Design, Synthesis of Some Novel Thiazolidin-4-one Derivatives Bearing Benzimidazole Nucleus and Biological Evaluation of their Possible in vitro Antiinflammatory as Cyclooxygenase Inhibitors and Antioxidant Activity

U. Sahoo; A.K. Seth; R. Balaraman; R. Velmurugan

doi:10.14233/ajchem.2015.17788

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

Issue Published : January 19, 2015

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

Design, Synthesis of Some Novel Thiazolidin-4-one Derivatives Bearing Benzimidazole Nucleus and Biological Evaluation of their Possible in vitro Antiinflammatory as Cyclooxygenase Inhibitors and Antioxidant Activity

https://doi.org/10.14233/ajchem.2015.17788

U. Sahoo

Department of Pharmacy, Sumandeep Vidyapeeth University, Vadodara-391 760, India

A.K. Seth

Department of Pharmacy, Sumandeep Vidyapeeth University, Vadodara-391 760, India

R. Balaraman

Department of Pharmacy, Sumandeep Vidyapeeth University, Vadodara-391 760, India

R. Velmurugan

Department of Biotechnology, Drug Discovery R&D, Century Pharmaceuticals Ltd., Vadodara-390 001, India

Corresponding Author(s) : U. Sahoo

sahoo.devurb@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 3 (2015): Vol 27 Issue 3
Article Published : January 18, 2015

Abstract

A series of 2-[2-(4-cyanophenyl)-6-substituted-1H-benzimidazol-1-yl]-N-[2-(substituted)-4-oxo-1,3- thiazolidin-3-yl]acetamide [9(I-XXXI)] were synthesized. Substituted o-phenylenediamine was reacted with substituted 4-cyanobenzaldehydes in the presence of sodium metabisulfite to furnish substituted 2-(4-cyanophenyl)-1H-benzimidazoles (1). When these substituted 2-(4-cyanophenyl)-1H-benzimidazoles were further treated with ethyl chloroacetate in KOH/DMSO, N-alkylated product (2-(4-cyanophenyl)-benzimidazol-1-yl)-acetic acid ethyl esters (2) was formed. To synthesize 2-(4-cyanophenyl)-benzimidazol-1-yl-acetic acid hydrazides (3) chemical reactions were conducted between hydrazine hydrate and the esters (2). When a mixture of 2-(4-cyanophenyl)-benzimidazol-1-yl)-acetic acid hydrazide (3) react with substituted aldehydes in ethanol was reflux, imines intermediates [4(I-XXXI)] was formed. To synthesize 9(I-XXXI) reactions were occurred between a mixture of imine intermediate and thioglycollic acid in dioxane. The structures of newly synthesized compounds 9(I-XXXI) was confirmed by spectroscopic techniques. All the synthesized compounds were screened for its in vitro antioxidant and antiinflammatory activity. The in vitro antioxidant and antiinflammatory activity might be attributed due to the presence of more electrons withdrawing group and moiety having more lipophilicity also more electronegativity in nature.

Keywords

o-Phenylenediamine 4-Cyanobenzaldehyde Thiazolidinone Antioxidant Antiinflammatory

Sahoo, U., Seth, A., Balaraman, R., & Velmurugan, R. (2015). Design, Synthesis of Some Novel Thiazolidin-4-one Derivatives Bearing Benzimidazole Nucleus and Biological Evaluation of their Possible in vitro Antiinflammatory as Cyclooxygenase Inhibitors and Antioxidant Activity. Asian Journal of Chemistry, 27(3), 961–968. https://doi.org/10.14233/ajchem.2015.17788

