The Synthesis, Characterization, and Biological Activities of Some Novel Schiff Bases Derived From 3-Acetyl-4-Hydroxy-2H-Chromen-2-One And 2-Aminooxadiazole Derivatives Have Been Investigated

Authors

  • Jadhav Rajpal L.  Chemistry Department, Swa. Sawarkar Mahavidyalaya, Beed, (MH), India
  • Ubale Sanjay B.  Chemistry Department, Deogiri College, Chhatrapati Sambhajinagar, (MH), India

DOI:

https://doi.org/10.32628/IJSRST52411174

Keywords:

Coumarin, 3-acetyl-4-hydroy chromen-2-one, 2-aminooxadiazole, 3, 4-oxadiazole, Schiff’s bases and anti-microbial activity.

Abstract

A set of five novel Schiff’s bases (5a-e) incorporating coumarin-1, 3, 4-oxadiazole derivative were synthesized through condensation reaction of 3-acetyl-4-hydroxy-2H-chromen-2-one with 2-aminooxadiazole derivatives as heterocyclic aromatic amines. The novel structures of these compounds were confirmed based on their elemental analysis and spectral data. All these investigated derivatives were tested against bacterial species S. aurous, E. coli, S. typhi, B. substilis using the Agar cup method, and against fungal species A. niger, P. chrysogenum, F. moneliforme and A. flavus using poison plate method. Schiff bases incorporating coumarin and 1,3,4-oxadiazole moieties have shown notable efficacy against both bacterial and fungal strains.

