Synthesis of some coumarinyl chalcones of pharmacological interest

B.S. Jayashree, S. Yusuf, D.V. Kumar

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Coumarins are group of secondary plant metabolites found to exhibit important pharmacological activities. Some of their 3-substituted derivatives such as novobiocin, coumaromycin and chartencin are known to exhibit antibacterial activity. The reports on chalcones address their useful biological activity. In the present study, three acetylcoumarins were condensed with different aromatic aldehydes to obtain coumarinyl chalcones. 3-Acetylcoumarins were synthesized by Pachmann reaction and were condensed with different substituted aromatic aldehyde to obtain coumarinyl chalcones (1-12). The synthesized test compounds were characterized by their TLC, melting point, IR, 1H NMR and Mass spectral studies and evaluated for various pharmacological activities such as, antioxidant, antiinflammatory, analgesic and antibacterial activity. Out of the randomly selected test compounds, none of them exhibited antioxidant activity. However, compounds 7 and 9 exhibited fairly good analgesic activity compared to that of standard diclofenac sodium. Further, three compounds were randomly selected for antiinflammatory activity and found to be moderately active. Finally, all the test compounds were screened for their antibacterial activity, out of which, few were found to be moderately active against gram positive organisms while compound 10; a bromo substituted derivative of coumarin has shown zone of inhibition at 18 when compared with that of the standard streptomycin showing inhibition at 10 against K. pneumonia. It was found that halogen substitution at 6th position on coumarinyl chalcones has greater influence on analgesic activity than unsubstituted ones, while for antiinflammatory activity unsubstituted ones are more appropriate. Further, compound 10 was found to be active against K. pneumonia. © 2009 by Mrs. Pushpa Agarwal, Managing Editor, Asian Journal of Chemistry, Sahibabad, India.
Original languageEnglish
Pages (from-to)5918-5922
Number of pages5
JournalAsian Journal of Chemistry
Volume21
Issue number8
Publication statusPublished - 2009

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Chalcones
Analgesics
Coumarins
Anti-Inflammatory Agents
Aldehydes
Antioxidants
Novobiocin
Halogens
Diclofenac
Streptomycin
Metabolites
Bioactivity
Melting point
Substitution reactions
Nuclear magnetic resonance
Derivatives

