Environmentally benign synthesis, molecular docking study, and ADME prediction of some novel aryl sulfones containing cyclic imide moiety as antimicrobial agents

References

• Lushniak, B. D. Antibiotic Resistance: A Public Health Crisis. Public Health Rep. 2014, 129, 314–316. DOI: 10.1177/003335491412900402.
   PubMed Web of Science ®Google Scholar
• Blair, J. M. A.; Webber, M. A.; Baylay, A. J.; Ogbolu, D. O.; Piddock, L. J. Molecular Mechanisms of Antibiotic Resistance. Nat. Rev. Microbiol. 2015, 13, 42–51. DOI: 10.1038/nrmicro3380.
   PubMed Web of Science ®Google Scholar
• Parvaiz, N.; Ahmad, F.; Yu, W.; MacKerell, A. D.; Azam, S. S. Discovery of Beta-Lactamase CMY-10 Inhibitors for Combination Therapy against Multi-Drug Resistant Enterobacteriaceae. PLoS One 2021, 16, e0244967. DOI: 10.1371/journal.pone.0244967.
   PubMed Web of Science ®Google Scholar
• Laronze, M.; Boisbrun, M.; Léonce, S.; Pfeiffer, B.; Renard, P.; Lozach, O.; Meijer, L.; Lansiaux, A.; Bailly, C.; Sapi, J.; Laronze, J.-Y. Synthesis and Anticancer Activity of New Pyrrolocarbazoles and Pyrrolo-β-Carbolines. Bioorg. Med. Chem. 2005, 13, 2263–2283. DOI: 10.1016/j.bmc.2004.12.045.
   PubMed Web of Science ®Google Scholar
• Amr, A. E. G. E.; Sabry, N. M.; Abdulla, M. M. Synthesis, Reactions, and anti-Inflammatory Activity of Heterocyclic Systems Fused to a Thiophene Moiety Using Citrazinic Acid as Synthon. Monatsh. Chem. 2007, 138, 699–707. DOI: 10.1007/s00706-007-0651-0.
   Web of Science ®Google Scholar
• Anizon, F.; Belin, L.; Moreau, P.; Sancelme, M.; Voldoire, A.; Prudhomme, M.; Ollier, M.; Sevère, D.; Riou, J. F.; Bailly, C.; et al. Syntheses and Biological Activities (Topoisomerase Inhibition and Antitumor and Antimicrobial Properties) of Rebeccamycin Analogues Bearing Modified Sugar Moieties and Substituted on the Imide Nitrogen with a Methyl Group. J. Med. Chem. 1997, 40, 3456–3465. DOI: 10.1021/jm9702084.
   PubMed Web of Science ®Google Scholar
• Zentz, F.; Valla, A.; Le Guillou, R.; Labia, R.; Mathot, A. G.; Sirot, D. Synthesis and Antimicrobial Activities of N-Substituted Imides. Farmaco 2002, 57, 421–426. DOI: 10.1016/S0014-827X(02)01217-X.
   PubMedGoogle Scholar
• Abdel-Aziz, A. A.-M. Novel and Versatile Methodology for Synthesis of Cyclic Imides and Evaluation of Their Cytotoxic, DNA Binding, Apoptotic Inducing Activities and Molecular Modeling Study. Eur. J. Med. Chem. 2007, 42, 614–626. DOI: 10.1016/j.ejmech.2006.12.003.
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz, A. A.-M.; ElTahir, K. E. H.; Asiri, Y. A. Synthesis, anti-Inflammatory Activity and COX-1/COX-2 Inhibition of Novel Substituted Cyclic Imides. Part 1: Molecular Docking Study. Eur. J. Med. Chem. 2011, 46, 1648–1655. DOI: 10.1016/j.ejmech.2011.02.013.
