A REVIEW OF INDAZOLE DERIVATIVES IN PHARMACOTHERAPY OF INFLAMMATION

VISHAL KUMAR, KAMINI GUPTA, ANUP KUMAR SIRBAIYA, MD AZIZUR RAHMAN

Abstract


ndazole is an important class of heterocyclic compound. This review is aimed to collect different synthetic methods and the anti-inflammatory data of indazole derivatives. Literature surveys on scientific national and international journals, books as well as electronic resources were performed. Different synthetic methods and the anti-inflammatory data of indazole derivatives were compiled in the present review. From the literature survey, the best method for the synthesis of indazole derivatives was found to be compound 45. The indazole derivatives had shown various pharmacological activities such as antibacterial, anti-emetic, anticancer, MAO inhibitors, anti-convulsant, anti-protozoal, anti-asthmatic, HIV protease inhibitors, Rho kinase inhibitors, antihypertensive and other activities. Indazole shows different pharmacological activities as well as good anti-inflammatory activity due to their structural similarities with biomolecules like adenine and guanine, hence easily interact with biopolymer in living system.

Keywords


Indazole, Anti-inflammatory, Benzydamine, Diazotization, Hetrocycles.

Full Text:

PDF

References


Thangadurai A, Minu M, Wakode S, Agrawal S, Narasimhan B. Indazole: A medicinally important heterocyclic moiety. Med Chem Res. 2012;21(7):1509-23. doi: 10.1007/s00044-011-9631-3.

Gaikawad DD, Chapolikar DA, Devlate GC, Warad DK, Tayade PA, Pawar PR, Domb JA. Synthesis of indazole motifs and their medicinal importance:an overview. Eur J Med Chem. 2014.

Catalan J, del Valle JC, Claramunt RM, Boyer G, Laynez J, Gomez J, Jimenez P, Tomas F, Elguero J. Acidity and basicity of indazole and its N-methyl derivatives in the ground and in the excited state. J Phys Chem. 1994;98(41):10606-12. doi: 10.1021/j100092a035.

Catalán J, De Paz JL, Elguero J. The structure of NH-benzazoles (1HBenzimidazoles, 1H-and 2H-Indazoles, 1H-and 2H-Benzotriazoles). J Chem Soc Perkin Trans. 1996;2:57.

Öğretir C, Funda Kaypak NF. Quantum chemical calculations on the annular tautomerism of some indazole derivatives. 1. A gas phase study. THEOCHEM. 2002;583(1-3):137-44. doi: 10.1016/S0166-1280(01)00806-5.

Denya I, Malan SF, Joubert J. Indazole derivatives and their therapeutic applications: a patent review (2013-2017). Expert Opin Ther Pat. 2018;28(6):441-53. doi: 10.1080/13543776.2018.1472240, PMID 29718740.

Doing J, Zhang Q, Wang Z, Huang G, Li S. Recent Advances in the Development of indazole - based Anticancer Agents. Chem Chem. 2018;13:1-19. doi: 10.1002/cmdc.201800253.

Shrivastava A, Chakraborty AK, Upmanyu N, et al. Recent progress in chemistry and biology of indazole and its derivatives: A brief review. Austin J Anal Pharm Chem. 2016;3(4):1076.

Tanitame A, Oyamada Y, Ofuji K, Kyoya Y, Suzuki K, Ito H, Kawasaki M, Nagai K, Wachi M, Yamagishi J. Design, synthesis and structure–activity relationship studies of novel indazole analogues as DNA gyrase inhibitors with Gram-positive antibacterial activity. Bioorg Med Chem Lett. 2004 Jun 7;14(11):2857-62. doi: 10.1016/j.bmcl.2004.03.044, PMID 15125947.

Minu M, Thangadurai A, Wakode SR, Agrawal SS, Narasimhan B. Synthesis, antimicrobial activity and QSAR studies of new 2, 3-disubstituted-3, 3a, 4, 5, 6, 7-hexahydro-2Hindazoles. Bioorg Med Chem Lett. 2009;19(11):2960-4. doi: 10.1016/j.bmcl.2009.04.052, PMID 19410452.

López-Vallejo F, Castillo R, Yépez-Mulia L, et al, Medina-Franco JL. Benzotriazoles and indazoles are scaffolds with biological activity against Entamoeba histolytica. J. Biomol. Screening. 2011;16(8):862-8. doi: 10.1177/1087057111414902, PMID 21821786.

Pérez-Villanueva J, Hernández-Campos A, Yépez-Mulia L, Méndez-Cuesta C, Méndez-Lucio O, Hernández-Luis F, Castillo R. Synthesis and antiprotozoal activity of novel 2-{[2-(1H-imidazol-1-yl)ethyl]sulfanyl}-1H-benzimidazole derivatives. Bioorg Med Chem Lett. 2013;23(14):4221-4. doi: 10.1016/j.bmcl.2013.05.012, PMID 23731944.

