Synthesis, antitumor and antibacterial activities of certain substituted pyrimidines bearing benzofuran

V.H. Babu, P.S. Kumar, K.K. Srinivasan, G.V. Bhat

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Benzofuran chalcones (2a-i) were prepared by the reaction of 2-acetylbenzofuran (1) with different aromatic aldehydes in the presence of a strong base. Cyclocondensation of benzofuran chalcones with guanidine hydrochloride, thiourea and urea resulted in the formation of various aminopyrimidines (3a-i), thiopyrimidines (4a-i) and hydroxy pyrimidines (5a-i), respectively. The structures of all the compounds (2,3,4,5 a-i) have been established on the basis of analytical and spectral data. All the compounds have been screened for antitumour and antimicrobial activities. Compounds 3b and 3d showed significant antitumour activity. While compounds 4d and 4h showed only moderate activity against Staphylococcus aureus at 500 μg/ml, compounds 4h, 4i, 5a, 5b, 5h and 5i showed promising activity against Candida albicans at 500 μg/ml concentrations.
Original languageEnglish
Pages (from-to)647-652
Number of pages6
JournalIndian Journal of Pharmaceutical Sciences
Volume66
Issue number5
Publication statusPublished - 2004

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Chalcones
Pyrimidines
Thiourea
Guanidine
Candida albicans
Aldehydes
Urea
Staphylococcus aureus
benzofuran
2-acetylbenzofuran
2-aminopyrimidine

Cite this

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abstract = "Benzofuran chalcones (2a-i) were prepared by the reaction of 2-acetylbenzofuran (1) with different aromatic aldehydes in the presence of a strong base. Cyclocondensation of benzofuran chalcones with guanidine hydrochloride, thiourea and urea resulted in the formation of various aminopyrimidines (3a-i), thiopyrimidines (4a-i) and hydroxy pyrimidines (5a-i), respectively. The structures of all the compounds (2,3,4,5 a-i) have been established on the basis of analytical and spectral data. All the compounds have been screened for antitumour and antimicrobial activities. Compounds 3b and 3d showed significant antitumour activity. While compounds 4d and 4h showed only moderate activity against Staphylococcus aureus at 500 μg/ml, compounds 4h, 4i, 5a, 5b, 5h and 5i showed promising activity against Candida albicans at 500 μg/ml concentrations.",
author = "V.H. Babu and P.S. Kumar and K.K. Srinivasan and G.V. Bhat",
note = "Cited By :9 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Babu, V. H.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal-576104, India; email: harinadhababu_v@yahoo.com References: Nasef, M., El-Naem, S.J.A., Ei-Shabrawy, O.A., (1992) Egypt J. Pharm. Sci, 33-34, p. 463; through (1994) Chem. Abst, 120, pp. 323143q; Habele, R.P., (1985) EP, 130, p. 151; through (1985) Chem. Abst, 103, p. 160521; Sonnatag C., Klutchko S. and Shavel J(Jr), U. S., 1972, 3, 649, 644; through (1977) Chem. Abst, 77, p. 5439; Klutchko S., Shovel J(Jr) and Van Strandtmann M., U. S., 1973, 3, 780, 0660; through (1974) Chem. Abst, 80, p. 82931; Grinev, N., Zotova, S.A., Golobova, T.M., (1985) Khim. Farm. Zh, 19, p. 227; through (1986) Chem. Abst, 104, p. 68700; Elliot, C., Anthony, V.M., (1986) Ger. Offen. DE, 3 (620), p. 354; through (1987) Chem. Abst, 107, pp. 7063j; Pesteellini, V., Ghelardoni, M., Ortolani, C., (1986) EP, 257, p. 171; through (1988) Chem. Abst, 109, p. 65205; Ghosh, M. N., In: Fundamentals of Experimental Pharmacology, Ed II., Scientific Book Agency, Kolkata, 1984, 153; Meyer, H., Ferrigni, N.R., Putnam, J.F., Jacobson, I.B., Nichole, D.E., Mc Laughlin, J.I., (1982) Planta Medica, 45, p. 31; Ferrigni, N.R., Mc Laughlin, J.I., (1984) J. Nat. Products, 47, p. 347; Chitnis, M.P., Bhatia, K.G., Phatak, M.K., Kesava Rao, K.V., (1980) Indian J. Expt. Biol, 18, p. 6; Gillespie, S.H., (1994) Medical Microbiology-Illustrated, p. 234. , Butterworth Heinemann, London",
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Synthesis, antitumor and antibacterial activities of certain substituted pyrimidines bearing benzofuran. / Babu, V.H.; Kumar, P.S.; Srinivasan, K.K.; Bhat, G.V.

