Ultra-Sonicated One-Pot Synthesis of Potent Bioactive Biscoumarin and Polycyclic Pyranodichromenone Scaffolds in Aqueous Media: A Complementary Tool to Organic Synthesis

Abstract

Present study involves the synthesis of bis-coumarins and novel polycyclic pyranodichromenones using a catalyst-free approach under ultrasonic irradiation in an aqueous medium. The chemical structures of the synthesized compounds were characterized using FTIR, ¹H NMR, and ¹³C NMR spectroscopy. The antibacterial and antifungal activities of the compounds were evaluated against Gram-positive (S. aureus, B. cereus) and Gram-negative bacteria (P. aeruginosa, E. coli), as well as the fungus C. albicans, using the disc diffusion method. Several compounds exhibited excellent activity against the tested microorganisms. Moreover, the antioxidant potential of the synthesized products was assessed using 2,2-diphenyl-1-picrylhydrazyl (DPPH), 2,2′-azino-bis(3-ethyl­benzothiazoline-6-sulfonic acid) (ABTS) free radical scavenging, and total antioxidant capacity (TAC) assays. Promising antioxidant activity was observed for certain compounds. Computational studies using density functional theory (DFT) were conducted to investigate the molecular reactivity and electronic properties of the synthesized compounds. Quantum mechanical parameters such as Ionization Potential (IP), Electron Affinity (EA), Mulliken Electronegativity (χ), Chemical Potential (μ), and Electrophilicity Index (ω) were calculated. The study highlights the efficiency and eco-friendliness of ultrasonic-assisted processes, contributing to the advancement of sustainable chemistry.

Key words

biscoumarins - polycyclic pyranodichromenones - one pot synthesis - antioxidant activity - antibacterial activity - antifungal activity - DFT

