Structure-Based Design, Synthesis and Antidepressant-Like Activity of Phenylthiazolyl-1H,2H,3H,4H-naphthalene Derivatives

Archana Uppal; Anita Singh; Preeti Kothiyal

doi:10.14233/ajchem.2015.18457

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Issue Published : December 27, 2014

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

Structure-Based Design, Synthesis and Antidepressant-Like Activity of Phenylthiazolyl-1H,2H,3H,4H-naphthalene Derivatives

https://doi.org/10.14233/ajchem.2015.18457

Archana Uppal

Shri Guru Ram Rai Institute of Technology and Science, Patel Nagar, Dehradun-248 001, India

Anita Singh

Department of Pharmacy, Kumaon University, Bhimtal Campus, Bhimtal-263 136, India

Preeti Kothiyal

Shri Guru Ram Rai Institute of Technology and Science, Patel Nagar, Dehradun-248 001, India

Corresponding Author(s) : Anita Singh

asingh25661@gmail.com

Asian Journal of Chemistry, Vol. 27 No. 1 (2015): Vol 27 Issue 1
Article Published : December 29, 2014

Abstract

In recent years, a bacterial homologue of SERT (LeuT) target protein was solved in complex with sertraline and offers promising pathway for the hit identification. Herein, we cover advanced computational methodology for hybrid class 1,2,3,4-tetrahydronaphalene and phenylthiazole derivatives using three two modules. First, these drug-like candidates were filtered by molecular properties from a training set of library. Second, compounds were prioritized according to previously optimized CDocker docking methodology. Finally, synthesized in silico actives were demonstrated enhanced antidepressant-like activity with reasonable non-toxicity using standard mice model (s).

Keywords

1 2 3 4-Tetrahydronaphthalene Phenylthiazole Molecular properties Docking

Uppal, A., Singh, A., & Kothiyal, P. (2014). Structure-Based Design, Synthesis and Antidepressant-Like Activity of Phenylthiazolyl-1H,2H,3H,4H-naphthalene Derivatives. Asian Journal of Chemistry, 27(1), 379–384. https://doi.org/10.14233/ajchem.2015.18457

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References

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References

C.L.M.L.J. Verlinde and W.G.J. Hol, Structure, 2, 577 (1994); doi:10.1016/S0969-2126(00)00060-5.

D. Kuntz, Science, 257, 1078 (1992); doi:10.1126/science.257.5073.1078.

B.S.P. Romano T. Kroemer, Curr. Protein Pept. Sci., 8, 312 (2007); doi:10.2174/138920307781369382.

E. Varkondi, F. Pinter, K. Robert, R. Schwab, N. Breza, L. Orfi, G. Keri and I. Petak, J. Recept. Signal Transduct. Res., 28, 295 (2008); doi:10.1080/10799890802084671.

C. Ketron, W.A. Denny, D.E. Graves and N. Osheroff, Biochemistry, 51, 1730 (2012); doi:10.1021/bi201159b.

Q.Z. Zheng, F. Zhang, K. Cheng, Y. Yang, Y. Chen, Y. Qian, H.J. Zhang, H.Q. Li, C.F. Zhou, S.Q. An, Q.C. Jiao and H.L. Zhu, Bioorg. Med. Chem., 18, 880 (2010); doi:10.1016/j.bmc.2009.11.037.

M. Buchanan, J.H. Shih, J.W. Astin, G.W. Rewcastle, J.U. Flanagan, P.S. Crosier and P.R. Shepherd, Clin. Sci., 122, 449 (2012); doi:10.1042/CS20110412.

G.E. Simon, Biol. Psychiatry, 54, 208 (2003); doi:10.1016/S0006-3223(03)00420-7.

R. Lanzenberger, G.S. Kranz, D. Haeusler, E. Akimova, M. Savli, A. Hahn, M. Mitterhauser, C. Spindelegger, C. Philippe, M. Fink, W. Wadsak, G. Karanikas and S. Kasper, Neuroimage, 63, 874 (2012); doi:10.1016/j.neuroimage.2012.07.023.

L.L. Brunton, D.K. Blumenthal, N. Murri, R.H. