Design, Synthesis, and In Silico Molecular Docking Study of Some Novel Thiochromene Derivatives with Antimicrobial Potential

References

• S. B. Levy, “The 2000 Garrod Lecture. Factors Impacting on the Problem of Antibiotic Resistance,” The Journal of Antimicrobial Chemotherapy 49, no. 1 (2002): 25–30.
   PubMed Web of Science ®Google Scholar
• S. Luthra, A. Rominski, and P. Sander, “The Role of Antibiotic-Target-Modifying and Antibiotic-Modifying Enzymes in Mycobacterium abscessus Drug Resistance,” Frontiers in Microbiology 9 (2018): 2179.
   PubMed Web of Science ®Google Scholar
• T. Parish, “Steps to Address Anti-Microbial Drug Resistance in Today's Drug Discovery,” Expert Opinion on Drug Discovery 14, no. 2 (2019): 91–4.
   PubMed Web of Science ®Google Scholar
• W.-B. Ho, L. R. Wright, E. D. Turtle, C. Mossman, and L. A. Flippin, “Thiochromene Derivatives as HIF Hydroxylase Inhibitors,” (Google Patents, 2015).
   Google Scholar
• N. Sakauchi, H. Furukawa, J. Shirai, A. Sato, H. Kuno, R. Saikawa, and M. Yoshida, “Identification of 3,4-Dihydro-2H-Thiochromene 1,1-Dioxide Derivatives with a Phenoxyethylamine Group as Highly Potent and Selective α1D Adrenoceptor Antagonists,” European Journal of Medicinal Chemistry 139 (2017): 114–27.
   PubMed Web of Science ®Google Scholar
• R. Roy, S. Rakshit, T. Bhowmik, S. Khan, A. Ghatak, S. Bhar. “Substituted 3-E-styryl-2 H-chromenes and 3-E-styryl-2 H-thiochromenes: synthesis, photophysical studies, anticancer activity, and exploration to tricyclic benzopyran skeleton,” The Journal of Organic Chemistry 79 (2014): 6603–6614
   PubMedGoogle Scholar
• A. G. Alshammari, A.-R. B. El-Gazzar, and H. N. Hafez, “Efficient Synthesis of a New Class of N-Nucleosides of 4H-Thiochromeno [2, 3-d] Pyrimidine-10-Sulfone as Potential Anticancer and Antibacterial Agents,” International Journal of Organic Chemistry 2013 (2013).
   Google Scholar
• A. Barakat, M. S. Islam, M. Ali, A. M. Al-Majid, S. Alshahrani, A. S. Alamary, S. Yousuf, and M. I. Choudhary, “Regio-and Stereoselective Synthesis of a New Series of Spirooxindole Pyrrolidine Grafted Thiochromene Scaffolds as Potential Anticancer Agents,” Symmetry 13, no. 8 (2021): 1426.
   Google Scholar
• P. T. Kaye, M. A. Musa, A. T. Nchinda, and X. W. Nocanda, “Novel Heterocyclic Analogues of the HIV‐1 Protease Inhibitor, Ritonavir,” Synthetic Communications 34, no. 14 (2004): 2575–89.
   Web of Science ®Google Scholar
• M. Ferraroni, F. Carta, A. Scozzafava, and C. T. Supuran, “Thioxocoumarins Show an Alternative Carbonic Anhydrase Inhibition Mechanism Compared to Coumarins,” Journal of Medicinal Chemistry 59, no. 1 (2016): 462–73.
   PubMed Web of Science ®Google Scholar
• R. Choubey, N. Choubey, and G. Garg, “Antimicrobial Activity of Newly Synthesized Pyrazolidine-3, 5-Dione Substituted Thiochromene Derivatives,” Research Journal of Pharmacy and Technology 8, no. 9 (2015): 1250–8.
   Google Scholar
• T. Ben Hadda, A. Kerbal, B. Bennani, G. A. Houari, M. Daoudi, A. C. L. Leite, V. H. Masand, R. D. Jawarkar, and Z. Charrouf, “Molecular Drug Design, Synthesis and Pharmacophore Site Identification of Spiroheterocyclic Compounds: Trypanosoma crusi Inhibiting Studies,” Medicinal Chemistry Research 22, no. 1 (2013): 57–69.
   Web of Science ®Google Scholar
• G. Wang, G. Yang, Z. Ma, W. Tian, B. Fang, and L. Li, Synthesis and Antifungal Activity of Some 6H-Thiochromeno [4, 3-b] Quinolines,” International Journal of Chemistry 2, no. 1 (2010): 19.
