SYNTHESIS, CHARACTERIZATION AND ANTIOXIDANT ACTIVITY OF NEW BIS N’-(1H-BENZIMIDAZOL-2-YL)-N-ALKYLAMIDINE DERIVATIVES
Abstract
New series of Bis N’-(1H-benzimidazol-2-yl)-N-alkyl amidine derivatives 2a-e were synthesized starting from (1H-benzimidazol-2-yl) iminoester 1 with two equivalents of ethane-1,2-diamine. The structures of compounds were elucidated by spectroscopic methods including IR, 1H NMR, 13C NMR, and 13C NMR Dept 135° of 2b, elemental analyses and mass spectral analysis. In the next step, the above mentioned compounds were screened for antioxidant activity. Their antioxidant activity was assessed using, the rapid and the most appropriate method, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging assay. The results indicated that bis amidines 2a-e tested possess good antioxidant activity. Compounds 2c and 2e showed excellent antioxidant activity, while compounds 2a, 2d and 2b showed the lowest one.
Keywords: Benzimidazole, Bis amidines, DPPH method, ethane-1,2-diamine , Iminoesters.
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Keywords:
Benzimidazole, Bis amidines, DPPH method, Ethylenediamine, IminoestersDOI
https://doi.org/10.22270/jddt.v6i5.1332References
Thomas MJ, The role of free radicals and antioxidants: how do we know that they are working, Critical Reviews in Food Science and Nutrition, 1995, 35(1-2), 21-39.
Azam F, Therapeutic Potential of Free Radical Scavengers in Neurological Disorders in Handbook of Free Radicals: Formation, Types and Effects; Chapter 2; Kozyrev D, Slutsky V, Eds.; Nova Science Publishers, Inc: Hauppauge, NY, USA; 2010. P. 57–97.
Singhal N, et al., Synthesis of amidine and bis amidine precursors, Phosphorus, Sulfur, and Silicon and the Related Elements,174, 2001, 8I-92
Panico A, Vicini P, Incerti M, Cardile V, Gentile B, Ronsisvalle G, Amidinobenzisothiazole derivatives with antidegenerative activity on cartilage, Il Farmaco, 2002, 57(8), 671-675.
Arya S, Kumar N, Roy P, Sondhi SM, .Synthesis of amidine and bis amidine derivatives and their evaluation for anti-inflammatory and anticancer activity, European journal of medicinal chemistry, 2013, 59.7-14.
Franca da Silva C, Batista MM, Batista DGJ, Mello de Souza E, Bernardino da Silva P, Melo de Oliveira G, Meuser A, Shareef AR, Boykin DW, Maria de Nazare CS, Antimicrobial Agents Chemotherapy, 2008, 52, 3307-3314.
Hu L, Arafa RK, Ismail MA, Patel A, Munde M, Wilson WD, Wenzler T, Brun R, Boykin DW, Synthesis and activity of azaterphenyl diamidines against Trypanosoma brucei rhodesiense and Plasmodim, Bioorganic & Medicinal Chemistry, 2009, 17, 6651-6658.
Madhusudhan G, Balraju V, Rajesh T, Narayana BV, Reddy RN, Synthesis of an amino moiety in trovafloxacin by using an in-expensive amidine base N, N-diethyacetaamidine, Indian Journal of Chemistry, Section B, 2009, 48B, 569-573.
Ismail MA, Arafa RK, Brun R, Wenzler T, Miao Y, Wilson WD, Generaux C, Bridges A, Hall JE, Boykin DW, Synthesis, DNA Affinity, and antiprotozoal activity of linear dications: terphenyl diamine and analogues, Journal of Medicinal Chemistry, 2006, 49, 5324-5332.
Calas M, Ouattara M, Piquet G, Ziora Z, Bordat Y, Ancelin ML, Escale R, Vial H, Potent antimalarial activity of 2-aminopyridinium salts, amidines, and guanidines, Journal of Medicinal Chemistry, 2007, 50, 6307-6315.
Han FS, Osajima IH, Cheung M, Tokuyama H, Fukuyama T, Novel structural motifs consisting of chiral thiazolines: Synthesis, molecular recognition, and anticancer activity, Chemistry European Journal, 2007, 13, 3026-3038.
Sasaki S, Fukushima J, Arai H, Kusakabe K, Hamajima K, Ishii N, Hirahara F, Okuda K, Kawamoto S, Ruysschaert JM, Vandenbranden M, Wahren B, Okuda K, Human immunodeficiency virus type-1-specific immune responses induced by DNA vaccination are greatly enhanced by mannan-coated diC14-amidine, European Journal Immuology,1997, 27, 3121-3129.
Panico A, Vinici P, Inert M, Cardile V, Gentile B, Ronsisvalle G, Amidinobenzisothiazole derivatives with antidegenerative activity on cartilage, Il Farmaco 2002, 57, 671-675.
Rudolph MJ, Illig CR, Subasinghe NL, Wilson KJ, Hoffman JB, Randle T, Green D, Molloy CT, Soll RM, Lewandowski F, Zhang M, Bone R, Spurlino JC, Deckman IC, Manthey C, Sharp C, Maguire D, Grasberger BL, Desjarlais RL, Zhou Z, Design and synthesis of 4,5-disubstituted-thiophene-2-amidines as potent urokinase inhibitors, Bioorganic Medicinal Chemistry Letters. 2002, 12, 491-495.
Abderrahim R, Baacar B, Benkhoud ML, Synhtese de (1,2a)benzimidazolo-1,3,5,2-triazaphosphorine-2-oxydes, Phosphorus, Sulfur and silicon and related elements, 2002, 117, 1033-1040.
Brand-Williams W, Cuvelier ME, Berset C, Use of a free radical method to evaluate antioxidant activity. LWT-Food Science Technology, 1995, 28(1), 25-30.
Koparir M, Orek C, Parlak AE, Söylemez A, Koparir P, Karatepe M, Dastan SD, Synthesis and biological activities of some novel aminomethyl derivatives of 4-substituted-5-(2- thienyl)-2,4-dihydro-3H-1,2,4-triazole-3-thiones, European Journal of Medicinal Chemistry, 2013, 63, 340-346.
Kumar A, Sharma P, Kumari P, Kalal BL, Exploration of antimicrobial and antioxidant potential of newly synthesized 2,3-disubstituted quinazoline-4(3H)-ones, Bioorganic Medicinal Chemistry Letters, 2011, 21, 4353-4357.
Furniss B S, Hannaford A J; Smith P W, Tatchell, A R, Vogel’s Text book of Practical Organic Chemistry, 5 edition, Longman Scientific and Technical, England; 1989. P 1162-1163.
Malki F, Touati A, Moulay S, Baltas M, Antioxidant and antimicrobial activities of two amidine derivatives, Mediterranean Journal of Biosciences, 2016, 1(2), 62-68.
Saini S, Neerupma D, Mittal A, Gaurav K, Synthesis and antioxidant activity of the 2-methyl benzimidazole, Journal of Drug Delivery & Therapeutics, 2016, 6(3),100-102.
Barbuceanu S, Carolina Ilies D, Saramet G, Uivarosi V, Draghici C, Radulescu V, Synthesis and Antioxidant Activity Evaluation of New Compounds from Hydrazinecarbothioamide and 1,2,4-Triazole Class Containing Diarylsulfone and 2,4-Difluorophenyl Moieties, International Journal of Molecular Sciences, 2014, 15, 10908-10925.
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