SYNTHESIS AND CHARACTERIZATION OF NEW COUMARIN DERIVATIVES CONTAINING VARIOUS MOIETIES WITH ANTIBACTERIAL ACTIVITIES

  • Shokhan Jamal Hamid Department of Pharmaceutical Chemistry, School of Pharmacy, Faculty of Medical Sciences, University of Sulaimani. Sulaimani-IRAQ
  • Ammar A. Razzak Mahmood Kubba Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad-Baghdad-IRAQ

Abstract

Objective: The purpose of this research is to evaluate the antibacterial activity of different moieties (Schiff bases, chalcones, hydrazones and hydrazinyl thiazole) derivatives, inserted at carbon 8 of 7-hydroxy-4-methyl coumarin, using in vitro, serial broth dilution method.

Methods: A series of new coumarin derivatives, including (Schiff bases, chalcones, hydrazones and hydrazinyl thiazole), were prepared from 7-hydroxy-4-methyl coumarin, by insertion of the formyl group, at carbon number 8 using Duff reaction. The structure of the new synthesized derivatives elucidated and confirmed utilizing the corresponding analytical and spectroscopic data; including FT-IR, 13C-NMR, and mass spectroscopy. All new coumarin derivatives have been screened for their preliminary antibacterial activity, by serial broth dilution method against two Gram-positive bacteria (Staphylococcus epidermidis and Staphylococcus hemolyticus) and two Gram-negative bacteria (Escherichia coli and Klebsiella pneumoniae).

Results: All the synthesized compounds have been found to exhibit considerable antibacterial activity in vitro. Among all the derivatives, compound (5a), showed the highest rate of inhibition, against (Escherichia coli), while compound (6a), showed the greatest anti-bacterial activity against (Staphylococcus hemolyticus), each with minimum inhibitory concentration of (25µg/ml), and the highest MIC of 200 µg/ml for compound 2, against. Klebsiella pneumoniae.

Conclusion: Our results displayed a substantial preliminary antibacterial activity of the new coumarin moieties, especially some hydrazones and chalcones at C8 of the coumarin nucleus, against Gram-positive and a Gram-negative bacteria with distinguished MIC.

 

Keywords: Coumarin, Duff reaction, Chalcones, Hydrazones, Schiff base, Antibacterial activity

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Author Biography

Ammar A. Razzak Mahmood Kubba, Department of Pharmaceutical Chemistry, College of Pharmacy, University of Baghdad-Baghdad-IRAQ

