The Antimicrobial Susceptibility test. Illus lea and Febiger, Philadelphia, USA, p. 180 (1976).
H.W. Seeley, P.J. Vandemark and P.J. van Demark, Microbes in Action: A Laboratory Manual of Microbiology (1970).