Synthesis of novel furobenzopyrone derivatives and evaluation of their antimicrobial and antiinflammatory activity

K. Srinivasan, Y. Neelima, A. Joseph, G. Sreejith, A. Ciraj, J. Rao

Research output: Contribution to journalArticle

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Abstract

Certain 4′-(4″-substituted phenyl)-4-methylfurobenzopyrones were synthesized and evaluated for antibacterial activity. Six of the synthesized compounds were also screened for their antiinflammatory activity. Substituted resorcinols were condensed with ethyl acetoacetate to afford different coumarins (2a-c). Various substituted phenacyl bromides (4a-g) were prepared by the bromination of para-substituted acetophenones. The coumarins (2a-c) and phenacyl bromides (4a-g) were condensed to give oxoethers (5a-s). These were cyclised by using 1 M sodium hydroxide to afford the desired furobenzopyrone derivatives (FCa-s). All the compounds have been evaluated for their antibacterial activity against different strains of gram positive and gram negative bacteria. All the compounds have shown good activity against Pseudomonas aeruginosa. Compounds, 3-(4-chlorophenyl)-5-methylfuro-[3,2-g][1] benzopyran-7-one, 3-(4-chlorophenyl)-5,9-dimethylfuro[3,2-g][1]benzopyran-7-one and 4,5-dimethyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCe, FCi, FCn) were active against E. coli. A few compounds showed moderate activity against Bacillus subtilis also. Antiinflammatory activity of six selected compounds was also tested using the carrageenan-induced rat paw oedema method. Among them, 5-methyl-3-p-tolylfuro[3,2-g][1]benzopyran-7-one (FCg) showed excellent activity. 5-Methyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCa) and 4,5-dimethyl-3-(4-nitrophenyl)-furo[3,2-g][1]benzopyran-7-one (FCc) showed activity comparable to that of the standard drug ibuprofen.
Original languageEnglish
Pages (from-to)326-331
Number of pages6
JournalIndian Journal of Pharmaceutical Sciences
Volume69
Issue number2
Publication statusPublished - 2007

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Benzopyrans
Anti-Inflammatory Agents
Coumarins
Resorcinols
Acetophenones
Sodium Hydroxide
Carrageenan
Ibuprofen
Halogenation
Bacillus subtilis
Gram-Negative Bacteria
Pseudomonas aeruginosa
Edema
Escherichia coli
Pharmaceutical Preparations

Cite this

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title = "Synthesis of novel furobenzopyrone derivatives and evaluation of their antimicrobial and antiinflammatory activity",
abstract = "Certain 4′-(4″-substituted phenyl)-4-methylfurobenzopyrones were synthesized and evaluated for antibacterial activity. Six of the synthesized compounds were also screened for their antiinflammatory activity. Substituted resorcinols were condensed with ethyl acetoacetate to afford different coumarins (2a-c). Various substituted phenacyl bromides (4a-g) were prepared by the bromination of para-substituted acetophenones. The coumarins (2a-c) and phenacyl bromides (4a-g) were condensed to give oxoethers (5a-s). These were cyclised by using 1 M sodium hydroxide to afford the desired furobenzopyrone derivatives (FCa-s). All the compounds have been evaluated for their antibacterial activity against different strains of gram positive and gram negative bacteria. All the compounds have shown good activity against Pseudomonas aeruginosa. Compounds, 3-(4-chlorophenyl)-5-methylfuro-[3,2-g][1] benzopyran-7-one, 3-(4-chlorophenyl)-5,9-dimethylfuro[3,2-g][1]benzopyran-7-one and 4,5-dimethyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCe, FCi, FCn) were active against E. coli. A few compounds showed moderate activity against Bacillus subtilis also. Antiinflammatory activity of six selected compounds was also tested using the carrageenan-induced rat paw oedema method. Among them, 5-methyl-3-p-tolylfuro[3,2-g][1]benzopyran-7-one (FCg) showed excellent activity. 5-Methyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCa) and 4,5-dimethyl-3-(4-nitrophenyl)-furo[3,2-g][1]benzopyran-7-one (FCc) showed activity comparable to that of the standard drug ibuprofen.",
author = "K. Srinivasan and Y. Neelima and A. Joseph and G. Sreejith and A. Ciraj and J. Rao",
note = "Cited By :4 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Srinivasan, K.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical SciencesIndia; email: pansrini@yahoo.co.in Chemicals/CAS: ibuprofen, 15687-27-1, 79261-49-7, 31121-93-4, 527688-20-6 References: Okuyama, E., Nishimura, S., Ohmori, S., Ozaki, Y., Satake, M., Yamazaki, M., (1993) Chem. Pharm. Bull, 41, p. 926; Nivsarkar, M., Desai, A., Mokal, R., (1996) Biochem. Mol. Biol. Int, 38, p. 625; Parrish, J.A., Fitzpatrick, T.B., Tanenbaum, L., Pathak, M.A., (1974) N. Engl. J. Med, 291, p. 1207; Shamshurin, A.A., (1941) Chem. Abstr, pp. 35-3994; Synthesis of phenacylbromides (1919) J. Amer. Chem. Soc, 41, p. 77; Andriana, C., Cristina, M., Adriano, G., (1999) J. Med. Chem, 42, p. 2936; (1982) Photochemotherapy of skin diseases: The science of photomedicine, p. 595. , Parrish, J.A, Stern, R.S, Pathak, M.A. and Fitzpatrick, T.B, Eds, Plenum press, New York; Lisa, D.V., Ornella, G., Sebastiano, M.M., Lourdes, S., Marta, T., (1999) J. Med. Chem, 42, p. 4405",
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journal = "Indian Journal of Pharmaceutical Sciences",
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Synthesis of novel furobenzopyrone derivatives and evaluation of their antimicrobial and antiinflammatory activity. / Srinivasan, K.; Neelima, Y.; Joseph, A.; Sreejith, G.; Ciraj, A.; Rao, J.

