Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives

M.A. Kadir; R. Ramli; M.S.M. Yusof; N. Ismail; N. Ngah

doi:10.14233/ajchem.2016.19430

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Issue Published : December 5, 2015

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

Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives

https://doi.org/10.14233/ajchem.2016.19430

M.A. Kadir

School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia; Institute of Marine Biotechnology, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia

R. Ramli

School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia

M.S.M. Yusof

School of Fundamental Science, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia

N. Ismail

Institute of Marine Biotechnology, Universiti Malaysia Terengganu, 21030 Kuala Terengganu, Terengganu, Malaysia

N. Ngah

Department of Chemistry, Kulliyyah of Science, International Islamic University Malaysia, Kuantan Campus, 25200 Kuantan, Pahang, Malaysia

Corresponding Author(s) : M.A. Kadir

maisara@umt.edu.my

Asian Journal of Chemistry, Vol. 28 No. 3 (2016): Vol 28 Issue 3
Article Published : December 5, 2015

Abstract

Four new thiourea compounds have been successfully synthesized and characterized from combination of lauroyl chloride, ammonium thiocyanate and simple amino acids in acetone. The structure of the respective compounds, namely 3-(3-dodecanoyl-thioureido)propionic acid (R1), 2-(3-dodecanoyl-thioureido)-3-methyl butyric acid (R2), (3-dodecanoyl-thioureido)acetic acid (R3) and 2-(3-dodecanoyl-thioureido)-3-phenyl propionic acid (R4) are confirmed by combination of spectroscopic techniques such as infrared, ultraviolet and nuclear magnetic resonance. The antibacterial activity of these compounds are investigated towards selected bacteria and the results show that compound R4 displays better antibacterial activity compared to R1-R3 and as well as to few reported compounds. Compound R4 shows good antibacterial activity towards two Gram-negative bacteria Escherichia coli and Salmonella typhimurium, with inhibition zone approximately 8 mm wide and minimum inhibitory concentration (MIC) 50 μg/mL, respectively. The good results given by R4 might be attributed by the presence of alkyl and phenyl group that increases the lipophilicity and stability of the compounds.

Keywords

Dodecanoyl Lauroyl thiourea Antibacterial activity Amino acids

Kadir, M., Ramli, R., Yusof, M., Ismail, N., & Ngah, N. (2015). Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives. Asian Journal of Chemistry, 28(3), 596–600. https://doi.org/10.14233/ajchem.2016.19430

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References

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References

N. Ngah, M. Kadir, B.M. Yamin and M.S.M. Yusof, Acta Crystallogr., E68, 1801 (2012); doi:10.1107/S160053681202168X.

M. Ghanei-Motlagh, M. Fayazi and M.A. Taher, Sens. Actuators B, 199, 133 (2014); doi:10.1016/j.snb.2014.03.086.

R. Rahamathullah, W.M. Khairul, H. Salleh, H.K. Adli, M. Isa and M.G. Tay, Int. J. Electrochem. Sci., 8, 3333 (2013).

H.M. Abosadiya, E.H. Anouar, S.A. Hasbullah and B.M. Yamin, Spectrochim. Acta A, 144, 115 (2015); doi:10.1016/j.saa.2015.01.092.

N.B. Patel and F.M. Shaikh, Saudi Pharm. J., 18, 129 (2010); doi:10.1016/j.jsps.2010.05.002.

W. Zheng, S.R. Yates, S.K. Papiernik and M. Guo, Environ. Sci. Technol., 38, 6855 (2004); doi:10.1021/es049384+.

X. Xu, X. Qian, Z. Li, Q. Huang and G. Chen, J. Fluor. Chem., 121, 51 (2003); doi:10.1016/S0022-1139(02)00330-5.

S. Manjula, N.M. Noolvi, K.V. Parihar, S.M. Reddy, V. Ramani, A.K. Gadad, G. Singh, N.G. Kutty and C.M. Rao, Eur. J. Med. Chem., 44, 2923 (2009); doi:10.1016/j.ejmech.2008.12.002.

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C.S. Shantharam, D.M. Suyoga Vardhan, R. Suhas, M.B. Sridhara and D.C. Gowda, Eur. J. Med. Chem., 60, 325 (2013); doi:10.1016/j.ejmech.2012.12.029.