Cite this

Jayashree, B.S. ; Yusuf, S. ; Kumar, D.V. / Synthesis of some coumarinyl chalcones of pharmacological interest. In: Asian Journal of Chemistry. 2009 ; Vol. 21, No. 8. pp. 5918-5922.
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abstract = "Coumarins are group of secondary plant metabolites found to exhibit important pharmacological activities. Some of their 3-substituted derivatives such as novobiocin, coumaromycin and chartencin are known to exhibit antibacterial activity. The reports on chalcones address their useful biological activity. In the present study, three acetylcoumarins were condensed with different aromatic aldehydes to obtain coumarinyl chalcones. 3-Acetylcoumarins were synthesized by Pachmann reaction and were condensed with different substituted aromatic aldehyde to obtain coumarinyl chalcones (1-12). The synthesized test compounds were characterized by their TLC, melting point, IR, 1H NMR and Mass spectral studies and evaluated for various pharmacological activities such as, antioxidant, antiinflammatory, analgesic and antibacterial activity. Out of the randomly selected test compounds, none of them exhibited antioxidant activity. However, compounds 7 and 9 exhibited fairly good analgesic activity compared to that of standard diclofenac sodium. Further, three compounds were randomly selected for antiinflammatory activity and found to be moderately active. Finally, all the test compounds were screened for their antibacterial activity, out of which, few were found to be moderately active against gram positive organisms while compound 10; a bromo substituted derivative of coumarin has shown zone of inhibition at 18 when compared with that of the standard streptomycin showing inhibition at 10 against K. pneumonia. It was found that halogen substitution at 6th position on coumarinyl chalcones has greater influence on analgesic activity than unsubstituted ones, while for antiinflammatory activity unsubstituted ones are more appropriate. Further, compound 10 was found to be active against K. pneumonia. {\circledC} 2009 by Mrs. Pushpa Agarwal, Managing Editor, Asian Journal of Chemistry, Sahibabad, India.",
author = "B.S. Jayashree and S. Yusuf and D.V. Kumar",
note = "Cited By :6 Export Date: 10 November 2017 CODEN: AJCHE Correspondence Address: Jayashree, B. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal-576104, India; email: jesolar2001@yahoo.co.in References: Harbome, J.B., William, C.A., (2000) Photochemistry, 55, p. 481; Kostova, I., (2007) Expert Opin. Drug Discov., 2, p. 1605; Manfredini, S., Bazzanini, R., Baraldi, P.G., Guarneri, M., Simoni, D., Marongiu, M.E., Pani, A., La Colla, P., (1992) J. Med. Chem., 35, p. 917; Chiang, C.C., Mouscadet, J.F., Tsai, H.J., Liu, C.T., Hsu, L.Y., (2007) Chem. Pharm. Bull (Tokyo), 55, p. 1740; Oblak, M., Kotnik, M., Solmajer, T., (2007) Curr. Med. Chem., 14, p. 2033; Sardari, S., Mori, Y., Horita, K., Micetich, R.G., Nishibe, S., Daneshtalab, M., (1999) Bioorg. Med. Chem., 7, p. 1933; Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., Nicolaides, D.N., (2004) Curr. Pharm. Design, 10, p. 3813; Gellert, M., Mizuuchi, K., O'Dea, M.H., Itoh, T., Tomizawa, J.-I., (1976) Proc. Natl. Acad. Sci. (USA), 73, p. 4474; Dey, P., (2006) Curr. Med. Chem., 13, p. 2909. , http://en.wikipedia.org/wiki/Iurmeric; Rai, K.M.L., Basavaraju, Y.B., Sadashivamurthy, B., (2007) Indian J. Pharm. Sci., 69, p. 116; Vibhute, Y.B., Baseer, M.A., (2003) Cheminform, 34; Blios, M.S., (1958) Nature, 181, p. 1191; Winter, C.A., Risley, E.A., Nuss, G.W., (1962) Proc. Soc. Exp. Biol. Med., 111, p. 544; Witkin, L.B., Heubner, C.F., Galdi, F., O'keefe, Spitaletta, P., Plummer, A.J., (1961) J. Pharmacol. Exp., 133, p. 400; Richardson, H., Emslie-Smith, E.H., Senior, B.W., (1968) Appl. Microbiol., 16, p. 1468",
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Synthesis of some coumarinyl chalcones of pharmacological interest. / Jayashree, B.S.; Yusuf, S.; Kumar, D.V.

In: Asian Journal of Chemistry, Vol. 21, No. 8, 2009, p. 5918-5922.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of some coumarinyl chalcones of pharmacological interest

AU - Jayashree, B.S.

AU - Yusuf, S.

AU - Kumar, D.V.

N1 - Cited By :6 Export Date: 10 November 2017 CODEN: AJCHE Correspondence Address: Jayashree, B. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal-576104, India; email: jesolar2001@yahoo.co.in References: Harbome, J.B., William, C.A., (2000) Photochemistry, 55, p. 481; Kostova, I., (2007) Expert Opin. Drug Discov., 2, p. 1605; Manfredini, S., Bazzanini, R., Baraldi, P.G., Guarneri, M., Simoni, D., Marongiu, M.E., Pani, A., La Colla, P., (1992) J. Med. Chem., 35, p. 917; Chiang, C.C., Mouscadet, J.F., Tsai, H.J., Liu, C.T., Hsu, L.Y., (2007) Chem. Pharm. Bull (Tokyo), 55, p. 1740; Oblak, M., Kotnik, M., Solmajer, T., (2007) Curr. Med. Chem., 14, p. 2033; Sardari, S., Mori, Y., Horita, K., Micetich, R.G., Nishibe, S., Daneshtalab, M., (1999) Bioorg. Med. Chem., 7, p. 1933; Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., Nicolaides, D.N., (2004) Curr. Pharm. Design, 10, p. 3813; Gellert, M., Mizuuchi, K., O'Dea, M.H., Itoh, T., Tomizawa, J.-I., (1976) Proc. Natl. Acad. Sci. (USA), 73, p. 4474; Dey, P., (2006) Curr. Med. Chem., 13, p. 2909. , http://en.wikipedia.org/wiki/Iurmeric; Rai, K.M.L., Basavaraju, Y.B., Sadashivamurthy, B., (2007) Indian J. Pharm. Sci., 69, p. 116; Vibhute, Y.B., Baseer, M.A., (2003) Cheminform, 34; Blios, M.S., (1958) Nature, 181, p. 1191; Winter, C.A., Risley, E.A., Nuss, G.W., (1962) Proc. Soc. Exp. Biol. Med., 111, p. 544; Witkin, L.B., Heubner, C.F., Galdi, F., O'keefe, Spitaletta, P., Plummer, A.J., (1961) J. Pharmacol. Exp., 133, p. 400; Richardson, H., Emslie-Smith, E.H., Senior, B.W., (1968) Appl. Microbiol., 16, p. 1468

