Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety

Bijo Mathew; A. Jerad Suresh; S. Anbazhagan

doi:10.14233/ajchem.2013.13187

Issue

Vol. 25 No. 4 (2013): Vol 25 Issue 4

Issue Published : November 1, 2012

This work is licensed under a Creative Commons Attribution 4.0 International License.

Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety

https://doi.org/10.14233/ajchem.2013.13187

Bijo Mathew

Department of Pharmaceutical Chemistry, Grace College of Pharmacy, Palakkad-678 004, India

A. Jerad Suresh

Department of Pharmaceutical Chemistry, Madras Medical College, Chennai-600 003, India

S. Anbazhagan

Department of Pharmaceutical Chemistry, Karuna College of Pharmacy, Palakkad-679 533, India

Corresponding Author(s) : Bijo Mathew

bijovilaventgu@gmail.com

Asian Journal of Chemistry, Vol. 25 No. 4 (2013): Vol 25 Issue 4
Article Published : November 1, 2012

Abstract

A series of (2E)-1-(H-benzimidazol-2-yl)-3-substituted phenyl 2-propen-1-one linked with barbitone (5a-g) are synthesized by both conventional method and microwave assisted method. The benzimidazole chalcones (4a-g) were prepared from the condensation of 2-acetyl benzimidazole (3a) with different aromatic aldehydes. These chalcones on reaction with barbituric acid in presence of acetic acid medium gave the a,b-unsaturated benzimidazole derivatives. The structures of the all the final compounds were established on the basis of IR, ¹H NMR, mass spectra and elemental analysis. The druglikeness and physicochemical properties of the derivatives were determined by actelion, molsoft, molinspiration and ACD ChemDraw Ultra 11.0 software. The final products possess a favourable drug likeness and drug score. All the final synthesized compounds were screened for their antioxidant properties like free radical scavenging by DPPH method. Among the synthesized compounds (5f), (5c) and (5d) were exhibited a good antioxidant activity and all the other derivatives showed a moderate activity.

Keywords

2-Acetyl benzimidazole Barbituric acid Chalcones Antioxidant activity

Mathew, B., Jerad Suresh, A., & Anbazhagan, S. (2012). Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety. Asian Journal of Chemistry, 25(4), 1853–1856. https://doi.org/10.14233/ajchem.2013.13187

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G.B. Bulkley, Surgery, 113, 479 (1993).

B. Halliwell and M. Guitteridge, Free Radicals in Biology and Medicine, edn. 3rd, Oxford Science Publication, Oxford University Press (1998).

K.F. Ansari and C. Lal, Eur. J. Med. Chem., 44, 4028 (2009).

V.M. Reddy and K.R. Reddy, Chem. Pharm. Bull., 58, 953 (2010).

K.F. Ansari and C. Lal, Eur. J. Med. Chem., 44, 2294 (2009).

K.G. Desai, and K.R. Desai, Bioorg. Med. Chem., 14, 827 (2006).

R.V. Shingalapur, K.M. Hosamani and R.S. Keri, Eur. J. Med. Chem., 44, 4244 (2009).

G.R. Jadhav, M.U. Shaikh, R.P. Kale and C.H. Gill, Eur. J. Med. Chem., 44, 2930 (2009).

M. Shaharyar, M.M. Abdullah, M.A. Bakht and J. Majeed, Eur. J. Med. Chem., 45, 114 (2010).

M.M. Ramla, M.A. Omar, A.M.M. El-Khamry and H.I. El-Diwani, Bioorg. Med. Chem., 14, 7324 (2006).

Y.H. Yang, M.S. Cheng, Q.H. Wang, H. Nie, N. Liao, J. Wang and H. Chen, Eur. J. Med.Chem., 44, 1808 (2009).

T.D. Penning, G.D. Zhu, V.B. Gandhi, S.J. Gong Thomas, W. Lubisch, R. Grandel, W. Wernet, C.H. Park, E.H. Fry, X. Liu, Y. Shi, V. Klinghofer, E.F. Johnson, C.K. Donawho, D.J. Frost, V.B. Diaz, J.J. Bouska, A.M. Olson and K.C. Marsh, Bioorg. Med. Chem., 16, 6965 (2008).

L. Garuti, M. Roberti, D. Pizzirani, A. Pession, E. Leoncini, V. Cenci and S. Hrelia, Farmaco, 59, 663 (2004).

N. Kaur, A. Kaur, Y. Bansal, D.I. Shah, G. Bansal and M. Singh, Bioorg. Med. Chem., 16, 10210 (2008).

A.R. Porcari, R.V. Devivar and L.S. Kucera, J. Med. Chem., 41, 1252 (1998).

M.T. Migawa, J.L. Girardet, J.A. Walker 2nd, G.W. Koszalka, S.D. Chamberlain, J.C. Drach and L.B. Townsend, J. Med. Chem., 41, 1242 (1998).

I. Tamm and P.B. Sehgal, Adv. Virus Res., 22, 187 (1978).

S. Budavari, The Merck Index, Merck, Rahway, NJ, USA, edn. 11 (1989).

Y. Furukawa, Eur. Patent, 22688 (1983).

S.L. Katz and A.W. Gay, US Patent 352 806 (1982).

W.G. Brouwer, E.E. Felauerand and A.R. Bell, US Patent, 779 982 990 (1991).

A.V. Moskovin, N.R. Reznikova and B.A. Ivin, Russ. J. Org. Chem., 38, 463 (2002).

J. Rajora, J. Yadav, R. Kumar and Y.K. Srivastava, Indian J. Chem., 49B, 989 (2010).

H.G. Sangani, K.B. Bhimani, R.C. Khunt and A.R. Parikh, J. Serb. Chem. Soc., 6, 587 (2006).

J.S. Biradar, B.S. Sasidhar and R. Parveen, J. Med. Chem., 45, 4074 (2010).

C.A. Lippinski, F. Lombardo, B.W. Dominy and P.J. Feeney, Adv. Drug. Deliv., 23, 3 (1997).

D.E. Clark, J. Pharm. Sci., 88, 815 (1999).

R. Bartzatt, S.L.G. Cirillo and J.D. Cirillo, Physiol. Chem. Phys. Med. NMR, 36, 85 (2004).

V. Weber, P. Coudert, C. Rubart and J.C. Garmian, Bioorg. Med. Chem., 10, 1647 (2002).

K. Shimada, K. Fujikawa, K. Yahara and T.J. Nakamura, Agri. Food. Chem., 40, 945 (1992).

Issue

Vol. 25 No. 4 (2013): Vol 25 Issue 4

Microwave Assisted Synthesis, Physico-chemical Properties and Antioxidant Activity of a,b-Unsaturated Benzimidazole Derivatives Incorporated with Baritone Moiety

Corresponding Author(s) : Bijo Mathew

Abstract

Keywords

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