Download Citation

References

B. C. Cantello, M. A. Cawthorne, G. P. Cottam, P. T. Duff, D. Haigh, R. M. Hindley, C. A. Lister, S. A. Smith and P. L. Thurlby, J. Med. Chem., 37, 3977 (1994); doi:10.1021/jm00049a017.
S.G. Kuçukguzel, E.E. Oruc, S. Rollas, F. Shin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.
G. Capan, N. Ulusoy, N. Ergenc and M. Kiraz, Monatsh. Chem., 130, 1399 (1999); doi:10.1007/PL00010200.
N.C. Desai, M.D. Shah and A.M. Bhavsar, Indian J. Chem., 47B, 1135 (2008).
F.A. Ragab, N.M. Eid and H.A. el-Tawab, Pharmazie, 52, 926 (1997).
M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, A. Trovato, M.T. Monforte and M.F. Taviano, Bioorg. Med. Chem. Lett., 11, 2791 (2001); doi:10.1016/S0960-894X(01)00476-0.
C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davis, R.Day, M.B. Ferraz, C.J. Hawkey, M.C. Hochberg, T.K. Kvien and T.J. Schnitzer, N. Engl. J. Med., 343, 1520 (2000); doi:10.1056/NEJM200011233432103.
F.E. Silverstein, G. Faich, J.L. Goldstein, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawal, W.F. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkowith, K.M. Verburg and G.S. Geis, JAMA, 284, 1247 (2000); doi:10.1001/jama.284.10.1247.
P. McGettigan and D. Henry, JAMA, 296, 1633 (2006); doi:10.1001/jama.296.13.jrv60011.
R.P. Mason, M.F. Walter, H.P. McNulty, S.F. Lockwood, J. Byun, C.A. Day and R.F. Jacob, J. Cardiovasc. Pharmacol., 47, S7 (2006).
M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, M.T. Monforte, A. Trovato, M.F. Taviano, N. Miceli, G. De Luca, S. Alcaro and F. Ortuso, Bioorg. Med. Chem., 11, 999 (2003); doi:10.1016/S0968-0896(02)00518-7.
A.A. Geronikaki, A.A. Lagunin, D.I. Hadjipavlou-Litina, P.T. Eleftheriou, D.A. Filimonov, V.V. Poroikov, I. Alam and A.K. Saxena, J. Med. Chem., 51, 1601 (2008); doi:10.1021/jm701496h.
T. Uchoa Fde, T.G. Da Silva, C. De Lima Mdo, S.L. Galdino, R.P. Ida and T.D. Costa, J. Pharm. Pharmacol., 61, 339 (2009).
P. Vicini, A. Geronikaki, M. Incerti, F. Zani, J. Dearden and M. Hewitt, Bioorg. Med. Chem., 16, 3714 (2008); doi:10.1016/j.bmc.2008.02.001.
N.D. Sonawane and A. S. Verkman, Bioorg. Med. Chem., 16, 8187 (2008); doi:10.1016/j.bmc.2008.07.044.
L.J. Knutsen, C.J. Hobbs, C.G. Earnshaw, A. Fiumana, J. Gilbert, S.L. Mellor, F. Radford, N.J. Smith, P.J. Birch, J.R. Burley, S.D. Ward and I.F. James, Bioorg. Med. Chem. Lett., 17, 662 (2007); doi:10.1016/j.bmcl.2006.10.098.
S.K. Chaudhari, M. Verma, A.K. Chaturvedi and S.S. Parmar, J. Pharm. Sci., 64, 614 (1975); doi:10.1002/jps.2600640408.
C. Dwivedi, T.K. Gupta and S.S. Parmar, J. Med. Chem., 15, 553 (1972); doi:10.1021/jm00275a031.
S. Nagar, H.H. Singh, J.N. Sinha and S.S. Parmar, J. Med. Chem., 16, 178 (1973); doi:10.1021/jm00260a027.
S. Demirayak, U.A. Mohsen and A.C. Karaburun, Eur. J. Med. Chem., 37, 255 (2002); doi:10.1016/S0223-5234(01)01313-7.
T. Yamori, A. Matsunaga, S. Sato, K. Yamazaki, A. Komi, K. Ishizu, I. Mita, H. Edatsugi, Y. Matsuba, K. Takezawa, O. Nakanishi, H. Kohno, Y. Nakajima, H. Komatsu, T. Andoh and T. Tsuruo, Cancer Res., 59, 4042 (1999).
M. Wang, J. Li, M. Rangarajan, Y. Shao, E.J. La Voie, T.-C. Huang and C.-T. Ho, J. Agric. Food Chem., 46, 4869 (1998); doi:10.1021/jf980614b.
B. Kar, R.S. Kumar, I. Karmakar, N. Dola, A. Bala, U.K. Mazumder and P.K. Hadar, Asian Paci. J. Trop. Biom, 2, S976 (2012); doi:10.1016/S2221-1691(12)60346-3.
M.H. Yang, K.D. Yoon, Y.W. Chin, J.H. Park and J. Kim, Bioorg. Med. Chem., 17, 2689 (2009); doi:10.1016/j.bmc.2009.02.057.
R.J. Kulmacz and W.E.M. Lands, Prostaglandins, 25, 531 (1983); doi:10.1016/0090-6980(83)90025-4.

References

B. C. Cantello, M. A. Cawthorne, G. P. Cottam, P. T. Duff, D. Haigh, R. M. Hindley, C. A. Lister, S. A. Smith and P. L. Thurlby, J. Med. Chem., 37, 3977 (1994); doi:10.1021/jm00049a017.

S.G. Kuçukguzel, E.E. Oruc, S. Rollas, F. Shin and A. Ozbek, Eur. J. Med. Chem., 37, 197 (2002); doi:10.1016/S0223-5234(01)01326-5.

G. Capan, N. Ulusoy, N. Ergenc and M. Kiraz, Monatsh. Chem., 130, 1399 (1999); doi:10.1007/PL00010200.

N.C. Desai, M.D. Shah and A.M. Bhavsar, Indian J. Chem., 47B, 1135 (2008).

F.A. Ragab, N.M. Eid and H.A. el-Tawab, Pharmazie, 52, 926 (1997).

