Synthesis and biological evaluation of some novel pyrazolines

V. Babu, Ch. Sridevi, A. Joseph, K. Srinivasan

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Chalcones (2a and 2b) were prepared from 2-acetyl benzofuran (1) and condensed with different aromatic acid hydrazides (3a-o) to get the corresponding pyrazolines (4a-o and 5a-o). The structures of all these compounds have been established on the basis of analytical and spectral data. Compounds have been screened for antiinflammatory, antioxidant and antibacterial studies. Among the 7 compounds that were screened for antiinflammatory activity, compounds 4g and 5m showed 83.4% and 80.5% inhibition of oedema volume, while the standard drug (ibuprofen) showed inhibition of 91.9%. Compounds 4k and 5h showed moderate activity of 72.8% and 59.6% respectively. All the 30 compounds were tested for antioxidant activity at 1000, 500, 250, 100, 50, 25 and 10 mg/ml concentrations against standard drug ascorbic acid. Compounds 4g, 4h, 4k, 4m, 5g, 5h, 5k and 5m showed excellent antioxidant activity as compared with ascorbic acid. Among the 30 compounds that were screened against two Gram +ve ( Staphylococcus aureus and Bacillus subtilis ) and two gram -ve ( Escherichia coli and Pseudomonas aeruginosa ) organisms, compounds possessing p-chloro, p-fluoro, 2-amino-5-bromo, 2-hydroxy-5-nitro and 3,5-dichloro substitutions on the phenyl ring showed good activity against Escherichia coli and Bacillus subtilis. The activity is comparable with that of the standard drug ciprofloxacin.
Original languageEnglish
Pages (from-to)470-473
Number of pages4
JournalIndian Journal of Pharmaceutical Sciences
Volume69
Issue number3
Publication statusPublished - 2007

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Antioxidants
Bacillus subtilis
Ascorbic Acid
Anti-Inflammatory Agents
Pharmaceutical Preparations
Chalcones
Escherichia coli
Ibuprofen
Ciprofloxacin
Pseudomonas aeruginosa
Staphylococcus aureus
Edema
Acids
compound 30
1-benzofuran

