Synthesis and Antibacterial Activity of Hydrazone Derivatives Bearing 3-(6,7-Dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)benzoicacid Scaffold

Gowrisankar Rao Kaki; B. Sreenivasulu; Aminul Islam; Dussa Nageshwar; Raghubabu Korupolu; B. Venkateshwara Rao

doi:10.14233/ajchem.2015.18877

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Issue Published : June 22, 2015

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

Synthesis and Antibacterial Activity of Hydrazone Derivatives Bearing 3-(6,7-Dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)benzoicacid Scaffold

https://doi.org/10.14233/ajchem.2015.18877

Gowrisankar Rao Kaki

Chemical Research and Development Department, APL Research Center, Aurobindo Pharma Ltd, Survey No: 71 and 72, Indrakaran Village, Sangareddy Mandal, Medak District, Hyderabad-502 329, India; Department of Engineering Chemistry, A.U. College of Engineering (A), Andhra University, Visakhapatnam-530 003, India

B. Sreenivasulu

Chemical Research and Development Department, APL Research Center, Aurobindo Pharma Ltd, Survey No: 71 and 72, Indrakaran Village, Sangareddy Mandal, Medak District, Hyderabad-502 329, India

Aminul Islam

Chemical Research and Development Department, APL Research Center, Aurobindo Pharma Ltd, Survey No: 71 and 72, Indrakaran Village, Sangareddy Mandal, Medak District, Hyderabad-502 329, India

Dussa Nageshwar

Chemical Research and Development Department, APL Research Center, Aurobindo Pharma Ltd, Survey No: 71 and 72, Indrakaran Village, Sangareddy Mandal, Medak District, Hyderabad-502 329, India

Raghubabu Korupolu

Department of Engineering Chemistry, A.U. College of Engineering (A), Andhra University, Visakhapatnam-530 003, India

B. Venkateshwara Rao

Department of Engineering Chemistry, A.U. College of Engineering (A), Andhra University, Visakhapatnam-530 003, India

Corresponding Author(s) : Gowrisankar Rao Kaki

gowrisankarkaki2014@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 10 (2015): Vol 27 Issue 10
Article Published : June 22, 2015

Abstract

The present work describes the synthesis and antibacterial activity of 3-(6,7-dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)benzohydrazide derivatives (7a-p) prepared from commercially available 4,5,6,7-tetrahydrothieno[3,2-c]pyridine (1). They were characterized by ¹H NMR, IR and mass spectral analysis. The synthesized compounds 7a-p, were tested against Gram negative and Gram positive bacterial strains viz; (i) Escherichia coli (MTCC 443), (ii) Pseudomonas aeruginosa (MTCC 424) (iii) Staphylococcus aureus (MTCC 96) and (iv) Streptococcus pyogenes (MTCC 442) using agar well diffusion method. Compounds 7g (R = 2-OH, 4-OCHF₂), 7h (R = 2-NO₂), 7i (R = 3-NO₂), 7j (R = 4-NO₂) and 7n (4-OH) displayed excellent antibacterial activity (zone of inhibition: 25-32 mm) against both the Gram positive and Gram negative bacterial strains. Compounds 7f (R = 2-F, 3-Cl), 7k (R = 2-OMe), 7l (R = 4-OMe), 7m (R = 4-OEt), 7o (R = 3-OMe), 7p (R = 3,4-OEt) showed good antibacterial activity (zone of inhibition: 19-26 mm).

Keywords

4 5 6 7-Tetrahydrothieno[3 2-c]pyridine 3-(Chlorosulfonyl)benzoicacid Hydrazones Antibacterial activity Norfloxacin

Rao Kaki, G., Sreenivasulu, B., Islam, A., Nageshwar, D., Korupolu, R., & Venkateshwara Rao, B. (2015). Synthesis and Antibacterial Activity of Hydrazone Derivatives Bearing 3-(6,7-Dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)benzoicacid Scaffold. Asian Journal of Chemistry, 27(10), 3586–3590. https://doi.org/10.14233/ajchem.2015.18877

