QSAR study by 1,2,4-triazoles using several physicochemical descriptors

Authors

  • Vesna Dimova Faculty of Technology and Metallurgy, Ss. Cyril & Methodius University, Skopje
  • Nada Perišić-Janjić Institute of Chemistry, Faculty of Sciences, Trg Dositeja Obradovića 3, 21000 Novi Sad

DOI:

https://doi.org/10.20450/mjcce.2009.223

Keywords:

QSAR, 1, 2, 4-triazole, surface tension, index of refraction, Q<sup>2</sup> values

Abstract

A QSAR study on the inhibition of Bacillus subtilis and Salmonella enteritidis by 1,2,4-triazoles using several physicochemical descriptors was performed. The 1,2,4-triazoles consist of 18 derivatives with N1-aryl- or N1- heteroaryl substituted rings and having aminomethyl or aminoethyl unit. The 6 best models were selected for the discussion. Initial regression analysis indicated that η plays a dominating role in modelling the activity in all proposed models. The correlation coefficients were 0.80 – 0.99 in all cases, and the standard deviation was below 0.42. Good cross-validation Q2 values were obtained (Q2 > 0.72). The ratio of PRESS/SSY ranges between 0.002–0.169, indicating that all proposed models are reliable QSAR models. A statistically significant result for the bacterial inhibitory activity of the chosen triazole derivatives against S. enteritidis, using the eight descriptors, was not obtained.

References

http://www.chem.swin.edu.au/modules/mod4/index.html (last accessed: 01.04.2008)

C. Hansch, A. Leo, Exploring QSAR: Fundamentals and Applications in Chemistry and Biology, American Chemical Society, Washington, DC, 1995.

M. Karelson, V. Lobanov, A. Katritzky, Quantum– Chemical Descriptors in QSAR/QSPR Studies, Chem. Rev., 96, 1027–1043 (1996).

M. Polyakova, L. Mei Jin, K. Ho Row, QSPR Models for Chromatographic Retention of some Azoles with Physicochemical properties, Bull. Korean Chem. Soc., 27, 211–218 (2006).

J–L. Xu, S–L. Gao, X–F. Zhang, Y–P. Xie, X–Y. Huang, X–G. Xie, QSAR Studies on 7–Substituted Fluoroquinolones, Chinese J. Struct. Chem., 26, 91–97 (2007).

P. Vasanthanathan, M. Lakshimi, M. Babu, A. Gupta, S. Kaskhedikar, QSAR Study of 3–Phenyl–5– acyloxymethyl–2H,5H–furan–2–ones as Antifungal Agents, Vhem. Pharm. Bull., 54, 583–587 (2006).

M. Tandon, J. P. Barthwal, T. N. Bhall, K P. Bhargava, Synthesis and Antiinflammatory Activity of Some New 3–(o–Substituted phenyl)–4–substituted–phenyl–5– alkyl/alkenyl–mercapto–1H–1,2,4–triazoles, Indian J. Chem., 20B, 1017–1018 (1981).

S. Rollas, Synthesis and Spectrometric Analysis of some 1,2,4–triazole–5–thiones, J. Fac. Pharm. Istanbul, 17, 155–163 (1981).

B. N. Goswami, J. C. S. Kataky, J. N. Baruah, Synthesis and Antibaceterial Activity of 1–(2,4–Dichlorobenzoyl)– 4–substituted Thiosemicarbazides, 1,2,4–Triazoles and Their Methyl Derivatives, J. Heterocyclic Chem., 21, 1225–1229 (1984).

A. R. Jalilian, S. Sattari, M. Bineshmarvasti, A. Shafiee, M. Daneshtalab, Synthesis and in vitro antifungal and cytotoxicity evaluation of thiazolo–4H–1,2,4–triazoles and 1,2,3–thiadiazolo–4H–1,2,4–triazoles–1,2,4–4H– triazoles–thiazoles–1,2,3–thiadiazoles, Arch. Der Pharmazie, 333, 347–354 (2000).

N. Guelerman, S. Rollas, M. Uelgen, Synthesis and in vitro microsomal metabolism of 4–ethyl–5–(4–fluorophenyl)– 2,4–dihydro–3H–1,2,4–triazole–3–thione and its potential metabolites, Boll. Chim. Farm., 137, 140–143 (1998).

S. M. Rabea, N. A. El–Koussi, H. Y. Hassan, T. Aboui– Fadi, Synthesis of 5–phenyl–1–(3–pyridyl)–1H–1,2,4– triazole–3–carboxylic Acid Derivatives of potential Anti– inflamatary Activity, Arch. der Pharmazie, 339, 32–40 (2006).

M. Wujec, M. Pitucha, M. Dobosz, U. Kosikowska, A. Malm, Synthesis and potential antimycotic activity of 4– substituted–3–(thiophene–2–yl–methyl)–1,2,4– triazoline–5–thiones, Acta Pharm., 54, 251–260 (2004).

G. Sahin, E. Palaska, P. Kelicen, R. Demirdamar G. Altmok, Synthesis of some new 1–acylthiosemicarbazides, 1,3,4–oxadiazoles, 1,3,4–thiadiazoles and 1,2,4–triazole– 3–thiones and their anti–inflamatory activities, Arzneim. Forsch., 51, 478–484 (2001).

