Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

G. Vijaya Bhasker; G.V. Satyanarayana; A. Latha; E. Laxminarayana; M. Thirumala Chary

doi:10.14233/ajchem.2018.20972

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Issue Published : February 28, 2018

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

Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

https://doi.org/10.14233/ajchem.2018.20972

G. Vijaya Bhasker

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

G.V. Satyanarayana

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

A. Latha

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

E. Laxminarayana

Department of Science & Humanities, Sreenidhi Institute of Science & Technology. Yamnampet, Ghatkesar, Hyderabad-501 301, India

M. Thirumala Chary

Department of Chemistry, Jawaharlal Nehru Technological University Hyderabad, Kukatpally, Hyderabad-500 085, India

Corresponding Author(s) : M. Thirumala Chary

mtcharya@yahoo.com

Asian Journal of Chemistry, Vol. 30 No. 4 (2018): Vol 30 Issue 4
Article Published : February 28, 2018

Abstract

2-Aminonicotinaldehyde (1) and 1-(3-nitrophenyl)ethanone (2) react each other in presence of piperidine to form 2-(3-nitrophenyl)-1,8-naphthyridine (3). Compound 3 on reduction with hydrazine hydrate offered 3-(1,8-naphthyridin-2-yl)aniline (4), which on condensation with different arylcarbamates results in formation of 1-[3-(1,8-naphthyridin-2-yl)phenyl]-3-arylurea derivatives (6a-q). The structures of all the compounds are confirmed by IR, NMR and mass spectral data. Further the newly synthesized compounds were evaluated for antimicrobial activity. The results obtained revealed that the tested compounds possess inhibitory effect on the growth of bacterial cells.

Keywords

Naphthyridine derivatives Piperidine Urea Antimicrobial activity

Bhasker, G. V., Satyanarayana, G., Latha, A., Laxminarayana, E., & Chary, M. T. (2018). Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives. Asian Journal of Chemistry, 30(4), 771–774. https://doi.org/10.14233/ajchem.2018.20972

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References

D. Bouzard, Recent Progress in the Chemical Synthesis of Antibiotics: Recent Advances in the Chemistry of Quinolines, Springer Verlag, Berlin. pp. 249 (1990).
C. Siporin, C.L. Heifetz and J.M. Domagala, The New Generation of Quinolines, M. Dekker, New York (1990).
P.A. Lowe, Naphthyridines, Pyridoquinolines, Anthyridines and Similar Compounds, Comprehensive Heterocyclic Chemistry, vol. II, pp. 581- 627 (1984).
A.S. Tomcufcik, W.E. Meyer and J.W. Marisco, Eur. Pat. Appl. EP 446604 (1991).
E.V. Brown, R.M. Novack and A.A. Hamdan, J. Org. Chem., 26, 2831 (1961); https://doi.org/10.1021/jo01066a050.
E.V. Brown, R.M. Novack and A.A. Hamdan, J. Natl. Cancer Inst., 26, 1461 (1961).
H. Egawa, T. Miyamoto, A. Minamida, Y. Nishimura, H. Okada, H. Uno and J. Matsumoto, J. Med. Chem., 27, 1543 (1984); https://doi.org/10.1021/jm00378a004.
J. Nezval and K. Halaèka, Experientia, 23, 1043 (1967); https://doi.org/10.1007/BF02136439.
E.M. Hawes, D.K.J. Gorecki and R.G. Gedir, J. Med. Chem., 20, 838 (1977); https://doi.org/10.1021/jm00216a021.
N. Suzuki and R. Dohmori, Chem. Pharm. Bull. (Tokyo), 27, 410 (1979); https://doi.org/10.1248/cpb.27.410.
R. Peters and I.G. Young, The Chemistry of Steroids, Wilmer Brother and Harman Ltd, Birkenhead, p. 112 (1960).
N. Suzuki, Pharm. Bull., 28, 761 (1980); https://doi.org/10.1248/cpb.28.761.
K.P. Jadav and D.B. Ingle, J. Indian Chem. Soc., 55, 424 (1978).
G.B. Barlin and W.L. Tan, Aust. J. Chem., 37, 1065 (1984); https://doi.org/10.1071/CH9841065.
R.S. Lodhi and S.D. Srivastsava, Indian J. Chem., 36B, 947 (1997).
S.S. Shankar, E. Laxminarayana, B. Srinivasulu and M.T. Chary, Indian J. Heterocycl. Chem., 18, 341 (2009).
E. Laxminarayana, A. Narender, S.S. Shankar and M.T. Chary, Int. J. Appl. Chem., 4, 237 (2008).
M.T. Chary, E. Laxminarayana, S.S. Shankar and A. Narender, Hetercycl. Commun., 15, 35 (2009); https://doi.org/10.1515/HC.2009.15.1.35.
A. Narender, M.T. Chary, E. Laxminarayana and V. Haripriya, Indian J. Chem., 52B, 440 (2013).
A. Narender, E. Laxminarayana and M.T. Chary, J Chil. Chem. Soc., 54, 289 (2009); https://doi.org/10.4067/S0717-97072009000400033.
A. Narender, E. Laxminarayana, S.S. Shankar and M.T. Chary, Hetercycl. Commun., 16, 187 (2010); https://doi.org/10.1515/HC.2010.16.2-3.187.
A. Narendar, E. Laxminarayana and M.T. Chary, Indian J. Heterocycl. Chem., 23, 239 (2014).
K.K. Anantoju, G. Tharikoppula, L. Eppakayala and T.C. Maringanti, Int. J. Chem. Anal. Sci., 4, 146 (2013); https://doi.org/10.1016/j.ijcas.2013.07.008.
M. Bucha, L. Eppakayala, T.C. Maringanti, G. Tharikoppula and S. Kethireddy, Org. Med. Chem. Lett., 4, 16 (2014); https://doi.org/10.1186/s13588-014-0016-8.

