QSAR STUDY OF PHENOTHIAZINES

Atena PÎRVAN-MOLDOVAN; Sara  ERSALI; Raluca  POP

Authors

Atena PÎRVAN-MOLDOVAN Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeș-Bolyai University, Cluj-Napoca, Romania. Corresponding author: diudea@chem.ubbcluj.ro. https://orcid.org/0000-0002-3092-3135
Sara ERSALI Department of Chemistry, Faculty of Chemistry and Chemical Engineering, Babeș-Bolyai University, Cluj-Napoca, Romania. Corresponding author: diudea@chem.ubbcluj.ro. https://orcid.org/0000-0001-9456-6678
Raluca POP Faculty of Pharmacy, “Victor Babeş” University of Medicine and Pharmacy, Timişoara, Romania. Email: pop.raluca@umft.ro. https://orcid.org/0000-0001-6795-0009

Keywords:

phenothiazine, hypermolecule, LD50, logP, topological indices

Abstract

A QSAR study on a set of 30 phenothiazines performed within a hypermolecule frame, to model their logP and LD₅₀ values, is reported. The initial set of molecules was split into a training set and the test set; Cluj topological indices and some quantum mechanical descriptors have been used to derive the models, which were next tested for predictability by LOO, external validation and similarity clustering.

References

M.V. Diudea, “Fenotiazine și medicamente structural înrudite”, PhD Thesis, Inst. Chem. Cluj, 1979.

S.M. Free, Jr, J.W. Wilson, J. Med. Chem., 1964, 7, 395.

H. Kubinyi, “QSAR: Hansch analysis and related approaches”, R. Mannhold, Krogsgaard-Larsen P., Timmerman H. (Eds.),VCH Publishers, New York, 1993.

M.V. Diudea, (Ed.), QSPR/QSAR “Studies by Molecular Descriptors”, NOVA, New York, 2001.

M.V. Diudea, MATCH Commun. Math. Comput. Chem., 1997, 35, 169.

M.V. Diudea, J. Chem. Inf. Comput. Sci., 1997, 37, 300.

O. Ursu, M.V. Diudea, TOPOCLUJ software program, Babes-Bolyai University, Cluj, 2005.

C.D. Moldovan, A. Costescu, G. Katona and M.V. Diudea, MATCH Commun. Math. Comput. Chem., 2008, 60, 977.

A.T. Balaban, A. Chiriac, I. Motoc, and Z. Simon, “Steric Fit in QSAR” (Lectures Notes in Chemistry, Vol. 15), Springer, Berlin, 1980.

A.A.Toropov, A.P.Toropova, Internet El. J. Molec. Design, 2002, 1, 108.

A.A.Toropov, A.P.Toropova, J. Mol. Struct. (Theochem), 2001, 538, 287.

P. Willett, J.M. Barnard, G.M. Downs, J. Chem. Inf. Comput. Sci., 1998, 38(6), 983.

Gaussian 09, Gaussian Inc Wallingford CT, Revision A.1 (2009) Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam NJ, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas Ö, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ.

L. Jäntschi, LOO Analysis (LOO: leave one out), Academic Direct Library of Software, 2005, Available at: http://l.academicdirect.org/Chemistry/SARs/SARs/loo/.

J.G. Topliss, R.J. Costello, J. Med. Chem., 1972, 15, 1066.