Abstract
A series of novel derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid bearing two identical substituted 1,3,4-oxadiazole, 1,3,4-thiadiazole, or 1,2,4-triazole moieties were synthesized and their molecular structures were confirmed by IR, 1H, 13C NMR spectroscopy, and elemental analysis data. The synthesized compounds were screened for their reducing power, free radical scavenging, plant growth regulating, and antimicrobial properties. 5,5′-((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione) showed excellent antioxidant activity, three times higher than that of the antibiotic control (cefazolin). 2,2′-((((Phenylazanediyl)bis(ethane-2,1-diyl))bis(4-phenyl-4H-1,2,4-triazole-5,3-diyl))bis(sulfanediyl))diacetate exhibited notable bactericidal activity against Pseudomonas aeruginosa with MBC and MIC values 7.3 µg/ml, whereas 12 compounds displayed significant fungicidal activity against Candida albicans with MIC value 3.9 µg/ml.
Graphical Abstract
Synthesis of compounds 2–27. R: 2, 5, 7, 10, 13, 15-27 C6H5–; 3, 8, 11 4-Cl-C6H4–; 4, 9, 12 CH3–; 6, 14 2.6-(CH3)2-C6H3–; R′: 15 CH3CH2–; 16 (CH3)2CH–; 17 (CH3)2CHCH2–; 18 CH3CH2CH2CH2–; 19 (CH3)2CHCH2CH2–; 20 CH3CH2CH2CH2CH2–; 21 NH2COCH2–; 22 C6H5CH2–; 23 C6H5COCH2–; 24 4-ClC6H4COCH2–; 25 4-NO2C6H4COCH2–; 26 C2H5OCOCH2–.
Similar content being viewed by others
References
J. Bostrom, A. Hogner, A. Llinas, E. Wellner, A.T. Plowright, J. Med. Chem. 55, 1817 (2012)
W. Xu, S. Yang, P. Bhadury, J. He, M. He, L. Gao, D. Hu, B. Song, Pest. Biochem. Physiol. 10, 6 (2011)
Y. Hu, C.-Y. Li, X.-M. Wang, Y.-H. Yang, H.-L. Zhu, Chem. Rev. 114, 5572 (2014)
R.A. Rane, S.D. Gutte, N.U. Sahu, Bioorg. Med. Chem. Lett. 22, 6429 (2012)
J. Sun, M.-H. Li, S.-S. Qian, F.-J. Guo, X.-F. Dang, X.-M. Wang, Y.-R. Xue, H.-L. Zhu, Bioorg. Med. Chem. Lett. 23, 2876 (2013)
I. Tumosienė, K. Kantminienė, A. Pavilonis, Ž. Maželienė, Z.J. Beresnevičius, Heterocycles 78, 59 (2009)
K.I. Bhat, K.S. Sufeera, K.P. Chaitanya, J. Young Pharm. 3, 310 (2011)
P. Singh, P.K. Jangra, Der Chem. Sin. 1, 118 (2010)
B. Kumar, V. Raj, A. Kumar, V. Singh, Int. J. Curr. Pharm. Res. 4, 9 (2012)
Y. Kotaiah, N. Harikrishna, K. Nagaraju, C.V. Rao, Eur. J. Med. Chem. 58, 340 (2012)
M. Juszczak, J. Matysiak, M. Szeliga, P. Pozarowski, A. Niewiadomy, J. Albrecht, W. Rzeski, Bioorg. Med. Chem. Lett. 22, 5466 (2012)
M.N. Noolvi, H.M. Patel, S. Kamboj, A. Kaur, V. Mann, Eur. J. Med. Chem. 56, 56 (2012)
T. Plech, M. Wujec, U. Kosikowska, A. Malm, B. Kaproń, Eur. J. Med. Chem. 47, 580 (2012)
S.-F. Barbuceanu, G. Saramet, G.L. Almajan, C. Draghici, F. Barbuceanu, G. Bancescu, Eur. J. Med. Chem. 49, 417 (2012)
