Synthesis and antibacterial evaluation of fused pyrazoles and Schiff bases

References

• Vardanyan, R. S.; Hruby, V. J. Synthesis of Essential Drugs; Elsevier Science, 2006. pp 425–498 https://www.sciencedirect.com/science/book/9780444521668
   Google Scholar
• Guerrini, G.; Ciciani, G.; Crocetti, L.; Daniele, S.; Ghelardini, C.; Giovannoni, M. P.; Iacovone, A.; Mannelli, L. D.; Martini, C.; Vergelli, C. Identification of a New Pyrazolo[1,5-a] Quinazoline Ligand Highly Affine to γ-Aminobutyric Type A (GABA A ) Receptor Subtype with Anxiolytic-Like and Antihyperalgesic Activity. J. Med. Chem. 2017, 60, 9691–9702. DOI: 10.1021/acs.jmedchem.7b01151.
   PubMed Web of Science ®Google Scholar
• Liu, Y.; Laufer, R.; Patel, N. K.; Ng, G.; Sampson, P. B.; Li, S.-W.; Lang, Y.; Feher, M.; Brokx, R.; Beletskaya, I.; et al. Discovery of Pyrazolo[1,5-a]Pyrimidine TTK Inhibitors: CFI-402257 Is a Potent, Selective, Bioavailable Anticancer Agent. ACS Med. Chem. Lett. 2016, 7, 671–675. DOI: 10.1021/acsmedchemlett.5b00485.
   PubMed Web of Science ®Google Scholar
• Baraldi, P. G.; Manfredini, S.; Romagnoli, R.; Stevanato, L.; Zaid, A. N.; Manservigi, R. Synthesis and Anti-HSV-1 Activity of 6 Substituted Pyrazolo[3,4-d]Pyridazin-7-one. Nucleotides 1998, 17, 2165–2173. DOI: 10.1080/07328319808004307.
   Web of Science ®Google Scholar
• El-Mekabaty, A.; Habib, O. M. O.; Moawad, E. B.; Hasel, A. M. Synthesis and Antioxidant Activity of New Pyrazolo[1,5-a]Pyrimidine Derivatives Incorporating a Thiazol-2-Yldiazenyl Moiety. J. Heterocyclic Chem. 2016, 53, 1820–1826. DOI: 10.1002/jhet.2492.
   Web of Science ®Google Scholar
• Abd El Razik, H. A.; Abdel Wahab, A. E. Synthesis and Biological Evaluation of Some Novel Fused Pyrazolopyrimidines as Potential Anticancer and Antimicrobial Agents. Arch. Pharm. Pharm. Med. Chem. 2011, 344, 184–196. DOI: 10.1002/ardp.201000188.
   PubMed Web of Science ®Google Scholar
• Sindhu, J.; Singh, H.; Khurana, J. M.; Bhardwaj, J. K.; Saraf, P.; Sharma, C. Synthesis and Biological Evaluation of Some Functionalized 1H-1,2,3-Triazole Tethered Pyrazolo[3,4-b]Pyridin-6(7H)-Ones as Antimicrobial and Apoptosis Inducing Agents. Med. Chem. Res. 2016, 25, 1813–1830. DOI: 10.1007/s00044-016-1604-0.
   Web of Science ®Google Scholar
• Gouda, M. A.; Berghot, M. A.; Abd El-Ghani, G. E.; Khalil, A. M. Synthesis and Antimicrobial Activities of Some New Thiazole and Pyrazole Derivatives Based on 4,5,6,7-Tetrahydrobenzothiophene Moiety. Eur. J. Med. Chem. 2010, 45, 1338–1345. DOI: 10.1016/j.ejmech.2009.12.020.
   PubMed Web of Science ®Google Scholar
• Dawane, B. S.; Konda, S. G.; Zangade, S. B. Design, Synthesis, and Characterization of Some Novel Pyrazolo [1,5-a]Pyrimidines as Potent Antimicrobial Agents. J. Heterocyclic Chem. 2010, 47, 1250–1254. DOI: 10.1002/jhet.413.
   Web of Science ®Google Scholar
• Hafez, H. N.; El-Gazzar, A. B. A.; Al-Hussain, S. A. Novel Pyrazole Derivatives with Oxa/Thiadiazolyl, Pyrazolyl Moieties and Pyrazolo[4,3-d]-Pyrimidine Derivatives as Potential Antimicrobial and Anticancer Agents. Bioorg. Med. Chem. Lett. 2016, 26, 2428–2433. DOI: 10.1016/j.bmcl.2016.03.117.
