Antioxidant analgesic and anti-inflammatory activities of some selected heteroaryl substituted Coumarins

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3 Citations (Scopus)

Abstract

Significant amounts of Coumarins, with benzopyrone ring units, are frequently present in plants. Simple coumarins and analogues are a large class of compounds with a wide spectrum of biological activity. Several series of coumarin derivatives were synthesized and five of the 5-(substituted phenyl)-1-phenyl- 2-pyrozoline-3″-yl) 6-halogen substituted coumarins were tested for in vivo analgesic and anti-inflammatory studies. The compounds were selected on the basis of log P values and in vitro radical scavenging activities. Anti-inflammatory activity was determined by carrageenan induced rat paw edema and analgesic activity was assessed by inhibition of hyperalgesia produced by carrageenan induced inflammation in the same rats by measuring the paw withdrawal latency. All compounds tested pharmacologically showed good analgesic and antiinflammatory activity in Wistar rats. The radical scavenging property may be one of the probable reasons for their analgesic and anti-inflammatory activity.

Original languageEnglish
Pages (from-to)404-410
Number of pages7
JournalPharmacologyonline
Volume2
Publication statusPublished - 2008

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Coumarins
Non-Steroidal Anti-Inflammatory Agents
Antioxidants
Carrageenan
Analgesics
Anti-Inflammatory Agents
Halogens
Hyperalgesia
Wistar Rats
Edema
Inflammation

