Synthesis and Evaluation of 2-Chloro-3-[3-(6-nitro-1H-benzimidazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]quinolines as Potent Antibacterial Agents

Indira M. Madawali; Navanath V. Kalyane; E.N. Gaviraj; B. Shivakumar

doi:10.14233/ajchem.2018.21126

Issue

Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018

Issue Published : March 29, 2018

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

Synthesis and Evaluation of 2-Chloro-3-[3-(6-nitro-1H-benzimidazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]quinolines as Potent Antibacterial Agents

https://doi.org/10.14233/ajchem.2018.21126

Indira M. Madawali

Department of Pharmaceutical Chemistry, B.L.D.E.A's S.S.M. College of Pharmacy and Research Centre, Vijayapur-586 103, India

Navanath V. Kalyane

Department of Pharmaceutical Chemistry, B.L.D.E.A's S.S.M. College of Pharmacy and Research Centre, Vijayapur-586 103, India

E.N. Gaviraj

Department of Pharmaceutical Chemistry, B.L.D.E.A's S.S.M. College of Pharmacy and Research Centre, Vijayapur-586 103, India

B. Shivakumar

Department of Pharmaceutical Chemistry, B.L.D.E.A's S.S.M. College of Pharmacy and Research Centre, Vijayapur-586 103, India

Corresponding Author(s) : B. Shivakumar

drbsk_2007@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018
Article Published : March 29, 2018

Abstract

New series of 2-chloro-3-[3-(6-nitro-1H-benzimidazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]quinolines (Va-k) have been synthesized by the reaction of 3-(2-chloroquinolin-3-yl)-1-(6-nitro-1H-benzimidazol-2-yl)prop-2-en-1-one (IVa-k) with hydrazine hydrate which in turn were obtained by the condensation of 1-(6-nitro-1H-benzimidazol-2-yl)ethanone (III) with different 2-chloroquinoline-3-carbaldehydes. 1-(6-Nitro-1H-benzimidazol-2-yl)ethanone was obtained by the oxidation of 1-(6-nitro-1H-benzimidazol- 2-yl)ethanol (II) prepared by the reaction of 4-nitro-1,2-phenylenediamine (I) with 2-hydroxypropanoic acid. The synthesized compounds were characterized by IR, ¹H NMR and mass spectral studies. These compounds were screened for their antibacterial activity by standard methods and found some of them active.

Keywords

Benzimidazoles Chalcones Quinolines Pyrazolines Antibacterial activity

Madawali, I. M., Kalyane, N. V., Gaviraj, E., & Shivakumar, B. (2018). Synthesis and Evaluation of 2-Chloro-3-[3-(6-nitro-1H-benzimidazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]quinolines as Potent Antibacterial Agents. Asian Journal of Chemistry, 30(5), 1023–1026. https://doi.org/10.14233/ajchem.2018.21126

Download Citation

References

Salahuddin, M. Shaharyar and A. Mazumder, Arab. J. Chem., 10, 157 (2017); https://doi.org/10.1016/j.arabjc.2012.07.017.
I.G. Mamedov, Y.V. Mamedov, V.N. Khrustalev, M.R. Bayramov and A.M. Maharramov, Indian J. Chem., 56B, 192 (2017).
A. Goyal, S. Sharma and J. Gaba, Indian J. Chem., 56B, 334 (2017).
A.K Tiwari, S. Fatma, A. Bishnoi, A. Srivastava, C.K.M. Tripathi, B. Banerjee. Indian J. Chem., 56B, 317 (2017).
T.A. Naik and K.H. Chikhalia, E-J. Chem., 4, 60 (2007); https://doi.org/10.1155/2007/507590.
V.M. Reddy and K.R. Reddy, Chin. Chem. Lett., 21, 1145 (2010); https://doi.org/10.1016/j.cclet.2010.06.017.
P.K. Dubey, K. Ramaiah, J.S. Grossert, D.L. Hooper and J. Ramanatham, J. Indian Chem. Soc., 76, 140 (1999).
M.M. Ali, S.A. Sana, K.C. Tasneem, K.C. Rajanna and P.K. Saiprakash, Synth. Commun., 32, 1351 (2002); https://doi.org/10.1081/SCC-120003631.
R.M. Singh and A. Srivastava, Indian J. Chem., 44B, 1868 (2005).
P.K. Dubey, J. Ramanatham, R. Kumar and R.C. Kumar, Indian J. Heterocycl. Chem., 9, 259 (2000).
S.N. Sawhney, D. Vir and A. Gupta. Indian J. Chem., 29B, 1107 (1990).
B.N.B. Vaidehi, K.G. Deepika, R.V. Satya, R.R. Bangaramma, R.H. Kumar, Y.R. Sudha and T.R. Kumar, Int. J. Res. Pharm. Chem., 2, 322 (2012).
P. Rajakumar and R. Raja, Tetrahedron Lett., 51, 4365 (2010); https://doi.org/10.1016/j.tetlet.2010.06.059.
P. Venkatesan and S. Sumathi, J. Heterocycl. Chem., 47, 81 (2010); https://doi.org/10.1002/jhet.268.
S. Tabassum, T.H.S. Kumara, J.P. Jasinski, S.N. Millikan, H.S. Yathirajan, P.S.S. Ganapathy, H.B.V. Sowmya, S.S. More, G. Nagendrappa, M. Kaur and G. Jose, J. Mol. Struct., 1070, 10 (2014); https://doi.org/10.1016/j.molstruc.2014.04.009.
E. Ramesh, T.K. Sree Vidhya and R. Raghunathan, Tetrahedron Lett., 49, 2810 (2008); https://doi.org/10.1016/j.tetlet.2008.02.128.
M. Nyerges, Á. Pintér, A. Virányi, G. Blaskó and L. Tõke, Tetrahedron, 61, 8199 (2005); https://doi.org/10.1016/j.tet.2005.06.032.
Z. Wang, Phillips-Ladenburg Benzimidazole Synthesis, In: Comprehensive Organic Name Reactions and Reagents, edn 2, Chap. 496, p. 2197, Wiley (2009).
J.B. Wright, Chem. Rev., 48, 397-541 (1951); https://doi.org/10.1021/cr60151a002.