In: Indian Journal of Pharmaceutical Sciences, Vol. 69, No. 2, 2007, p. 326-331.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Joseph, A.

AU - Sreejith, G.

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N1 - Cited By :4 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Srinivasan, K.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical SciencesIndia; email: pansrini@yahoo.co.in Chemicals/CAS: ibuprofen, 15687-27-1, 79261-49-7, 31121-93-4, 527688-20-6 References: Okuyama, E., Nishimura, S., Ohmori, S., Ozaki, Y., Satake, M., Yamazaki, M., (1993) Chem. Pharm. Bull, 41, p. 926; Nivsarkar, M., Desai, A., Mokal, R., (1996) Biochem. Mol. Biol. Int, 38, p. 625; Parrish, J.A., Fitzpatrick, T.B., Tanenbaum, L., Pathak, M.A., (1974) N. Engl. J. Med, 291, p. 1207; Shamshurin, A.A., (1941) Chem. Abstr, pp. 35-3994; Synthesis of phenacylbromides (1919) J. Amer. Chem. Soc, 41, p. 77; Andriana, C., Cristina, M., Adriano, G., (1999) J. Med. Chem, 42, p. 2936; (1982) Photochemotherapy of skin diseases: The science of photomedicine, p. 595. , Parrish, J.A, Stern, R.S, Pathak, M.A. and Fitzpatrick, T.B, Eds, Plenum press, New York; Lisa, D.V., Ornella, G., Sebastiano, M.M., Lourdes, S., Marta, T., (1999) J. Med. Chem, 42, p. 4405

PY - 2007

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N2 - Certain 4′-(4″-substituted phenyl)-4-methylfurobenzopyrones were synthesized and evaluated for antibacterial activity. Six of the synthesized compounds were also screened for their antiinflammatory activity. Substituted resorcinols were condensed with ethyl acetoacetate to afford different coumarins (2a-c). Various substituted phenacyl bromides (4a-g) were prepared by the bromination of para-substituted acetophenones. The coumarins (2a-c) and phenacyl bromides (4a-g) were condensed to give oxoethers (5a-s). These were cyclised by using 1 M sodium hydroxide to afford the desired furobenzopyrone derivatives (FCa-s). All the compounds have been evaluated for their antibacterial activity against different strains of gram positive and gram negative bacteria. All the compounds have shown good activity against Pseudomonas aeruginosa. Compounds, 3-(4-chlorophenyl)-5-methylfuro-[3,2-g][1] benzopyran-7-one, 3-(4-chlorophenyl)-5,9-dimethylfuro[3,2-g][1]benzopyran-7-one and 4,5-dimethyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCe, FCi, FCn) were active against E. coli. A few compounds showed moderate activity against Bacillus subtilis also. Antiinflammatory activity of six selected compounds was also tested using the carrageenan-induced rat paw oedema method. Among them, 5-methyl-3-p-tolylfuro[3,2-g][1]benzopyran-7-one (FCg) showed excellent activity. 5-Methyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCa) and 4,5-dimethyl-3-(4-nitrophenyl)-furo[3,2-g][1]benzopyran-7-one (FCc) showed activity comparable to that of the standard drug ibuprofen.

AB - Certain 4′-(4″-substituted phenyl)-4-methylfurobenzopyrones were synthesized and evaluated for antibacterial activity. Six of the synthesized compounds were also screened for their antiinflammatory activity. Substituted resorcinols were condensed with ethyl acetoacetate to afford different coumarins (2a-c). Various substituted phenacyl bromides (4a-g) were prepared by the bromination of para-substituted acetophenones. The coumarins (2a-c) and phenacyl bromides (4a-g) were condensed to give oxoethers (5a-s). These were cyclised by using 1 M sodium hydroxide to afford the desired furobenzopyrone derivatives (FCa-s). All the compounds have been evaluated for their antibacterial activity against different strains of gram positive and gram negative bacteria. All the compounds have shown good activity against Pseudomonas aeruginosa. Compounds, 3-(4-chlorophenyl)-5-methylfuro-[3,2-g][1] benzopyran-7-one, 3-(4-chlorophenyl)-5,9-dimethylfuro[3,2-g][1]benzopyran-7-one and 4,5-dimethyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCe, FCi, FCn) were active against E. coli. A few compounds showed moderate activity against Bacillus subtilis also. Antiinflammatory activity of six selected compounds was also tested using the carrageenan-induced rat paw oedema method. Among them, 5-methyl-3-p-tolylfuro[3,2-g][1]benzopyran-7-one (FCg) showed excellent activity. 5-Methyl-3-phenylfuro[3,2-g][1]benzopyran-7-one (FCa) and 4,5-dimethyl-3-(4-nitrophenyl)-furo[3,2-g][1]benzopyran-7-one (FCc) showed activity comparable to that of the standard drug ibuprofen.

M3 - Article

VL - 69

SP - 326

EP - 331

JO - Indian Journal of Pharmaceutical Sciences

JF - Indian Journal of Pharmaceutical Sciences

SN - 0250-474X

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