Dept. of Pharmaceutical Chemistry at College of Pharmacy

Lecturer

References

Sentha SM. Synthesis of coumarin and 4-methyl coumarin. Chem Rev 1945;36:2.
2. Darren Holling, Graham Sandford, Andrei S Batsanov, Dmitril S Yufit, Judith AK Howard. Direct fluorination of coumarin, 6-methyl-coumarin, and 7-alkoxy-coumarins. J Fluorine Chem 2005;126(9-10):1377-83.
3. Pangal A, Gazge M, Mane V, Shaikh JA. Various pharmacological aspects of coumarin derivatives: a review. Int J Pharm Biol 2013;2(6):168-94.
4. Lin P-Y, Yeh K-S, Su C-L, Sheu S-Y, Chen T, Ou K-L, et al. Synthesis and antibacterial activities of novel 4-hydroxy-7-hydroxy-and 3-carboxycoumarin derivatives. Molecules 2012;17:10846-63.
5. Swamy BHMJ, Nandini HGM, Pramod N. Synthesis, characterization and antifungal activity of coumarin carbohydrazide containing quinoline derivatives. Int J Res Pharm Nan Sci 2013;2(2):195-2.
6. Darla MM, Krishna BS, Rao KU, Reddy NB, Srivash MK, Adeppa K, et al. Synthesis and bio-evaluation of novel 7-hydroxy coumarin derivatives via Knoevenagel reaction. Res Chem Intermed 2015;41:1115-33.
7. Al-Kawkabani A, Boutemeur-Kheddis B, Makhloufi-Chebli M, Hamdi M, Talhi O, Silva AMS. Synthesis of novel 2H,8H-pyrano [2,3-f] chromene-2,8-diones from 8-formyl-7-hydroxy-4-methylcoumarin. Tetrahedron Lett 2013;54:5111–4.
8. Aly MRES, Fodah HAER, Saleh SY. Antiobesity, antioxidant and cytotoxicity activities of newly synthesized chalcone derivatives and their metal complexes. Eur J Med Chem 2014;76:517-30.
9. Syam S, Abdelwahab SI, Al-Mamary MA, Mohan S. Synthesis of chalcones with anticancer activities. Molecules 2012;17:6179-95.
10. Singh I, Kaur H, Kumar S, Kumar A, Lata S, Kumar A. Synthesis of new coumarin derivatives as antibacterial agents. Int J Chem Tech Res 2010;2:1745-52.
11. Mantri N, Jadon G. Two Synthesized mannich bases of 7-hydroxy-4-methyl coumarin with a different secondary amine. Int J Adv Res Pharm Biosci 2013;3(2):117-26.
12. Manidhar DM, Rao KUM, Reddy NB, Sundar CS, Reddy CS. Synthesis of new 8-formyl-4-methyl-7-hydroxy coumarin derivatives. J Korean Chem Soc 2012;56(4):459-63.
13. Lamani KSS, Kotresh O, Phaniband MA, Kadakol JC. Synthesis, characterization and antimicrobial properties of Schiff bases derived from condensation of 8-formyl-7-hydroxy-4-methylcoumarin and substituted triazole derivatives. E J Chem 2009;6:239-46.
14. Kumar DN, Sharma P, pareek A. Synthesis of new Schiff-base complexes and their applications. Int J Appl Res St 2013;2:307.
15. Sashidhara KV, Kumar A, Kumar M, Sarkar J, Sinha S. Synthesis and in vitro evaluation of novel coumarin–chalcone hybrids as potential anticancer agents. Bioorg Med Chem Lett 2010;20:7205–11.
16. Serda M, Musiol R, Polanski J. New thiosemicarbazones based on the quinoline scaffold as anticancer iron chelators. 14thInternational Electronic Conference on Synthetic Organic Chemistry, (ECSOC-14). Szkolna, Poland; 2010.
17. Gomha SM, Khalil KD. A convenient ultrasound-promoted synthesis of some new thiazole derivatives bearing a coumarin nucleus and their cytotoxic activity. Molecules 2012;17:9335-47.
18. Mohamed HM, El-Wahab AHFA, Ahmed KA, El-Agrody AM, Bedair AH, Eid FA, et al. Synthesis, reactions and antimicrobial activities of 8-ethoxycoumarin derivatives. Molecules 2012;17:971-88.
19. Pingaew R, Prachayasittikul S, Ruchirawat S. Synthesis, Cytotoxic and antimalarial activities of benzoyl thiosemicarbazone analogs of isoquinoline and related compounds. Molecules 2010;15:988-96.
20. Sudhir S Sawant, Vijaya Pawar, Shirish Janrao, Ramesh S Yamgar, Y Nivid. Synthesis and characterization of transition metal complexes of novel Schiff base 8-[(Z)-{[3-(N-methylamino) propyl] imino} methyl]-7-hydroxy-4-methyl-2H-chromene-one][NMAPIMHMC] and their biological activities. Int J Res Pharm Chem 2013;3(3):636-44.
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How to Cite
Hamid, S. J., and A. A. R. Mahmood Kubba. “SYNTHESIS AND CHARACTERIZATION OF NEW COUMARIN DERIVATIVES CONTAINING VARIOUS MOIETIES WITH ANTIBACTERIAL ACTIVITIES”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 8, no. 8, June 2015, pp. 70-74, https://innovareacademics.in/journals/index.php/ijpps/article/view/5947.
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