Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents

S. Panda, P.V.R. Chowdary

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

A number of chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in NaOH solution in ethanol. These chalcones were immediately reacted with urea, thiourea and guanidine hydrochloride in presence of concentrated hydrochloric acid as reagent to obtain the corresponding hydroxy, thio and amino pyrimidines. The synthesized heterocyclics were characterized on the basis of physical, chemical tests and spectroscopic data and were tested for the acute antiinflammatory activity, antioxidant, antibacterial activity using carragenan-induced rat paw oedema method, DPPH (diphenylpicrylhydrazyl) radical scavenging method and cup plate method using Muller-Hinton agar media respectively. Evaluation of the compounds revealed remarkable antiinflammatory activity reflected by their ability to reduce the carragenan-induced inflammation in rats, appreciable antioxidant activity and also antibacterial activity was observed.
Original languageEnglish
Pages (from-to)208-215
Number of pages8
JournalIndian Journal of Pharmaceutical Sciences
Volume70
Issue number2
DOIs
Publication statusPublished - 2008

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Chalcones
Anti-Inflammatory Agents
Antioxidants
Anti-Bacterial Agents
Thiourea
Pyrimidines
Hydrochloric Acid
Guanidine
Agar
Urea
Edema
Ethanol
Inflammation
pyrimidine
indole-3-carbaldehyde
acetophenone

Cite this

@article{1ead5deb5913422f8b42936ff5220f71,
title = "Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents",
abstract = "A number of chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in NaOH solution in ethanol. These chalcones were immediately reacted with urea, thiourea and guanidine hydrochloride in presence of concentrated hydrochloric acid as reagent to obtain the corresponding hydroxy, thio and amino pyrimidines. The synthesized heterocyclics were characterized on the basis of physical, chemical tests and spectroscopic data and were tested for the acute antiinflammatory activity, antioxidant, antibacterial activity using carragenan-induced rat paw oedema method, DPPH (diphenylpicrylhydrazyl) radical scavenging method and cup plate method using Muller-Hinton agar media respectively. Evaluation of the compounds revealed remarkable antiinflammatory activity reflected by their ability to reduce the carragenan-induced inflammation in rats, appreciable antioxidant activity and also antibacterial activity was observed.",
author = "S. Panda and P.V.R. Chowdary",
note = "Cited By :23 Export Date: 10 November 2017 CODEN: IJSID Correspondence Address: Panda, S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Mahe Manipal-576 104, India; email: sivashankarpanda@yahoo.com Chemicals/CAS: 1,1 diphenyl 2 picrylhydrazyl, 1898-66-4; acetophenone, 98-86-2; alcohol, 64-17-5; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7; guanidine, 113-00-8, 25215-10-5, 50-01-1; hydrochloric acid, 7647-01-0; ibuprofen, 15687-27-1; indole 3 aldehyde, 487-89-8; sodium hydroxide, 1310-73-2; thiourea, 62-56-6; urea, 57-13-6 References: Patel, D.H., Mistry, B.D., Desai, K.R., Synthesis and antimicrobial activity of pyrazolo[3,4-d]pyrimidines (2003) Indian J Hetero Chem, 13, pp. 179-180; Kreutzberger, A., Sellheim, M., Antimycotics, XIX, 4,6-Disubstituted 2-(cyanamino)pyrimidines Indian (1985) J Hetero Chem, 22, pp. 721-723; Shanker, K., Gupta, G.P., Singh, S., Synthesis of novel pyrimidinediones and thiazolidinones as cardiovascular agents (1985) Indian J Chem, 24, pp. 1094-1097; Lather, V., Chowdary, P.V., Synthesis and antimicrobial activity of N1(arylidine hydrazidomethyl)-indoles,2-(substituted aryl)-3-(N1-indolyl acetamidyl)-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, 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 Hetero Chem, 9, pp. 107-112; Klohr, S.E., Cassady, M.J., An intramolecular photocyclization to form the azepino[3,4,5-cd]indole system (1988) Synthetic Communication, 18, pp. 671-674; 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 Exp Biol, 111, pp. 544-547; Newbould, B.B., Chemotherapy of arthritis induced in rats by mycobacterial adjuvant (1963) Brit J Pharmacol, 21, pp. 127-136; Seeley, H.W., Van Denmark, P.J., (1975) Microbes in action: A laboratory manual of microbiology, , Mumbai: D B Taraporevala Sons and Co Pvt Ltd;; Kavanagh, F., (1963) Analytical microbiology, pp. 313-346. , New York",
year = "2008",
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language = "English",
volume = "70",
pages = "208--215",
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Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents. / Panda, S.; Chowdary, P.V.R.

In: Indian Journal of Pharmaceutical Sciences, Vol. 70, No. 2, 2008, p. 208-215.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Synthesis of novel indolyl-pyrimidine antiinflammatory, antioxidant and antibacterial agents

AU - Panda, S.

AU - Chowdary, P.V.R.

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PY - 2008

Y1 - 2008

N2 - A number of chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in NaOH solution in ethanol. These chalcones were immediately reacted with urea, thiourea and guanidine hydrochloride in presence of concentrated hydrochloric acid as reagent to obtain the corresponding hydroxy, thio and amino pyrimidines. The synthesized heterocyclics were characterized on the basis of physical, chemical tests and spectroscopic data and were tested for the acute antiinflammatory activity, antioxidant, antibacterial activity using carragenan-induced rat paw oedema method, DPPH (diphenylpicrylhydrazyl) radical scavenging method and cup plate method using Muller-Hinton agar media respectively. Evaluation of the compounds revealed remarkable antiinflammatory activity reflected by their ability to reduce the carragenan-induced inflammation in rats, appreciable antioxidant activity and also antibacterial activity was observed.

AB - A number of chalcones were synthesized by reacting indole-3-aldehyde, prepared by Vilsemeir Haack reaction with 4-substituted acetophenone in NaOH solution in ethanol. These chalcones were immediately reacted with urea, thiourea and guanidine hydrochloride in presence of concentrated hydrochloric acid as reagent to obtain the corresponding hydroxy, thio and amino pyrimidines. The synthesized heterocyclics were characterized on the basis of physical, chemical tests and spectroscopic data and were tested for the acute antiinflammatory activity, antioxidant, antibacterial activity using carragenan-induced rat paw oedema method, DPPH (diphenylpicrylhydrazyl) radical scavenging method and cup plate method using Muller-Hinton agar media respectively. Evaluation of the compounds revealed remarkable antiinflammatory activity reflected by their ability to reduce the carragenan-induced inflammation in rats, appreciable antioxidant activity and also antibacterial activity was observed.

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DO - 10.4103/0250-474X.41457

M3 - Article

VL - 70

SP - 208

EP - 215

JO - Indian Journal of Pharmaceutical Sciences

JF - Indian Journal of Pharmaceutical Sciences

SN - 0250-474X

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ER -