   Google Scholar
• N. P. Badiger, S. L. Gaonkar, and N. S. Shetty, “Synthesis of Some New Thienopyrimidines and Triazole Fused Thienopyrimidines and Their Antimicrobial Activities,” ” International Journal of Chemical and Pharmaceutical Sciences 6 (2015): 59–62.
   Google Scholar
• D.-J. Wang, Z. Hou, H. Xu, R. An, X. Su, and C. Guo, “Design, Synthesis, and Biological Evaluation of 4-Chloro-2H-Thiochromenes Featuring Nitrogen-Containing Side Chains as Potent Antifungal Agents,” Bioorganic & Medicinal Chemistry Letters 28, no. 22 (2018): 3574–8.
   PubMed Web of Science ®Google Scholar
• R. Mishra, N. Sachan, N. Kumar, I. Mishra, and P. Chand, “Thiophene Scaffold as Prospective Antimicrobial Agent: A Review,” Journal of Heterocyclic Chemistry 55, no. 9 (2018): 2019–34.
   Web of Science ®Google Scholar
• N. A. Elkanzi, R. B. Bakr, and A. A. Ghoneim, “Design, Synthesis, Molecular Modeling Study, and Antimicrobial Activity of Some Novel Pyrano [2, 3‐b] Pyridine and Pyrrolo [2, 3‐b] Pyrano [2.3‐d] Pyridine Derivatives,” Journal of Heterocyclic Chemistry 56 (2019): 406–16.
   Google Scholar
• R. B. Bakr and N. A. Elkanzi, “Preparation of Some Novel Thiazolidinones, Imidazolinones, and Azetidinone Bearing Pyridine and Pyrimidine Moieties with Antimicrobial Activity,” Journal of Heterocyclic Chemistry 57, no. 7 (2020): 2977–89.
   Web of Science ®Google Scholar
• E. M. Sharshira and N. M. M. Hamada, “Synthesis and Antimicrobial Evaluation of Some Pyrazole Derivatives,” Molecules (Basel, Switzerland) 17, no. 5 (2012): 4962–71.
   PubMed Web of Science ®Google Scholar
• B. P. Bandgar, S. S. Gawande, R. G. Bodade, N. M. Gawande, and C. N. Khobragade, “Synthesis and Biological Evaluation of a Novel Series of Pyrazole Chalcones as Anti-Inflammatory, Antioxidant and Antimicrobial Agents,” Bioorganic & Medicinal Chemistry 17, no. 24 (2009): 8168–73.
   PubMed Web of Science ®Google Scholar
• M. A. Elsherif, A. S. Hassan, G. O. Moustafa, H. M. Awad, and N. M. Morsy, “Antimicrobial Evaluation and Molecular Properties Prediction of Pyrazolines Incorporating Benzofuran and Pyrazole Moieties,” Journal of Applied Pharmaceutical Science 10 (2020): 37–43.
   Google Scholar
• M. V. Raimondi, S. Cascioferro, D. Schillaci, and S. Petruso, “Synthesis and Antimicrobial Activity of New Bromine-Rich Pyrrole Derivatives Related to Monodeoxypyoluteorin,” European Journal of Medicinal Chemistry 41, no. 12 (2006): 1439–45.
   PubMed Web of Science ®Google Scholar
• M. Maruthapandi, K. Sharma, J. H. Luong, and A. Gedanken, “Antibacterial Activities of Microwave-Assisted Synthesized Polypyrrole/Chitosan and Poly (pyrrole-N-(1-Naphthyl) Ethylenediamine) Stimulated by C-Dots,” Carbohydrate Polymers 243 (2020): 116474.
   PubMed Web of Science ®Google Scholar
• D. Unluer, A. A. Kamiloglu, S. Direkel, E. Bektas, H. Kantekin, and K. Sancak, “Synthesis and Characterization of Metallophthalocyanine with Morpholine Containing Schiff Base and Determination of Their Antimicrobial and Antioxidant Activities,” Journal of Organometallic Chemistry 900 (2019): 120936.
   Web of Science ®Google Scholar
• H. Bektaş, Ş. Ceylan, N. Demirbaş, Ş. Alpay-Karaoğlu, and B. B. Sökmen, “Antimicrobial and Antiurease Activities of Newly Synthesized Morpholine Derivatives Containing an Azole Nucleus,” Medicinal Chemistry Research : An International Journal for Rapid Communications on Design and Mechanisms of Action of Biologically Active Agents 22, no. 8 (2013): 3629–39.
   PubMed Web of Science ®Google Scholar
• S. Shahzadi, S. Ali, M. H. Bhatti, M. Fettouhi, and M. Athar, “Chloro-Diorganotin (IV) Complexes of 4-Methyl-1-Piperidine Carbodithioic Acid: Synthesis, X-Ray Crystal Structures, Spectral Properties and Antimicrobial Studies,” Journal of Organometallic Chemistry 691, no. 8 (2006): 1797–802.
