SYNTHESIS OF 1-BENZOYL-3-PHENYL-1H-PYRAZOLE-4-CARBALDEHYDE AND EVALUATION OF THEIR ANTIOXIDANT AND ANTI-INFLAMMATORY ACTIVITY

BONO NAGA SUDHA; N YELLA SUBBAIAH; MANCHALA MAHALAKSHMI

doi:10.22159/ajpcr.2021.v14i10.41779

Authors

BONO NAGA SUDHA Department of Pharmaceutical Chemistry, CES College of pharmacy, Kurnool-518218, Andhra Pradesh, India.
N YELLA SUBBAIAH Department of Pharmaceutical Chemistry, CES College of pharmacy, Kurnool-518218, Andhra Pradesh, India.
MANCHALA MAHALAKSHMI Department of Pharmaceutical Chemistry, CES College of pharmacy, Kurnool-518218, Andhra Pradesh, India.

DOI:

https://doi.org/10.22159/ajpcr.2021.v14i10.41779

Keywords:

Pyrazoles, Hydrazones, Vilsmier-Haack reaction, Antioxidant and anti-inflammatory activity

Abstract

Objective: The main objective of this study is to synthesize a series of 1-Benzoyl-3-phenyl-1H-pyrazole-4-carbaldehyde (4a-e) derivatives and evaluation of the synthesized compounds for their antioxidant and anti-inflammatory activity.

Methods: A series of substituted acetophenones are condensed with hydrazides to the corresponding hydrazones which are subsequently cyclized by using vilsmier-Haack reaction to give final series of 1-Benzoyl-3-phenyl-1H-pyrazole-4-carbaldehyde (4a-e) derivatives respectively. All newly synthesized compounds were characterized on the basis of infrared, proton nuclear magnetic resonance and mass spectral data and screened for their antioxidant and anti-inflammatory activities.

Results: In view of the significant biological activity profile of Pyrazole, the synthesized compounds (4a-e) were evaluated for their antioxidant potency by DPPH, Nitric oxide, Hydroxyl radical scavenging, and Hydrogen Peroxide method. Compounds 4c and 4e showed potent antioxidant activity then standard. Synthesized compounds were also screened for anti-inflammatory activity. Among all the molecules 4c, 4e, and 4d showed significant activity as compared to standard drug diclofenac sodium.

Conclusion: in this study, we synthesized 1-Benzoyl-3-phenyl-1H-pyrazole-4-carbaldehyde (4a-e) derivatives. Further, these derivatives showed significant antioxidant and anti-inflammatory activity. Among them, two molecules 4c and 4e have shown near action to the standard.

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References

Noe FF, Fowden A. Heterocyclic amino acid, Β-pyrazol-lylalanine, was isolated from the seeds of watermelon (Citrullus vulgaris) and its structure confirmed by comparison with synthetic material. Biochem J 1960;77:543-6.

Abdel Aziz SA, El-Sayed Ali T, El-Mahdy KM, Abde-Karim SM. Synthesis and antimicrobial activities of some novel bis-pyrazole derivatives containing a hydrophosphoryl unit. Eur J Chem 2011;2:25- 35.

Shridhar M, Isloor MA, Akhila DS, Hoong-Kun F. Synthesis, characterization and antibacterial activity of some new pyrazole schiff bases. Arab J Chem 2013;6:335-40.

Yassin FA. Novel pyrazolyl pyridazine derivatives likely to possess anti-inflammatory activity. J Microb Antimicrob 2010;2:93-99.

Abdel Aziz M, Rahma Gel DA, Hassan AA. Synthesis of novel pyrazole derivatives and evaluation of their antidepressant and anticonvulsant activities. Eur J Chem 2009;44:3480-4.

Unnat P, Amit D. Synthesis and antitubercular activity of novel pyrazole-quinazolinone hybrid analogs. Med Chem Res 2013;22:3364- 71.

Pathak RB, Chovatia PT, Parekh HH. Synthesis, antitubercular and antimicrobial evaluation of 3-(4-chlorophenyl) 4-substituted pyrazole derivatives. Bioorg Med Chem Lett 2012;22:5129-33.

Tzanetou E, Liekens S, Kasiotis KM, Fokialakis N, Haroutounian SA. Novel pyrazole and indazole derivatives, synthesis and evaluation of their anti-proliferative and anti-angiogenic activities. Arch Pharm 2012;345:804-11.

Anadarajagopal K, Sunilson JA, Illavarasu A, Thangavelpandian N, Kalirajan R. Antiepileptic and antimicrobial activities of novel 1-(unsubstituted/substituted)-3,5-dimethyl-1h-pyrazole derivatives. Int J ChemTech Res 2010;2:45-9.

Brian ST, Antony JH, Peter WG, Austin RR. Vogel’s: Practical Organic Chemistry. 5th ed. New York: Longman Scientific Technical; 1989. p. 1077.

Altarejos J, Salido S, Bonilla MP, Palomino PJ, Beek TA, Nogueras M. Preliminary assay on the free radical scavenging activity of olive wood extracts. Fitoterapia 2005;76:348-51.

Marcocci L, Maguire JJ, Droy-Lefaiz MT, Packer L. The nitric oxide-scavenging properties of Ginkgo biloba eztract EGB 761. Biochem Biophys Res Commun 1994;201:748-55.

Sakanaka S, Tachibana Y, Okada Y. Preparation and antioxidant properties of extracts of Japanese persimmon leaf tea (kakinoha-cha). Food Chem 2005;89:569-75.

Bozin B, Mimica-Duki N, Samojlik I, Goran A, Igic R. Phenolics as antioxidants in garlic (Allium sativum Linn. Alliaceae). Food Chem 2008;111:925-9.

Olfert ED, Cross BM, McWilliam AA. Guide to the Care and Use of Experimental Animals. 2nd ed., Vol. 1. Ottawa, Ontario: Canadian Council on Animal Care; 1993.

Winter CA, Risley EA, Nuss GW. Carrageenin-induced edema in hind paw of the rat as an assay for anti-inflammatory drugs. Exp Biol Med 1962;111:544-7.