M. Ibrahim, M. Yusof and N. Amin, Molecules, 19, 5191 (2014); doi:10.3390/molecules19045191.

W. Yang, H. Liu, M. Li, F. Wang, W. Zhou and J. Fan, J. Inorg. Biochem., 116, 97 (2012); doi:10.1016/j.jinorgbio.2012.08.001.

M.M. Zhao, X.Y. Dong, G. Li, Y.H. Yang, Y.J. Zhang and X.Q. Yang, Asian J. Chem., 25, 7548 (2013); doi:10.14233/ajchem.2013.15157.

T.J. Egan, K.R. Koch, P.L. Swan, C. Clarkson, D.A. Van Schalkwyk and P.J. Smith, J. Med. Chem., 47, 2926 (2004); doi:10.1021/jm031132g.

N. Selvakumaran, S.W. Ng, E.R. Tiekink and R. Karvembu, Inorg. Chim. Acta, 376, 278 (2011); doi:10.1016/j.ica.2011.06.031.

A.M. Plutin, R. Mocelo, A. Alvarez, R. Ramos, E.E. Castellano, M.R. Cominetti, A.E. Graminha, A.G. Ferreira and A.A. Batista, J. Inorg. Biochem., 134, 76 (2014); doi:10.1016/j.jinorgbio.2014.01.022.

G. Kurt, F. Sevgi and B. Mercimek, Chem. Pap., 63, 548 (2009); doi:10.2478/s11696-009-0055-1.

I.J. Kang, L.W. Wang, S.J. Hsu, C.C. Lee, Y.C. Lee, Y.S. Wu, A. Yueh, J.C. Wang, T.A. Hsu, Y.S. Chao and J.-H. Chern, Bioorg. Med. Chem. Lett., 19, 6063 (2009); doi:10.1016/j.bmcl.2009.09.037.

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E.J. Waheed, J. Al-Nahrain Univ., 15, 1 (2012).

C. Limban, M.C.B. Chifiriuc, A.V. Missir, I.C. Chiriţă and C. Bleotu, Molecules, 13, 567 (2008); doi:10.3390/molecules13030567.

M.S.M. Yusof, R.H. Jusoh, W.M. Khairul and B.M. Yamin, J. Mol. Struct., 975, 280 (2010); doi:10.1016/j.molstruc.2010.04.037.

S. Saeed, N. Rashid, P.G. Jones and A. Tahir, J. Heterocycl. Chem., 48, 74 (2011); doi:10.1002/jhet.510.

J. Liu, S. Yang, X. Li, H. Fan, P. Bhadury, W. Xu, J. Wu and Z. Wang, Molecules, 15, 5112 (2010); doi:10.3390/molecules15085112.

N.I.M. Halim, K. Kassim, A.H. Fadzil and B.M. Yamin, APCBEE Procedia, 3, 129 (2012); doi:10.1016/j.apcbee.2012.06.058.

M. Ghorab, Z.H. Ismail, S.M. Abdel‐Gawad and A.A. Aziem, Heteroatom Chem., 15, 57 (2004); doi:10.1002/hc.10212.

N. Joondan, S. Jhaumeer-Laulloo and P. Caumul, Microbiol. Res., 169, 675 (2014); doi:10.1016/j.micres.2014.02.010.

L.C. Chen, W.D. Chiang, W.C. Chen, H.H. Chen, Y.W. Huang, W.J. Chen and S.B. Lin, Food Chem., 135, 2397 (2012); doi:10.1016/j.foodchem.2012.06.122.

A.J. Hoey, C.M. Jackson, G.G. Pegg and M.N. Sillence, Br. J. Pharmacol., 119, 564 (1996); doi:10.1111/j.1476-5381.1996.tb15709.x.

Z. Zhong, R. Xing, S. Liu, L. Wang, S. Cai and P. Li, Carbohydr. Res., 343, 566 (2008); doi:10.1016/j.carres.2007.11.024.

K. Shivakumara, K. Prakasha and D. Gowda, E-J. Chem., 6, S473 (2009); doi:10.1155/2009/267296.

L. Vidal, V. Thuault, A. Mangas, R. Coveñas, A. Thienpont and M. Geffard, J. Amino Acids, Article ID 672367 (2014); doi:10.1155/2014/672367.

Issue

Vol. 28 No. 3 (2016): Vol 28 Issue 3

Synthesis, Spectroscopic Studies and Antibacterial Activity of New Lauroyl Thiourea Amino Acid Derivatives

Corresponding Author(s) : M.A. Kadir

Abstract

Keywords

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