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References

P. Collet, J.S. Hulot and G. Montalescot, Lancet, 373, 1172 (2009); doi:10.1016/S0140-6736(09)60682-6.
S.C. Gujarathi, A.R. Shah, S.C. Jagdale, P.A. Datar, V.P. Choudhari and B.S. Kuchekar, Int. J. Pharm. Sci. Rev. Res., 3, 115 (2010).
G.L. Grunewald, M.R. Seim, S.R. Bhat, M.E. Wilson and K.R. Criscione, Bioorg. Med. Chem., 16, 542 (2008); doi:10.1016/j.bmc.2007.08.066.
W.L. Baker and C.M. White, Am. J. Cardiovasc. Drugs, 9, 213 (2009); doi:10.2165/1131209-000000000-00000.
K. Huber, U. Yasothan, B. Hamad and P. Kirkpatrick, Nat. Rev. Drug Discov., 8, 449 (2009); doi:10.1038/nrd2899.
M. Taniuchi, H.I. Kurz and J.M. Lasala, Circulation, 104, 539 (2001); doi:10.1161/hc3001.093435.
H.S. Andersen, O.H. Olsen, L.F. Iversen, A.L.P. Sørensen, S.B. Mortensen, M.S. Christensen, S. Branner, T.K. Hansen, J.F. Lau, L. Jeppesen, E.J. Moran, J. Su, F. Bakir, L. Judge, M. Shahbaz, T. Collins, T. Vo, M.J. Newman, W.C. Ripka and N.P.H. Møller, J. Med. Chem., 45, 4443 (2002); doi:10.1021/jm0209026.
D.H. Boschelli, B. Wu, A.C.B. Sosa, J.J. Chen, J.M. Golas and F. Boschelli, Bioorg. Med. Chem. Lett., 15, 4681 (2005); doi:10.1016/j.bmcl.2005.07.061.
A.M.R. Bernardino, L.C. da Silva Pinheiro, C.R. Rodrigues, N.I. Loureiro, H.C. Castro, A. Lanfredi-Rangel, J. Sabatini-Lopes, J.C. Borges, J.M. Carvalho, G.A. Romeiro, V.F. Ferreira, I.C.P.P. Frugulhetti and M.A. Vannier-Santos, Bioorg. Med. Chem., 14, 5765 (2006); doi:10.1016/j.bmc.2006.03.013.
L.N. Tumey, D.H. Boschelli, J. Lee and D. Chaudhary, Bioorg. Med. Chem. Lett., 18, 4420 (2008); doi:10.1016/j.bmcl.2008.06.040.
F.A. Attaby, M.A.A. Elneairy and M.S. Elsayed, Phosphorus Sulfur Silicon Rel. Elem., 149, 49 (1999); doi:10.1080/10426509908037022.
R.C. Moellering Jr., Int. J. Antimicrob. Agents, 37, 2 (2011); doi:10.1016/j.ijantimicag.2010.08.018.
A.D. So, N. Gupta and O. Cars, BMJ, 340, 2071 (2010); doi:10.1136/bmj.c2071.
A. Coates, Y. Hu, R. Bax and C. Page, Nat. Rev. Drug Discov., 1, 895 (2002); doi:10.1038/nrd940.
H.S. Seleem, G.A. El-Inany, B.A. El-Shetary, M.A. Mousa and F.I. Hanafy, Chem. Cent. J., 5, 20 (2011); doi:10.1186/1752-153X-5-20.
A.B. Samel and N.R. Pai, J. Chem. Pharm. Res., 2, 60 (2010).
S.A.M. Shedid, H.M. Hassan, F.A. Kora and R.M. El- Eisawy. J. Chem. Pharm. Res., 3, 388 (2011).
M. Asif and A. Husain, J. Appl. Chem., Article ID 247203 (2013); doi:10.1155/2013/247203.
P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera and R. Loddo, Eur. J. Med. Chem., 41, 624 (2006); doi:10.1016/j.ejmech.2006.01.010.
J. Mao, Y. Wang, B. Wan, A.P. Kozikowski and S.G. Franzblau, ChemMedChem, 2, 1624 (2007); doi:10.1002/cmdc.200700112.
F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, F. Ortuso, M.C. Cardia and S. Distinto, J. Med. Chem., 50, 707 (2007); doi:10.1021/jm060869d.
K.T. Joshi, J.M. Patel and A.M. Pancholi, Alfa Universal: An Int. J. Chem., 2, 118 (2011).
R. Narisetty, K.B. Chandrasekhar, S. Mohanty and B. Balram, Lett. Drug Des. Discov., 10, 620 (2013); doi:10.2174/1570180811310070009.
M. Mohan, M.P. Gupta, L. Chandra and N.K. Jha, Inorg. Chim. Acta, 151, 61 (1988); doi:10.1016/S0020-1693(00)83485-4.
M.J. Pelczar Jr., R.D. Reid and E.C.S. Chan, Cultivation of Bacteria. In: Microbiology, Tata McGraw Hill Publishing Co. Ltd., New Delhi, edn 4, p. 103 (1982).
B.P. Nariya, R.N. Bhalodia, V.J. Shukla and B.M. Nariya, Int. J. PharmTech. Res., 2, 2522 (2010).
M.L. Rao, A.R. Reddy, G. Goverdhan, K. Mukkanti and B. Rakeshwar, Der Pharma Chem., 4, 479 (2012).

References

P. Collet, J.S. Hulot and G. Montalescot, Lancet, 373, 1172 (2009); doi:10.1016/S0140-6736(09)60682-6.

S.C. Gujarathi, A.R. Shah, S.C. Jagdale, P.A. Datar, V.P. Choudhari and B.S. Kuchekar, Int. J. Pharm. Sci. Rev. Res., 3, 115 (2010).

G.L. Grunewald, M.R. Seim, S.R. Bhat, M.E. Wilson and K.R. Criscione, Bioorg. Med. Chem., 16, 542 (2008); doi:10.1016/j.bmc.2007.08.066.

W.L. Baker and C.M. White, Am. J. Cardiovasc. Drugs, 9, 213 (2009); doi:10.2165/1131209-000000000-00000.