   PubMed Web of Science ®Google Scholar
• Abdel-Aziz, A. A.-M.; El-Azab, A. S.; Attia, S. M.; Al-Obaid, A. M.; Al-Omar, M. A.; El-Subbagh, H. I. Synthesis and Biological Evaluation of Some Novel Cyclic-Imides as Hypoglycaemic, Anti-Hyperlipidemic Agents. Eur. J. Med. Chem. 2011, 46, 4324–4329. DOI: 10.1016/j.ejmech.2011.07.002.
   PubMed Web of Science ®Google Scholar
• Nettleton, D. E.; Doyle, T. W.; Krishnan, B.; Matsumoto, G. K.; Clardy, J. Isolation and Structure of Rebeccamycin – A New Antitumor Antibiotic from Nocardia Aerocoligenes. Tetrahedron Lett. 1985, 26, 4011–4014. DOI: 10.1016/S0040-4039(00)89280-1.
   Web of Science ®Google Scholar
• Bush, J. A.; Long, B. H.; Catino, J. J.; Bradner, W. T.; Tomita, K. Production and Biological Activity of Rebeccamycin, a Novel Antitumor Agent. J. Antibiot. 1987, 40, 668–678. DOI: 10.7164/antibiotics.40.668.PMID3112080.
   PubMed Web of Science ®Google Scholar
• Cechinel Filho, V.; Campos, F.; Corrêa, R.; Yunes, R.; Nunes, R. Chemical Aspects and Therapeutic Potential of Cyclic Imides: A Literature Review. Quím. Nova 2003, 26, 230–241. DOI: 10.1590/S0100-40422003000200016.
   Web of Science ®Google Scholar
• Kamiński, K.; Obniska, J.; Chlebek, I.; Wiklik, B.; Rzepka, S. Design, Synthesis and Anticonvulsant Properties of New N-Mannich Bases Derived from 3-Phenylpyrrolidine-2,5-Diones. Bioorg. Med. Chem. 2013, 21, 6821–6830. DOI: 10.1016/j.bmc.2013.07.029.
   PubMed Web of Science ®Google Scholar
• Cybulski, J.; Chilmonczyk, Z.; Szelejewski, W.; Wojtasiewicz, K.; Wrobel, J. An Efficient Synthesis of Buspirone and Its Analogues. Arch. Pharm. Pharm. Med. Chem. 1992, 325, 313–315. DOI: 10.1002/ardp.19923250513.
   Web of Science ®Google Scholar
• Grib, S.; Berredjem, M.; Otmane Rachedi, K.; Djouad, S. E.; Bouacida, S.; Bahadi, R.; Ouk, T. S.; Kadri, K.; Ben Hadda, T.; Belhani, B. Novel N-Sulfonylphthalimides: Efficient Synthesis, X-Ray Characterization, Spectral Investigations, POM Analyses, DFT Computations and Antibacterial Activity. J. Mol. Struct. 2020, 1217, 128423. DOI: 10.1016/j.molstruc.2020.128423.
   Web of Science ®Google Scholar
• Abdel-Aziz, A. M.; El-Azab, A. S.; Ceruso, M.; Supuran, C. T. Carbonic Anhydrase Inhibitory Activity of Sulfonamides and Carboxylic Acids Incorporating Cyclic Imide Scaffolds. Bioorg. Med. Chem. Lett. 2014, 24, 5185–5189. DOI: 10.1016/j.bmcl.2014.09.076.
   PubMed Web of Science ®Google Scholar
• Al-Sanea, M. M.; Elkamhawy, A.; Paik, S.; Lee, K.; El Kerdawy, A. M.; Syed Nasir Abbas, B.; Joo Roh, E.; Eldehna, W. M.; Elshemy, H. A. H.; Bakr, R. B.; et al. Sulfonamide-Based 4-Anilinoquinoline Derivatives as Novel Dual Aurora Kinase (AURKA/B) Inhibitors: Synthesis, Biological Evaluation and In Silico Insights. Bioorg. Med. Chem. 2020, 28, 115525–115533. DOI: 10.1016/j.bmc.2020.115525.
