Synthesis and Biological Evaluation of 4-(4-Chlorophenyl)cyclohexane Carbohydrazide Derivatives as Anti-Bacterial Agents

G. Venkatasatyanarayana; V. Lakshmana Rao; M. Thirumala Chary; B. Ram; B. Balram; E. Laxminarayana

doi:10.14233/ajchem.2015.18731

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Issue Published : March 17, 2015

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

Synthesis and Biological Evaluation of 4-(4-Chlorophenyl)cyclohexane Carbohydrazide Derivatives as Anti-Bacterial Agents

https://doi.org/10.14233/ajchem.2015.18731

G. Venkatasatyanarayana

Mylan Laboratories Limited, Hyderabad-500 034, India; JNTUH College of Engineering, Nachupally (Kondagattu), Kodimyal mandal, Karimnagar-505 327, India; Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India

V. Lakshmana Rao

Mylan Laboratories Limited, Hyderabad-500 034, India

M. Thirumala Chary

JNTUH College of Engineering, Nachupally (Kondagattu), Kodimyal mandal, Karimnagar-505 327, India

B. Ram

Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India

B. Balram

Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India

E. Laxminarayana

Green Evolution Laboratories, Wangapally Village, Nalgonda-500 085, India

Asian Journal of Chemistry, Vol. 27 No. 6 (2015): Vol 27 Issue 6
Article Published : March 18, 2015

Abstract

The present paper describes the synthesis and antibacterial activity of novel hydrazone derivatives 4a-s derived from 4-(4-chlorophenyl)-cyclohexane carboxylic acid. All the ninteen newly synthesized novel hydrazone derivatives 4a-s were evaluated for their in vitro antibacterial activity against Staphylococcus aureus and S. pyogenes (Gram-positive bacteria) and Escherichia coli and Pseudomonas aeruginosa (Gram-negative bacteria). Antibacterial activity data revealed that the basic scaffold with R = nitrogen heterocyclic ring such as pyridine, quinoline, imidazole and indole showed significant antibacterial activity (excellent activity), whereas the hetrocyclic ring like benzo[b]furan, furan, thiophene moiety showed good antibacterial activity.

Keywords

Atovaquone Cyclohexanecarbohydrazide Hydrazones Antibacterial Activity

Venkatasatyanarayana, G., Lakshmana Rao, V., Thirumala Chary, M., Ram, B., Balram, B., & Laxminarayana, E. (2015). Synthesis and Biological Evaluation of 4-(4-Chlorophenyl)cyclohexane Carbohydrazide Derivatives as Anti-Bacterial Agents. Asian Journal of Chemistry, 27(6), 2267–2272. https://doi.org/10.14233/ajchem.2015.18731

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References

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S. Gemma, G. Kukreja, M. Fattorusso, C. Persico, M. Romano, M. Altarelli, L. Savini, G. Campiani, E. Fattorusso, N. Basilico, D. Taramelli, V. Yardley and S. Butini, Bioorg. Med. Chem. Lett., 16, 5384 (2006); doi:10.1016/j.bmcl.2006.07.060.

L.F. Lindoy and S.E. Livingstone, Coord. Chem. Rev., 2, 173 (1967); doi:10.1016/S0010-8545(00)80204-0.

G. Uppal, S. Bala, S. Kamboj and M. Saini, Der Pharma Chem., 3, 250 (2011).

S. Rollas and S.G. Küçükgüzel, Molecules, 12, 1910 (2007); doi:10.3390/12081910.

R. Narang, B. Narasimhan and S. Sharma, Curr. Med. Chem., 19, 569 (2012); doi:10.2174/092986712798918789.

V.J. Negi, A.K. Sharma, J.S. Negi and V. Ra, Int. J. Pharm. Chem., 4, 100 (2012).

E.J. Corey and D. Enders, Tetrahedron Lett., 17, 3 (1976); doi:10.1016/S0040-4039(00)71307-4.

H.G. Aslan, S. Özcan and N. Karacan, Spectrochim. Acta A, 98, 329 (2012); doi:10.1016/j.saa.2012.08.043.

S.A. Khan, Eur. J. Med. Chem., 43, 2040 (2008); doi:10.1016/j.ejmech.2007.12.008.