A. R. Katritzky, S. Rachwal, B. Rachwal, The Chemistry of N–substituted Benzotriazoles. Part 4. A Novel and Versatile Method for the Mono–N–alkylation of Aromatic and Heteroaromatic Amines, J. Chem. Soc. Perkin Trans. I, 1, 805–809 (1987).

F. Collino, S. Volpe, Mannich bases of benzimidazoles, benzotriazoles and their analogs having pharmacological activity, Boll. Chim. Farm., 121, 328–331 (1982).

J. Cruz, E. Gracia–Ochoa, M. Castro, Experimental and Theoretical Study of the 3–Amino–1,2,4–triazole and 2– Aminothiazole Corrosion Inhibitors in Carbon Steel, J. Electrochem. Soc., 150, B26–B35 (2003).

M. A. Quraishi, D. Jamal, Fatty acid triazoles: Novel corrosion inhibitors for oil well steel (N–80) and mild steel, J. Am. Oil Chem. Soc., 77, 1107–1111 (2000).

R. L. Sung, B. H. Zoleski, U. S. P. 4 (278), 553 (1981); (Chem. Abstr. 1981, 95, 118196h).

E. E. Dolgopolyi, E. A. Eminov, U.S.S.R.P. 761, 543 (1980); (Chem. Abstr. 1981, 94, 50010g).

Nippon Oil Co. Ltd., Jpn. P. 81 (163), 195 (1981); (Chem. Abstr. 1982, 96, 194998a).

J. Chim, U. S. P. 4 (264), 436 (1981); (Chem. Abstr. 1981, 95, 159907j).

M. Lazarevic, V. Dimova, D. Molnar Gabor, V. Kakurinov, K. Colanceska, Synthesis of some N1–aryl/heteroarylaminomethyl/ ethyl–1,2,4–triazoles and their antibacterial and antifungal activities, Heterocyclic Communications, 7 (6), 577–582 (2001).

K. Colanceska, V. Dimova, V. Kakurinov, D. Molnar– Gabor, A. Buzarovska, Synthesis and antibacterial and antifungal activity of 4–substituted–5–aryl–1,2,4– triazole, Molecules, 6, 815–824 (2001).

N. Perisic–Janjic, M. Acinski, N. Janjic, M. Lazarevic, V. Dimova, Study of the lipophilicity of some 1,2,4–triazole derivatives by RPHPLC and TLC, Journal of Planar Chromatography, 13, 281–284 (2000).

B. Spasovska-Gerasimova, S. Ilievska, K. Čolančeska, M. Lazarevic, V. Dimova, Tretment of cotton textile material with N1–

–(1,2,4–triazole–1–yl)methyl)–4–amino– 1,2,4–triazole for imparting antimicrobial properties, Vlákna a textil, 9 (2), 46–49 (2002).

S. Rollas, N. Kalyoncuoglu, D. Sür–Altiner, Y. Yegenoglu, 5–(4–Aminophenyl)–4–substituted–2,4–dihydro– 3H–1,2,4–triazole–3–thiones: Synthesis and antibacerial and antifungal activities, Pharmazie, 48, 308– 309 (1993).

ACD-Lab software for calculationg the referred physicochemical properties, Chemsketh S.O., http: //www.acdlabs.com (last accessed: 01.04.2008)

http://www.syrres.com/esc/est_kowdemo.htm (last accessed: 01.04.2008)

Atkins, P.W. Quanta; Oxford University Press; Oxford, 1991.

Origin – program package, Version 5,0, Microcal Software Inc., USA, 1997.

V. Dimova, K. Colanceska Ragenovic, V. Kakurinov, QSAR of some N1–aryl/heteroarylaminometyl/ethyl– 1,2,4–triazoles. Part II: Antimicrobial activity against Bacillus subtilis, Int. J. Mol. Sci., 7, 119–129 (2006).

V. Dimova, K. Čolančeska, V. Kakurinov, QSAR of some N1–aryl/hetero–arylaminomethyl/ethyl–1,2,4–triazoles. Part III: Antimicrobial activity against Salmonella enteritidis, Bull. Chem. Technol. Macedonia, 25 (1), 1–7 (2006).

Downloads

Published

2009-06-15

How to Cite

Dimova, V., & Perišić-Janjić, N. (2009). QSAR study by 1,2,4-triazoles using several physicochemical descriptors. Macedonian Journal of Chemistry and Chemical Engineering, 28(1), 79–89. https://doi.org/10.20450/mjcce.2009.223

Issue

Vol. 28 No. 1 (2009)

Section

Organic Chemistry

License

The authors agree to the following licence: Attribution-NonCommercial 4.0 International (CC BY-NC 4.0)

  • Adapt — remix, transform, and build upon the material
  • for any purpose, even commercially.
The licensor cannot revoke these freedoms as long as you follow the license terms.

 Under the following terms:

  • Attribution — You must give appropriate credit, provide a link to the license, and indicate if changes were made. You may do so in any reasonable manner, but not in any way that suggests the licensor endorses you or your use.

  • NonCommercial — You may not use the material for commercial purposes.