   PubMedGoogle Scholar
• Abraham, D. J.; (Ed.), Burger’s Medicinal Chemistry and Drug Discovery; John Wiley & Sons: Hoboken, NJ, 2003.
   Google Scholar
• Gadad, A. K.; Mahajanshetti, C. S.; Nimbalkar, S.; Raichurkar, A. Synthesis and Antibacterial Activity of Some 5-Guanylhydrazone/Thiocyanato-6-Arylimidazo [2,1-b]-1,3,4-Thiadiazole-2-Sulfonamide Derivatives. Eur. J. Med. Chem. 2000, 35, 853–857. DOI: 10.1016/S0223-5234(00)00166-5.
   PubMed Web of Science ®Google Scholar
• Zani, F.; Vicini, P. Antimicrobial Activity of Some 1, 2-Benzisothiazoles Having a Benzenesulfonamide Moiety. Arch. Pharm. Pharm. Med. Chem. 1998, 331, 219–223. DOI: 10.1002/(sici)1521-4184(199806)331:6 < 219::aid-ardp219 > 3.0.co;2-u.
   PubMed Web of Science ®Google Scholar
• Majumdar, K. C.; Mondal, S.; De, N. Synthesis of Polycyclic Sultams by Palladium-Catalyzed Intramolecular Cyclization. Synthesis 2009, 2009, 3127–3135. DOI: 10.1055/s-0029-1216888.
   Google Scholar
• Dhumad, A. M.; Jassem, A. M.; Alharis, R. A.; Almashal, F. A. Design, Cytotoxic Effects on Breast Cancer Cell Line (MDA-MB 231), and Molecular Docking of Some Maleimide-Benzenesulfonamide Derivatives. J. Indian. Chem. Soc. 2021, 98, 100055–100064. DOI: 10.1016/j.jics.2021.100055.
   Web of Science ®Google Scholar
• Shaki, H.; Khosravi, A.; Gharanjig, K.; Mahboubi, A. Synthesis and Biological Properties of Novel Cationic Fluorescent Dye. Int. J. Tech. Res Appl. 2015, 29, 103–106. e-ISSN: 2320–8163.
   Google Scholar
• Jan, M. S.; Sajjad, A.; Fida, H.; Ashfaq, A.; Fawad, M.; Umer, R.; Obaid-Ur-Rahman, A.; Farhat, U.; Muhammad, A.; Sadiq, A. Design, Synthesis, In-Vitro, In-Vivo and In-Silico Studies of Pyrrolidine-2,5-Dione Derivatives as Multitarget Anti-Inflammatory Agents. Eur. J. Med. Chem. 2020, 186, 111863–111868. DOI: 10.1016/j.ejmech.2019.111863.
   PubMed Web of Science ®Google Scholar
• Jafari, E.; Jarah-Najafabadi, N. T.; Jahanian-Najafabadi, A.; Poorirani, S.; Hassanzadeh, F.; Sadeghian-Rizi, S. Synthesis and Evaluation of Antimicrobial Activity of Cyclic Imides Derived from Phthalic and Succinic Anhydrides. Res. Pharm. Sci. 2017, 12, 526–534. DOI: 10.4103/1735-5362.217433.
   PubMedGoogle Scholar
• Deshpande, S. R.; Maybhate, S. P.; Likhite, A. P.; Chaudhary, P. M. A Facile Synthesis of N-Substituted Maleimides. Indian J. Chem. 2010, 49B, 487–488. ISSN: 0975–0975.
   Google Scholar
• Haval, K. P.; Mhaske, S. B.; Argade, N. P. Cyanuric Chloride: Decent Dehydrating Agent for an Exclusive and Efficient Synthesis of Kinetically Controlled Isomaleimides. Tetrahedron 2006, 62, 937–942. DOI: 10.1016/j.tet.2005.10.027.
