Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 53, 2023 - Issue 3
258
Views
8
CrossRef citations to date
0
Altmetric
Articles

One-pot synthesis and antibacterial screening of new (nicotinonitrile-thiazole)-based mono- and bis(Schiff bases) linked to arene units

, ORCID Icon & ORCID Icon
Pages 245-261 | Received 25 Aug 2022, Published online: 02 Jan 2023

References

  • Sanad, S. M. H.; Ahmed, A. A. M.; Mekky, A. E. M. Synthesis, In-Vitro and In-Silico Study of Novel Thiazoles as Potent Antibacterial Agents and MurB Inhibitors. Arch. Pharm. 2020, 353, e1900309. DOI: 10.1002/ardp.201900309.
  • Laxminarayan, R.; Duse, A.; Wattal, C.; Zaidi, A. K. M.; Wertheim, H. F. L.; Sumpradit, N.; Vlieghe, E.; Hara, G. L.; Gould, I. M.; Goossens, H.; et al. Antibiotic Resistance-the Need for Global Solutions. Lancet Infect. Dis. 2013, 13, 1057–1098. DOI: 10.1016/S1473-3099(13)70318-9.
  • Antimicrobial resistance. https://www.who.int/news-room/fact-sheets/detail/antimicrobial-resistance (accessed Oct 13, 2020).
  • Wright, P. M.; Seiple, I. B.; Myers, A. G. The Evolving Role of Chemical Synthesis in Antibacterial Drug Discovery. Angew. Chem. Int. Ed. Engl. 2014, 53, 8840–8869. DOI: 10.1002/anie.201310843.
  • Ahmed, A. A. M.; Mekky, A. E. M.; Sanad, S. M. H. Effective Synthesis of New Benzo-Fused Macrocyclic and Heteromacrocyclic Bis(Schiff Bases). J. Iran. Chem. Soc. 2022, 19, 1711–1722. DOI: 10.1007/s13738-021-02409-3.
  • Nath, B. D.; Islam, M. M.; Karim, M. R.; Rahman, S.; Shaikh, M. A. A.; Georghiou, P. E.; Menelaou, M. Recent Progress in Metal‐Incorporated Acyclic Schiff‐Base Derivatives: Biological Aspects. ChemistrySelect 2022, 7, e202104290. DOI: 10.1002/slct.202104290.
  • Khalil, T. E.; Elbadawy, H. A.; Attia, A. A.; El-Sayed, D. S. Synthesis, Spectroscopic, and Computational Studies on Molecular Charge-Transfer Complex of 2-((2-Hydroxybenzylidene) Amino)-2-(Hydroxymethyl) Propane-1,3-Diol with Chloranilic Acid: Potential Antiviral Activity Simulation of CT-Complex against SARS-CoV-2. J. Mol. Struct. 2022, 1251, 132010. DOI: 10.1016/j.molstruc.2021.132010.
  • Hashem, H. E.; Nath, A.; Kumer, A. Synthesis, Molecular Docking, Molecular Dynamic, Quantum Calculation, and Antibacterial Activity of New Schiff Base-Metal Complexes. J. Mol. Struct. 2022, 1250, 131915. DOI: 10.1016/j.molstruc.2021.131915.
  • Siwach, A.; Verma, P. K. Therapeutic Potential of Oxadiazole or Furadiazole Containing Compounds. BMC Chem. 2020, 14, 70. DOI: 10.1186/s13065-020-00721-2.
  • Alsafi, M. A.; Al-Dhuwayin, B. H.; El-Sofany, W. I.; Rateb, H. S.; Flefel, E. M. Functionalization of Novel Anti-Microbial Drug Based on Molecular Docking Study for Nicotinonitrile Analogs Prepared by Microwave Irradiation. J. Mol. Struct. 2022, 1264, 133261. DOI: 10.1016/j.molstruc.2022.133261.
  • Morsy, H. A.; Mohammed, S. M.; Abdel Hamid, A. M.; Moustafa, A. H.; El-Sayed, H. A. Click Synthesis of 1,2,3-Triazole Nucleosides Based on Functionalized Nicotinonitriles. Russ. J. Org. Chem. 2020, 56, 143–147. DOI: 10.1134/S1070428020010224.