   PubMed Web of Science ®Google Scholar
• Bondock, S.; Rabie, R.; Etman, H. A.; Fadda, A. A. Synthesis and Antimicrobial Activity of Some New Heterocycles Incorporating Antipyrine Moiety. Eur. J. Med. Chem. 2008, 43, 2122–2129. DOI: 10.1016/j.ejmech.2007.12.009.
   PubMed Web of Science ®Google Scholar
• Iftikhar, B.; Javed, K.; Khan, M. S. U.; Akhter, Z.; Mirza, B.; Mckee, V. Synthesis, Characterization and Biological Assay of Salicylaldehyde Schiff Base Cu(II) Complexes and Their Precursors. J. Mol. Struct. 2018, 1155, 337–348. DOI: 10.1016/j.molstruc.2017.11.022.
   Web of Science ®Google Scholar
• Murtaza, G.; Mumtaz, A.; Khan, F. A.; Ahmad, S.; Azhar, S.; Khan, S. A.; Najam-Ul-Haq, M.; Atif, M.; Khan, S. A.; Maalik, A.; et al. Recent Pharmacological Advancements in Schiff Bases: A Review. Acta Pol Pharm 2014, 71, 531–535.,
   PubMed Web of Science ®Google Scholar
• Kumar, K. S.; Ganguly, S.; Veerasamy, R.; De Clercq, E. Synthesis, Antiviral Activity and Cytotoxicity Evaluation of Schiff Bases of Some 2-Phenyl Quinazoline-4(3)H-Ones. Eur. J. Med. Chem. 2010, 45, 5474–5479. DOI: 10.1016/j.ejmech.2010.07.058.
   PubMed Web of Science ®Google Scholar
• Sridevi, C.; Selvaraj, M.; Mani, V.; Mohammad, J. I.; Selvarajan, K. K.; Akhtar, S. S.; Marikannan, M.; Raj, S.; Teh, L. K.; Salleh, M. Z. Synthesis of Azomethines Derived from Cinnamaldehyde and Vanillin: In Vitro Aetylcholinesterase Inhibitory, Antioxidant and Insilico Molecular Docking Studies. Med. Chem. Res. 2018, 27, 807–816.
   Web of Science ®Google Scholar
• Ameri, A.; Khodarahmi, G.; Hassanzadeh, F.; Forootanfar, H.; Hakimelahi, G.-H. Novel Aldimine-Type Schiff Bases of 4-Amino-5-[(3,4,5-Trimethoxyphenyl)Methyl]-1,2,4-Triazole-3-Thione/Thiol: Docking Study, Synthesis, Biological Evaluation, and anti-Tubulin Activity. Arch. Pharm. (Weinheim) 2016, 349, 662–681. DOI: 10.1002/ardp.201600021.
   PubMed Web of Science ®Google Scholar
• Shanty, A. A.; Philip, J. E.; Sneha, E. J.; Kurup, M. R. P.; Balachandran, S.; Mohanan, P. V. Synthesis, Characterization and Biological Studies of Schiff Bases Derived from Heterocyclic Moiety. Bioorg. Chem. 2017, 70, 67–73. DOI: 10.1016/j.bioorg.2016.11.009.
   PubMed Web of Science ®Google Scholar
• da Silva, C. M.; Silva, M. M.; Reis, F. S.; Ruiz, A. T. G.; de Carvalho, J. E.; Santos, J. C. C.; Figueiredo, I. M.; Alves, R. B.; Modolo, L. V.; Fátima, Â. Studies on Free Radical Scavenging, Cancer Cell Antiproliferation, and Calf Thymus DNA Interaction of Schiff Bases. J. Photochem. Photobiol. B, Biol. 2017, 172, 129–138. DOI: 10.1016/j.jphotobiol.2017.05.020.
   PubMed Web of Science ®Google Scholar
• Rahim, F.; Ullah, H.; Taha, M.; Wadood, A.; Javed, M. T.; Rehman, W.; Nawaz, M.; Ashraf, M.; Ali, M.; Sajid, M.; et al. Synthesis and in Vitro Acetylcholinesterase and Butyrylcholinesterase Inhibitory Potential of Hydrazide Based Schiff Bases. Bioorg. Chem. 2016, 68, 30–40. DOI: 10.1016/j.bioorg.2016.07.005.
