Design, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents

He Dian; De-Bin Zhou; Jian-Ping Mou; Zhu-Qing Yang; Jia Zhong; Xiao-Quan Ding; Chong Li; Xiao-Hong Wang; Jian-Gang Zhang

doi:10.14233/ajchem.2014.16594

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Issue Published : September 30, 2014

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

Design, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents

https://doi.org/10.14233/ajchem.2014.16594

He Dian

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

De-Bin Zhou

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China; The First Hospital of PLA, Lanzhou 730030, P.R. China

Jian-Ping Mou

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Zhu-Qing Yang

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Jia Zhong

Department of Pharmacy, Pulmonary Hospital of Lanzhou, Lanzhou 730046, P.R. China

Xiao-Quan Ding

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Chong Li

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Xiao-Hong Wang

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Jian-Gang Zhang

Institute of Medicinal Chemistry, School of Pharmacy, Lanzhou University, Lanzhou 73000, P.R. China

Corresponding Author(s) : He Dian

hed@lzu.edu.cn

Asian Journal of Chemistry, Vol. 26 No. 21 (2014): Vol 26 Issue 21
Article Published : October 1, 2014

Abstract

A series of N-(pyridin-4-yl) salicylamides derivatives were prepared through acylation of the corresponding acetylsalicyloyl chlorides with substituted 4-amino-pyridines. These compounds were evaluated in vitro for antimycobacterial activities against Mycobacterium tuberculosis (TB) and Mycobacterium avium (A) by the minimum inhibitory concentrations (MIC) values. Eight of the compounds exhibited lower MIC against A than the one of isoniazide. Meanwhile, four of the compounds exhibited good anti-TB activity compared to isoniazide. Antimycobacterial activities of N-(pyridin-4-yl) salicylamides were influenced by the balance between hydrophobicity and electron withdrawing substituent effects on the phenyl and pyridine ring. These studies show that the compounds might serve as prospective wide-spectrum antimycobacterial substances.

Keywords

Mycobacterium tuberculosis N-(pyridin-4-yl) salicylamides Activity evaluation Synthesis

Dian, H., Zhou, D.-B., Mou, J.-P., Yang, Z.-Q., Zhong, J., Ding, X.-Q., … Zhang, J.-G. (2014). Design, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents. Asian Journal of Chemistry, 26(21), 7269–7275. https://doi.org/10.14233/ajchem.2014.16594

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References

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References

K. Waisser, J. Hladuvkova, J. Kunes, L. Kubicova, V. Klimesova, P. Karajannis and J. Kaustova, Chem. Pap., 55, 121 (2001).

K. Waisser, O. Bures, P. Holý, J. Kunes, R. Oswald, L. Jirásková, M. Pour, V. Klimesová, L. Kubicová and J. Kaustová, Arch. Pharm., 336, 53 (2003); doi:10.1002/ardp.200390004.

D.J. Hlasta, J.P. Demers, B.D. Foleno, S.A. Fraga-Spano, J. Guan, J.J. Hilliard, M.J. Macielag, K.A. Ohemeng, C.M. Sheppard, Z. Sui, G.C. Webb, M.A. Weidner-Wells, H. Werblood and J.F. Barrett, Bioorg. Med. Chem. Lett., 8, 1923 (1998); doi:10.1016/S0960-894X(98)00326-6.

J.B. Stock, A.J. Ninfa and A.M. Stock, Microbiol. Rev., 53, 450 (1989).

J.A. Hoch and T.J. Silhavy, Two-Component Signal Transduction, ASM Press: Washington, DC, pp 305-317 (1995).

R.A. Goldschmidt, M.J. Macielag and D.J. Hlasta, Curr. Pharm. Des., 3, 125 (1997).

M.J. Macielag, J.P. Demers, S.A. Fraga-Spano, D.J. Hlasta, S.G. Johnson, R.M. Kanojia, R.K. Russell, Z. Sui, M.A. Weidner-Wells, H. Werblood, B.D. Foleno, R.M. Goldschmidt, M.J. Loeloff, G.C. Webb and J.F. Barrett, J. Med. Chem., 41, 2939 (1998); doi:10.1021/jm9803572.

I.M. Ota and A. Varshavsky, Science, 262, 566 (1993); doi:10.1126/science.8211183.

K. Waisser, M. Pesina, P. Holý, M. Pour, O. Bures, J. Kunes, V. Klimesová, V. Buchta, P. Kubanová and J. Kaustová, Arch. Pharm., 336, 322 (2003); doi:10.1002/ardp.200300725.

K. Waisser, M. Perina, V. Klimešová and J. Kaustová, Coll. Czech. Chem. Commun., 68, 1275 (2003); doi:10.1135/cccc20031275.

K. Waisser, K. Drazková, J. Kunes, V. Klimesová and J. Kaustová, IL Farmaco, 59, 615 (2004); doi:10.1016/j.farmac.2004.02.003.

F. Doucet-Populaire, J.O. Capobianco, D. Zakula, V. Jarlier and R.C. Goldman, J. Antimicrob. Chemother., 41, 179 (1998); doi:10.1093/jac/41.2.179.

R.C. Goldman and F. Scaglione, Curr. Drug Targets Infect. Disord., 4, 241 (2004); doi:10.2174/1568005043340812.

Z.J. Zhu, O. Krasnykh, D. Pan, V. Petukhova, G. Yu, Y. Liu, H. Liu, S. Hong, Y. Wang, B. Wan, W. Liang and S.G. Franzblau, Tuberculosis, 88(Suppl. 1), 549 (2008); doi:10.1016/S1472-9792(08)70036-2.

M. Botta, M. Artico, S. Massa, A. Gambacorta, M.E. Marongiu, A. Pani and P. Lacolla, Eur. J. Med. Chem., 27, 251 (1992); doi:10.1016/0223-5234(92)90009-P.

Chinese Anti-tuberculosis Association, J. Chinese Anti-tuberc. Assoc., 18, 28 (1996).

Issue

Vol. 26 No. 21 (2014): Vol 26 Issue 21

Design, Synthesis and Activity Evaluation of N-(pyridin-4-yl) Salicylamides as Antimycobacterial Agents

Corresponding Author(s) : He Dian

Abstract

Keywords

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