In: Indian Journal of Pharmaceutical Sciences, Vol. 66, No. 5, 2004, p. 647-652.

Research output: Contribution to journalArticle

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N1 - Cited By :9 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Babu, V. H.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal-576104, India; email: harinadhababu_v@yahoo.com References: Nasef, M., El-Naem, S.J.A., Ei-Shabrawy, O.A., (1992) Egypt J. Pharm. Sci, 33-34, p. 463; through (1994) Chem. Abst, 120, pp. 323143q; Habele, R.P., (1985) EP, 130, p. 151; through (1985) Chem. Abst, 103, p. 160521; Sonnatag C., Klutchko S. and Shavel J(Jr), U. S., 1972, 3, 649, 644; through (1977) Chem. Abst, 77, p. 5439; Klutchko S., Shovel J(Jr) and Van Strandtmann M., U. S., 1973, 3, 780, 0660; through (1974) Chem. Abst, 80, p. 82931; Grinev, N., Zotova, S.A., Golobova, T.M., (1985) Khim. Farm. Zh, 19, p. 227; through (1986) Chem. Abst, 104, p. 68700; Elliot, C., Anthony, V.M., (1986) Ger. Offen. DE, 3 (620), p. 354; through (1987) Chem. Abst, 107, pp. 7063j; Pesteellini, V., Ghelardoni, M., Ortolani, C., (1986) EP, 257, p. 171; through (1988) Chem. Abst, 109, p. 65205; Ghosh, M. N., In: Fundamentals of Experimental Pharmacology, Ed II., Scientific Book Agency, Kolkata, 1984, 153; Meyer, H., Ferrigni, N.R., Putnam, J.F., Jacobson, I.B., Nichole, D.E., Mc Laughlin, J.I., (1982) Planta Medica, 45, p. 31; Ferrigni, N.R., Mc Laughlin, J.I., (1984) J. Nat. Products, 47, p. 347; Chitnis, M.P., Bhatia, K.G., Phatak, M.K., Kesava Rao, K.V., (1980) Indian J. Expt. Biol, 18, p. 6; Gillespie, S.H., (1994) Medical Microbiology-Illustrated, p. 234. , Butterworth Heinemann, London

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N2 - Benzofuran chalcones (2a-i) were prepared by the reaction of 2-acetylbenzofuran (1) with different aromatic aldehydes in the presence of a strong base. Cyclocondensation of benzofuran chalcones with guanidine hydrochloride, thiourea and urea resulted in the formation of various aminopyrimidines (3a-i), thiopyrimidines (4a-i) and hydroxy pyrimidines (5a-i), respectively. The structures of all the compounds (2,3,4,5 a-i) have been established on the basis of analytical and spectral data. All the compounds have been screened for antitumour and antimicrobial activities. Compounds 3b and 3d showed significant antitumour activity. While compounds 4d and 4h showed only moderate activity against Staphylococcus aureus at 500 μg/ml, compounds 4h, 4i, 5a, 5b, 5h and 5i showed promising activity against Candida albicans at 500 μg/ml concentrations.

AB - Benzofuran chalcones (2a-i) were prepared by the reaction of 2-acetylbenzofuran (1) with different aromatic aldehydes in the presence of a strong base. Cyclocondensation of benzofuran chalcones with guanidine hydrochloride, thiourea and urea resulted in the formation of various aminopyrimidines (3a-i), thiopyrimidines (4a-i) and hydroxy pyrimidines (5a-i), respectively. The structures of all the compounds (2,3,4,5 a-i) have been established on the basis of analytical and spectral data. All the compounds have been screened for antitumour and antimicrobial activities. Compounds 3b and 3d showed significant antitumour activity. While compounds 4d and 4h showed only moderate activity against Staphylococcus aureus at 500 μg/ml, compounds 4h, 4i, 5a, 5b, 5h and 5i showed promising activity against Candida albicans at 500 μg/ml concentrations.

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JO - Indian Journal of Pharmaceutical Sciences

JF - Indian Journal of Pharmaceutical Sciences

SN - 0250-474X

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