   PubMed Web of Science ®Google Scholar
• Hassan, A. S.; Awad, H. M.; Magd-El-Din, A. A.; Hafez, T. S. Synthesis and in Vitro Antitumor Evaluation of Novel Schiff Bases. Med. Chem. Res. 2018, 27, 915–927. DOI: 10.1007/s00044-017-2113-5.
   Web of Science ®Google Scholar
• Hassan, A. S.; Mady, M. F.; Awad, H. M.; Hafez, T. S. Synthesis and Antitumor Activity of Some New Pyrazolo[1,5-a]Pyrimidines. Chin. Chem. Lett. 2017, 28, 388–393. DOI: 10.1016/j.cclet.2016.10.022.
   Web of Science ®Google Scholar
• Hassan, A. S.; Hafez, T. S.; Ali, M. M.; Khatab, T. K. Design, synthesis and cytotoxic activity of some new pyrazolines bearing benzofuran and pyrazole moieties. Res. J. Pharm. Biol. Chem. Sci. 2016, 7, 4 7–429. http://www.rjpbcs.com/pdf/2016_7(4)/[60].pdf
   Google Scholar
• Abd El-All, A. S.; Hassan, A. S.; Osman, S. A.; Yosef, H. A. A.; Abdel-Hady, W. H.; El-Hashash, M. A.; Atta-Allah, S. R.; Ali, M. M.; El Rashedy, A. A. Synthesis, Characterization and Biological Evaluation of New Fused Triazine Derivatives Based on 6-Methyl-3-Thioxo-1,2,4-Triazin-5-One. Acta Pol. Pharm. 2016, 73, 79–92.
   PubMed Web of Science ®Google Scholar
• Hassan, A. S.; Hafez, T. S.; Osman, S. A. M.; Ali, M. M. Synthesis and in vitro cytotoxic activity of novel pyrazolo[1,5-a]pyrimidines and related Schiff bases.. Turk. J. Chem. 2015, 39, 1102–1113. DOI: 10.3906/kim-1504-12.
   Web of Science ®Google Scholar
• Hassan, A. S.; Osman, S. A.; Hafez, T. S. 5-Phenyl-2-furaldehyde: Synthesis, Reactions and Biological Activities. Egypt. J. Chem. 2015, 58, 113–139.
   Google Scholar
• Hassan, A. S.; Hafez, T. S. Osman, S. A. Synthesis, characterization, and cyotoxicity of some new 5-aminopyrazole and pyrazolo[1,5-a]pyrimidine derivatives. Sci. Pharm. 2015, 83, 27–39. DOI: 10.3797/scipharm.1409-14.
   PubMedGoogle Scholar
• Osman, S. A.; Mousa, H. A.; Yosef, H. A. A.; Hafez, T. S.; El-Sawy, A. A.; Abdallah, M. M.; Hassan, A. S. Synthesis, Characterization and Cytotoxicity of Mixed Ligand Mn(II), Co(II) and Ni(II) Complexes. J. Serb. Chem. Soc. 2014, 79, 953–964. DOI: 10.2298/JSC130813134O.
   Web of Science ®Google Scholar
• Osman, S. A.; Yosef, H. A. A.; Hafez, T. S.; El-Sawy, A. A.; Mousa, H. A.; Hassan, A. S. Synthesis and antibacterial activity of some novel chalcones, pyrazoline and 3-cyanopyridine derivatives based on khellinone as well as Ni(II), Co(II) and Zn(II) complexes. Aust. J. Basic & Appl. Sci. 2012, 6, 852–863.
   Google Scholar
• Elgemeie, G. H.; Elsayed, S. H.; Hassan, A. S. Design and Synthesis of the First Thiophene Thioglycosides. Synth. Commun. 2009, 39, 1781–1792. DOI: 10.1080/00397910802590928.
   Web of Science ®Google Scholar
• Hassan, A. S.; Masoud, D. M.; Sroor, F. M.; Askar, A. A. Synthesis and Biological Evaluation of Pyrazolo[1,5-a]Pyrimidine-3-Carboxamide as Antimicrobial Agents. Med. Chem. Res. 2017, 26, 2909–2919. DOI: 10.1007/s00044-017-1990-y.
   Web of Science ®Google Scholar
• Hassan, A. S.; Hafez, T. S. J. App. Pharm. Sci. 2018, 8, 156–165.