K. Huber, U. Yasothan, B. Hamad and P. Kirkpatrick, Nat. Rev. Drug Discov., 8, 449 (2009); doi:10.1038/nrd2899.

M. Taniuchi, H.I. Kurz and J.M. Lasala, Circulation, 104, 539 (2001); doi:10.1161/hc3001.093435.

H.S. Andersen, O.H. Olsen, L.F. Iversen, A.L.P. Sørensen, S.B. Mortensen, M.S. Christensen, S. Branner, T.K. Hansen, J.F. Lau, L. Jeppesen, E.J. Moran, J. Su, F. Bakir, L. Judge, M. Shahbaz, T. Collins, T. Vo, M.J. Newman, W.C. Ripka and N.P.H. Møller, J. Med. Chem., 45, 4443 (2002); doi:10.1021/jm0209026.

D.H. Boschelli, B. Wu, A.C.B. Sosa, J.J. Chen, J.M. Golas and F. Boschelli, Bioorg. Med. Chem. Lett., 15, 4681 (2005); doi:10.1016/j.bmcl.2005.07.061.

A.M.R. Bernardino, L.C. da Silva Pinheiro, C.R. Rodrigues, N.I. Loureiro, H.C. Castro, A. Lanfredi-Rangel, J. Sabatini-Lopes, J.C. Borges, J.M. Carvalho, G.A. Romeiro, V.F. Ferreira, I.C.P.P. Frugulhetti and M.A. Vannier-Santos, Bioorg. Med. Chem., 14, 5765 (2006); doi:10.1016/j.bmc.2006.03.013.

L.N. Tumey, D.H. Boschelli, J. Lee and D. Chaudhary, Bioorg. Med. Chem. Lett., 18, 4420 (2008); doi:10.1016/j.bmcl.2008.06.040.

F.A. Attaby, M.A.A. Elneairy and M.S. Elsayed, Phosphorus Sulfur Silicon Rel. Elem., 149, 49 (1999); doi:10.1080/10426509908037022.

R.C. Moellering Jr., Int. J. Antimicrob. Agents, 37, 2 (2011); doi:10.1016/j.ijantimicag.2010.08.018.

A.D. So, N. Gupta and O. Cars, BMJ, 340, 2071 (2010); doi:10.1136/bmj.c2071.

A. Coates, Y. Hu, R. Bax and C. Page, Nat. Rev. Drug Discov., 1, 895 (2002); doi:10.1038/nrd940.

H.S. Seleem, G.A. El-Inany, B.A. El-Shetary, M.A. Mousa and F.I. Hanafy, Chem. Cent. J., 5, 20 (2011); doi:10.1186/1752-153X-5-20.

A.B. Samel and N.R. Pai, J. Chem. Pharm. Res., 2, 60 (2010).

S.A.M. Shedid, H.M. Hassan, F.A. Kora and R.M. El- Eisawy. J. Chem. Pharm. Res., 3, 388 (2011).

M. Asif and A. Husain, J. Appl. Chem., Article ID 247203 (2013); doi:10.1155/2013/247203.

P. Vicini, M. Incerti, I.A. Doytchinova, P. La Colla, B. Busonera and R. Loddo, Eur. J. Med. Chem., 41, 624 (2006); doi:10.1016/j.ejmech.2006.01.010.

J. Mao, Y. Wang, B. Wan, A.P. Kozikowski and S.G. Franzblau, ChemMedChem, 2, 1624 (2007); doi:10.1002/cmdc.200700112.

F. Chimenti, E. Maccioni, D. Secci, A. Bolasco, P. Chimenti, A. Granese, O. Befani, P. Turini, S. Alcaro, F. Ortuso, M.C. Cardia and S. Distinto, J. Med. Chem., 50, 707 (2007); doi:10.1021/jm060869d.

K.T. Joshi, J.M. Patel and A.M. Pancholi, Alfa Universal: An Int. J. Chem., 2, 118 (2011).

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

M. Mohan, M.P. Gupta, L. Chandra and N.K. Jha, Inorg. Chim. Acta, 151, 61 (1988); doi:10.1016/S0020-1693(00)83485-4.

M.J. Pelczar Jr., R.D. Reid and E.C.S. Chan, Cultivation of Bacteria. In: Microbiology, Tata McGraw Hill Publishing Co. Ltd., New Delhi, edn 4, p. 103 (1982).

B.P. Nariya, R.N. Bhalodia, V.J. Shukla and B.M. Nariya, Int. J. PharmTech. Res., 2, 2522 (2010).

M.L. Rao, A.R. Reddy, G. Goverdhan, K. Mukkanti and B. Rakeshwar, Der Pharma Chem., 4, 479 (2012).

Issue

Vol. 27 No. 10 (2015): Vol 27 Issue 10

Synthesis and Antibacterial Activity of Hydrazone Derivatives Bearing 3-(6,7-Dihydrothieno[3,2-c]pyridin-5(4H)-ylsulfonyl)benzoicacid Scaffold

Corresponding Author(s) : Gowrisankar Rao Kaki

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