Synthesis of Some New Heteroarylamino-3-Nitro-2H-[1]-Benzopyran-2-ones and their Antibacterial Activity
Keywords:
Thiazolidin-4-one, benzopyran-2-one, condensiation, antibacterial, inhibition zones.Abstract
Novel derivatives of benzopyran-2-ones are synthesized by catalytic condensation reaction. 4-(3-Hydroxy-2-pyridinylamino)- 3-nitro-2H-[1]-benzopyran-2-one 4a, 4-(4-methyl-3-nitro-2-pyridinylamino)-3-nitro-2H-[1]-benzopyran-2-one, 4b and 4-(pyrimidinylamono)-3-nitro-2H-[1]-benzopyran-2-ones 4(c, d) are synthesized by condensation of 4-Chlor-3-nitro-2H-[1]-benzopyran-2-one 2 and corresponding heteroarylamines 3(a-d ) under reflux reaction conditions. Alkali hydrolysis of 4(a-d ) afforded the 2-hydroxy-? -nitroacetophenone 5. Structural characterization of the synthesized products is done on the basis of spectrometric data. Antibacterial activity of the compounds 4(a-d) against S. aureus, E. coli and Klebsiella was examined by measuring the inhibition zones around the disks marked with the corresponding product solutions in N,N-DMF concentration 2 mg/mL , 4 mg/mL and 6 mg/mL. Compounds 4a and 4c have shown significant antibacterial activity against S. aureus, compounds 4b and 4d exhibited significant activity against E. coli whereas compound 4d was more active against Klebsiella.
References
[1] F. M. Dean, Naturally Occurring Oxygen Rong Compounds, Butterworth, London, 1963.
[2] D. M. X. Donnelly, and Boland, in The Flavonoids: Advances in Research since 1986, ed. J. B. Harborne, Chapman and Hall, London, 1994, 239 – 258.
[3] M. M. Darla, B.S. Krishna, K. U.Rao, N. B. Reddy, M. K. Srivash, K. Adeppa, Ch. S. Sundar, C. S. Reddy, K. Misra, Synthesis and bio-evaluation of novel 7-hydroxy coumarin derivatives via Knoevenagel reaction, Research on Chemical Intermediates, Vol. 41, Issue 2, pp 1115–1133, 2015.
[4] X. Hea, Y. Y. Chena, J. B. Shi, W. J Tang, Z. X. Pan, Z. Q. Dong, B. A. Song, J. Li, , X. H. Liu, New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO, Bioorganic & Medicinal Chemistry, Vol. 22, Issue 14, pp 3732–3738, 2014.
[5] R.D.H. Murray, J.Hendez, S.A.Brown, The Natural Coumarins, Willey, New York, 1982.
[6] D. M. Manidhar, R. Kesharwani, N. Bakthavatchala, K. Misra, Designing, synthesis, and characterization of some novel coumarin derivatives as probable anticancer drugs, Med Chem Res. 22: 4146–4157, 2013.
[7] Y.K. Tyagi, A. Kumar, H.G. Raj, P. Vohra, G. Gupta, R.K. Gupta, Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. Eur. J. Med. Chem. 40, 413–420, 2005.
[8] H. Osman, A. Arshad, C. K. Lam, M. C. Bagley, Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives, Chemistry Central Journal, 6:32, 1186/1752-153X, 2012.
[9] S.V. Rodriguez, R. F.Guinez, M. J. Matos, L. Santana, E. Uriarte, M. Lapier, J. D. Maya, C. O. Azar, Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties, Med. Chem. Commun., 4, 993-1000. 2013.
[10] D. Yu, M. Suzuki, L. Xie, S.L. Natschke, K.H. Lee, Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Reiv., 23, 322–345, 2003.
[11] J. N. Modranka, E. Nawrot, J. Graczik, In vivo antitumor, in vitro anti- bacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem., 41 1301–1309, 2006.
[12] R. S. Araújo, F. Q. Guerra, E. O. Lima, C. A. Simone, J. F. Tavares, L. Scotti, M. T. Scotti, T. M. Aquino, R. O. Moura, F. J. Mendonça, J. M. Barbosa-Filho, Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity, Int J Mol Sci. 10;14(1):1293-309, 2013.