M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, A. Trovato, M.T. Monforte and M.F. Taviano, Bioorg. Med. Chem. Lett., 11, 2791 (2001); doi:10.1016/S0960-894X(01)00476-0.

C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davis, R.Day, M.B. Ferraz, C.J. Hawkey, M.C. Hochberg, T.K. Kvien and T.J. Schnitzer, N. Engl. J. Med., 343, 1520 (2000); doi:10.1056/NEJM200011233432103.

F.E. Silverstein, G. Faich, J.L. Goldstein, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawal, W.F. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkowith, K.M. Verburg and G.S. Geis, JAMA, 284, 1247 (2000); doi:10.1001/jama.284.10.1247.

P. McGettigan and D. Henry, JAMA, 296, 1633 (2006); doi:10.1001/jama.296.13.jrv60011.

R.P. Mason, M.F. Walter, H.P. McNulty, S.F. Lockwood, J. Byun, C.A. Day and R.F. Jacob, J. Cardiovasc. Pharmacol., 47, S7 (2006).

M.G. Vigorita, R. Ottana, F. Monforte, R. Maccari, M.T. Monforte, A. Trovato, M.F. Taviano, N. Miceli, G. De Luca, S. Alcaro and F. Ortuso, Bioorg. Med. Chem., 11, 999 (2003); doi:10.1016/S0968-0896(02)00518-7.

A.A. Geronikaki, A.A. Lagunin, D.I. Hadjipavlou-Litina, P.T. Eleftheriou, D.A. Filimonov, V.V. Poroikov, I. Alam and A.K. Saxena, J. Med. Chem., 51, 1601 (2008); doi:10.1021/jm701496h.

T. Uchoa Fde, T.G. Da Silva, C. De Lima Mdo, S.L. Galdino, R.P. Ida and T.D. Costa, J. Pharm. Pharmacol., 61, 339 (2009).

P. Vicini, A. Geronikaki, M. Incerti, F. Zani, J. Dearden and M. Hewitt, Bioorg. Med. Chem., 16, 3714 (2008); doi:10.1016/j.bmc.2008.02.001.

N.D. Sonawane and A. S. Verkman, Bioorg. Med. Chem., 16, 8187 (2008); doi:10.1016/j.bmc.2008.07.044.

L.J. Knutsen, C.J. Hobbs, C.G. Earnshaw, A. Fiumana, J. Gilbert, S.L. Mellor, F. Radford, N.J. Smith, P.J. Birch, J.R. Burley, S.D. Ward and I.F. James, Bioorg. Med. Chem. Lett., 17, 662 (2007); doi:10.1016/j.bmcl.2006.10.098.

S.K. Chaudhari, M. Verma, A.K. Chaturvedi and S.S. Parmar, J. Pharm. Sci., 64, 614 (1975); doi:10.1002/jps.2600640408.

C. Dwivedi, T.K. Gupta and S.S. Parmar, J. Med. Chem., 15, 553 (1972); doi:10.1021/jm00275a031.

S. Nagar, H.H. Singh, J.N. Sinha and S.S. Parmar, J. Med. Chem., 16, 178 (1973); doi:10.1021/jm00260a027.

S. Demirayak, U.A. Mohsen and A.C. Karaburun, Eur. J. Med. Chem., 37, 255 (2002); doi:10.1016/S0223-5234(01)01313-7.

T. Yamori, A. Matsunaga, S. Sato, K. Yamazaki, A. Komi, K. Ishizu, I. Mita, H. Edatsugi, Y. Matsuba, K. Takezawa, O. Nakanishi, H. Kohno, Y. Nakajima, H. Komatsu, T. Andoh and T. Tsuruo, Cancer Res., 59, 4042 (1999).

M. Wang, J. Li, M. Rangarajan, Y. Shao, E.J. La Voie, T.-C. Huang and C.-T. Ho, J. Agric. Food Chem., 46, 4869 (1998); doi:10.1021/jf980614b.

B. Kar, R.S. Kumar, I. Karmakar, N. Dola, A. Bala, U.K. Mazumder and P.K. Hadar, Asian Paci. J. Trop. Biom, 2, S976 (2012); doi:10.1016/S2221-1691(12)60346-3.

M.H. Yang, K.D. Yoon, Y.W. Chin, J.H. Park and J. Kim, Bioorg. Med. Chem., 17, 2689 (2009); doi:10.1016/j.bmc.2009.02.057.

R.J. Kulmacz and W.E.M. Lands, Prostaglandins, 25, 531 (1983); doi:10.1016/0090-6980(83)90025-4.

Issue

Vol. 27 No. 3 (2015): Vol 27 Issue 3

Design, Synthesis of Some Novel Thiazolidin-4-one Derivatives Bearing Benzimidazole Nucleus and Biological Evaluation of their Possible in vitro Antiinflammatory as Cyclooxygenase Inhibitors and Antioxidant Activity

Corresponding Author(s) : U. Sahoo

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents