Synthesis and Molecular Docking for Antiinflammatory Studies of 2-(Arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amines

Mallaiah Bucha; Laxminarayana Eppakayala; Ramesh Malothu; Karunakar Rao Kudle; Ramchander Merugu

doi:10.14233/ajchem.2018.20784

Issue

Vol. 30 No. 1 (2018): Vol 30 Issue 1

Issue Published : November 30, 2017

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

Synthesis and Molecular Docking for Antiinflammatory Studies of 2-(Arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amines

https://doi.org/10.14233/ajchem.2018.20784

Mallaiah Bucha

Sreenidhi Institute of Science and Technology (Autonomous) Yamnampet, Ghatkesar, Hyderabad-501 301, India

Laxminarayana Eppakayala

Sreenidhi Institute of Science and Technology (Autonomous) Yamnampet, Ghatkesar, Hyderabad-501 301, India

Ramesh Malothu

Jawaharlal Nehru Technological University, Kakinada-533 003, India

Karunakar Rao Kudle

Department of Biochemistry, Osmania University, Hyderabad-500 007, India

Ramchander Merugu

University College of Science, Mahatma Gandhi University, Nalgonda-508 254, India

Corresponding Author(s) : Laxminarayana Eppakayala

elxnkits@yahoo.co.in

Asian Journal of Chemistry, Vol. 30 No. 1 (2018): Vol 30 Issue 1
Article Published : November 30, 2017

Abstract

1-Chloro-2,4-dinitrobenzene (1) was reacted with aliphatic amines (2) in ethanol as solvent under reflux condition for 16-24 h to form N-alkyl-2,4-dinitroaniline (3). Compound 3 undergoes reduction to from N-alkyl-4-nitrobenzene-1,2-diamine (4). Compound 4 was treated with carboxylic acid (5) to offered N-(2-(alkylamino)-5-nitrophenyl)-2-arylacetamide (6) which on cyclization gave 2-(arylmethyl)-1-ethyl-5-nitro-1H-benzo[d]imidazole (7). Finally, compound 7 undergoes reduction give 2-(arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amine (8). The synthesized compounds were characterized by using spectral analyses. The compounds synthesized were confirmed by spectral analyses. Molecular docking of 5COX with the ligand using docking server, predicted the compound to be a potential anti-inflammatory compound.

Keywords

N-alkyl-4-nitrobenzene-1,2-diamine Benzimidazole Antiinflammatory activity Molecular docking

Bucha, M., Eppakayala, L., Malothu, R., Kudle, K. R., & Merugu, R. (2017). Synthesis and Molecular Docking for Antiinflammatory Studies of 2-(Arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amines. Asian Journal of Chemistry, 30(1), 29–33. https://doi.org/10.14233/ajchem.2018.20784

Download Citation

References

H. Zarrinmayeh,A.M. Nunes, P.L. Ornstein, D.M. Zimmerman, M.B. Arnold, D.A. Schober, S.L. Gackenheimer, R.F. Bruns, P.A. Hipskind, T.C. Britton, B.E. Cantrell and D.R. Gehlert, J. Med. Chem., 41, 2709 (1998); https://doi.org/10.1021/jm9706630.
M. Hranjec, M. Kralj, I. Piantanida, M. Sedic, L. Suman, K. Pavelic and G. Karminski-Zamola, J. Med. Chem., 50, 5696 (2007); https://doi.org/10.1021/jm070876h.
M. Hasegawa, N. Nishigaki, Y. Washio, K. Kano, P.A. Harris, H. Sato, I. Mori, R.I. West, M. Shibahara, H. Toyoda, L. Wang, R.T. Nolte, J.M. Veal and M. Cheung, J. Med. Chem., 50, 4453 (2007); https://doi.org/10.1021/jm0611051.
J. Falco, M. Pique, M. Gonzalez, I. Buira, E. Mendez, J. Terencio, C. Pérez, M. Príncep, A. Palomer and A. Guglietta, Eur. J. Med. Chem., 41, 985 (2006); https://doi.org/10.1016/j.ejmech.2006.03.031.
A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva and V.A. Anisimova, Pharm. Chem. J., 33, 232 (1999); https://doi.org/10.1007/BF02510042.
M.A. Phillips, J. Chem. Soc., 2393 (1928); https://doi.org/10.1039/JR9280002393.
M.R. Grimmet,A.R. Katritzky and C.W.J. Rees, Heterocyclic Chemistry Oxford, UK, vol. 5. p. 457 (1984).
A. Czarny, W.D. Wilson and D.W. Boykin, J. Heterocycl. Chem., 33, 1393 (1996); https://doi.org/10.1002/jhet.5570330463.
R.R. Tidwell, J.D. Geratz, O. Dann, G. Volz, D. Zeh and H. Loewe, J. Med. Chem., 21, 613 (1978); https://doi.org/10.1021/jm00205a005.
Z. Wu, P. Rea and G. Wickham, Tetrahedron Lett., 41, 9871 (2000); https://doi.org/10.1016/S0040-4039(00)01732-9.
B.H. Kim, R. Han, J.S. Kim, Y.M. Jun, W. Baik and B.M. Lee, Heterocycles, 62, 41 (2004); https://doi.org/10.3987/COM-03-9903.
B. Gangadasu, P. Narender, S.B. Kumar, M. Ravinder, B.A. Rao, C. Ramesh, B.C. Raju and V.J. Rao, Tetrahedron, 62, 8398 (2006); https://doi.org/10.1016/j.tet.2006.06.026.
B.E. Maryanoff, W. Ho, D.F. McComsey, A.B. Reitz, P.P. Grous, S.O. Nortey, R.P. Shank, B. Dubinsky, R.J.J. Taylor and J.F. Gardocki, J. Med. Chem., 38, 16 (1995); https://doi.org/10.1021/jm00001a005.
H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov and P.E. Bourne, Nucleic Acids Res., 28, 235 (2000); https://doi.org/10.1093/nar/28.1.235.
Z. Bikadi, L. Demko and E. Hazai, Arch. Biochem. Biophys., 461, 225 (2007); https://doi.org/10.1016/j.abb.2007.02.020.