[13] M. Mazzei, E. Nieddu, M. Miele, A. Balbi, M. Ferrone, M. Fermeglia, et al., Synthesis of Mannich bases of 7-hydroxycoumarin and screened against Fla- viviridae, Bioorg. Med. Chem. 16 2591–2605, 2008.
[14] S. A. Mayekar, V. V. Mulwad, Synthesis and antibacterial activity of 6-(5phenyl- {1,3,4}thiadiazol-2-ylimino)-benzopyran-2-ones. Indian J. Chem. 47 (B) 1438–1442, 2008.
[15] N. C. Desai, H. M. Satodiya, K. M. Rajpara, V. V. Joshi, H. V. Vaghani, Microwave assisted synthesis of new coumarin based 3-cyanopyridine scaffolds bearing sulfonamide group having antimicrobial activity, Indian Journal of Chemistry, 52B, 904-914, 2013.
[16] S. Rehman, M. Ikram, R. J. Baker, M. Zubair, E. Azad, S. Min, K. Riaz, K. H. Mok, S. Rehman, Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives, Chemistry Central Journal, 7:68, 1186/1752-153X, 2013.
[17] S. A. Mayekar, V. V. Mulwad, Synthesis and antibacterial activity of 6-(5phenyl- {1,3,4}thiadiazol-2-ylimino)-benzopyran-2-ones, Indian J. Chem. 47 (B) 1438–1442, 2008.
[18] K. V. Sashidhara, A. Kumar, R. P. Dodda, N. N. Krishna, P. Agarwal, K. Srivastava, S. K. Puri, Coumarin-trioxane hybrids: synthesis and evaluation as a new class of antimalarial scaffolds, Bioorg Med Chem Lett. 15;22(12):3926-3930, 2012.
[19] H. Osman, A. Arshad, C. K. Lam, M. C. Bagley, Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives, Chemistry Central Journal, 6:32, 1186/1752-153X, 2012.
[20] S. V. Rodriguez, R. F. Guinez, M. J. Matos, L. Santana, E. Uriarte, M. Lapier, J. D. Maya, C. O. Azar, Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties, Med. Chem. Commun., 4, 993-1000, 2013.
[21] J. Nawrot-Modranka, E. Nawrot, J. Graczik, In vivo antitumor, in vitro anti- bacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem. 41 1301–1309, 2006.
[22] D. Yu, M. Suzuki, L. Xie, S. L. Natschke, K. H. Lee, Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Reiv. 23 322–345, 2003.
[23] M. Atmaca, H. M. Bilgin, B. D. Obay, H. Diken, M. Kelle, E. Kale, The hepatoprotective effect of coumarin and coumarin derivates on carbon tetrachloride-induced hepatic injury by antioxidative activities in rats. J Physiol Biochem. 67(4), 569-76, 2011.
[24] B. Ahmed, S. A. Khan, T. Alam, Synthesis and antihepatotoxic activity of some heterocyclic compounds containing the 1,4-dioxane ring system. Pharmazie, 58(3), 173-176, 2003.
[25] T. Okamoto, T. Kobayashi, S. Yoshida, Synthetic Derivatives of Osthole for the Prevention of Hepatitis, Medicinal Chemistry, 3, 35-44, 2007.
[26] S. Rajasekaran, G. K. Rao, S. Pai, A. Rajan, Design, synthesis, antibacterial and in vitro antioxidant activity of substituted 2H-benzopyran-2-one derivatives, International Journal of ChemTech Research, 3, 2, 555-559, 2011.
[27] R. Hoti, V. Kalaj, I. Vehapi, H. Ismaili, V. Thaçi, M. Bicaj, Novel Pyrimidin-2-yl-benzylidene imines and 2-[(pyrimidin-ylimino)-methyl]-phenoles and their antibacterial activity, The FASEB Journal,Experimental Biology, 2010, lb487, Anaheim Ca. Apr. 2010,
[28] R. Hoti, A. Nura-Lama, Gj. Mulliqi-Osmani, N. Tronia, F. Gashi, H. Ismaili V. Thaçi, Synthesis of 4-Triazolylamino- and 4-Benzothiazolylamino-3- nitro-2H-[1]-Benzopyran-2-ones and their Antimicrobial Activity, Orbital: The Electronic Journal of Chemistry, Vol. 6, No.3, July-September, 2014.