References

D. Bouzard, Recent Progress in the Chemical Synthesis of Antibiotics: Recent Advances in the Chemistry of Quinolines, Springer Verlag, Berlin. pp. 249 (1990).

C. Siporin, C.L. Heifetz and J.M. Domagala, The New Generation of Quinolines, M. Dekker, New York (1990).

P.A. Lowe, Naphthyridines, Pyridoquinolines, Anthyridines and Similar Compounds, Comprehensive Heterocyclic Chemistry, vol. II, pp. 581- 627 (1984).

A.S. Tomcufcik, W.E. Meyer and J.W. Marisco, Eur. Pat. Appl. EP 446604 (1991).

E.V. Brown, R.M. Novack and A.A. Hamdan, J. Org. Chem., 26, 2831 (1961); https://doi.org/10.1021/jo01066a050.

E.V. Brown, R.M. Novack and A.A. Hamdan, J. Natl. Cancer Inst., 26, 1461 (1961).

H. Egawa, T. Miyamoto, A. Minamida, Y. Nishimura, H. Okada, H. Uno and J. Matsumoto, J. Med. Chem., 27, 1543 (1984); https://doi.org/10.1021/jm00378a004.

J. Nezval and K. Halaèka, Experientia, 23, 1043 (1967); https://doi.org/10.1007/BF02136439.

E.M. Hawes, D.K.J. Gorecki and R.G. Gedir, J. Med. Chem., 20, 838 (1977); https://doi.org/10.1021/jm00216a021.

N. Suzuki and R. Dohmori, Chem. Pharm. Bull. (Tokyo), 27, 410 (1979); https://doi.org/10.1248/cpb.27.410.

R. Peters and I.G. Young, The Chemistry of Steroids, Wilmer Brother and Harman Ltd, Birkenhead, p. 112 (1960).

N. Suzuki, Pharm. Bull., 28, 761 (1980); https://doi.org/10.1248/cpb.28.761.

K.P. Jadav and D.B. Ingle, J. Indian Chem. Soc., 55, 424 (1978).

G.B. Barlin and W.L. Tan, Aust. J. Chem., 37, 1065 (1984); https://doi.org/10.1071/CH9841065.

R.S. Lodhi and S.D. Srivastsava, Indian J. Chem., 36B, 947 (1997).

S.S. Shankar, E. Laxminarayana, B. Srinivasulu and M.T. Chary, Indian J. Heterocycl. Chem., 18, 341 (2009).

E. Laxminarayana, A. Narender, S.S. Shankar and M.T. Chary, Int. J. Appl. Chem., 4, 237 (2008).

M.T. Chary, E. Laxminarayana, S.S. Shankar and A. Narender, Hetercycl. Commun., 15, 35 (2009); https://doi.org/10.1515/HC.2009.15.1.35.

A. Narender, M.T. Chary, E. Laxminarayana and V. Haripriya, Indian J. Chem., 52B, 440 (2013).

A. Narender, E. Laxminarayana and M.T. Chary, J Chil. Chem. Soc., 54, 289 (2009); https://doi.org/10.4067/S0717-97072009000400033.

A. Narender, E. Laxminarayana, S.S. Shankar and M.T. Chary, Hetercycl. Commun., 16, 187 (2010); https://doi.org/10.1515/HC.2010.16.2-3.187.

A. Narendar, E. Laxminarayana and M.T. Chary, Indian J. Heterocycl. Chem., 23, 239 (2014).

K.K. Anantoju, G. Tharikoppula, L. Eppakayala and T.C. Maringanti, Int. J. Chem. Anal. Sci., 4, 146 (2013); https://doi.org/10.1016/j.ijcas.2013.07.008.

M. Bucha, L. Eppakayala, T.C. Maringanti, G. Tharikoppula and S. Kethireddy, Org. Med. Chem. Lett., 4, 16 (2014); https://doi.org/10.1186/s13588-014-0016-8.

Issue

Vol. 30 No. 4 (2018): Vol 30 Issue 4

Synthesis and Antimicrobial Activity of Novel 1-[3-(1,8-Naphthyridin-2-yl)phenyl]-3-arylurea Derivatives

Corresponding Author(s) : M. Thirumala Chary

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