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Pharmacology

Cite this

@article{0af1216626574e44afc7acd362e92952,
title = "Antioxidant analgesic and anti-inflammatory activities of some selected heteroaryl substituted Coumarins",
abstract = "Significant amounts of Coumarins, with benzopyrone ring units, are frequently present in plants. Simple coumarins and analogues are a large class of compounds with a wide spectrum of biological activity. Several series of coumarin derivatives were synthesized and five of the 5-(substituted phenyl)-1-phenyl- 2-pyrozoline-3″-yl) 6-halogen substituted coumarins were tested for in vivo analgesic and anti-inflammatory studies. The compounds were selected on the basis of log P values and in vitro radical scavenging activities. Anti-inflammatory activity was determined by carrageenan induced rat paw edema and analgesic activity was assessed by inhibition of hyperalgesia produced by carrageenan induced inflammation in the same rats by measuring the paw withdrawal latency. All compounds tested pharmacologically showed good analgesic and antiinflammatory activity in Wistar rats. The radical scavenging property may be one of the probable reasons for their analgesic and anti-inflammatory activity.",
author = "Jayashree, {B. S.} and Sameer Arora and Yogendra Nayak",
note = "Cited By :3 Export Date: 10 November 2017 Correspondence Address: Jayashree, B.S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal 576104, India; email: jesolar2001@yahoo.co.in Chemicals/CAS: acetylsalicylic acid, 493-53-8, 50-78-2, 53663-74-4, 53664-49-6, 63781-77-1; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7 Tradenames: bsj 3; bsj 4; bsja 1; bsja 4; sa 3 Manufacturers: Sigma References: Kulkarni, M.V., Kulkarni, G.M., Lin, C.H., Sun, C.M., Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents (2006) Curr Med Chem, 13 (23), pp. 2795-2818; Curini, M., Cravotto, G., Epifano, F., Giannone, G., Chemistry and biological activity of natural and synthetic prenyloxycoumarins (2006) Curr Med Chem, 13 (2), pp. 199-222; Santana L, Uriarte E, Roleira F, Milhazes N, Borges F. Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity. Curr Med Chem 2004;11(24):3239-3261; Lacy, A., O'Kennedy, R., Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer (2004) Curr Pharm Des, 10 (30), pp. 3797-3811; Budzisz, E., Małecka, M., Lorenz, I.P., Mayer, P., Kwiecień, R.A., Paneth, P., Krajewska, U., R{\'o}zalski, M., Synthesis, cytotoxic effect, and structure-activity relationship of Pd(II) complexes with coumarin derivatives (2006) Inorg Chem, 45 (24), pp. 9688-9695; Leonetti, F., Favia, A., Rao, A., Aliano, R., Paluszcak, A., Hartmann, R.W., Carotti, A., Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors (2004) J Med Chem, 47 (27), pp. 6792-6803; Chen, S., Cho, M., Karlsberg, K., Zhou, D., Yuan, Y.C., Biochemical and biological characterization of a novel anti-aromatase coumarin derivative (2004) J Biol Chem, 279 (46), pp. 48071-48078; Santana, L., Uriarte, E., Gonz{\'a}lez-D{\'i}az, H., Zagotto, G., Soto-Otero, R., M{\'e}ndez-Alvarez, E., A QSAR model for in silico screening of MAO-A inhibitors. Prediction, synthesis, and biological assay of novel coumarins (2006) J Med Chem, 49 (3), pp. 1149-1156; Chimenti, F., Secci, D., Bolasco, A., Chimenti, P., Granese, A., Befani, O., Turini, P., Ortuso, F., Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study (2004) Bioorg Med Chem Lett, 14 (14), pp. 3697-3703; Shen, Q., Peng, Q., Shao, J., Liu, X., Huang, Z., Pu, X., Ma, L., Gu, L., Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors (2005) Eur J Med Chem, 40 (12), pp. 1307-1315; Zavrsnik, D., Muratović, S., Spirtović, S., QSAR and QSPR study of derivatives 4-arylaminocoumarin (2003) Bosn J Basic Med Sci, 3 (3), pp. 59-63; Khan KM, Saify ZS, Khan MZ, Zia-Ullah, Choudhary IM, Atta-Ur-Rahman, Perveen S, Chohan ZH, Supuran CT. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem 2004;19(4):373-379; Maxwell, A., The interaction between coumarin drugs and DNA gyrase (1993) Mol Microbiol, 9 (4), pp. 681-686; Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., Nicolaides, D.N., Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities (2004) Curr Pharm Des, 10 (30), pp. 3813-3833; Kontogiorgis, C.A., Savvoglou, K., Hadjipavlou-Litina, D.J., Antiinflammatory and antioxidant evaluation of novel coumarin derivatives (2006) J Enzyme Inhib Med Chem, 21 (1), pp. 21-29; Jackson, S.A., Sahni, S., Lee, L., Luo, Y., Nieduzak, T.R., Liang, G., Chiang, Y., Rebello, S.S., Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase (2005) Bioorg Med Chem, 13 (8), pp. 2723-2739; Venugopala, K.N., Jayashree, B.S., Synthesis and characterization of carboxamides of 2′-amino-4′- (6-bromo-3-oumarinyl) thiazole for their analgesic and antiinflammatory activity (2003) Ind J Heterocyclic Chem, 12, pp. 307-310; Jayashree, B.S., Jerald, J., Venugopala, K.N., Synthesis and characterization of schiff bases of 2′-amino-4′- (3-coumarinyl) thiazole as potential NSAIDs (2004) Oriental J Chem, 20 (1), pp. 123-126; Venugopala, K.N., Jayashree, B.S., Attimarad, M., Synthesis and evaluation of some substituted 2-arylamino coumarinyl thiazoles as potential NSAIDs (2004) Asian J Chem, 16 (2), pp. 872-876; Venugopala, K.N., Jayashree, B.S., Synthesis and characterization of schiff bases of aminothiazolyl bromocoumarin for their analgesic and anti-inflammatory activity (2004) Asian J Chem, 16 (1), pp. 407-411; Jayashree, B.S., Anuradha, D., Venugopala, K.N., Synthesis and Characterization of Schiff bases of 2′-Amino-4′-(6-chloro-3-coumarinyl) thiazole as potential NSAIDs (2005) Asian J Chem, 17 (3), pp. 2093-2097; Jayashree, B.S., Sahu, A.R., Murthy, S.M., Venugopala, K.N., Synthesis, Characterization and Determination of Partition Coefficient of Some Triazolo thiadiazinyl coumarin for their Antimicrobial Activity (2007) Asian J Chem, 19 (1), pp. 73-78; Jayashree, B.S., Arora, S., Venugopala, K.N., Microwave assisted synthesis of some of the substituted coumarinyl chalcones as reaction intermediates for biologically important coumarinyl hetererocycles (2008) Asian J Chem, 20 (1), pp. 1-7; Rajakumar, D.V., Rao, M.N., Antioxidant properties of phenyl styryl ketones (1995) Free Radic Res, 22 (4), pp. 309-317; Jain, N.K., Patil, C.S., Singh, A., Kulkarni, S.K., A simple technique to evaluate inflammatory pain along with anti-inflammatory studies in carrageenan-induced paw edema (2001) Ind J Pharmacology, 33 (2), pp. 114-115",
year = "2008",
language = "English",
volume = "2",
pages = "404--410",
journal = "Pharmacologyonline",
issn = "1827-8620",
publisher = "SILAE (Italo-Latin American Society of Ethnomedicine)",

}

TY - JOUR

T1 - Antioxidant analgesic and anti-inflammatory activities of some selected heteroaryl substituted Coumarins

AU - Jayashree, B. S.

