Structure Activity Relationships, QSAR Modeling and Drug-Like Calculations of TP Inhibition of 1,3,4-Oxadiazoline-2-Thione Derivatives

Almi, Zineb; Belaidi, Salah; Lanez, Touhami; Tchouar, Noureddine

doi:10.18052/www.scipress.com/ILCPA.37.113

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Structure Activity Relationships, QSAR Modeling and Drug-Like Calculations of TP Inhibition of 1,3,4-Oxadiazoline-2-Thione Derivatives

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Abstract:

QSAR studies have been performed on twenty-one molecules of 1,3,4-oxadiazoline-2-thiones. The compounds used are among the most thymidine phosphorylase (TP) inhibitors. A multiple linear regression (MLR) procedure was used to design the relationships between molecular descriptor and TP inhibition of the 1,3,4-oxadiazoline-2-thione derivatives. The predictivity of the model was estimated by cross-validation with the leave-one-out method. Our results suggest a QSAR model based of the following descriptors: logP, HE, Pol, MR, MV, and MW, qO1, SAG, for the TP inhibitory activity. To confirm the predictive power of the models, an external set of molecules was used. High correlation between experimental and predicted activity values was observed, indicating the validation and the good quality of the derived QSAR models.

Info:

Periodical:

International Letters of Chemistry, Physics and Astronomy (Volume 37)

Pages:

113-124

DOI:

https://doi.org/10.18052/www.scipress.com/ILCPA.37.113

Citation:

Z. Almi et al., "Structure Activity Relationships, QSAR Modeling and Drug-Like Calculations of TP Inhibition of 1,3,4-Oxadiazoline-2-Thione Derivatives", International Letters of Chemistry, Physics and Astronomy, Vol. 37, pp. 113-124, 2014

Online since:

August 2014

Authors:

Zineb Almi, Salah Belaidi, Touhami Lanez, Noureddine Tchouar

Keywords:

1,3,4-Oxadiazoline-2-Thionederivative, Drug-Like, MLR, QSAR, SAR, TP Inhibitory

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Open Access

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

References:

M. J. S. Dewar, E. G. Zoebisch, E. F. Healy, J.J.P. Stewart, J. Am. Chem. Soc. 107 (1985).

N. Melkemi, S. Belaidi, J. Comput. Theor. Nanosci. 11 (2014) 801-806.

V. A. McNally, M. Rajabi, A. Gbaj, I. J. Stratford, P. N. Edwards, K. T. Douglas, R. A. Bryce, M. Jaffar, S. Freeman, J. Pharm. Pharmacol. 59 ( 2007) 537.

P.A., Schwartz, M.J., Vetticatt, V.L., Schramm, Biochemistry 50 (2011) 1412.

M. Joydeep, Ch. Raja, S. Saikat, V. anjay, De. Biplab, T. K. Ravi, Der. Pharma. Chemica 1(2) (2009) 188-198.

P. Joachim, M. Nathalie, K. Christine, M. Gerald, Bioorg & Med. Chemistry 20 (2012) 5343-5351.

S. A. Shahzad. M. Yar , M. Bajda, B. Jadoon , Z. Ali Khan, S. A. Raza Naqvi, A. J. Shaikh, K. Hayat, A. Mahmmod, N. Mahmood, S. Filipek. Bioorg. Med. Chem. 22 (2014) 1008-1015.

Hyperchem (Molecular Modeling System) Hypercube, Inc., 1115 Nw, 4th Street, Gainesville, Fl 32601; Usa, (2007).

Gaussian 09, Revision B. 01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H. P. Hratchian, A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, R. L. Martin, K. Morokuma, V. G. Zakrzewski, G. A. Voth, P. Salvador, J. J. Dannenberg, S. Dapprich, A. D. Daniels, O. Farkas, J. B. Foresman, J. V. Ortiz, J. Cioslowski and D. J. Fox, Gaussian, Inc., Wallingford CT, (2010).

V. N. Viswanadhan, A. K. Ghose, G. R. Revankar, And R. K. Robins, J. Chem. Inf. Comp. Sci. 29 (1989) 163.

K. Ghose, G. M. Crippen, J. Chem. Inf. Comput. Sci. 27 (1987) 21.

N. Bodor, Z. Gabanyi, and C. K. Wong, J. Am. Chem. Soc. 111 (1989) 3783.

A. Gavezzotti, J. Am. Chem. Soc. 105 (1983) 5220.

K. J. Miller, J. Am. Chem. Soc. 112 (1990) 8533.

SPSS software packages, SPSS Inc., 444 North Michigan Avenue, Suite 3000, Chicago, Illinoi, 60611, USA.

J. Wang, X.Q. Xie, T. Hou, X. Xu, Fast J. Phys. Chem. A. 111 (2007) 4443-4448.

G. L. Patrick, An Introduction to Médicinal Chemistry, Oxford University Press, Oxford 1995, 140-141.

N. I. Zhokhova, I. I. Baskin, V. A. Palyulin, A. N. Zefirov, N. S. Zefirov. Russ. Chem. B+. 52 (2003) 1061.

R. Mazri, S. Belaidi, A. Kerassa, T. Lanez, International Letters of Chemistry, Physics and Astronomy 14(2) (2014) 146-167.

J. Petit, N. Maurice, C. Kaiser, G. Maggiora, Bioorg. Med. Chem. 20 (2012) 5343-5351.

G. Thirunarayanan, International Letters of Chemistry, Physics and Astronomy 5 (2014) 89-98.

G. Alamelumangai, N. Santhi, International Letters of Chemistry, Physics and Astronomy 5 (2014) 124-133.

Dipti L. Namera, Umed C. Bhoya, International Letters of Chemistry, Physics and Astronomy 11(2) (2014) 159-166.

Hasmukh R. Khunt, Piyush P. Pipaliya, Satish M. Ghelani, Jayesh S. Babariya, Yogesh T. Naliapara, International Letters of Chemistry, Physics and Astronomy 12 (2014) 20-25. ( Received 28 July 2014; accepted 06 August 2014 ).

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