B. Chandrakantha, A.M. Isloor, P. Shetty, H.K. Fun, G. Hegde, Eur. J. Med. Chem. 71, 316 (2014)
A. Cansız, A. Cetin, C. Orek, M. Karatepe, K. Sarac, A. Kus, P. Koparir, Spectrochim. Acta A Mol. Biomol. Spectrosc. 97, 606 (2012)
V. Mathew, J. Keshavayya, V.P. Vaidya, M.H. Moinuddin, Khan. J. Coord. Chem. 61, 2629 (2008)
E.S. Il’inykh, D.G. Kim, Chem. Heterocycl. Com. 47, 636 (2011)
I. Tumosienė, I. Jonuškienė, K. Kantminienė, Z.J. Beresnevičius, Monatsh. Chem. 145, 319 (2014)
J. Stefańska, M. Struga, S. Tyski, J. Kossakowski, M. Dobosz, Pol. J. Microbiol. 57, 179 (2008)
R. Nunna, D. Ramachandran, V.B. Modi, K.J. Goswami, Der. Pharma Chemica 4, 639 (2012)
G.W. Ware, D.M. Whitacre, An. Introduction to Herbicides (2nd ed.) (Extracted from The Pesticide Book, 6th ed. (2004), Published by MeisterPro Information Resources, A division of Meister Media Worldwide, Willoughby, Ohio, USA), http://ipmworld.umn.edu/chapters/whitacreherb.htm. Accessed 30 June 2015
K.D. Patel, S.M. Prajapati, S.N. Panchal, H.D. Patel, Synthetic Commun. 44, 1859 (2014)
S.C. Holm, B.F. Straub, Org. Prep. Proc. Int. 43, 319 (2011)
I. Tumosienė, Z.J. Beresnevičius, Monatsh. Chem. 140, 1523 (2009)
I. Tumosienė, I. Jonuškienė, K. Kantminienė, Z.J. Beresnevičius, Monatsh. Chem. 143, 1441 (2012)
I. Tumosiene, Z.J. Beresnevicius, Chem. Heterocycl. Comp. 43, 1148 (2007)
L.N. Madhu, K.N. Suchetha, B.K. Sarojini, DIT 3, 297 (2011)
V. Jaishree, N. Ramdas, J. Sachin, B. Ramesh, J. Saudi Chem. Soc. 16, 371 (2012)
A.M. Snow, A.E. Ghaly, Am. J. Environ. Sci. 4, 89 (2008)
K.A. Sazanova, D.I. Bashmakov, A. Brazaitytė, Č. Bobinas, P. Duchovskis, A.S. Lukatkin, Zemdirbyste-Agriculture 99, 273 (2012)
A. Franklin, J. Acar, F. Anthony, R. Gupta, T. Nicholls, Y. Tamura, S. Thompson, E.J. Thelfall, D. Vose, M. van Vuuren, D.G. White, H.C. Wegener, M.L. Costarrica, Rev. Sci. Tech. Off. Int. Epiz. 20, 859 (2001)
B. Goodson, A. Ehrhardt, S. Ng, J. Nuss, K. Johnson, M. Giedlin, R. Yamamoto, A. Krebber, M. Ladner, M.B. Giacona, C. Vitt, J. Winter, Antimicrob. Agents Chemother. 43, 1429 (1999)
A. Petersen, F.M. Aarestrup, M. Hofshagen, H. Sipilä, A. Franklin, E. Gunnarsson, Microb. Drug Resist. 9, 381 (2003)
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Tumosienė, I., Jonuškienė, I., Kantminienė, K. et al. Synthesis and biological activity of 1,3,4-oxa(thia)diazole, 1,2,4-triazole-5-(thio)one and S-substituted derivatives of 3-((2-carboxyethyl)phenylamino)propanoic acid. Res Chem Intermed 42, 4459–4477 (2016). https://doi.org/10.1007/s11164-015-2290-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-015-2290-0