Cedillo-Rivera R, Chávez B, González-Robles A, Tapia A, Yépez-Mulia L. In vitro effect of nitazoxanide against Entamoeba histolytica, Giardia intestinalis and Trichomonas vaginalis trophozoites. J Eukaryot Microbiol. 2002;49(3):201-8. doi: 10.1111/j.1550-7408.2002.tb00523.x, PMID 12120985.

Orlando BJ, Malkowski MG. Crystal structure of rofecoxib bound to human cyclooxygenase-2. Acta Crystallogr F Struct Biol Commun. 2016;72(10):772-6. doi: 10.1107/S2053230X16014230, PMID 27710942.

Cheekavolu C, Muniappan M. In vivo and in vitro antiinflammatory activity of indazole and its derivatives. J Clin Diagn Res. 2016;10(9), FF01–FF06. doi: 10.7860/JCDR/2016/19338.8465, PMID 27790461.

Woods KW, Fischer JP, Claiborne A, Li T, Thomas SA, Zhu GD, Diebold RB, Liu X, Shi Y, Klinghofer V, Han EK, Guan R,Magnone SR, Johnson EF, Bouska JJ, Olson AM, de Jong R, Oltersdorf T, Luo Y, Rosenberg SH, Giranda VL, Li Q. Synthesis and SAR of indazolepyridine based protein kinase B/Akt inhibitors. Bioorg Med Chem. 2006;14(20):6832-46. doi: 10.1016/j.bmc.2006.06.047, PMID 16843670.

Patel M, Rodgers JD, McHugh RJ, Johnson BL, Cordova BC, Klabe RM, Bacheler LT, Erickson-Viitanen S, Ko SS. Unsymmetrical cyclic ureas as HIV-1 protease inhibitors: novel biarylindazoles as P2/P2’ substituents. Bioorg Med Chem Lett. 1999;9(22):3217-20. doi: 10.1016/s0960-894x(99)00564-8, PMID 10576691.

Moore PK, Babbedge RC, Wallace PZ, Gaffen ZA, Hart SL. 7-nitro indazole, an inhibitor of nitric oxide synthase, exhibits anti-nociceptive activity in the mouse without increasing blood pressure. Br J Pharmacol. 1993;108(2):296-7. doi: 10.1111/j.1476-5381.1993.tb12798.x, PMID 7680591.

Tzvetkov NT, Hinz S, Küppers P, Gastreich M, Müller CE. Indazole-and indole5-carboxamides: selective and reversible monoamine oxidase B inhibitors with subnanomolar potency. J Med Chem. 2014;57(15):6679-703. doi: 10.1021/jm500729a, PMID 24955776.

Ali Na, Zakir S, Patel M, Farooqui M. Synthesis of new alpha aminophosphonate system bearing indazole moiety and their biological activity. Eur J Med Chem. 2012;50:39-43. doi: 10.1016/j.ejmech.2012.01.024, PMID 22341789.

Janardhanan CJ, Mishra KR, Das G, Sini S, jayamurthy P, suresh HC, Praveen KV, Manoj N, Babu PB. Functionalizable 1H-Indazole by palladium catalyzed Aza-Nenitzescu reaction: pharmacophores to donor acceptor type multi-luminescent fluorophores. Asian J Org Chem. 2018;7:1-12.

Drizin I, Gomtsyan A, Bayburt K E, G.Schmidt R. Zhu Zheng G. J Perner R, DiDomenico S, R.Koenig J, C. Turner K, K. Jinkerson T, S. Brown J, G. Keddy R, A. McDonald H, Honore P, T.Wismer C, C. Marsh K, M. Wetter J, S. Polakowski J, A. Segreti J, F. Jarvis M, R. Faltynek C, Hung Lee C, "Structure - Activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists" Bioorganic and Medicinal Chemistry 14(2006) 4740 – 4749.

Jin T, Yamamoto Y. An efficient, Facile, and General Synthesis of 1H-Indazoles by 1,3-Dipolar Cycloaddition of Arynes with Diazomethane Derivatives. Angew Chem Int Ed Engl. 2007;46(18)'3323-3325. doi: 10.1002/anie.200700101, PMID 17385767.

Wang J, Liu Z, Wang L, Tan H, Zhou S, Fu T, Xia Y, Zhang Y. Synthesis of 1H-Indazoles from N-tosylhydrazones and nitro aromatic compounds. Vol. 09. Royal Society of Chemistry; 2014. p. 05-57.

Wang J, Liu Z, Wang L, Tan H, Zhou S, Fu T, Xia Y, Zhang Y. Synthesis of 1H-Indazoles from N-tosylhydrazones and nitro aromatic compounds. Vol. 09. Royal Society of Chemistry; 2014. p. 05-57.

Larock C R, Liu Z. Shi F, D.G. Martinez P, Raminelli C, Synthesis of indazole by the [3+2] Cycloaddition of Diazo compound with Arynes and Subsequent acyl Migration. J Org Chem. 2008;73:219-26.

Chang J, Yu W, Yang X, Wang Z, Wei W. Divergent synthesis of 1H-Indazoles and 1H-pyrazoles from hydrazones via iodine - mediated intramolecular aryl and sp3 C - H amination. Adv Synth Cat.