References

H. Zarrinmayeh,A.M. Nunes, P.L. Ornstein, D.M. Zimmerman, M.B. Arnold, D.A. Schober, S.L. Gackenheimer, R.F. Bruns, P.A. Hipskind, T.C. Britton, B.E. Cantrell and D.R. Gehlert, J. Med. Chem., 41, 2709 (1998); https://doi.org/10.1021/jm9706630.

M. Hranjec, M. Kralj, I. Piantanida, M. Sedic, L. Suman, K. Pavelic and G. Karminski-Zamola, J. Med. Chem., 50, 5696 (2007); https://doi.org/10.1021/jm070876h.

M. Hasegawa, N. Nishigaki, Y. Washio, K. Kano, P.A. Harris, H. Sato, I. Mori, R.I. West, M. Shibahara, H. Toyoda, L. Wang, R.T. Nolte, J.M. Veal and M. Cheung, J. Med. Chem., 50, 4453 (2007); https://doi.org/10.1021/jm0611051.

J. Falco, M. Pique, M. Gonzalez, I. Buira, E. Mendez, J. Terencio, C. Pérez, M. Príncep, A. Palomer and A. Guglietta, Eur. J. Med. Chem., 41, 985 (2006); https://doi.org/10.1016/j.ejmech.2006.03.031.

A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva and V.A. Anisimova, Pharm. Chem. J., 33, 232 (1999); https://doi.org/10.1007/BF02510042.

M.A. Phillips, J. Chem. Soc., 2393 (1928); https://doi.org/10.1039/JR9280002393.

M.R. Grimmet,A.R. Katritzky and C.W.J. Rees, Heterocyclic Chemistry Oxford, UK, vol. 5. p. 457 (1984).

A. Czarny, W.D. Wilson and D.W. Boykin, J. Heterocycl. Chem., 33, 1393 (1996); https://doi.org/10.1002/jhet.5570330463.

R.R. Tidwell, J.D. Geratz, O. Dann, G. Volz, D. Zeh and H. Loewe, J. Med. Chem., 21, 613 (1978); https://doi.org/10.1021/jm00205a005.

Z. Wu, P. Rea and G. Wickham, Tetrahedron Lett., 41, 9871 (2000); https://doi.org/10.1016/S0040-4039(00)01732-9.

B.H. Kim, R. Han, J.S. Kim, Y.M. Jun, W. Baik and B.M. Lee, Heterocycles, 62, 41 (2004); https://doi.org/10.3987/COM-03-9903.

B. Gangadasu, P. Narender, S.B. Kumar, M. Ravinder, B.A. Rao, C. Ramesh, B.C. Raju and V.J. Rao, Tetrahedron, 62, 8398 (2006); https://doi.org/10.1016/j.tet.2006.06.026.

B.E. Maryanoff, W. Ho, D.F. McComsey, A.B. Reitz, P.P. Grous, S.O. Nortey, R.P. Shank, B. Dubinsky, R.J.J. Taylor and J.F. Gardocki, J. Med. Chem., 38, 16 (1995); https://doi.org/10.1021/jm00001a005.

H.M. Berman, J. Westbrook, Z. Feng, G. Gilliland, T.N. Bhat, H. Weissig, I.N. Shindyalov and P.E. Bourne, Nucleic Acids Res., 28, 235 (2000); https://doi.org/10.1093/nar/28.1.235.

Z. Bikadi, L. Demko and E. Hazai, Arch. Biochem. Biophys., 461, 225 (2007); https://doi.org/10.1016/j.abb.2007.02.020.

Issue

Vol. 30 No. 1 (2018): Vol 30 Issue 1

Synthesis and Molecular Docking for Antiinflammatory Studies of 2-(Arylmethyl)-1-ethyl-1H-benzo[d]imidazol-5-amines

Corresponding Author(s) : Laxminarayana Eppakayala

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents