Synthesis, Characterization and Antioxidant Evaluation of New N-Α-Chloroacetylsalicyloyl-N-Antipyrine Benzamide

Authors

  • Elham Abdalrahem Bin Selim Chemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
  • Mohammed Hadi Al–Douh Chemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen
  • Faten Abdulaziz Bin Hawiel Chemistry Department, Faculty of Science, Hadhramout University, Mukalla, Hadhramout, Yemen

DOI:

https://doi.org/10.22401/b72ypg13

Keywords:

Benzamide , 4-Aminoantipyrine , Acetylsalicylic Acid, Antioxidant

Abstract

The new compound N-α-chloroacetylsalicyloyl-N-antipyrine benzamide was synthesized by a reaction of N-benzylidene antipyrine amine and O-acetyl salicyloyl chloride. On the other hand, N-benzylidene antipyrine amine was obtained by a coupling reaction between benzaldehyde and 4-aminoantipyrine, while O-acetyl salicyloyl chloride resulted from acylation reaction of aspirin starting from salicylic acid. All synthesized compounds were characterized by using m.ps., UV-Vis., FTIR, MS, and 1HNMR spectroscopic methods. The method of DPPH was also used as testing to measure the radical scavenging of the new compound. It showed very powerful antioxidant activity with IC50 value of 29 ppm. Moreover, its antibacterial activity  was tested against three types of bacteria.

References

Costanzo, L.S.; “Physiology”. 6th ed.; Wolters Kluwer Health: Philadelphia, USA, 2016. ISBN: 978-1-4511-8795-3

Steinberg, M.I.; Lacefield, W.B.; Robertson, D.W.; “Class I and III antiarrhythmic drugs”. Ann. Rep. Med. Chem., 21: 95-108, 1986. DOI: 10.1016/S0065-7743(08)61120-3

Asif, M.; “Pharmacological potential of benzamide analogues and their uses in medicinal chemistry”. Mod. Chem. Appl., 4(4): 1000194, 1-10, 2016. DOI: 10.4172/2329-6798. 1000194

Barrett, K.T.; Miller, S.J.; “Enantioselective synthesis of atropisomeric benzamides through peptide-catalyzed bromination”. J. Am. Chem. Soc., 135(8): 2963-2966, 2013. DOI: 10.1021/ ja400082x

Barrett, K.T.; Miller, S.J.; “Regioselective derivatizations of a tribrominated atrop isomeric benzamide scaffold”. Org. Lett., 17(3): 580-583, 2015. DOI: 10.1021/ol503593y

Marechal, M.D.; Carato, P.; Larchanche, P.E.; Ravez, S.; Boulahjar, R.; Barczyk, A.; Oxombre, B.; Vermersch, P.; Melnyk, P.; “Synthesis and pharmacological evaluation of benzamide derivatives as potent and selective sigma-1 protein ligands”. Eur. J. Med. Chem., 138: 964-978, 2017.

DOI: 10.1016/j.ejmech.2017.07.014

Al–Douh, M.H.; “Synthesis and Characterization of Some Barbituric Acid Derivatives via Schiff Bases”. M.Sc. Thesis. University of Babylon, Babylon, Iraq, 2002.

Al–Douh, M.H.; Al–Fatlawy, A.A.; Abid, O.H.; “Synthesis and characterization of some 2-(N-benzoyl-N-pyrid-4-yl aminobenzyl)-amino barbituric acids via Schiff's bases”. Hadh. Studies Res., 4(2): 37-49, 2003.

Al–Douh, M.H.; Al–Fatlawy, A.A.; Abid O.H.; “Synthesis and characterization of some 2-(N-benzoyl-N-pyrid-3-yl aminobenzyl)-amino barbituric acids via N-benzylidene pyridine-3-amines”. Fac. Sci. Bull., 16(10): 83-94, 2003.

Al–Douh, M.H.; Al–Fatlawy, A.A.; Abid, O.H.; “Synthesis and characterization of some 2-(N-benzoyl-N-pyrid-2-yl aminobenzyl)-amino barbituric acids via N-benzylidene pyridine-2-amines”. Univ. Aden J. Nat. Appl. Sci., 8(1): 181-194, 2004.