Bounce A. R, Annor-Gyamfi JK, Kumar Gnanasekaran K, Synthesis of 1-Aryl-5-nitro-1H-Indazoles and a General one-pot Route to 1-aryl-1H-Indazoles. Molecules. 2018;23:674.

Finar IL. stereochemistry and the chemistry of natural products. J Org Chem “vol 2. 5th ed, Pearson publication, page no.628.

Lefebvre V, Cailly T, Fabis F, Rault S. Two step Synthesis of substituted 3-Aminoindazoles from 2-Bromobenzonitriles. J Org Chem. 2010;75(8):2730-2. doi: 10.1021/jo100243c, PMID 20232925.

Schindler R, Fleischhauer I, Höfgen N, Sauer W, Egerland U, Poppe H, Heer S, Szelenyi I, Kutscher B, Engel J. 1,5-Disubstituted Indazole-3-ols with anti-inflammatory activity. Pharm MedChem. 1998;331(1):13-21. doi: 10.1002/(SICI)1521-4184(199801)331:1<13::AID-ARDP13>3.0.CO;2-M, PMID 9507697.32. Rosati O, Curini M, Marcotullio MC, Macchiarulo A, Perfumi M, Mattioli L, Rismondo F, Cravotto G. Synthesis docking studies and anti-inflammatory activity of 4, 5,6,7-tetrahydro-2H-Indazole derivatives. Bioorg Med Chem. 2007;15(10):3463-73. doi: 10.1016/j.bmc.2007.03.006, PMID 17382550.

Baiocchi L, Corsi G, Palazzo G. Synthesis and reactions of 1-H-indazol-3-oles and 1,2-dihydro-3H-indazol-3-ones. Synthesis. 1978;9:633-48.

Moretti GP, Foresta P. Preparation of (S)-2-amino-6- fluoro-7-methyoxytetraline for treatment of septic shock. PCT Int Appl Wo. 1998, Chem [abst], 129;98(33):762 (Cl. C 07C217/74)6 Aug. PMID 161424p.

Abouzid KA, el-Abhar HS. Synthesis and antiinflammatory activity of novel indazolones. Arch Pharm Res. 2003;26(1):1-8. doi: 10.1007/BF03179922, PMID 12568349.

Abouzid KA, el-Abhar HS. Synthesis and antiinflammatory activity of novel indazolones. Arch Pharm Res. 2003;26(1):1-8. doi: 10.1007/BF03179922, PMID 12568349.

Abouzid KA, el-Abhar HS. Synthesis and antiinflammatory activity of novel indazolones. Arch Pharm Res. 2003;26(1):1-8. doi: 10.1007/BF03179922, PMID 12568349.

Nagakura M, Ota T, Shimidzu N, Kawamura K, Eto Y, Wada Y. Synthesis and anti-inflammatory actions of 4, 5,6,7-Tetrahydroindazole-5-carboxylic acids. J Med Chem bol 22 no 1. 1979:48-52. doi: 10.1021/jm00187a012, PMID 423183.39. Gomtsyan A, Bayburt EK, Schmidt RG, Surowy CS, Honore P, Marsh KC, Hannick SM, McDonald HA, Wetter JM, Sullivan JP, Jarvis MF, Faltynek CR, Lee CH. Identification of (R)-1-(5-tert-butyl-2,3-dihydro-1H-inden-1-yl)-3-(1H-indazol-4-yl)urea (ABT-102) as a potent TRPV1 antagonist for pain management. J Med Chem. 2008;51(3):392-5. doi: 10.1021/jm701007g, PMID 18183945.

Schenone S, Bruno O, Ranise A, Brullo C, Bondavalli F, Filippelli W, Mazzeo F, Capuano A, Falcone G. 2-Aryl-3-phenylamino-4,5-dihydro-2h-ben[g]indazole with analgesic activity. Il Farmaco. 2003;58(9):845-9. doi: 10.1016/S0014-827X(03)00142-3.

Nasar NA. M, A. Said S, "Novel 3,3a4,5,6,7,-Hexahydroindazole and Arylthiazolylpyrazoline derivatives as Anti-inflammatory Agents", Pharm. Med Chem;3003(336):551-9.

Drizin I, Gomtsyan A, Bayburt K E, G.Schmidt R. Zhu Zheng G. J Perner R, DiDomenico S, R.Koenig J, C. Turner K, K. Jinkerson T, S. Brown J, G. Keddy R, A. McDonald H, Honore P, T.Wismer C, C. Marsh K, M. Wetter J, S. Polakowski J, A. Segreti J, F. Jarvis M, R. Faltynek C, Hung Lee C, "Structure - Activity studies of a novel series of 5,6-fused heteroaromatic ureas as TRPV1 antagonists" Bioorganic and Medicinal Chemistry 14(2006) 4740 – 4749.


Refbacks

  • There are currently no refbacks.


© Copyright 2016. All Rights Reserved - Innovatpublisher CC BY Creative commons