Cite this

Babu, V. ; Sridevi, Ch. ; Joseph, A. ; Srinivasan, K. / Synthesis and biological evaluation of some novel pyrazolines. In: Indian Journal of Pharmaceutical Sciences. 2007 ; Vol. 69, No. 3. pp. 470-473.
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title = "Synthesis and biological evaluation of some novel pyrazolines",
abstract = "Chalcones (2a and 2b) were prepared from 2-acetyl benzofuran (1) and condensed with different aromatic acid hydrazides (3a-o) to get the corresponding pyrazolines (4a-o and 5a-o). The structures of all these compounds have been established on the basis of analytical and spectral data. Compounds have been screened for antiinflammatory, antioxidant and antibacterial studies. Among the 7 compounds that were screened for antiinflammatory activity, compounds 4g and 5m showed 83.4{\%} and 80.5{\%} inhibition of oedema volume, while the standard drug (ibuprofen) showed inhibition of 91.9{\%}. Compounds 4k and 5h showed moderate activity of 72.8{\%} and 59.6{\%} respectively. All the 30 compounds were tested for antioxidant activity at 1000, 500, 250, 100, 50, 25 and 10 mg/ml concentrations against standard drug ascorbic acid. Compounds 4g, 4h, 4k, 4m, 5g, 5h, 5k and 5m showed excellent antioxidant activity as compared with ascorbic acid. Among the 30 compounds that were screened against two Gram +ve ( Staphylococcus aureus and Bacillus subtilis ) and two gram -ve ( Escherichia coli and Pseudomonas aeruginosa ) organisms, compounds possessing p-chloro, p-fluoro, 2-amino-5-bromo, 2-hydroxy-5-nitro and 3,5-dichloro substitutions on the phenyl ring showed good activity against Escherichia coli and Bacillus subtilis. The activity is comparable with that of the standard drug ciprofloxacin.",
author = "V. Babu and Ch. Sridevi and A. Joseph and K. Srinivasan",
note = "Cited By :30 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Babu, V.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal - 576 104, India; email: pansrini@yahoo.co.in Chemicals/CAS: ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; ciprofloxacin, 85721-33-1; ibuprofen, 15687-27-1 References: Nasef, A.M., El Naem, S.I., El Shabrawy, O.A., Synthesis and analgesic activity of benzofuran carboxamide derivatives (1992) Egypt J Pharm Sci, 33, p. 463; Chakrabarthi, K.J., Richard, E.J., Peter, G.T., Janette, H., Terrence, H.A., 5-acyl-3- substituted benzofuran-2(3H)-ones as potential antiinflammatory agents (1987) J Med Chem, 30, p. 1663; Shah, M., Patel, P., Korgaokar, S., Parekh, H., Synthesis of pyrazolines, isoxazoles and cynopyridines as potential antimicrobial agents (1996) Indian J Chem, 35, p. 1282; Shenoy, G.G., Bhat, A.R., Bhat, V.G., Kotian, M., Synthesis and antimicrobial activities of 1,3,5-trisubstituted -2- pyrazolines (2001) Indian J Heterocyclic Chem, 10, p. 197; Singh, G.B., Andatra Singh, S.J., Khajuria, C.S., synthesis and antiinflammatory activity of 1-acetyl-3-(2,4- dimethoxyphenyl)-5-phenyl-2-pyrazolines (1993) J. Indian Chem Soc, 70, p. 266; Vidya VP, Agasimuddin YS. Synthesis of some benzofuro(3,2-d)-pyramidines and benzofuro(3.,2.:4,5)pyramido(1,2-b) benzo(d)thiazoles. Indian J Chem 1981;20:114-7; Sreejayan, N., Rao, M.N.A., (1993) Int J Pharma, 100, p. 93; Winter, C.A., Risely, E.A., Nuss, G.W., (1962) Proc Soc Exp Biol, 111, p. 54719; Gillespie, S.H., (1994) Medical Microbiology-Illustrated, , 1st ed. Butterworth Heinemann;",
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pages = "470--473",
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number = "3",

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Babu, V, Sridevi, C, Joseph, A & Srinivasan, K 2007, 'Synthesis and biological evaluation of some novel pyrazolines', Indian Journal of Pharmaceutical Sciences, vol. 69, no. 3, pp. 470-473.

Synthesis and biological evaluation of some novel pyrazolines. / Babu, V.; Sridevi, Ch.; Joseph, A.; Srinivasan, K.

In: Indian Journal of Pharmaceutical Sciences, Vol. 69, No. 3, 2007, p. 470-473.

Research output: Contribution to journalArticle

TY - JOUR

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AU - Babu, V.

AU - Sridevi, Ch.

AU - Joseph, A.

AU - Srinivasan, K.

N1 - Cited By :30 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Babu, V.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE, Manipal - 576 104, India; email: pansrini@yahoo.co.in Chemicals/CAS: ascorbic acid, 134-03-2, 15421-15-5, 50-81-7; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; ciprofloxacin, 85721-33-1; ibuprofen, 15687-27-1 References: Nasef, A.M., El Naem, S.I., El Shabrawy, O.A., Synthesis and analgesic activity of benzofuran carboxamide derivatives (1992) Egypt J Pharm Sci, 33, p. 463; Chakrabarthi, K.J., Richard, E.J., Peter, G.T., Janette, H., Terrence, H.A., 5-acyl-3- substituted benzofuran-2(3H)-ones as potential antiinflammatory agents (1987) J Med Chem, 30, p. 1663; Shah, M., Patel, P., Korgaokar, S., Parekh, H., Synthesis of pyrazolines, isoxazoles and cynopyridines as potential antimicrobial agents (1996) Indian J Chem, 35, p. 1282; Shenoy, G.G., Bhat, A.R., Bhat, V.G., Kotian, M., Synthesis and antimicrobial activities of 1,3,5-trisubstituted -2- pyrazolines (2001) Indian J Heterocyclic Chem, 10, p. 197; Singh, G.B., Andatra Singh, S.J., Khajuria, C.S., synthesis and antiinflammatory activity of 1-acetyl-3-(2,4- dimethoxyphenyl)-5-phenyl-2-pyrazolines (1993) J. Indian Chem Soc, 70, p. 266; Vidya VP, Agasimuddin YS. Synthesis of some benzofuro(3,2-d)-pyramidines and benzofuro(3.,2.:4,5)pyramido(1,2-b) benzo(d)thiazoles. Indian J Chem 1981;20:114-7; Sreejayan, N., Rao, M.N.A., (1993) Int J Pharma, 100, p. 93; Winter, C.A., Risely, E.A., Nuss, G.W., (1962) Proc Soc Exp Biol, 111, p. 54719; Gillespie, S.H., (1994) Medical Microbiology-Illustrated, , 1st ed. Butterworth Heinemann;