References

  1. R.D.H. Murray, J. Mendez, and S.A. Brown, "The Natural Coumarins," John Wiley & Sons, Ltd., New York, (1982); b) R.D.H. Murray, Progress in the Chemistry of Organic Natural Products, Vol. 35, 199 (1978).
  2. B. Naser- Hijazi; B. Stolze; K.S. Zanker.; Second Proceedings of the International Society of Coumarin Investigators; Springer: Berlin, Germany (1994).
  3. R. O’Kennedy and R.D. Thornes; Coumarins: Biology, applications and mode of action; John Wiley & Sons, New York (1997).
  4. C. Gnerre, M. Catto, F. Leonetti, P.A. Weber, P.A. Carrupt, C. Altomare, A. Carotti, B. Testa; Inhibition of monoamine oxidases by functionalized coumarin derivatives; biological activity; J. Med. Chem.; Vol. 43(25); 4747-58 (2000).
  5.  M. Zahradnik: “The Production and Application of Fluorescent Brightening Agents”, John Wiley & Sons, New York, USA (1992).
  6. S. Hesse; G. Kirsch: “Synthesis, reactivity and antimicrobial activity of Coumarinic and Chromonic heterocycles; Tetrahedron Letter.: Vol. 43, 1213-1215 (2002).
  7. D. Patel, P. Kumari, and N. Patel: “Synthesis, characterization and biological evaluation of some thiazolidinone derivatives as antimicrobial agents”: J. Chemical and Pharm. Res., Vol. 2(5); 84–91 (2010).
  8. V. K. Gupta and V. Arya; “A review on potential diuretics of Indian medicinal Plants”: J. Chem. Pharm. Res., Vol. 3(1):613-620 (2011).
  9. Y.S. Ranganath; V.H. Babu; G. Sandeep; R. Parameshwar; “Synthesis and evaluation of some novel furocoumarin derivatives for radical scavenging profile and cytotoxic studies”: J. Chem. Pharma. Res.; Vol. 3(4), p. 62-68 (2011).
  10. L.A. Singer and N.P. Kong: Vinyl Radicals, Stereoselectivity in Hydrogen Atom Transfer to Equilibrated Isomeric Vinyl Radicals1; J. American Chem. Soc.; Vol.: 88 (22), 5213-5219 (1966).
  11. S. Carboni; V. Malaguzzi; A. Marzili: “Ferulenol a new coumarin derivative from ferula Communis”; Tetrahedron Letter; Vol. 5, 2783–2785(1964).
  12. C.P. Raptopoulou; A.N. Papadopoulos; D.A. Malamatari; E. Loannidis; G. Molsidis; A. Terzis; D.P. Kessissoglou: “Ni (II) and Cu (II) Schiff base complexes with an extended H-bond network”; Inorg. ChimicaActa; Vol. 272 (1-2); 283-290 (1998).
  13. Y.K. Vaghasiya; R.S. Nair; M. Baluja; S.S. Chanda: “Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine”; J. Serb. Chem. Soc.; Vol.69, (12); 991–998 (2004).
  14. K. Vashi; H.B. Naik: “Synthesis of novel Schiff base and azetidinone derivatives and their antibacterial activity”; E-Journal of Chemistry; Vol. 1, (5), 272-276 (2004).
  15. H.M. Safwat; F.A. Ragab; N.M. Eid; G.M. Abdel; “Synthesis, anti-tumor and antimicrobial activities of 3-chloro-9-(p-N-substituted sulfamoylphenylaminoethylene) acridines”; Egyptian J. Pharm. Sci.; Vol.29, 99–110 (1988).
  16. R. Mtrei; M. Yadawe; S.A. Patil; “Synthesis of biologically active p-bis (amino-5-mercapto-1,2,4- triazol-3-yl) benzene and its Schiff base: a new class of bis-triazole”;Orient J Chem; Vol.12: 101- 102 (1996).
  17. D.R. Shkawat; S.S. Sabnis; C.V. Deliwala; “Potential anticancer agents, Schiff bases from p-(3- azaspiro [5,5] undec 3 yl) benzaldehydes”; Bull HaffkineInst; Vol.1: 35-39 (1973).
  18. C.T. Barboiu; M. Luca; C. Pop; E. Brewster; M.E. Dinculescu; “Functionalized Derivatives of Benzocrown Ethers, II. † Supramolecular Complexes of L‐Amino Acids as Efficient Activators of the Zinc Enzyme Carbonic Anhydrase; 22 Aug.1997; Eur. J. Med. Chem.,Vol. 31, 597 (1996).
  19. R.Pignatello; A. Pianicol; P Mazzone; M Pinzzotto; AGarozzo; P.M. Furneri: “Schiff bases of N-hydroxy-N-aminoguianidines as antiviral, antibacterial and anticancer agents”, Eur.J. med. Chem; Vol. 29, (10), 781-785 (1994).
  20. J. Wu; X. Liu; X. Cheng; Y. Cao; D. Wang; Z. Li; W. Xu; Ch. Pannecouque; M. Witvrouw; E.De Clercq. Molecules, Vol.12, 2003 (2007).