  • Lahsasni, S. A.; Al Korbi, F. H.; Aljaber, N. A. Synthesis, Characterization and Evaluation of Antioxidant Activities of Some Novel Chalcones Analogues. Chem. Cent. J. 2014, 8, 32. DOI: 10.1186/1752-153X-8-32.
  • Hamdy, N. A.; Gamal-Eldeen, A. M. New Pyridone, Thioxopyridine, Pyrazolopyridine and Pyridine Derivatives That Modulate Inflammatory Mediators in Stimulated RAW 264.7 Murine Macrophage. Eur. J. Med. Chem. 2009, 44, 4547–4556. DOI: 10.1016/j.ejmech.2009.06.023.
  • Maqbool, M.; Manral, A.; Jameel, E.; Kumar, J.; Saini, V.; Shandilya, A.; Tiwari, M.; Hoda, N.; Jayaram, B. Development of Cyanopyridine–Triazine Hybrids as Lead Multitarget Anti-Alzheimer Agents. Bioorg. Med. Chem. 2016, 24, 2777–2788. DOI: 10.1016/j.bmc.2016.04.041.
  • Liu, J.; Zuo, D.; Jing, T.; Guo, M.; Xing, L.; Zhang, W.; Zhao, J.; Shen, J.; Gong, P.; Zhang, D.; Zhai, X. Synthesis, Biological Evaluation and Molecular Modeling of Imidazo[1,2-a]Pyridine Derivatives as Potent Antitubulin Agents. Bioorg. Med. Chem. 2017, 25, 4088–4099. DOI: 10.1016/j.bmc.2017.05.057.
  • El-Sayed, N. S.; Shirazi, A. N.; El-Meligy, M. G.; El-Ziaty, A. K.; Rowley, D.; Sun, J.; Nagib, Z.; Parang, A. K. Synthesis of 4-Aryl-6-Indolylpyridine-3-Carbonitriles and Evaluation of Their Antiproliferative Activity. Tetrahedron Lett. 2014, 55, 1154–1158. DOI: 10.1016/j.tetlet.2013.12.081.
  • Hu, Y. Y.; Wang, J.; Li, T. J.; Bheemanaboina, R. R. Y.; Ansari, M. F.; Cheng, Y.; Zhou, C. H. An Unexpected Discovery toward Novel Membrane Active Sulfonyl Thiazoles as Potential MRSA DNA Intercalators. Future Med. Chem. 2020, 12, 1709–1727. DOI: 10.4155/fmc-2019-0303.
  • Rostom, S. A.; El-Ashmawy, I. M.; Abd El Razik, H. A.; Badr, M. H.; Ashour, H. M. Design and Synthesis of Some Thiazolyl and Thiadiazolyl Derivatives of Antipyrine as Potential Non-Acidic Anti-Inflammatory, Analgesic and Antimicrobial Agents. Bioorg. Med. Chem. 2009, 17, 882–895. DOI: 10.1016/j.bmc.2008.11.035.
  • Luzina, E. L.; Popov, A. V. Synthesis and Anticancer Activity of N-Bis(Trifluoromethyl)alkyl-N′-Thiazolyl and N-Bis(Trifluoromethyl)alkyl-N′-Benzothiazolyl Ureas. Eur. J. Med. Chem. 2009, 44, 4944–4953. DOI: 10.1016/j.ejmech.2009.08.007.
  • Turan-Zitouni, G.; Chevallet, P.; Kilic, F. S.; Erol, K. Synthesis of Some Thiazolyl-Pyrazoline Derivatives and Preliminary Investigation of Their Hypotensive Activity. Eur. J. Med. Chem. 2000, 35, 635–641. DOI: 10.1016/S0223-5234(00)00152-5.
  • Khan, M.; Hameed, S.; Akhtar, T.; Al-Masoudi, N. A.; Al-Masoudi, W. A.; Jones, P. G.; Pannecouque, C. Synthesis, Crystal Structure, Anti-HIV, and Antiproliferative Activity of New Oxadiazole and Thiazole Analogs. Med. Chem. Res. 2016, 25, 2399–2409. DOI: 10.1007/s00044-016-1669-9.