   Web of Science ®Google Scholar
• M. R. Aouad, “Click Synthesis and Antimicrobial Screening of Novel Isatin-1, 2, 3-Triazoles with Piperidine, Morpholine, or Piperazine Moieties,” Organic Preparations and Procedures International 49, no. 3 (2017): 216–27.
   Web of Science ®Google Scholar
• N. O. Boadi, M. Degbevi, S. A. Saah, M. Badu, L. S. Borquaye, and N. K. Kortei, “Antimicrobial Properties of Metal Piperidine Dithiocarbamate Complexes against Staphylococcus aureus and Candida albicans,” Scientific African 12 (2021): e00846.
   Google Scholar
• W. Kasekarn, R. Sirawaraporn, T. Chahomchuen, A. F. Cowman, and W. Sirawaraporn, “Molecular Characterization of Bifunctional Hydroxymethyldihydropterin Pyrophosphokinase-Dihydropteroate Synthase from Plasmodium falciparum,” Molecular and Biochemical Parasitology 137, no. 1 (2004): 43–53.
   PubMed Web of Science ®Google Scholar
• V. Gorelova, L. Ambach, F. Rébeillé, C. Stove, and D. Van Der Straeten, “Folates in Plants: Research Advances and Progress in Crop Biofortification,” Frontiers in Chemistry 5 (2017): 21.
   PubMed Web of Science ®Google Scholar
• M. W. Irvine, Agents Acting on Pyrimidine Metabolism. Antimalarial Agents (UK: Elsevier, 2020), 133–85.
   Google Scholar
• H. Yang, X. Zhang, Y. Liu, L. Liu, J. Li, G. Du, et al. “Synthetic biology-driven microbial production of folates: Advances and perspectives,” Bioresource Technology 324 (2021): 124624.
   Google Scholar
• C. R. Bourne, “Utility of the Biosynthetic Folate Pathway for Targets in Antimicrobial Discovery,” Antibiotics (Basel, Switzerland) 3, no. 1 (2014): 1–28.
   PubMedGoogle Scholar
• K. Pal, A. Heinsch, A. Berkessel, and A. L. Koner, “Differentiation of Folate-Receptor-Positive and Negative Cells Using a Substrate Mimicking Fluorescent Probe,” Microscopy 3 (2017): 6.
   Google Scholar
• S. H. Satuluri, S. K. Katari, C. Pasala, and U. Amineni, “Novel and Potent Inhibitors for Dihydropteroate Synthase of Helicobacter pylori,” Journal of Receptor and Signal Transduction Research 40, no. 3 (2020): 246–56.
   PubMed Web of Science ®Google Scholar
• J. R. Suh, A. K. Herbig, and P. J. Stover, “New Perspectives on Folate Catabolism,” Annual Review of Nutrition 21 (2001): 255–82.
   PubMed Web of Science ®Google Scholar
• N. A. A. Elkanzi, H. Hrichi, R. B. Bakr, O. Hendawy, M. M. Alruwaili, E. D. Alruwaili, R. W. Almamtrfi, and H. K. Alsharary, “Synthesis, In Vitro Evaluation and Molecular Docking of New Pyrazole Derivatives Bearing 1, 5, 10, 10a-Tetrahydrobenzo [g] Quinoline-3-Carbonitrile Moiety as Potent Antibacterial Agents,” Journal of the Iranian Chemical Society 18, no. 4 (2021): 977–15.
   Web of Science ®Google Scholar
• A. A. Ghoneim, A. F. El-Farargy, and R. B. Bakr, “Design, Synthesis, Molecular Docking of Novel Substituted Pyrimidinone Derivatives as Anticancer Agents,” Polycyclic Aromatic Compounds (2020): 1–17.
   Web of Science ®Google Scholar
• N. A. Elkanzi and R. B. Bakr, “Microwave Assisted, Antimicrobial Activity and Molecular Modeling of Some Synthesized Newly Pyrimidine Derivatives Using 1, 4-Diazabicyclo [2.2. 2] Octane as a Catalyst,” Letters in Drug Design & Discovery 17, no. 12 (2020): 1538–51.
   Google Scholar
• H. Hrichi, E. N. A. Ahmed, and B. R. Badawy, “Novel β-Lactams and Thiazolidinone Derivatives from 1, 4-Dihydroquinoxaline Schiff’s Base: Synthesis, Antimicrobial Activity and Molecular Docking Studies,” Chemistry Journal of Moldova 15, no. 1 (2020): 86–94.
