Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles

S.S. Panda, P.V.R. Chowdary, B.S. Jayashree

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in ethanolic KOH solution. These chalcones were immediately reacted with hydroxylamine hydrochloride in presence of glacial acetic acid as reagent to obtain the corresponding isoxazole derivatives. The synthesized heterocycles were characterized on the basis of physical, chemical tests and spectroscopic data. These compounds were tested for the acute antiinflammatory activity and antibacterial activity using carrageenan-induced rat paw edema method and cup-plate method, respectively.
Original languageEnglish
Pages (from-to)684-687
Number of pages4
JournalIndian Journal of Pharmaceutical Sciences
Volume71
Issue number6
DOIs
Publication statusPublished - 2009

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Chalcones
Isoxazoles
Anti-Inflammatory Agents
Hydroxylamine
Carrageenan
Acetic Acid
Edema
acetophenone
indole-3-carbaldehyde

Cite this

@article{b62808ad835d4616a1742234231677b7,
title = "Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles",
abstract = "Chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in ethanolic KOH solution. These chalcones were immediately reacted with hydroxylamine hydrochloride in presence of glacial acetic acid as reagent to obtain the corresponding isoxazole derivatives. The synthesized heterocycles were characterized on the basis of physical, chemical tests and spectroscopic data. These compounds were tested for the acute antiinflammatory activity and antibacterial activity using carrageenan-induced rat paw edema method and cup-plate method, respectively.",
author = "S.S. Panda and P.V.R. Chowdary and B.S. Jayashree",
note = "Cited By :17 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Panda, S. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE Manipal-576 104, India; email: sivashankarpanda@yahoo.com Chemicals/CAS: acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; ciprofloxacin, 85721-33-1; hydroxylamine, 7803-49-8; ibuprofen, 15687-27-1 References: Jung, H.K., Doddareddya, M.R., Cha, J.H., Rhim, H., Cho, Y.S., Koh, H.Y., Synthesis and biological evaluation of novel T-type Ca2+ channel blockers (2004) Bioorg Med Chem, 12, pp. 3965-3970; Popat, K.H., Nirmavat, K.S., Kachhadia, V.V., Joshi, H.S., Synthesis and biological activity of 3-aryl-5-(3'-bromo/chlorophenyl) isoxazoles (2003) J Indian Chem Soc, 80, pp. 707-708; Norman, B.H., Lander, P.A., Gruber, J.M., Kroin, J.S., Cyclohexyl-linked tricyclic isoxazoles are potent and selective modulators of the multidrug resistance protein (MRP1) (2005) Bioorg Med Chem Lett, 15, pp. 5526-5530; Raman, K., Pandey, B.R., Barthwal, J.P., Parmar, S.S., Antiinflammatory and antiproteolytic properties of 1,3-disubstituted-5- (2-arylindol-3-yl)-2- pyrazolines (1980) Eur J Med Chem Chem Ther, 15, pp. 567-569; Kumar, A., Sinha, J.N., Bhargava, K.P., Shanker, K., Synthesis of 1-acetyl- 5-aryl-3-[ortho-(3-chloro-2-indol-3-yl-4-oxo-1- azetidinyl)phenyl]2- pyrazolines (1984) Indian J Chem, 23 B, pp. 589-591; Gupta, D.P., Kumar, P., Ahmad, S., Shanker, K., Synthesis, antiacetylcholinesterase, and anthelmintic activities of newer indolyl derivatives (1990) Indian J Chem, 29 B, pp. 194-196; Lather, V., Chowdary, P.V.R., Synthesis and antimicrobial activity of N1-(arylidine hydrazidomethyl)-indoles,2-(substitutedaryl)-3-(N1- indolylacetamidyl)-4-oxo- thiazolidines and 5-benzylidine derivatives of thiazolidinones (2003) Indian J Pharm Sci, 65, pp. 576-579; Gadaginamath, G.S., Shyadligeri, A.S., Kavali, R.R., Chemoselectivity of indoledicarboxylates towards hydrazine hydrate: Part III- synthesis and antimicrobial activity of novel 4-thiazolidinonylindoles (1999) Indian J Chem, 38 B, pp. 156-159; Renukadevi, P., Biradar, J.S., Synthesis and antimicrobial activity of 3,5-disubstituted-2-[1'-phenyl- 5'-thioalkyl-s-triazol-2'-yl]indoles and 3,5-disubstituted-2-[1'-substituted aminomethyl-4'-phenyl-5',4'- phenyl-5'(4'H)-thion-s-triazol-3-yl]indoles (1999) Indian J Heterocycl Chem, 9, pp. 107-112; Panda, S.S., Chowdary, P.V., Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents (2008) Indian J Pharm Sci, 70, pp. 208-215; Winter, C.A., Risley, E.A., Nuss, G.W., Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs (1962) Proc Soc Expt Biol, 111, pp. 544-547; Clarke, G.M., Cooke, D., (1998) A Basic Course in Statistics, pp. 520-546. , 4th ed. London: Arnold; Kavanagh, F., (1963) Analytical Microbiology, pp. 313-346. , New York Academic Press",
year = "2009",
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volume = "71",
pages = "684--687",
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Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles. / Panda, S.S.; Chowdary, P.V.R.; Jayashree, B.S.