  • Zablotskaya, A.; Segal, I.; Germane, S.; Shestakova, I.; Domracheva, I.; Nesterova, A.; Geronikaki, A.; Lukevics, E. Silyl Modification of Biologically Active Compounds. 8. Trimethylsilyl Ethers of Hydroxyl-Containing Thiazole Derivatives. Chem. Heterocycl. Compd. 2002, 38, 859–866. DOI: 10.1023/A:1020698107686.
  • Britschgi, M.; Greyerz, S.; Burkhart, C.; Pichler, W. J. Molecular Aspects of Drug Recognition by Specific T Cells. Curr. Drug Targets 2003, 4, 1–11. DOI: 10.2174/1389450033347082.
  • Mekky, A. E. M.; Sanad, S. M. H.; El-Idreesy, T. T. New Thiazole and Thiazole-Chromene Hybrids Possessing Morpholine Units: Piperazine-Mediated One-Pot Synthesis of Potential Acetylcholinesterase Inhibitors. Synth. Commun. 2021, 51, 3332–3344. DOI: 10.1080/00397911.2021.1970774.
  • Mekky, A. E. M.; Sanad, S. M. H. Microwave‐Assisted Synthesis of Novel Bis(Thiazoles) Incorporating Piperazine Moiety. J. Heterocycl. Chem. 2019, 56, 1560–1566. DOI: 10.1002/jhet.3531.
  • Kadhim, G. N.; Dim, I.; Ahmad, H. F. S.; Abood, A. S. A.; Hanoon, M. M.; Kadhum, A. A. H.; Shaker, L. M.; Alamiery, A. A.; Isahak, W. N. R. W. Bacterial Inhibitory Activity of a New Schiff Base Derived from Thiazole Complemented with Gravimetrical and Theoretical Investigations. Int. J. Corros. Scale Inhib. 2022, 11, 307–321. DOI: 10.17675/2305-6894-2022-11-1-18.
  • Lemilemu, F.; Bitew, M.; Demissie, T. B.; Eswaramoorthy, R.; Endale, M. Synthesis, Antibacterial and Antioxidant Activities of Thiazole-Based Schiff Base Derivatives: A Combined Experimental and Computational Study. BMC Chem. 2021, 15, 67. DOI: 10.1186/s13065-021-00791-w.
  • Sanad, S. M. H.; Mekky, A. E. M. Novel Nicotinonitriles and Thieno[2,3‐b]Pyridines as Potent Biofilm and COX‐2 Inhibitors: Synthesis, In Vitro and In Silico Studies. ChemistrySelect 2020, 5, 8494–8503. DOI: 10.1002/slct.202001208.
  • Mishra, R.; Panday, A. K.; Choudhury, L. H.; Pal, J.; Subramanian, R.; Verma, A. Multicomponent Reactions of Arylglyoxal, 4-Hydroxycoumarin, and Cyclic 1,3-C,N-Binucleophiles: Binucleophile-Directed Synthesis of Fused Five- and Six-Membered N-Heterocycles. Eur. J. Org. Chem. 2017, 2017, 2789–2800. DOI: 10.1002/ejoc.201700115.
  • Ibarra, I. A.; Islas-Jácome, A.; González-Zamora, E. Synthesis of Polyheterocycles via Multicomponent Reactions. Org. Biomol. Chem. 2018, 16, 1402–1418. DOI: 10.1039/c7ob02305g.
  • Dey, S.; Wong, C. H. Programmable One-Pot Synthesis of Heparin Pentasaccharides Enabling Access to Regiodefined Sulfate Derivatives. Chem. Sci. 2018, 9, 6685–6691. DOI: 10.1039/c8sc01743c.
  • Dey, S.; Lo, H. J.; Wong, C. H. Programmable One-Pot Synthesis of Heparin Pentasaccharide Fondaparinux. Org. Lett. 2020, 22, 4638–4642. DOI: 10.1021/acs.orglett.0c01386.
  • Dey, S.; Lo, H. J.; Wong, C. H. An Efficient Modular One-Pot Synthesis of Heparin-Based Anticoagulant Idraparinux. J. Am. Chem. Soc. 2019, 141, 10309–10314. DOI: 10.1021/jacs.9b03266.