A. Kamal, S. Kaleem Ahmed, K. Srinivasa Reddy, M.N.A. Khan, R.V.C.R.N.C. Shetty, B. Siddhardha, U.S.N. Murthy, I.A. Khan, M. Kumar, S. Sharma and A.B. Ram, Bioorg. Med. Chem. Lett., 17, 5419 (2007); doi:10.1016/j.bmcl.2007.07.027.

V.N. Telvekar, A. Belubbi, V.K. Bairwa and K. Satardekar, Bioorg. Med. Chem. Lett., 22, 2343 (2012); doi:10.1016/j.bmcl.2012.01.067.

S. Gemma, L. Savini, M. Altarelli, P. Tripaldi, L. Chiasserini, S.S. Coccone, V. Kumar, C. Camodeca, G. Campiani, E. Novellino, S. Clarizio, G. Delogu and S. Butini, Bioorg. Med. Chem., 17, 6063 (2009); doi:10.1016/j.bmc.2009.06.051.

L.T. Maillard, S. Bertout, O. Quinonéro, G. Akalin, G. Turan-Zitouni, P. Fulcrand, F. Demirci, J. Martinez and N. Masurier, Bioorg. Med. Chem. Lett., 23, 1803 (2013); doi:10.1016/j.bmcl.2013.01.039.

M.D. Altıntop, A. Özdemir, G. Turan-Zitouni, S. Ilgın, Ö. Atlı, G. İşcan and Z.A. Kaplancıklı, Eur. J. Med. Chem., 58, 299 (2012); doi:10.1016/j.ejmech.2012.10.011.

B. Tian, M. He, S. Tang, I. Hewlett, Z. Tan, J. Li, Y. Jin and M. Yang, Bioorg. Med. Chem. Lett., 19, 2162 (2009); doi:10.1016/j.bmcl.2009.02.116.

A.A. Mohamed Eissa, G.A. Soliman and M.H. Khataibeh, Chem. Pharm. Bull. (Tokyo), 60, 1290 (2012); doi:10.1248/cpb.c12-00516.

G. Rajitha, N. Saideepa and P. Praneetha, Indian J. Chem., 50B, 729 (2011).

N.R. Bhairab, P.S. Girij, L.S. Piyush, K.R. Manoj, R. Mitra and A. Trivedi, Indian J. Chem., 52B, 1299 (2013).

V.S. Latter and W.E. Gutteridge, US Patent 4981874 (1991).

O. Cirioni, A. Giacometti, M. Balducci, F. Burzacchini and G. Scalise, J. Antimicrob. Chemother., 36, 740 (1995); doi:10.1093/jac/36.4.740.

A.T. Hudson and C.L.Yeates. EP Patent, 445141 (1996).

S. Looareesuwan, C. Viravan, H. Webster, D.E. Kyle, D.B. Hutchinson and C.J. Canfield, Am. J. Trop. Med. Hyg., 54, 62 (1996).

J.M. Andrews, Antimicrob. Chemother., 48(suppl 1), 5 (2001); doi:10.1093/jac/48.suppl_1.5.

K.T. Chung, W.R. Thomasson and C.D. Wu-Yuan, J. Appl. Bacteriol., 69, 498 (1990); doi:10.1111/j.1365-2672.1990.tb01541.x.

C. Azoro, World J. Biotechnol., 3, 347 (2002).

R. Narisetty, K. Chandrasekhar, S. Mohanty and B. Balram, Lett. Drug Des. Discov., 10, 620 (2013); doi:10.2174/1570180811310070009.

P.A. Villanova, National Committee for Clinical Laboratory, Standards Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria that Grow Aerobically Approved Standard, edn 3, NCCLS Publication M7-A3 (1993).

G.V. Satyanarayana, V.L. Rao, M.T. Chary, B. Ram, B. Balram and V. Chinmaiyee, J. Applicable Chem., 3, 1232 (2014).

Issue

Vol. 27 No. 6 (2015): Vol 27 Issue 6

Synthesis and Biological Evaluation of 4-(4-Chlorophenyl)cyclohexane Carbohydrazide Derivatives as Anti-Bacterial Agents

Abstract

Keywords

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