   Web of Science ®Google Scholar
• Le, Z. G.; Chen, Z. C.; Hu, Y.; Zheng, Q. G. Organic Reactions in Ionic Liquids: Ionic Liquid-Promoted Efficient Synthesis of N-Alkyl and N-Arylimides. Synthesis 2004, 2004, 995–998. DOI: 10.1055/s-2004-822337.
   Google Scholar
• Arif, R.; Nayab, P. S.; Rahisuddin, P. Synthesis, Characterization, DNA Binding, Antibacterial, and Antioxidant Activity of New Bis-Phthalimides. Russ. J. Gen. Chem. 2016, 86, 1374–1380. DOI: 10.1134/S1070363216060232.
   Web of Science ®Google Scholar
• Paterson, M. J.; Eggleston, I. M. Convenient Preparation of N-Maleoyl Amino Acid Succinimido Esters Using N-Trifluoroacetoxysuccinimide. Synth. Commun. 2008, 38, 303–308. DOI: 10.1080/00397910701750151.
   Web of Science ®Google Scholar
• Kondo, T.; Nomura, M.; Ura, Y.; Wada, K.; Mitsudo, T. Ruthenium-Catalyzed [2 + 2 + 1] Cocyclization of Isocyanates, Alkynes, and CO Enables the Rapid Synthesis of Polysubstituted Maleimides. J. Am. Chem. Soc. 2006, 128, 14816–14817. DOI: 10.1021/ja066305g.
   PubMed Web of Science ®Google Scholar
• Shetgiri, N. P.; Nayak, B. K. Synthesis and Antimicrobial Activity of Some Succinimides. Indian J. Chem. 2005, 44B, 1933–1936. ISSN: 0975–0975.
   Google Scholar
• Bougheloum, C.; Belghiche, R.; Messalhi, A. Synthesis of New Substituted N-Sulfonyl Pyrrolidine-2,5-Dione Using Dawson-Type Heteropolyacid as Catalyst. Phosphorus Sulfur Silicon Relat. Elem. 2015, 190, 269–276. DOI: 10.1080/10426507.2014.947413.
   Web of Science ®Google Scholar
• Bougheloum, C.; Guezane Lakoud, S.; Belghiche, R.; Messalhi, A. Simple, Rapid and Clean Condensation of Sulfonamide and Maleic Anhydride Derivatives: Synthesis of Novel 1H-Pyrrole-2,5-Diones Under Heterogeneous Conditions. Phosphorus Sulfur Silicon Relat. Elem. 2016, 191, 1344–1350. DOI: 10.1080/10426507.2016.1193504.
   Web of Science ®Google Scholar
• Bougheloum, C.; Barbey, C.; Berredjem, M.; Messalhi, A.; Dupont, N. Synthesis and Structural Study of N-Acetyl-1,2,3,4-Tetrahydroisoquinoline-2-Sulfonamide Obtained Using H6P2W18O62 as Acidic Solid Catalyst. J. Mol. Struct. 2013, 1041, 6–15. DOI: 10.1016/j.molstruc.2013.02.018.
   Web of Science ®Google Scholar
• Bougheloum, C.; Alioua, S.; Belghiche, R.; Benali, N.; Messalhi, A. An Efficient Green Synthesis of New Benzothiazoles Containing Sulfonamide or Cyclic Imide Moieties. J. Heterocyclic Chem. 2020, 57, 120–131. DOI: 10.1002/jhet.3753.
   Web of Science ®Google Scholar
• Benali, N.; Bougheloum, C.; Alioua, S.; Belghiche, R.; Messalhi, A. Efficient N-Acylation of Sulfonamides Using Cesium Salt of Wells–Dawson Heteropolyacid as Catalyst: Synthesis of New N-Acyl Sulfonamides and Cyclic Imides. Synth. Commun. 2018, 48, 3099–3112. DOI: 10.1080/00397911.2018.1535077.