References

Salahuddin, M. Shaharyar and A. Mazumder, Arab. J. Chem., 10, 157 (2017); https://doi.org/10.1016/j.arabjc.2012.07.017.

I.G. Mamedov, Y.V. Mamedov, V.N. Khrustalev, M.R. Bayramov and A.M. Maharramov, Indian J. Chem., 56B, 192 (2017).

A. Goyal, S. Sharma and J. Gaba, Indian J. Chem., 56B, 334 (2017).

A.K Tiwari, S. Fatma, A. Bishnoi, A. Srivastava, C.K.M. Tripathi, B. Banerjee. Indian J. Chem., 56B, 317 (2017).

T.A. Naik and K.H. Chikhalia, E-J. Chem., 4, 60 (2007); https://doi.org/10.1155/2007/507590.

V.M. Reddy and K.R. Reddy, Chin. Chem. Lett., 21, 1145 (2010); https://doi.org/10.1016/j.cclet.2010.06.017.

P.K. Dubey, K. Ramaiah, J.S. Grossert, D.L. Hooper and J. Ramanatham, J. Indian Chem. Soc., 76, 140 (1999).

M.M. Ali, S.A. Sana, K.C. Tasneem, K.C. Rajanna and P.K. Saiprakash, Synth. Commun., 32, 1351 (2002); https://doi.org/10.1081/SCC-120003631.

R.M. Singh and A. Srivastava, Indian J. Chem., 44B, 1868 (2005).

P.K. Dubey, J. Ramanatham, R. Kumar and R.C. Kumar, Indian J. Heterocycl. Chem., 9, 259 (2000).

S.N. Sawhney, D. Vir and A. Gupta. Indian J. Chem., 29B, 1107 (1990).

B.N.B. Vaidehi, K.G. Deepika, R.V. Satya, R.R. Bangaramma, R.H. Kumar, Y.R. Sudha and T.R. Kumar, Int. J. Res. Pharm. Chem., 2, 322 (2012).

P. Rajakumar and R. Raja, Tetrahedron Lett., 51, 4365 (2010); https://doi.org/10.1016/j.tetlet.2010.06.059.

P. Venkatesan and S. Sumathi, J. Heterocycl. Chem., 47, 81 (2010); https://doi.org/10.1002/jhet.268.

S. Tabassum, T.H.S. Kumara, J.P. Jasinski, S.N. Millikan, H.S. Yathirajan, P.S.S. Ganapathy, H.B.V. Sowmya, S.S. More, G. Nagendrappa, M. Kaur and G. Jose, J. Mol. Struct., 1070, 10 (2014); https://doi.org/10.1016/j.molstruc.2014.04.009.

E. Ramesh, T.K. Sree Vidhya and R. Raghunathan, Tetrahedron Lett., 49, 2810 (2008); https://doi.org/10.1016/j.tetlet.2008.02.128.

M. Nyerges, Á. Pintér, A. Virányi, G. Blaskó and L. Tõke, Tetrahedron, 61, 8199 (2005); https://doi.org/10.1016/j.tet.2005.06.032.

Z. Wang, Phillips-Ladenburg Benzimidazole Synthesis, In: Comprehensive Organic Name Reactions and Reagents, edn 2, Chap. 496, p. 2197, Wiley (2009).

J.B. Wright, Chem. Rev., 48, 397-541 (1951); https://doi.org/10.1021/cr60151a002.

Issue

Vol. 30 No. 5 (2018): Vol 30 Issue 5, 2018

Synthesis and Evaluation of 2-Chloro-3-[3-(6-nitro-1H-benzimidazol-2-yl)-4,5-dihydro-1H-pyrazol-5-yl]quinolines as Potent Antibacterial Agents

Corresponding Author(s) : B. Shivakumar

Abstract

Keywords

Full Article

Download Citation

References

Table Of Contents