AU - Arora, Sameer

AU - Nayak, Yogendra

N1 - Cited By :3 Export Date: 10 November 2017 Correspondence Address: Jayashree, B.S.; Department of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal 576104, India; email: jesolar2001@yahoo.co.in Chemicals/CAS: acetylsalicylic acid, 493-53-8, 50-78-2, 53663-74-4, 53664-49-6, 63781-77-1; carrageenan, 9000-07-1, 9049-05-2, 9061-82-9, 9064-57-7 Tradenames: bsj 3; bsj 4; bsja 1; bsja 4; sa 3 Manufacturers: Sigma References: Kulkarni, M.V., Kulkarni, G.M., Lin, C.H., Sun, C.M., Recent advances in coumarins and 1-azacoumarins as versatile biodynamic agents (2006) Curr Med Chem, 13 (23), pp. 2795-2818; Curini, M., Cravotto, G., Epifano, F., Giannone, G., Chemistry and biological activity of natural and synthetic prenyloxycoumarins (2006) Curr Med Chem, 13 (2), pp. 199-222; Santana L, Uriarte E, Roleira F, Milhazes N, Borges F. Furocoumarins in medicinal chemistry. Synthesis, natural occurrence and biological activity. Curr Med Chem 2004;11(24):3239-3261; Lacy, A., O'Kennedy, R., Studies on coumarins and coumarin-related compounds to determine their therapeutic role in the treatment of cancer (2004) Curr Pharm Des, 10 (30), pp. 3797-3811; Budzisz, E., Małecka, M., Lorenz, I.P., Mayer, P., Kwiecień, R.A., Paneth, P., Krajewska, U., Rózalski, M., Synthesis, cytotoxic effect, and structure-activity relationship of Pd(II) complexes with coumarin derivatives (2006) Inorg Chem, 45 (24), pp. 9688-9695; Leonetti, F., Favia, A., Rao, A., Aliano, R., Paluszcak, A., Hartmann, R.W., Carotti, A., Design, synthesis, and 3D QSAR of novel potent and selective aromatase inhibitors (2004) J Med Chem, 47 (27), pp. 6792-6803; Chen, S., Cho, M., Karlsberg, K., Zhou, D., Yuan, Y.C., Biochemical and biological characterization of a novel anti-aromatase coumarin derivative (2004) J Biol Chem, 279 (46), pp. 48071-48078; Santana, L., Uriarte, E., González-Díaz, H., Zagotto, G., Soto-Otero, R., Méndez-Alvarez, E., A QSAR model for in silico screening of MAO-A inhibitors. Prediction, synthesis, and biological assay of novel coumarins (2006) J Med Chem, 49 (3), pp. 1149-1156; Chimenti, F., Secci, D., Bolasco, A., Chimenti, P., Granese, A., Befani, O., Turini, P., Ortuso, F., Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study (2004) Bioorg Med Chem Lett, 14 (14), pp. 3697-3703; Shen, Q., Peng, Q., Shao, J., Liu, X., Huang, Z., Pu, X., Ma, L., Gu, L., Synthesis and biological evaluation of functionalized coumarins as acetylcholinesterase inhibitors (2005) Eur J Med Chem, 40 (12), pp. 1307-1315; Zavrsnik, D., Muratović, S., Spirtović, S., QSAR and QSPR study of derivatives 4-arylaminocoumarin (2003) Bosn J Basic Med Sci, 3 (3), pp. 59-63; Khan KM, Saify ZS, Khan MZ, Zia-Ullah, Choudhary IM, Atta-Ur-Rahman, Perveen S, Chohan ZH, Supuran CT. Synthesis of coumarin derivatives with cytotoxic, antibacterial and antifungal activity. J Enzyme Inhib Med Chem 2004;19(4):373-379; Maxwell, A., The interaction between coumarin drugs and DNA gyrase (1993) Mol Microbiol, 9 (4), pp. 681-686; Fylaktakidou, K.C., Hadjipavlou-Litina, D.J., Litinas, K.E., Nicolaides, D.N., Natural and synthetic coumarin derivatives with anti-inflammatory/ antioxidant activities (2004) Curr Pharm Des, 10 (30), pp. 3813-3833; Kontogiorgis, C.A., Savvoglou, K., Hadjipavlou-Litina, D.J., Antiinflammatory and antioxidant evaluation of novel coumarin derivatives (2006) J Enzyme Inhib Med Chem, 21 (1), pp. 21-29; Jackson, S.A., Sahni, S., Lee, L., Luo, Y., Nieduzak, T.R., Liang, G., Chiang, Y., Rebello, S.S., Design, synthesis and characterization of a novel class of coumarin-based inhibitors of inducible nitric oxide synthase (2005) Bioorg Med Chem, 13 (8), pp. 2723-2739; Venugopala, K.N., Jayashree, B.S., Synthesis and characterization of carboxamides of 2′-amino-4′- (6-bromo-3-oumarinyl) thiazole for their analgesic and antiinflammatory activity (2003) Ind J Heterocyclic Chem, 12, pp. 307-310; Jayashree, B.S., Jerald, J., Venugopala, K.N., Synthesis and characterization of schiff bases of 2′-amino-4′- (3-coumarinyl) thiazole as potential NSAIDs (2004) Oriental J Chem, 20 (1), pp. 123-126; Venugopala, K.N., Jayashree, B.S., Attimarad, M., Synthesis and evaluation of some substituted 2-arylamino coumarinyl thiazoles as potential NSAIDs (2004) Asian J Chem, 16 (2), pp. 872-876; Venugopala, K.N., Jayashree, B.S., Synthesis and characterization of schiff bases of aminothiazolyl bromocoumarin for their analgesic and anti-inflammatory activity (2004) Asian J Chem, 16 (1), pp. 407-411; Jayashree, B.S., Anuradha, D., Venugopala, K.N., Synthesis and Characterization of Schiff bases of 2′-Amino-4′-(6-chloro-3-coumarinyl) thiazole as potential NSAIDs (2005) Asian J Chem, 17 (3), pp. 2093-2097; Jayashree, B.S., Sahu, A.R., Murthy, S.M., Venugopala, K.N., Synthesis, Characterization and Determination of Partition Coefficient of Some Triazolo thiadiazinyl coumarin for their Antimicrobial Activity (2007) Asian J Chem, 19 (1), pp. 73-78; Jayashree, B.S., Arora, S., Venugopala, K.N., Microwave assisted synthesis of some of the substituted coumarinyl chalcones as reaction intermediates for biologically important coumarinyl hetererocycles (2008) Asian J Chem, 20 (1), pp. 1-7; Rajakumar, D.V., Rao, M.N., Antioxidant properties of phenyl styryl ketones (1995) Free Radic Res, 22 (4), pp. 309-317; Jain, N.K., Patil, C.S., Singh, A., Kulkarni, S.K., A simple technique to evaluate inflammatory pain along with anti-inflammatory studies in carrageenan-induced paw edema (2001) Ind J Pharmacology, 33 (2), pp. 114-115