American Chemical Society Reagent Chemicals “4-Aminoantipyrine (Ampyrone)”. Am. Chem. Soc., 4: 1-2, 2017. DOI: 10.1021/ acsreagents.4013

European Molecular Biology Laboratory “4-Aminoantipyrine”. Chem. Entities Biol. Inter., ChEBI: 59026, 2018.

https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:59026.

Dhanaraj, C.J.; Raj, S.S.S.; “Synthesis, characterization and biological studies of Schiff base metal complexes derived from 4-amino antipyrine, acetamide and p-phenylene diamine”. Inorg. Chem. Comm., 119: 108087, 2020. DOI: 10.1016/j.inoche.2020.108087

Whalen, K.; “Lippincott's Illustrated Review Pharmacology”. Wolters Kluwer: Pvt. Ltd., New Delhi, India, 2019. ISBN: 978-93-88313-20-9

Al-Labban, H.M.Y.; Sadiq, H.M.; Aljanaby, A.A.J.; “Synthesis, characterization and study biological activity of some Schiff bases derivatives from 4-amino antipyrine as a starting material”. J. Phys.: Conf. Ser., 1294: 052007, 2019. DOI: 10.1088/1742-6596/1294/5/052 007

Wilcox, J.C.F.; “Experimental Organic Chemistry”. Theory and Practice: Macmillan Publishing Company, New York, USA, 1984. ISBN: 0024276006

Mohrig, J.R.; Hammond, C.N.; Schatz, P.F.; “Techniques in Organic Chemistry”. 3rd Ed., WH. Freeman and Company: New York, USA, 2010. ISBN: 9781429219563

Maher, F.; “Kinetic study for the effect of new inhibitors on the activity of purified GPT from blood of cardiovascular patients”. Karbala Intern. J. Modern Sci., 5(2): 4, 2019. DOI: 10.33640/2405-609X.1011

Nariya, P.; Bhalodia, N.; Shukla, V.; Acharya, R.; Nariya, M.; “In vitro evaluation of antioxidant activity of Cordia dichotoma (Forst f.) bark”. AYU, 34(1): 124-128, 2013. DOI: 10. 4103/0974-8520.115451

Al-Majedy, Y.K.; Ibraheem, H.H.; Jassim, L.S.; Al-Amiery, A.A.; “Antioxidant activity of coumarine compounds”. ANJS, 22(1): 1-8, 2019. DOI: 0.22401/ANJS.22.1.01

Al-Majedy, Y.K.; Mahdi, A.; “Synthesis of phenyl-1,3,4-thiadiazol-2-amine derivatives with in vitro antioxidant activity”. ANJS, 23(2): 33-38, 2020.

DOI: 10.22401/ANJS.23.2.05

Mukherjee, S.; Pawar, N.; Kulkarni, O.; Nagarkar, B.; Thopte, S.; Bhujbal, A.; Pawar, P.; “Evaluation of free-radical quenching properties of standard ayurvedic formulation Vayasthapana rasayana”. BMC Complementary and Alternative Med., 11(38): 2-6, 2011. DOI: 10.1186/1472-6882-11-38

Yas, N.T.; Muslim, R.F.; Awad, M.A.; “Synthesis and characterization of novel Hg(II) complexes with new Schiff bases”. Materials Today: Proceedings, 45: 5544-5550, 2021. DOI: 10.1016/j.matpr.2021.02.302

Molyneux, P.; “The use of the stable free radical diphenylpicrylhydrazyl (DPPH) for estimating antioxidant activity”. Songklanakarin J. Sci. and Tech., 26(2): 211-219, 2004.

Kumari, P.K.; Umakanth, A.V.; Narsaiah, T.B.; Uma, A.; “Exploring anthocyanins, antioxidant capacity and glucosidase inhibition in bran and flour extracts of selected Sorghum genotypes”. Food Biosci., 41: 100979, 2021. DOI: 10.1016/j.fbio.2021.100979

Downloads

Published

2024-06-15

Issue

Section

Articles

How to Cite

(1)
Synthesis, Characterization and Antioxidant Evaluation of New N-Α-Chloroacetylsalicyloyl-N-Antipyrine Benzamide. ANJS 2024, 27 (2), 11-19. https://doi.org/10.22401/b72ypg13.

Most read articles by the same author(s)