  • Mekky, A. E. M.; Sanad, S. M. H. [3 + 2] Cycloaddition Synthesis of New (Nicotinonitrile-Chromene)-Based Bis(Pyrazole) Hybrids as Potential Acetylcholinesterase Inhibitors. J. Heterocycl. Chem. 2022. DOI: 10.1002/jhet.4590.
  • Sanad, S. M. H.; Mekky, A. E. M. Ultrasound-Mediated Synthesis of New (Piperazine-Chromene)-Linked Bis(Thieno[2,3-b]Pyridine) Hybrids as Potential Anti-Acetylcholinesterase. ChemistrySelect 2022, 7, e202203020. DOI: 10.1002/slct.202203020.
  • Sanad, S. M. H.; Mekky, A. E. M. [3 + 2] Cycloaddition Synthesis of New (Nicotinonitrile-Chromene) Hybrids Linked to Pyrazole Units as Potential Acetylcholinesterase Inhibitors. Synth. Commun. 2022, 52, 1672–1684. DOI: 10.1080/00397911.2022.2109974.
  • Sanad, S. M. H.; Mekky, A. E. M.; Ahmed, A. A. M. Tandem Synthesis, Cytotoxicity and In Silico Study of New 1,3,4-Oxadiazoles as Potential Thymidylate Synthase Inhibitors. Arch. Pharm. 2022, 355, e2200170. DOI: 10.1002/ardp.202200170.
  • Mekky, A. E. M.; Sanad, S. M. H. New Thiazole-Based Bis(Schiff Bases) Linked to Arene Units as Potential MRSA Inhibitors. Synth. Commun. 2022, 52, 2205–2218. DOI: 10.1080/00397911.2022.2134800.
  • Mekky, A. E. M.; Sanad, S. M. H.; Abdelfattah, A. M. Tandem Synthesis, Antibacterial Evaluation and SwissADME Prediction Study of New Bis(1,3,4-Oxadiazoles) Linked to Arene Units. Mendeleev Commun. 2022, 32, 612–614. DOI: 10.1016/j.mencom.2022.09.014.
  • Mohammad, H.; Reddy, P. N.; Monteleone, D.; Mayhoub, A. S.; Cushman, M.; Seleem, M. N. Synthesis and Antibacterial Evaluation of a Novel Series of Synthetic Phenylthiazole Compounds against Methicillin-Resistant Staphylococcus aureus (MRSA). Eur. J. Med. Chem. 2015, 94, 306–316. DOI: 10.1016/j.ejmech.2015.03.015.
  • Kamal, A.; Rahim, A.; Riyaz, S.; Poornachandra, Y.; Balakrishna, M.; Kumar, C. G.; Hussaini, S. M. A.; Sridhar, B.; Machiraju, P. K. Regioselective Synthesis, Antimicrobial Evaluation and Theoretical Studies of 2-Styryl Quinolines. Org. Biomol. Chem. 2015, 13, 1347–1357. DOI: 10.1039/c4ob02277g.
  • Daina, A.; Michielin, O.; Zoete, V. A. SwissADME: A Free Web Tool to Evaluate Pharmacokinetics, Drug-Likeness and Medicinal Chemistry Friendliness of Small Molecules. Sci. Rep. 2017, 7, 42717. DOI: 10.1038/srep42717.
  • Arnott, J. A.; Planey, S. L. The Influence of Lipophilicity in Drug Discovery and Design. Expert Opin. Drug Discov. 2012, 7, 863–875. DOI: 10.1517/17460441.2012.714363.
  • Cheng, T.; Zhao, Y.; Li, X.; Lin, F.; Xu, Y.; Zhang, X.; Li, Y.; Wang, R.; Lai, L. Computation of Octanol-Water Partition Coefficients by Guiding an Additive Model with Knowledge. J. Chem. Inf. Model. 2007, 47, 2140–2148. DOI: 10.1021/ci700257y.
  • Lipinski, C. A.; Lombardo, F.; Dominy, B. W.; Feeney, P. J. Experimental and Computational Approaches to Estimate Solubility and Permeability in Drug Discovery and Development Settings. Adv. Drug Deliv. Rev. 2001, 46, 3–26. DOI: 10.1016/s0169-409x(00)00129-0.