In: Indian Journal of Pharmaceutical Sciences, Vol. 71, No. 6, 2009, p. 684-687.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis, antiinflammatory and antibacterial activity of novel indolyl-isoxazoles

AU - Panda, S.S.

AU - Chowdary, P.V.R.

AU - Jayashree, B.S.

N1 - Cited By :17 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Panda, S. S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, MAHE Manipal-576 104, India; email: sivashankarpanda@yahoo.com Chemicals/CAS: acetic acid, 127-08-2, 127-09-3, 64-19-7, 71-50-1; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; ciprofloxacin, 85721-33-1; hydroxylamine, 7803-49-8; ibuprofen, 15687-27-1 References: Jung, H.K., Doddareddya, M.R., Cha, J.H., Rhim, H., Cho, Y.S., Koh, H.Y., Synthesis and biological evaluation of novel T-type Ca2+ channel blockers (2004) Bioorg Med Chem, 12, pp. 3965-3970; Popat, K.H., Nirmavat, K.S., Kachhadia, V.V., Joshi, H.S., Synthesis and biological activity of 3-aryl-5-(3'-bromo/chlorophenyl) isoxazoles (2003) J Indian Chem Soc, 80, pp. 707-708; Norman, B.H., Lander, P.A., Gruber, J.M., Kroin, J.S., Cyclohexyl-linked tricyclic isoxazoles are potent and selective modulators of the multidrug resistance protein (MRP1) (2005) Bioorg Med Chem Lett, 15, pp. 5526-5530; Raman, K., Pandey, B.R., Barthwal, J.P., Parmar, S.S., Antiinflammatory and antiproteolytic properties of 1,3-disubstituted-5- (2-arylindol-3-yl)-2- pyrazolines (1980) Eur J Med Chem Chem Ther, 15, pp. 567-569; Kumar, A., Sinha, J.N., Bhargava, K.P., Shanker, K., Synthesis of 1-acetyl- 5-aryl-3-[ortho-(3-chloro-2-indol-3-yl-4-oxo-1- azetidinyl)phenyl]2- pyrazolines (1984) Indian J Chem, 23 B, pp. 589-591; Gupta, D.P., Kumar, P., Ahmad, S., Shanker, K., Synthesis, antiacetylcholinesterase, and anthelmintic activities of newer indolyl derivatives (1990) Indian J Chem, 29 B, pp. 194-196; Lather, V., Chowdary, P.V.R., Synthesis and antimicrobial activity of N1-(arylidine hydrazidomethyl)-indoles,2-(substitutedaryl)-3-(N1- indolylacetamidyl)-4-oxo- thiazolidines and 5-benzylidine derivatives of thiazolidinones (2003) Indian J Pharm Sci, 65, pp. 576-579; Gadaginamath, G.S., Shyadligeri, A.S., Kavali, R.R., Chemoselectivity of indoledicarboxylates towards hydrazine hydrate: Part III- synthesis and antimicrobial activity of novel 4-thiazolidinonylindoles (1999) Indian J Chem, 38 B, pp. 156-159; Renukadevi, P., Biradar, J.S., Synthesis and antimicrobial activity of 3,5-disubstituted-2-[1'-phenyl- 5'-thioalkyl-s-triazol-2'-yl]indoles and 3,5-disubstituted-2-[1'-substituted aminomethyl-4'-phenyl-5',4'- phenyl-5'(4'H)-thion-s-triazol-3-yl]indoles (1999) Indian J Heterocycl Chem, 9, pp. 107-112; Panda, S.S., Chowdary, P.V., Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents (2008) Indian J Pharm Sci, 70, pp. 208-215; Winter, C.A., Risley, E.A., Nuss, G.W., Carrageenin-induced edema in hind paw of the rat as an assay for antiiflammatory drugs (1962) Proc Soc Expt Biol, 111, pp. 544-547; Clarke, G.M., Cooke, D., (1998) A Basic Course in Statistics, pp. 520-546. , 4th ed. London: Arnold; Kavanagh, F., (1963) Analytical Microbiology, pp. 313-346. , New York Academic Press

PY - 2009

Y1 - 2009

N2 - Chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in ethanolic KOH solution. These chalcones were immediately reacted with hydroxylamine hydrochloride in presence of glacial acetic acid as reagent to obtain the corresponding isoxazole derivatives. The synthesized heterocycles were characterized on the basis of physical, chemical tests and spectroscopic data. These compounds were tested for the acute antiinflammatory activity and antibacterial activity using carrageenan-induced rat paw edema method and cup-plate method, respectively.

AB - Chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in ethanolic KOH solution. These chalcones were immediately reacted with hydroxylamine hydrochloride in presence of glacial acetic acid as reagent to obtain the corresponding isoxazole derivatives. The synthesized heterocycles were characterized on the basis of physical, chemical tests and spectroscopic data. These compounds were tested for the acute antiinflammatory activity and antibacterial activity using carrageenan-induced rat paw edema method and cup-plate method, respectively.

U2 - 10.4103/0250-474X.59554

DO - 10.4103/0250-474X.59554

M3 - Article

VL - 71

SP - 684

EP - 687

JO - Indian Journal of Pharmaceutical Sciences

JF - Indian Journal of Pharmaceutical Sciences

SN - 0250-474X

IS - 6

ER -