ANTIOXIDANT POTENTIAL OF PIPERIDINE CONTAINING COMPOUNDS-A SHORT REVIEW

Authors

  • Manjusha R K Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati 517502, Andhra Pradesh, India.
  • Shaheen Begum Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati 517502, Andhra Pradesh, India.
  • Arifa Begum Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati 517502, Andhra Pradesh, India.
  • Bharathi K Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati 517502, Andhra Pradesh, India.

DOI:

https://doi.org/10.22159/ajpcr.2018.v11i8.26536

Keywords:

Piperidine nitroxides, Substituted piperidines, Unsaturated piperidines, N-acyl substituted piperidines, Diaryl substituted piperidinones, Piperidinone oximes, Piperidine hydrazides

Abstract

Piperidine is a saturated heterocyclic ring, considered as a privileged scaffold in view of its role in wide range of biological activities. Piperidine is good candidate molecule for obtaining potent antioxidant agents. The planar nature of this heterocyclic nucleus allows the introduction of substituent groups at different positions on the ring. In the present review, the antioxidant profile of piperidine containing compounds has been focused. The compounds were classified into naturally occurring piperidines, unsaturated piperidines, N-substituted piperidines, piperamides, piperanols, piperidine oximes, and hydrazides.

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Author Biography

Manjusha R K, Department of Pharmaceutical Chemistry, Institute of Pharmaceutical Technology, Sri Padmavati Mahila Visvavidyalayam (Women’s University), Tirupati 517502, Andhra Pradesh, India.

Department of Pharmaceutical Chemistry

References

Kumar D, Singh V. Study of heterocyclic compound piperidine. Int J Res Sci Tech 2014; 3:25-8.

Przedborski S, Jackson-Lewis V, Djaldetti R, Liberatore G, Vila M, Vukosavic S, et al. The parkinsonian toxin MPTP: Action and mechanism. Restor Neurol Neurosci 2000;16:135-42.

Aridoss G, Parthiban P, Ramachandran R, Prakash M, Kabilan S, Jeong YT, et al. Synthesis and spectral characterization of a new class of N-(N-methylpiperazinoacetyl)-2,6-diarylpiperidin-4-ones: Antimicrobial, analgesic and antipyretic studies. Eur J Med Chem 2009;44:577-92.

Prashanth MK, Revanasiddappa HD, Lokanatha Rai KM, Veeresh B. Synthesis, characterization, antidepressant and antioxidant activity of novel piperamides bearing piperidine and piperazine analogues. Bioorg Med Chem Lett 2012;22:7065-70.

Kiasalari Z, Khalili M, Roghani M, Ahmadi A, Mireie M. Antioxidant and antiepileptic activity of 1-[1-(3-Methoxyphenyl) (Tetralyl)] piperidine as a new derivative of phencyclidine on pentylentetrazole-induced kindling mice. Iran J Pathol 2013;9:138-48.

Paulrasu K, Arul D, Manikandan P, Amirthaganesan S, Kuppusamy M, Balasankar T, et al. Synthesis of 4-methyl- N’-(3-alkyl-2r,6C-diaryl piperidin-4-ylidene) -1,2,3-thiadiazole-5-carbohydrazides with antioxidant, antitumor and antimicrobial activities. Org Biomol Chem 2014;12:5911-21.

Frietas RM, Silva FO, Silva MG, Feng D. Antioxidant mechanisms of iso-cassine in suppressing seizures induced by pilocarpine. Braz J Pharmacog 2011;21:437-43.

Parthiban P, Aridoss G, Rathika P, Ramkumar V, Kabilan S. Synthesis, stereochemistry and antimicrobial studies of novel oxime ethers of aza/ diazabicycles. Bioorg Med Chem Lett 2009;19:6981-5.

Baumann M, Baxendale IR. An overview of the synthetic routes to the best selling drugs containing 6-membered heterocycles. Beilstein J Org Chem 2013;9:2265-319.

Bendary E, Francis RR, Ali HM, Sarwat MI, El Hady S. Antioxidant and structure-activity relationships (SARs) of some phenolic and anilines compounds. Ann Agric Sci 2013;58:173-81.

Hajhashemi V, Vaseghi G, Pourfarzam M, Abdollahi A. Are antioxidants helpful for disease prevention? Res Pharm Sci 2010;5:1-8.