   Web of Science ®Google Scholar
• R. B. Bakr, N. A. Elkanzi, A. A. Ghoneim, and S. Moustafa, “Synthesis, Molecular Docking Studies and In Vitro Antimicrobial Evaluation of Novel Pyrimido [1, 2-a] Quinoxaline and Triazino [4, 3-a]-Quinoxaline Derivatives,” Heterocycles 96, no. 11 (2018): 1941–57.
   Web of Science ®Google Scholar
• N. A. A. Elkanzi, A. A. Ghoneim, and R. B. Bakr, “Design, Efficient Synthesis and Antimicrobial Evaluation of Some Novel Pyrano [2, 3-b][1, 8] Naphthyridine and Pyrrolo [2, 3-f][1, 8] Naphth-Yridine Derivatives,” Pharma Chemica 11 (2019): 6–13.
   Google Scholar
• A. A. Ghoneim, N. A. Ahmed Elkanzi, and R. B. Bakr, “Synthesis and Studies Molecular Docking of Some New Thioxobenzo [g] Pteridine Derivatives and 1, 4-Dihydroquinoxaline Derivatives with Glycosidic Moiety,” Journal of Taibah University for Science 12, no. 6 (2018): 774–82.
   Web of Science ®Google Scholar
• I. H. El Azab and N. A. Elkanzi, “Synthesis and Pharmacological Evaluation of Some New Chromeno [3, 4‐c] Pyrrole‐3, 4‐Dione‐Based N‐Heterocycles as Antimicrobial Agents,” Journal of Heterocyclic Chemistry 54, no. 2 (2017): 1404–14.
   Web of Science ®Google Scholar
• I. H. El Azab and N. A. Elkanzi, “Design, Synthesis, and Antimicrobial Evaluation of New Annelated Pyrimido [2, 1-c][1, 2, 4] Triazolo [3, 4-f][1, 2, 4] Triazines,” Molecules 25, no. 6 (2020): 1339.
   Web of Science ®Google Scholar
• M. A. Abdelgawad, A. Musa, A. H. Almalki, S. I. Alzarea, E. M. Mostafa, M. M. Hegazy, G. Mostafa-Hedeab, M. M. Ghoneim, D. G. T. Parambi, R. B. Bakr, et al, “Novel Phenolic Compounds as Potential Dual EGFR and COX-2 Inhibitors: Design, Semisynthesis, In Vitro Biological Evaluation and In Silico Insights,” Drug Design,” Drug Design, Development and Therapy 15 (2021): 2325–37.
   PubMed Web of Science ®Google Scholar
• I. H. El Azab, R. B. Bakr, and N. A. Elkanzi, “Facile One-Pot Multicomponent Synthesis of Pyrazolo-Thiazole Substituted Pyridines with Potential anti-Proliferative Activity: Synthesis, In Vitro and In Silico Studies,” Molecules 26, no. 11 (2021): 3103.
   PubMed Web of Science ®Google Scholar
• I. H. El Azab, H. S. El-Sheshtawy, R. B. Bakr, and N. A. A. Elkanzi, “New 1, 2, 3-Triazole-Containing Hybrids as Antitumor Candidates: Design, Click Reaction Synthesis, DFT Calculations, and Molecular Docking Study,” Molecules 26, no. 3 (2021): 708.
   PubMed Web of Science ®Google Scholar
• K. N. Al-Shammri, N. A. Elkanzi, W. A. Arafa, I. O. Althobaiti, R. B. Bakr, and S. M. N. Moustafa, “Novel Indan-1, 3-Diones Derivatives: Design, Green Synthesis, Effect against Tomato Damping-off Disease Caused by Fusarium oxysporum and In Silico Molecular Docking Study,” Arabian Journal of Chemistry (2022): 103731.
   Google Scholar
• M. A. Abdelgawad, M. M. Al-Sanea, A. Musa, M. Elmowafy, A. K. El-Damasy, A. A. Azouz, M. M. Ghoneim, and R. B. Bakr, “Docking Study, Synthesis, and anti-Inflammatory Potential of Some New Pyridopyrimidine-Derived Compounds,” Journal of Inflammation Research 15 (2022): 451–63.
   PubMedGoogle Scholar
• R. B. Bakr, I. H. E. Azab, and N. A. Elkanzi, “Thiochromene Candidates: Design, Synthesis, Antimicrobial Potential and In Silico Docking Study,” Journal of the Iranian Chemical Society (2021): 1–11.
   Web of Science ®Google Scholar
• S. A. Komykhov, K. S. Ostras, A. R. Kostanyan, S. M. Desenko, V. D. Orlov, and H. Meier, “The Reaction of Amino‐Imidazoles,‐Pyrazoles and‐Triazoles with α, β‐Unsaturated Nitriles,” Journal of Heterocyclic Chemistry 42, no. 6 (2005): 1111–6.
   Google Scholar