[29] Bauer, A. W. et al. , Antibiotic suscepetibility testing by standardized single disc method, American journal of clinical pathology, 44, , 493: 496, 1966.
[2] D. M. X. Donnelly, and Boland, in The Flavonoids: Advances in Research since 1986, ed. J. B. Harborne, Chapman and Hall, London, 1994, 239 – 258.
[3] M. M. Darla, B.S. Krishna, K. U.Rao, N. B. Reddy, M. K. Srivash, K. Adeppa, Ch. S. Sundar, C. S. Reddy, K. Misra, Synthesis and bio-evaluation of novel 7-hydroxy coumarin derivatives via Knoevenagel reaction, Research on Chemical Intermediates, Vol. 41, Issue 2, pp 1115–1133, 2015.
[4] X. Hea, Y. Y. Chena, J. B. Shi, W. J Tang, Z. X. Pan, Z. Q. Dong, B. A. Song, J. Li, , X. H. Liu, New coumarin derivatives: Design, synthesis and use as inhibitors of hMAO, Bioorganic & Medicinal Chemistry, Vol. 22, Issue 14, pp 3732–3738, 2014.
[5] R.D.H. Murray, J.Hendez, S.A.Brown, The Natural Coumarins, Willey, New York, 1982.
[6] D. M. Manidhar, R. Kesharwani, N. Bakthavatchala, K. Misra, Designing, synthesis, and characterization of some novel coumarin derivatives as probable anticancer drugs, Med Chem Res. 22: 4146–4157, 2013.
[7] Y.K. Tyagi, A. Kumar, H.G. Raj, P. Vohra, G. Gupta, R.K. Gupta, Synthesis of novel amino and acetyl amino-4-methylcoumarins and evaluation of their antioxidant activity. Eur. J. Med. Chem. 40, 413–420, 2005.
[8] H. Osman, A. Arshad, C. K. Lam, M. C. Bagley, Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives, Chemistry Central Journal, 6:32, 1186/1752-153X, 2012.
[9] S.V. Rodriguez, R. F.Guinez, M. J. Matos, L. Santana, E. Uriarte, M. Lapier, J. D. Maya, C. O. Azar, Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties, Med. Chem. Commun., 4, 993-1000. 2013.
[10] D. Yu, M. Suzuki, L. Xie, S.L. Natschke, K.H. Lee, Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Reiv., 23, 322–345, 2003.
[11] J. N. Modranka, E. Nawrot, J. Graczik, In vivo antitumor, in vitro anti- bacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem., 41 1301–1309, 2006.
[12] R. S. Araújo, F. Q. Guerra, E. O. Lima, C. A. Simone, J. F. Tavares, L. Scotti, M. T. Scotti, T. M. Aquino, R. O. Moura, F. J. Mendonça, J. M. Barbosa-Filho, Synthesis, Structure-Activity Relationships (SAR) and in Silico Studies of Coumarin Derivatives with Antifungal Activity, Int J Mol Sci. 10;14(1):1293-309, 2013.
[13] M. Mazzei, E. Nieddu, M. Miele, A. Balbi, M. Ferrone, M. Fermeglia, et al., Synthesis of Mannich bases of 7-hydroxycoumarin and screened against Fla- viviridae, Bioorg. Med. Chem. 16 2591–2605, 2008.
[14] S. A. Mayekar, V. V. Mulwad, Synthesis and antibacterial activity of 6-(5phenyl- {1,3,4}thiadiazol-2-ylimino)-benzopyran-2-ones. Indian J. Chem. 47 (B) 1438–1442, 2008.
[15] N. C. Desai, H. M. Satodiya, K. M. Rajpara, V. V. Joshi, H. V. Vaghani, Microwave assisted synthesis of new coumarin based 3-cyanopyridine scaffolds bearing sulfonamide group having antimicrobial activity, Indian Journal of Chemistry, 52B, 904-914, 2013.
[16] S. Rehman, M. Ikram, R. J. Baker, M. Zubair, E. Azad, S. Min, K. Riaz, K. H. Mok, S. Rehman, Synthesis, characterization, in vitro antimicrobial, and U2OS tumoricidal activities of different coumarin derivatives, Chemistry Central Journal, 7:68, 1186/1752-153X, 2013.