PY - 2009

Y1 - 2009

N2 - Coumarins are group of secondary plant metabolites found to exhibit important pharmacological activities. Some of their 3-substituted derivatives such as novobiocin, coumaromycin and chartencin are known to exhibit antibacterial activity. The reports on chalcones address their useful biological activity. In the present study, three acetylcoumarins were condensed with different aromatic aldehydes to obtain coumarinyl chalcones. 3-Acetylcoumarins were synthesized by Pachmann reaction and were condensed with different substituted aromatic aldehyde to obtain coumarinyl chalcones (1-12). The synthesized test compounds were characterized by their TLC, melting point, IR, 1H NMR and Mass spectral studies and evaluated for various pharmacological activities such as, antioxidant, antiinflammatory, analgesic and antibacterial activity. Out of the randomly selected test compounds, none of them exhibited antioxidant activity. However, compounds 7 and 9 exhibited fairly good analgesic activity compared to that of standard diclofenac sodium. Further, three compounds were randomly selected for antiinflammatory activity and found to be moderately active. Finally, all the test compounds were screened for their antibacterial activity, out of which, few were found to be moderately active against gram positive organisms while compound 10; a bromo substituted derivative of coumarin has shown zone of inhibition at 18 when compared with that of the standard streptomycin showing inhibition at 10 against K. pneumonia. It was found that halogen substitution at 6th position on coumarinyl chalcones has greater influence on analgesic activity than unsubstituted ones, while for antiinflammatory activity unsubstituted ones are more appropriate. Further, compound 10 was found to be active against K. pneumonia. © 2009 by Mrs. Pushpa Agarwal, Managing Editor, Asian Journal of Chemistry, Sahibabad, India.

AB - Coumarins are group of secondary plant metabolites found to exhibit important pharmacological activities. Some of their 3-substituted derivatives such as novobiocin, coumaromycin and chartencin are known to exhibit antibacterial activity. The reports on chalcones address their useful biological activity. In the present study, three acetylcoumarins were condensed with different aromatic aldehydes to obtain coumarinyl chalcones. 3-Acetylcoumarins were synthesized by Pachmann reaction and were condensed with different substituted aromatic aldehyde to obtain coumarinyl chalcones (1-12). The synthesized test compounds were characterized by their TLC, melting point, IR, 1H NMR and Mass spectral studies and evaluated for various pharmacological activities such as, antioxidant, antiinflammatory, analgesic and antibacterial activity. Out of the randomly selected test compounds, none of them exhibited antioxidant activity. However, compounds 7 and 9 exhibited fairly good analgesic activity compared to that of standard diclofenac sodium. Further, three compounds were randomly selected for antiinflammatory activity and found to be moderately active. Finally, all the test compounds were screened for their antibacterial activity, out of which, few were found to be moderately active against gram positive organisms while compound 10; a bromo substituted derivative of coumarin has shown zone of inhibition at 18 when compared with that of the standard streptomycin showing inhibition at 10 against K. pneumonia. It was found that halogen substitution at 6th position on coumarinyl chalcones has greater influence on analgesic activity than unsubstituted ones, while for antiinflammatory activity unsubstituted ones are more appropriate. Further, compound 10 was found to be active against K. pneumonia. © 2009 by Mrs. Pushpa Agarwal, Managing Editor, Asian Journal of Chemistry, Sahibabad, India.

M3 - Article

VL - 21

SP - 5918

EP - 5922

JO - Asian Journal of Chemistry

JF - Asian Journal of Chemistry

SN - 0970-7077

IS - 8

ER -