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N2 - Chalcones (2a and 2b) were prepared from 2-acetyl benzofuran (1) and condensed with different aromatic acid hydrazides (3a-o) to get the corresponding pyrazolines (4a-o and 5a-o). The structures of all these compounds have been established on the basis of analytical and spectral data. Compounds have been screened for antiinflammatory, antioxidant and antibacterial studies. Among the 7 compounds that were screened for antiinflammatory activity, compounds 4g and 5m showed 83.4% and 80.5% inhibition of oedema volume, while the standard drug (ibuprofen) showed inhibition of 91.9%. Compounds 4k and 5h showed moderate activity of 72.8% and 59.6% respectively. All the 30 compounds were tested for antioxidant activity at 1000, 500, 250, 100, 50, 25 and 10 mg/ml concentrations against standard drug ascorbic acid. Compounds 4g, 4h, 4k, 4m, 5g, 5h, 5k and 5m showed excellent antioxidant activity as compared with ascorbic acid. Among the 30 compounds that were screened against two Gram +ve ( Staphylococcus aureus and Bacillus subtilis ) and two gram -ve ( Escherichia coli and Pseudomonas aeruginosa ) organisms, compounds possessing p-chloro, p-fluoro, 2-amino-5-bromo, 2-hydroxy-5-nitro and 3,5-dichloro substitutions on the phenyl ring showed good activity against Escherichia coli and Bacillus subtilis. The activity is comparable with that of the standard drug ciprofloxacin.

AB - Chalcones (2a and 2b) were prepared from 2-acetyl benzofuran (1) and condensed with different aromatic acid hydrazides (3a-o) to get the corresponding pyrazolines (4a-o and 5a-o). The structures of all these compounds have been established on the basis of analytical and spectral data. Compounds have been screened for antiinflammatory, antioxidant and antibacterial studies. Among the 7 compounds that were screened for antiinflammatory activity, compounds 4g and 5m showed 83.4% and 80.5% inhibition of oedema volume, while the standard drug (ibuprofen) showed inhibition of 91.9%. Compounds 4k and 5h showed moderate activity of 72.8% and 59.6% respectively. All the 30 compounds were tested for antioxidant activity at 1000, 500, 250, 100, 50, 25 and 10 mg/ml concentrations against standard drug ascorbic acid. Compounds 4g, 4h, 4k, 4m, 5g, 5h, 5k and 5m showed excellent antioxidant activity as compared with ascorbic acid. Among the 30 compounds that were screened against two Gram +ve ( Staphylococcus aureus and Bacillus subtilis ) and two gram -ve ( Escherichia coli and Pseudomonas aeruginosa ) organisms, compounds possessing p-chloro, p-fluoro, 2-amino-5-bromo, 2-hydroxy-5-nitro and 3,5-dichloro substitutions on the phenyl ring showed good activity against Escherichia coli and Bacillus subtilis. The activity is comparable with that of the standard drug ciprofloxacin.

M3 - Article

VL - 69

SP - 470

EP - 473

JO - Indian Journal of Pharmaceutical Sciences

JF - Indian Journal of Pharmaceutical Sciences

SN - 0250-474X

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