   Web of Science ®Google Scholar
• (a) Reddy, K. M.; Babu, N. S.; Suryanarayana, I.; Prasad, P. S.; Lingaiah, N. The Silver Salt of 12-Tungstophosphoric Acid: An Efficient Catalyst for the Three-Component Coupling of an Aldehyde, an Amine and an Alkyne. Tetrahedron Lett. 2006, 47, 7563–7566. DOI: 10.1016/j.tetlet.2006.08.094.
   Web of Science ®Google Scholar
  (b) Poźniczek, J.; Lubańska, A.; Mucha, D.; Bielański, A. Cesium Partly Substituted Salts CsxH6P2W18O62 of Wells–Dawson Heteropolyacid as Catalysts for Ethyl-Tert-Butyl Ether Synthesis. J. Mol. Catal. A: Chem. 2006, 257, 99–104. DOI: 10.1016/j.molcata.2006.04.036.
   Google Scholar
• Thakur, A.; Sharma, A.; Sharma, A. Efficient Synthesis of Xanthenedione Derivatives Using Cesium Salt of Phosphotungstic Acid as a Heterogeneous and Reusable Catalyst in Water. Synth. Commun. 2016, 46, 1766–1771. DOI: 10.1080/00397911.2016.1226340.
   Web of Science ®Google Scholar
• (a) Driowya, M.; Puissant, A.; Robert, G.; Auberger, P.; Benhida, R.; Bougrin, K. Ultrasound-Assisted One-Pot Synthesis of anti-CML Nucleosides Featuring 1,2,3-Triazole Nucleobase under Iron-Copper Catalysis. Ultrason. Sonochem. 2012, 19, 1132–1138. DOI: 10.1016/j.ultsonch.2012.04.007.
   PubMed Web of Science ®Google Scholar
  (b) Pasha, M. A.; Nagashree, S. A One-Pot Three-Component Synthesis of 4, 6-Diarylpyrimidin-2 (1H)-Ones (DAPMs) Using Atomized Sodium in THF under Sonic Condition. Ultrason. Sonochem. 2014, 21, 1279–1283. DOI: 10.1016/j.ultsonch.2013.12.021.
   PubMed Web of Science ®Google Scholar
  (c) Arafa, W. A.; Shaker, R. M. A Facile Green Chemistry Approaches towards the Synthesis of bis-Schiff Bases Using Ultrasound versus Microwave and Conventional Method without Catalyst. Arkivoc 2016, 2016, 187–201. DOI: 10.3998/ark.5550190.p009.464.
   Google Scholar
• Friedman, L.; Little, R.; Reichle, W. p-Toluenesulfonic Acid, Hydrazide. Org. Synth. 1960, 40, 93. DOI: 10.15227/orgsyn.040.0093.
   Google Scholar
• Govindan, K.; Chen, N. Q.; Chuang, Y. W.; Lin, W. Y. Unlocking Amides through Selective C–N Bond Cleavage: Allyl Bromide-Mediated Divergent Synthesis of Nitrogen-Containing Functional Groups. Org. Lett. 2021, 23, 9419–9424. DOI: 10.1021/acs.orglett.1c03541.
   PubMed Web of Science ®Google Scholar
• Parsons, W. H.; Rutland, N. T.; Crainic, J. A.; Cardozo, J. M.; Chow, A. S.; Andrews, C. L.; Sheehan, B. K. Development of Succinimide-Based Inhibitors for the Mitochondrial Rhomboid Protease PARL. Bioorg. Med. Chem. Lett. 2021, 49, 128290–128298. DOI: 10.1016/j.bmcl.2021.128290.
   PubMed Web of Science ®Google Scholar
• 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.