Marambaud P, Zhao H, Davies P. Resveratrol promotes clearance of Alzheimer’s disease amyloid-beta peptides. J Biol Chem 2005;280:37377-82.

Moon JK, Shibamoto T. Antioxidant assays for plant and food components. J Agric Food Chem 2009;57:1655-66.

Nakatani N, Inatani R, Ohta H, Nishioka A. Chemical constituents of peppers (Piper spp.) and application to food preservation: Naturally occurring antioxidative compounds. Environ Health Perspect 1986;67:135-42.

Trnka J, Blaikie FH, Logan A, Smith RA, Murphy MP. Antioxidant properties of Mito TEMPOL and its hydroxylamine. Free Rad Res 2009;43:4-12.

Kim JH, Shyam PK, Kim MJ, Lee HJ, Lee JT, Jang HY, et al. Enantioselective synthesis and antioxidant activity of 3,4,5-substituted piperidine derivatives. Bioorg Med Chem Lett 2016;26:3119-21.

Elanchezhian B, Manivannan N, Selvanathan G. Synthesis, spectral characterization and antioxidant activities of 3’-Methyl-2’,6’-diphenyl- 1,3-dihydrospiro[benzo[D]imidazole-2,4’-piperidine]. Int J Pharm Chem Biol Sci 2014;4:620-7.

Alexidis AN, Rekka EA, Demopoulos VJ, Kourounakis PN. Novel 1, 4 substituted piperidine derivatives. Synthesis and correlation of antioxidant activity with structure and lipophilicity. J Pharm Pharmacol 1995;47:131-7.

Kumar KA, Rai KM, Kumar G, Mylarappa BN. A facile route for the synthesis of ethyl, N-aryl-2,6-dioxo-piperid-3-ene-4-carboxylates and their biological activity. Int J Pharm Pharm Sci 2012;4:564-8.

Manohar S, Thakur A, Bhatia R, Walia S, Ponnan P, Rawat DS, et al. Antibacterial and antioxidant activity evaluation of novel symmetrical and unsymmetrical C5-curcuminoids. Indian J Chem 2015;54B:1235 46.

Khalid H, Rehman AU, Abbasi MA, Khan KM. Synthesis, spectral characterization and structure-activity relationship studies on some sulfonamides bearing piperidine nucleus. Int J Pharm Pharm Sci 2012;4:443-8.

Jahan S, Akhtar S, Kamil A, Saify ZS, Mushtaq N, Arif M, et al. Antibacterial, antifungal and antioxidant activities of derivatives of alkyl piperidine. FUUAST J Biol 2012;2:29-35.

Bandgar BP, Patil SA, Totre JV, Korbad BL, Gacche RN, Hote BS, et al. Synthesis and biological evaluation of nitrogen-containing benzophenone analogues as TNF-alpha and IL-6 inhibitors with antioxidant activity. Bioorg Med Chem Lett 2010;20:2292-6.

Prachayasittikul S, Worachartcheewan A, Lawung R, Ruchirawat S, Prachayasittikul V. Activities of thiotetrahydropyridines as antioxidant and antimicrobial agents. EXCLI J 2009;8:107-14.

Naicker L, Venugopala KN, Shode F, Odhav B. Antimicrobial and antioxidant activities of piperidine derivatives. Afr J Pharm Pharmacol 2015;9:783-92.

Gangadhara S, Prasad C, Venkateswarlu P. Synthesis, antimicrobial and antioxidant activity of piperidine analog containing transcinnamamides. Indo Am J Pharm Res 2015;5:1-8.

Karthik CS, Mallesha L, Mallu P. Synthesis and in vitro biological activity of [1-(Substituted-benzoyl)-piperidin-4-yl]-(2, 4- difluoro-phenyl)-methanoneoximes. Int J Chem Environ Biol Sci 2015;3:169 74.

Chamarthi N, Sudhamani H, Basha SK, Nagam V, Tartte V. Synthesis and characterization of new thiourea and urea derivatives of 6-fluoro- 3-(piperidin-4-yl) benzo[d]isoxazole: In vitro antimicrobial and antioxidant activity. J Chem Sci 2015;127:1739-46.

Shivaprasad CM, Jagadish S, Swaroop TR, Mohan CD, Roopashree R, Rangappa KS, et al. New synthetic benzisoxazole deriatives as antimicrobial, antioxidant and antiinflammatory agents. Eur J Chem 2013;4:402-7.