   Google Scholar
• El-Naggar, M.; Hassan, A. S.; Awad, H. M.; Mady, M. F. Design, Synthesis and Antitumor Evaluation of Novel Pyrazolopyrimidines and Pyrazoloquinazolines. Molecules 2018, 23, 1249. DOI: 10.3390/molecules23061249.
   PubMed Web of Science ®Google Scholar
• Moustafa, G. O.; El-Sawy, A. A.; Abo-Ghalia, M. H. Synthesis of novel cyclopeptide candidates: I-cyclo-[Nα-isophthaloyl-bis-(Glycine-amino acid)-L-lysine] derivatives with expected anticancer activity. Egypt. J. Chem. 2013, 5, 473–494.
   Google Scholar
• Abo-Ghalia, M. H.; Moustafa, G. O.; Alwasidi, A. S.; Naglah, A. M. Cytotoxic Investigation of IsophthaloylCyclopentapeptides. Lat. Am. J. Pharm. 2017, 36, 1957–1962.
   Web of Science ®Google Scholar
• Naglah, A. M.; Moustafa, G. O.; Al-Omar, M. A.; Al-Salem, H. S. A.; Hozzein, W. N. Synthesis, Characterization and in Vitro Antimicrobial Investigation of Novel Amino Acids and Dipeptides Based on Dibenzofuran-2-Sulfonyl-Chloride. J. Comput. Theor. Nanosci. 2017, 14, 3183–3190. DOI: 10.1166/jctn.2017.6613.
   Google Scholar
• Al-Salem, H. S. A.; Naglah, A. M.; Moustafa, G. O.; Mahmoud, A. Z.; Al-Omar, M. A. J. Synthesis of Novel Tripeptides Based on Dibenzofuran-2-Sulfonyl-[Aromatic and Hydroxy Aromatic Residues]: Towards Antimicobial and Antifungal Agents. Comput. Theor. Nanosci. 2017, 14, 3958–3966. DOI: 10.1166/jctn.2017.6702.
   Google Scholar
• Moustafa, G.; Khalaf, H.; Naglah, A.; Al-Wasidi, A.; Al-Jafshar, N.; Awad, H. Synthesis, Molecular Docking Studies, in Vitro Antimicrobial and Antifungal Activities of Novel Dipeptide Derivatives Based on N-(2-(2-Hydrazinyl-2-Oxoethylamino)-2-Oxoethyl)-Nicotinamide. Molecules 2018, 23, 761. DOI: 10.3390/molecules23040761.
   PubMed Web of Science ®Google Scholar
• Elgemeie, G. H.; Elsayed, S. H.; Hassan, A. S. Direct Route to a New Class of Acrylamide Thioglycosides and Their Conversions to Pyrazole Derivatives. Synth. Commun 2008, 38, 2700–2706. DOI: 10.1080/00397910802222605.
   Web of Science ®Google Scholar
• Hafez, T. S.; Osman, S. A.; Yosef, H. A. A.; Abd El-All, A. S.; Hassan, A. S.; El-Sawy, A. A.; Abdallah, M. M.; Youns, M. Synthesis, Structural Elucidation, and in Vitro Antitumor Activities of Some Pyrazolopyrimidines and Schiff Bases Derived from 5-Amino-3-(arylamino)-1H-pyrazole-4-carboxamides. Sci. Pharm. 2013, 81, 339–357. DOI: 10.3797/scipharm.1211-07.
   PubMedGoogle Scholar
• Cambridge Crystallographic Data Center. Crystal data for compound 15b was deposited to the (CCDC 1817564). https://www.ccdc.cam.ac.uk/
   Google Scholar
• Hassan, A. S.; Moustafa, G. O.; Awad, H. M. Synthesis and in vitro anticancer activity of pyrazolo[1,5-a]pyrimidines and pyrazolo[3,4-d][1,2,3]triazines. Synth. Commun. 2017, 47, 1963–1972. DOI: 10.1080/00397911.2017.1358368.
   Web of Science ®Google Scholar
• Cappuccino, J. G.; Sherman, N. New Delhi; Pearson Education, Inc.: India, 2004. pp 282–283
   Google Scholar
• Cooper, K. The theory of antibiotic inhibition zones. Analytical microbiology. Academic press: New York and London, 1963; pp 1–85.
   Google Scholar