Publikationsverlauf

Eingereicht: 04. Mai 2023

Angenommen nach Revision: 14. Juni 2023

Artikel online veröffentlicht:
20. Juli 2023

• References

• 1 Cioc RC, Ruijter E, Orru RV. A. Green Chem. 2014; 16: 2958
• 2 Zhi S, Ma X, Zhang W. Org. Biomol. Chem. 2019; 17: 7632
• 3 Saranya S, Rohit KR, Radhika S, Anilkumar G. Org. Biomol. Chem. 2019; 17: 8048
• 4 Weber L. Curr. Med. Chem. 2002; 9: 2085
• 5 Hulme C, Gore V. Curr. Med. Chem. 2003; 10: 51
• 6 Mohammadi-Khanaposhtani M, Yahyavi H, Barzegaric E, Imanparast S, Heravi MM, Ali Faramarzi M, Foroumadi A, Adibi H, Larijani B, Mahdavi M. Polycycl. Arom. Comp. 2018; 40: 915
• 7 Li M, Li J, Liu B, Zhou Y, Li X, Xue X, Hou Z, Luo X. Eur. J. Pharmacol. 2013; 721: 151
• 8 Kalalbandi VK. A, Bijjaragi SC, Seetharamappa J. ChemistrySelect 2018; 3: 3925
• 9 Emami S, Dadashpour S. Eur. J. Med. Chem. 2015; 102: 611
• 10 Sahar A, Khan ZA, Ahmad M, Zahoor AF, Mansha A, Iqbal A. Trop J. Pharm. Res. 2017; 16: 203
• 11 Ibrar A, Zaib S, Khan I, Jabeen F, Iqbal J, Saeed A. RSC Adv. 2015; 5: 89919
• 12 Kostova I. Eur. J. Med. Chem. 2001; 36: 339
• 13 Abid O.-R, Babar TM, Ali FI, Ahmed S, Wadood A, Rama NH, Uddin R, Zaheer-ul-Haq, Khan A, Choudhary MI. ACS Med. Chem. Lett. 2010; 1: 145
• 14 Waheed M, Ahmed N. Tetrahedron Lett. 2016; 57: 3785
• 15 Yan L, Kong Z, Shen W, Du W, Zhou Y, Qi Z. RSC Adv. 2016; 6: 5636
• 16 Teli P, Sethiya A, Agarwal S. ChemistrySelect 2019; 4: 13772
• 17 Brahmachari G, Begam S. ChemistrySelect 2019; 4: 5415
• 18 Daneshvar N, Goli-Jolodar O, Karimi-Chayjani R, Nikoo Langarudi MS, Shirini F. ChemistrySelect 2019; 4: 1562
• 19 Azizi N, Abbasi F, Abdoli-Senejani M. ChemistrySelect 2018; 3: 3797
• 20 Abbasi F, Azizi N, Abdoli-Senejani MJ. Iran. Chem. Soc. 2017; 14: 2097
• 21 Kauthale SS, Tekale SU, Jadhav KM, Pawar RP. Mol. Divers. 2016; 20: 763
• 22 Maleki B. Org. Prep. Proced. Int. 2016; 48: 303
• 23 Nadaf AN, Shivashankar K. J. Heterocycl. Chem. 2018; 55: 1375
• 24 Shirini F, Lati MP. J. Iran. Chem. Soc. 2016; 14: 75
• 25 Rezaei R, Sheikhi MR. Res. Chem. Intermed. 2013; 41: 1283
• 26 Gilanizadeh M, Zeynizadeh B. Polycycl. Arom. Comp. 2019; 41: 15
• 27 Biglari M, Shirini F, Mahmoodi NO, Zabihzadeh M, Safarpoor Nikoo La garudi M, Alipour Khoshdel M. Polycycl. Aromat. Compd. 2020; 42: 1452
• 28 Zeynizadeh B, Gilanizadeh M. New J. Chem. 2019; 43: 18794
• 29 Metwally NH, Abdallah SO, Mohsen MM. A. Bioorg. Chem. 2020; 97: 103672
• 30 Mahmoodi NO, Jalalifard Z, Fathanbari GP. J. Chin. Chem. Soc. 2019; 67: 172
• 31 Poor Heravi MR, Fakhr F. Tetrahedron Lett. 2011; 52: 6779
• 32 Kalinski C, Lemoine H, Schmidt J, Burdack C, Kolb J, Umkehrer M, Ross G. Synthesis 2008; 4007
• 33 Emelen KV, De Wit T, Hoornaert GJ, Compernolle F. Tetrahedron 2002; 58: 4225
• 34 Dou G, Shi C, Shi D. J. Comb. Chem. 2008; 10: 810
• 35 Wu H, Lin W, Wan Y, Xin H, Shi D, Shi Y, Yuan R, Bo R, Yin W. J. Comb. Chem. 2009; 12: 31
• 36 Liu H, Dou G, Shi D. J. Comb. Chem. 2010; 12: 292
• 37 Verma M, Thakur A, Sharma R, Bharti R. Curr. Org. Synth. 2022; 19: 86
• 38 Thakur A, Verma M, Bharti R, Sharma R. Tetrahedron 2022; 119: 132813
• 39 Thakur A, Bharti R, Sharma R. Orbital: E-J. Chem. 2021; 13: 335
• 40 Verma M, Thakur A, Kapil S, Sharma R, Sharma A, Bharti R. Mol. Diversity 2022; 27: 889
• 41 Thakur A, Verma M, Bharti R, Sharma R. Curr. Org. Chem. 2022; 26: 299
• 42 Hogg N. Semin. Reprod. Med. 1998; 16: 241
• 43 Bhardwaj P, Thakur MS, Kapoor S, Bhardwaj AK, Sharma A, Saxena S, Chaurasia OP, Kumar R. Pharmacogn. J. 2019; 11: 536
• 44 Soare JR, Dinis TC. P, Cunha AP, Almeida L. Free Radic. Res. 1997; 26: 469
• 45 Prieto P, Pineda M, Aguilar M. Anal. Biochem. 1999; 269: 337
• 46 Thakur A, Verma M, Setia P, Bharti R, Sharma R, Sharma A, Negi NP, Anand V, Bansal R. Res. Chem. Intermed. 2022; 49: 859
• 47 Thakral, A.; Bharti, R.; Thakur, A.; Verma, M.; Sharma, R. Mater. Today: Proc. 2022, in print.
• 48 Makhlouf J, Louis H, Benjamin I, Ukwenya E, Valkonen A, Smirani W. J. Mol. Struc. 2023; 1272: 134223
• 49 Sahu, B.; Bharti, R.; Thakur, A.; Verma, M.; Sharma, R. Mater Today: Proc. 2022, in print.
• 50 Koopmans T. Physica 1934; 1: 104