PY - 2008

Y1 - 2008

N2 - Significant amounts of Coumarins, with benzopyrone ring units, are frequently present in plants. Simple coumarins and analogues are a large class of compounds with a wide spectrum of biological activity. Several series of coumarin derivatives were synthesized and five of the 5-(substituted phenyl)-1-phenyl- 2-pyrozoline-3″-yl) 6-halogen substituted coumarins were tested for in vivo analgesic and anti-inflammatory studies. The compounds were selected on the basis of log P values and in vitro radical scavenging activities. Anti-inflammatory activity was determined by carrageenan induced rat paw edema and analgesic activity was assessed by inhibition of hyperalgesia produced by carrageenan induced inflammation in the same rats by measuring the paw withdrawal latency. All compounds tested pharmacologically showed good analgesic and antiinflammatory activity in Wistar rats. The radical scavenging property may be one of the probable reasons for their analgesic and anti-inflammatory activity.

AB - Significant amounts of Coumarins, with benzopyrone ring units, are frequently present in plants. Simple coumarins and analogues are a large class of compounds with a wide spectrum of biological activity. Several series of coumarin derivatives were synthesized and five of the 5-(substituted phenyl)-1-phenyl- 2-pyrozoline-3″-yl) 6-halogen substituted coumarins were tested for in vivo analgesic and anti-inflammatory studies. The compounds were selected on the basis of log P values and in vitro radical scavenging activities. Anti-inflammatory activity was determined by carrageenan induced rat paw edema and analgesic activity was assessed by inhibition of hyperalgesia produced by carrageenan induced inflammation in the same rats by measuring the paw withdrawal latency. All compounds tested pharmacologically showed good analgesic and antiinflammatory activity in Wistar rats. The radical scavenging property may be one of the probable reasons for their analgesic and anti-inflammatory activity.

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M3 - Article

VL - 2

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EP - 410

JO - Pharmacologyonline

JF - Pharmacologyonline

SN - 1827-8620

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