Shivaprasad CM, Jagadish S, Swaroop TR, Mohan CD, Roopashree R, Rangappa KS, et al. Synthesis of new benzisoxazole derivatives and their antimicrobial, antioxidant and anti-inflammatory activities. Eur J Chem 2014;5:91-5.

Kumar KA, Pavithra G, Renuka N, Kumar GV. Piperidone analogs: Synthesis and their diverse biological applications. Int Res J Pharm App Sci 2012;2:145-54.

Nithya P, Madhavi C. Antioxidant activity of 3-arylidene-4-piperidones in the 1,1-diphenyl-2-picrylhydrazyl scavenging assay. J Taibah Univ Sci 2017;11:40-5.

Karthik N, Nithiya S, Jayabharathi J. Novel piperidone derivatives: Synthesis, spectral and evaluation of antioxidant activity. Int J Drug Dev Res 2011;3:122-7.

Premalatha B, Elavarasan S, Bhakiaraj D, Chellakili B, Gopalakrishnan M. Synthesis, antimicrobial and antioxidant activity of novel 2,6-diphenyl-1-3-alkylpiperidin-4-one-O-[2,4,6-tritertiarybutyl-cyclohexa-2,5-dienon-4-yl]oximes. J Appl Chem 2013;2:1509-15.

Tharini K, Sangeetha P. Antioxidant and anti-inflammatory activity of 3,3-dimethyl 2,6- dimethyl piperidine4-one oxime. Int J Chem Sci 2015;13:1794-804.

Harini ST, Kumar HV, Peethambar SK, Rangaswamy J, Naik N. Novel 2,6-bis (4-methoxyphenyl)-1- methyl piperidin-4-one oxime esters: Synthesis and a new insight into their antioxidant and antimicrobial potential. Med Chem Res 2014;23:1887-98.

Harini ST, Kumar HV, Rangaswamy J, Naik N. Synthesis, antioxidant and antimicrobial activity of novel vanillin derived piperidin-4-one oxime esters: Preponderant role of the phenyl ester substituents on the piperidin-4-one oxime core. Bioorg Med Chem Lett 2012;22:7588-92.

Harini ST, Kumar HV, Rangaswamy J, Naik N. Synthesis of thiazole-based substituted piperidinone oximes: Profiling of antioxidant and antimicrobial activity. Russ J Bioorg Chem 2017;43:186-96.

Karaman N, Oruc-Emre EE, Sicak Y, Catıkkas B, Karakucuk A, Ozturk M, et al. Microwave-assisted synthesis of new sulfonylhydrazones, screening of biological activities and investigation of structure-activity relationship. Med Chem Res 2016;25:1590-607.

Allen NS, Ortiz RA, Anderson GJ. Comparison of the thermal and light stabilising action of novel imine and piperazine based hindered piperidine stabilisers in polyolefins. Polym Degrad Stab 1994;46:85 91.

Vasavirama K, Upender M. Piperine: A valuable alkaloid from Piper species. Int J Pharm Pharm Sci 2014;6:34-8.

Kumar KS, Mohan CD, Jagadish S, Rakesh KS, Hanumappa A, Basappa B, et al. Synthesis and acetylcholinesterase/butyrylcholinesterase inhibition activity of arecoline-, 4-thiazolidinone- and piperidine-based conjugates. Asian J Pharm Clin Res 2015;8:142-8.

Perumal P, Sivakkumar T, Kannappan N, Manavalan R. Synthesis, spectroscopic characterization and antimicrobial activity of 2,6 di-substituted piperidine-4-one derivatives. Int J Pharm Pharm Sci 2013; 5 suppl2:317-21.

Rajbir K, Saroj A. Alkaloids-important therapeutic secondary metabolites of plant origin. J Citation Rep 2015;2:1-8.

Published

07-08-2018

How to Cite

K, M. R., S. Begum, A. Begum, and B. K. “ANTIOXIDANT POTENTIAL OF PIPERIDINE CONTAINING COMPOUNDS-A SHORT REVIEW”. Asian Journal of Pharmaceutical and Clinical Research, vol. 11, no. 8, Aug. 2018, pp. 66-73, doi:10.22159/ajpcr.2018.v11i8.26536.

Issue

Section

Review Article(s)