  21. P. Sengupta; M. Mal; S. Mandal; J. Singh; and T. K. Maity: “Evaluation of antibacterial and antifungal activity of some 1, 3, 4 oxadiazoles,” Iranian J. of Pharmacology and Therapeutics, Vol. 7, (2), 165–167 (2008).
  22. N. Bhardwaj; S. K. Saraf; P. Sharma; and P. Kumar: “Syntheses, evaluation and characterization of some 1, 3, 4-oxadiazoles as antimicrobial agents,” E-J. of Chem., Vol. 6, (4),1133–1138 (2009).
  23.  A. A. Kadi; N. R. El-Brollosy; O. A. Al-Deeb; E. E. Habib; T. M. Ibrahim and A. A. El-Emam: “Synthesis, antimicrobial, and anti-inflammatory activities of novel 2-(1-adamantyl)-5-substituted-1,3,4-oxadiazoles and 2-(1-adamantylamino)-5-substituted-1,3,4-thiadiazoles,” Eur. J. of Med.Chem., Vol. 42, (2), 235–242 (2007).
  24. B. Chandrakantha; P. Shetty; V. Nambiyar; N. Isloor; A. M. Isloor: Eur. J. Med. Chem., Vol. 45, 1206e1210 (2010).
  25. T. Akhtar, S. Hameed, N. A. Al-Masoudi, R. Loddo, and P. L. Colla, “In vitro antitumor and antiviral activities of new benzothiazole and 1,3,4-oxadiazole-2-thione derivatives,” Acta Pharmaceutica, Vol. 58, (2), 135–149 (2008).
  26. M. J. Ahsan, J. Sharma, S. Bhatia, P. K. Goyal, K. Shankhala, and M. Didel, “Synthesis of 2, 5-disubstituted-1, 3, 4-oxadiazole analogs as novel anticancer and antimicrobial agents,” Lett. in Drug Design and Disc., Vol. 11, (4), 413–419, (2013).
  27. M. J. Ahsan, R. V. P. Singh,M. Singhet al., “Synthesis, anticancer and molecular docking studies of 2-(4-chlorophenyl)-5-aryl-1,3, 4-oxadiazole analogues,” Medicinal Chemistry, vol. 33, no. 3, pp. 294–297, (2013).
  28. Salahuddin, M. Shaharyar, A. Majumdar, and M. J. Ahsan, “Synthesis, characterization and anticancer evaluation of 2-(naphthalen-1-ylmethyl/naphthalen-2-yloxymethyl)-1- [5- (substituted phenyl)- [1,3,4] oxadiazol-2-ylmethyl]-1Hbenzimidazole,” Arabian Journal of Chemistry, (2013).
  29.  M. J. Ahsan, J. G. Samy, H. Khalilullah et al., “Molecular properties prediction and synthesis of novel 1,3,4-oxadiazole analogues as potent antimicrobial and antitubercular agents,” Bioorganic and Medicinal Chemistry Letters, vol. 21, no. 24, pp. 7246–7250, (2011).
  30. M. J. Ahsan, J. G. Samy, C. B. Jain, K. R. Dutt, H. Khalilullah, and M. S. Nomani, “Discovery of novel antitubercular 1,5-dimethyl-2-phenyl-4-([5-(arylamino)- 1,3,4-oxadiazol-2-yl] methylamino)-1,2-dihydro-3H-pyrazol-3-one analogues,” Bioorganic and Medicinal Chemistry Letters, vol. 22, no. 2, pp. 969–972, (2012).
  31. M. A. Bakht, M. S. Yar, S. G. Abdel-Hamid, S. I. Al Qasoumi, and A. Samad, “Molecular properties prediction, synthesis and antimicrobial activity of some newer oxadiazole derivatives,” European Journal of Medicinal Chemistry, vol. 45, no. 12, pp. 5862–5869, (2010).
  32. M. Khan, T. Akhtar, N. A. Al-Masoudi, H. Stoeckli-Evans, and S. Hameed, “Synthesis, crystal structure and anti-HIV activity of 2-adamantyl/adamantylmethyl-5-aryl-1,3,4-oxadiazoles,” Medicinal Chemistry, vol. 8, no. 6, pp. 1190–1197, (2012).
  33. G. C. Ramaprasad, B. Kalluraya, B. Sunil Kumar, and S. Mallya, “Synthesis of new oxadiazole derivatives as antiinflammatory, analgesic, and antimicrobial agents,” Medicinal Chemistry Research, vol. 22, no. 11, pp. 5381–5389, (2013).
  34. Y. Li, H. Zhu, K. Chen et al., “Synthesis, insecticidal activity, and structure-activity relationship (SAR) of anthranilic diamides analogs containing oxadiazole rings,” Organic and Biomolecular Chemistry, vol. 11, no. 24, pp. 3979–3988, (2013).
  35. Borg, S.; Estenne-Bouhtou, G.; Luthman, K.; Csoeregh, I.; Hesselink,W.; Hacksell,U. J. Org. Chem.1995, 60, 3112e3120.
  36. Khan, M. T. H.; Choudhary, M. I.; Khan, K. M.; Rani, M. Bioorg. Med. Chem., 13, 3385e3395 (2005).
  37. A. Ramazani, A. Rezaei, Org. Lett. Vol.12, 2852e2855 (2010).