   PubMedGoogle Scholar
• Jadhav, P. B.; Yadav, A. R.; Gore, M. G. Concept of Drug Likeness in Pharmaceutical Research. Int. J. Pharm. Bio. Sci. 2015, 6, 142–154. ID: 168400804.
   Google Scholar
• Veber, D. F.; Johnson, S. R.; Cheng, H. Y.; Smith, B. R.; Ward, K. W.; Kopple, K. D. Molecular Properties That Influence the Oral Bioavailability of Drug Candidates. J. Med. Chem. 2002, 45, 2615–2623. DOI: 10.1021/jm020017n.
   PubMed Web of Science ®Google Scholar
• Qiu, X.; Janson, C. A.; Smith, W. W.; Green, S. M.; McDevitt, P.; Johanson, K.; Carter, P.; Hibbs, M.; Lewis, C.; Chalker, A.; et al. Crystal Structure of Staphylococcus aureus Tyrosyl-tRNA Synthetase in Complex with a Class of Potent and Specific Inhibitors. Protein Sci. 2001, 10, 2008–2016. DOI: 10.1110/ps.18001.
   PubMed Web of Science ®Google Scholar
• G-Dayanandan, N.; Paulsen, J. L.; Viswanathan, K.; Keshipeddy, S.; Lombardo, M. N.; Zhou, W.; Lamb, K. M.; Sochia, A. E.; Alverson, J. B.; Priestley, N. D.; et al. Propargyl-Linked Antifolates Are Dual Inhibitors of Candida albicans and Candida glabrata. J Med Chem 2014, 57, 2643–2656. DOI: 10.1021/jm401916j.
   PubMed Web of Science ®Google Scholar
• (a) Aggarwal, S.; Devgun, M.; Narang, R.; Lal, R.; Rana, A. C.; Goyal, R.; Singh, L.; Sharma, S. Molecular Docking Studies of Thiazolopyrimidine Derivatives as Antimicrobial Agents. J. Adv. Sci. Res. 2021, 12, 285–291. ISSN: 0976–9595.
   Google Scholar
  (b) Jays, J.; Mohan, S.; Saravanan, J. Molecular Docking Studies of Novel Aminopyrimidines as Potent Antifungal Agents. Chem. Methodol. 2019, 3, 442–450. DOI: 10.22034/chemm.2018.151655.1100.
   Google Scholar
• Clinical Laboratory Standards Institute/NCCLS. Methods of Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically. Approved Standard. 10th ed. CLSI Document M07 - A10; Clinical and Laboratory Standards Institute: Wayne, PA, 2015.
   Google Scholar
• Trott, O.; Olson, A. J. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. J. Comput. Chem. 2010, 31, 455–461. DOI: 10.1002/jcc.21334.
   PubMed Web of Science ®Google Scholar
• Biovia. Discovery Studio Modeling Environment; Dassault Systemes Biovia Corp.: San Diego, CA, 2017.
   Google Scholar
• Meliani, S.; Toumi, S.; Djahoudi, H.; Deghdegh, K.; Amoura, K.; Djahoudi, A. Synergistic Combination of Colistin with Imipenem, Amikacine or Ciprofloxacin against Acinetobacter baumannii and Pseudomonas aeruginosa Carbapenem-Resistant Isolated in Annaba Hospital Algeria. Biocell 2020, 44, 175–182. DOI: 10.32604/biocell.2020.09097.
   Web of Science ®Google Scholar
• Mellouk, F. Z.; Bakour, S.; Meradji, S.; Al-Bayssari, C.; Bentakouk, M. C.; Zouyed, F.; Djahoudi, A.; Boutefnouchet, N.; Rolain, J. M. First Detection of VIM-4-Producing Pseudomonas aeruginosa and OXA-48-Producing Klebsiella pneumoniae in Northeastern (Annaba, Skikda) Algeria. Microb. Drug Resist. 2017, 23, 335–344. DOI: 10.1089/mdr.2016.0032.
   PubMed Web of Science ®Google Scholar