[17] S. A. Mayekar, V. V. Mulwad, Synthesis and antibacterial activity of 6-(5phenyl- {1,3,4}thiadiazol-2-ylimino)-benzopyran-2-ones, Indian J. Chem. 47 (B) 1438–1442, 2008.
[18] K. V. Sashidhara, A. Kumar, R. P. Dodda, N. N. Krishna, P. Agarwal, K. Srivastava, S. K. Puri, Coumarin-trioxane hybrids: synthesis and evaluation as a new class of antimalarial scaffolds, Bioorg Med Chem Lett. 15;22(12):3926-3930, 2012.
[19] H. Osman, A. Arshad, C. K. Lam, M. C. Bagley, Microwave-assisted synthesis and antioxidant properties of hydrazinyl thiazolyl coumarin derivatives, Chemistry Central Journal, 6:32, 1186/1752-153X, 2012.
[20] S. V. Rodriguez, R. F. Guinez, M. J. Matos, L. Santana, E. Uriarte, M. Lapier, J. D. Maya, C. O. Azar, Synthesis of coumarin–chalcone hybrids and evaluation of their antioxidant and trypanocidal properties, Med. Chem. Commun., 4, 993-1000, 2013.
[21] J. Nawrot-Modranka, E. Nawrot, J. Graczik, In vivo antitumor, in vitro anti- bacterial activity and alkylating properties of phosphorohydrazine derivatives of coumarin and chromone. Eur. J. Med. Chem. 41 1301–1309, 2006.
[22] D. Yu, M. Suzuki, L. Xie, S. L. Natschke, K. H. Lee, Recent progress in the development of coumarin derivatives as potent anti-HIV agents. Med. Res. Reiv. 23 322–345, 2003.
[23] M. Atmaca, H. M. Bilgin, B. D. Obay, H. Diken, M. Kelle, E. Kale, The hepatoprotective effect of coumarin and coumarin derivates on carbon tetrachloride-induced hepatic injury by antioxidative activities in rats. J Physiol Biochem. 67(4), 569-76, 2011.
[24] B. Ahmed, S. A. Khan, T. Alam, Synthesis and antihepatotoxic activity of some heterocyclic compounds containing the 1,4-dioxane ring system. Pharmazie, 58(3), 173-176, 2003.
[25] T. Okamoto, T. Kobayashi, S. Yoshida, Synthetic Derivatives of Osthole for the Prevention of Hepatitis, Medicinal Chemistry, 3, 35-44, 2007.
[26] S. Rajasekaran, G. K. Rao, S. Pai, A. Rajan, Design, synthesis, antibacterial and in vitro antioxidant activity of substituted 2H-benzopyran-2-one derivatives, International Journal of ChemTech Research, 3, 2, 555-559, 2011.
[27] R. Hoti, V. Kalaj, I. Vehapi, H. Ismaili, V. Thaçi, M. Bicaj, Novel Pyrimidin-2-yl-benzylidene imines and 2-[(pyrimidin-ylimino)-methyl]-phenoles and their antibacterial activity, The FASEB Journal,Experimental Biology, 2010, lb487, Anaheim Ca. Apr. 2010,
[28] R. Hoti, A. Nura-Lama, Gj. Mulliqi-Osmani, N. Tronia, F. Gashi, H. Ismaili V. Thaçi, Synthesis of 4-Triazolylamino- and 4-Benzothiazolylamino-3- nitro-2H-[1]-Benzopyran-2-ones and their Antimicrobial Activity, Orbital: The Electronic Journal of Chemistry, Vol. 6, No.3, July-September, 2014.
[29] Bauer, A. W. et al. , Antibiotic suscepetibility testing by standardized single disc method, American journal of clinical pathology, 44, , 493: 496, 1966.
Downloads
Published
2016-07-16
How to Cite
Hoti, R., Vehapi, I., Mulliqi-Osmani, G., Ismaili, H., & Thaci, V. (2016). Synthesis of Some New Heteroarylamino-3-Nitro-2H-[1]-Benzopyran-2-ones and their Antibacterial Activity. American Scientific Research Journal for Engineering, Technology, and Sciences, 22(1), 1–9. Retrieved from https://asrjetsjournal.org/index.php/American_Scientific_Journal/article/view/1789
Issue
Section
Articles
License
Authors who submit papers with this journal agree to the following terms.