  • Lipinski, C. A. Lead-and Drug-Like Compounds: The Rule-of-Five Revolution. Drug Discov. Today Technol. 2004, 1, 337–341. DOI: 10.1016/j.ddtec.2004.11.007.
  • Teague, S.; Davis, A.; Leeson, P.; Oprea, T. The Design of Lead-Like Combinatorial Libraries. Angew. Chem. Int. Ed. 1999, 38, 3743–3748. DOI: 10.1002/(SICI)1521-3773(19991216)38:243.0.CO;2-U.
  • Gad, E. M.; Nafie, M. S.; Eltamany, E. H.; Hammad, M. S. A. G.; Barakat, A.; Boraei, A. T. A. Discovery of New Apoptosis-Inducing Agents for Breast Cancer Based on Ethyl 2-Amino-4,5,6,7-Tetrahydrobenzo[b]Thiophene-3-Carboxylate: Synthesis, In Vitro, and In Vivo Activity Evaluation. Molecules 2020, 25, 2523. DOI: 10.3390/molecules25112523.
  • Elsherif, M. A.; Hassan, A. S.; Moustafa, G. O.; Awad, H. M.; Morsy, N. M. Antimicrobial Evaluation and Molecular Properties Prediction of Pyrazolines Incorporating Benzofuran and Pyrazole Moieties. J. Appl. Pharm. Sci. 2020, 10, 37–43. DOI: 10.7324/JAPS.2020.102006.
  • Wang, J. C. A Journey in the World of DNA Rings and beyond. Annu. Rev. Biochem. 2009, 78, 31–54. DOI: 10.1146/annurev.biochem.78.030107.090101.
  • Schoeffler, A. J.; Berger, J. M. DNA Topoisomerases: Harnessing and Constraining Energy to Govern Chromosome Topology. Q. Rev. Biophys. 2008, 41, 41–101. DOI: 10.1017/S003358350800468X.
  • Collin, F.; Karkare, S.; Maxwell, A. Exploiting Bacterial DNA Gyrase as a Drug Target: Current State and Perspectives. Appl. Microbiol. Biotechnol. 2011, 92, 479–497. DOI: 10.1007/s00253-011-3557-z.
  • Khan, T.; Sankhe, K.; Suvarna, V.; Sherje, A.; Patel, K.; Dravyakar, B. DNA Gyrase Inhibitors: Progress and Synthesis of Potent Compounds as Antibacterial Agents. Biomed. Pharmacother. 2018, 103, 923–938. DOI: 10.1016/j.biopha.2018.04.021.
  • Sissi, C.; Palumbo, M. Effects of Magnesium and Related Divalent Metal Ions in Topoisomerase Structure and Function. Nucleic Acids Res. 2009, 37, 702–711. DOI: 10.1093/nar/gkp024.
  • Aldred, K. J.; Kerns, R. J.; Osheroff, N. Mechanism of Quinolone Action and Resistance. Biochemistry 2014, 53, 1565–1574. DOI: 10.1021/bi5000564.
  • Morris, G. M.; Huey, R.; Lindstrom, W.; Sanner, M. F.; Belew, R. K.; Goodsell, D. S.; Olson, A. J. AutoDock4 and AutoDockTools4: Automated Docking with Selective Receptor Flexibility. J. Comput. Chem. 2009, 30, 2785–2791. DOI: 10.1002/jcc.21256.
  • Sanad, S. M. H.; Mekky, A. E. M. Synthesis, In-Vitro Antibacterial and Anticancer Screening of Novel Nicotinonitrile-Coumarin Hybrids Utilizing Piperazine Citrate. Synth. Commun. 2020, 50, 1468–1485. DOI: 10.1080/00397911.2020.1743318.
  • Sanad, S. M. H.; Mekky, A. E. M.; Said, A. Y.; Elneairy, M. A. A. Pyridine-2(1H)-Thiones: Versatile Precursors for One-Pot Synthesis of New Nicotinonitrile-Thiazole Hybrids. J. Heterocycl. Chem. 2021, 58, 1461–1471. DOI: 10.1002/jhet.4272.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.