  38. M. V. Girgaonkar and S. G. Shirodkar; “Synthesis, characterization and Antimicrobial activity of some new Schiff’s bases derived from 3-acetyl-4-hydroxy-2H-chromen-2-one and primary aromatic amines; J. of Chem. and Pharm. Res., Vol. 4, (1), 260-264 (2012).
  39. V. V. Kodgire, S. S. Chandole and S. G. Shirodkar; “Synthesis, characterization and antimicrobial study of some new schiff’s bases derived from 3-acetyl-4-hydroxy-2H chromen-2-one” J. of Chem. and Pharm. Res., Vol. 7, (4), 199-203(2015).
  40. V. V. Kodgire, S. B. Patwari, S. S. Chandole1 and S. G. Shirodkar; “Characterization and antimicrobial study of some new N'-(1-(4-hydroxy-2-oxo-2H-chromen-3-yl) ethylidene) arylhydrazide synthesized from 3-acetyl-4-hydroxy-2H-chromen-2-one” J. of Chem. and Pharm. Res; Vol. 7, (12) 515-518 (2015).
  41. M. S. Mote, S. B. Patwari and S. P. Pachling; “Synthesis, characterization and antimicrobial activity of some new schiff’s bases of 3-acetyl-4-hydroxy-2H-chromen-2-one and amino pyridines” J. of Chem. and Pharm. Res; Vol. 5(5) 267-270 (2013).
  42. R.L. Jadhav; H.U. Joshi; S.B. Ubale; “Synthesis, characterization and biological activities of some novel Schiff bases derived from 3-acetyl-4-hydroxy-2H-chromen-2-one and 5-(4-substituted phenyl)-1,3,4-thiadiazol-2-amine” J. of Interdis.Cycle Res. Vol. XIII, (X), (Oct-2021).
  43. R.L. Jadhav; H.U. Joshi; S.B. Ubale; “Synthesis, characterization and biological activities of some novel Schiff bases derived from 3-acetyl-4-hydroxy-2H-chromen-2-one and 2- amino 5-(4-halo substituted phenyl)-1, 3, 4-thiadiazole” The Inter. J. of analytical and expt. modal analysis Vol. XIII, (XI), (Nov. 2021).
  44. a)Klosa J., Preparation of 4-hydroxycoumarin ketones with the help of phosphoroxychloride, Arch Pharm BerDtsch Pharm Ges, Vol. 289(2), 104-10 (1956) b) Stephen J. F., and Marcus E.,Concerning the postulated rearrangement of 4-acyloxy-and 4-aroyloxycoumarins to 5-acyl-and 5-aroyl-4-hydroxycoumarins, J Org.Chem.; Volume 34(9); 2764-2766 (1969).
  45. Iman A. Gad El-Karim; Mahasen S. Amine; Amal A. Mahmoud; Alaa S. Gouda: Fatty Acids in Heterocyclic Synthesis. Part XIV: Synthesis of Surface-Active Agents from Some Novel Class of Oxadiazole, Thiadiazole and Triazole Derivatives Having Microbiological Activities; J. Surfact Deterg.; Vol.17; 509–523 (2014).
  46. R. J. Nahi, and Z. I. Kuwait; Synthesis, Characterization and Thermal Behavior Study of New 1,2,3-Triazole Derivatives Containing 1,3,4-Oxadiazole Ring; Nahi et. al., Orient. J. Chem., Vol. (35) 1, 416-422 (2019).
  47. Eid E. Salama; Synthesis of new 2-amino-1,3,4-oxadiazole derivatives with anti-salmonella typhi activity evaluation; Salama BMC Chemistry; Vol. 14(30);1-8) (2020).
  48. R.J. Cruickshank; R.R. Duguid; Swain Medical; Medical Microbiology; Churchill Livingstone; Vol. 1 (1998).
  49. V. Mutalk and M.A. Phaniband; “Synthesis, characterization, fluorescent and antimicrobial properties of new Lanthanide (III) complexes derived from coumarin Schiff base; J. Chem. Pharm. Res, Vol. 3(2), 313 (2011).

International Journal of Scientific Research in Science and Technology

Downloads

Published

2024-02-29

Issue

Volume 11, Issue 1, January-February-2024

Section

Research Articles

License

Copyright (c) IJSRST

Creative Commons License

This work is licensed under a Creative Commons Attribution 4.0 International License.

How to Cite

[1]
Jadhav Rajpal L., Ubale Sanjay B. "The Synthesis, Characterization, and Biological Activities of Some Novel Schiff Bases Derived From 3-Acetyl-4-Hydroxy-2H-Chromen-2-One And 2-Aminooxadiazole Derivatives Have Been Investigated" International Journal of Scientific Research in Science and Technology(IJSRST), Online ISSN : 2395-602X, Print ISSN : 2395-6011,Volume 11, Issue 1, pp.479-488, January-February-2024. Available at doi : https://doi.org/10.32628/IJSRST52411174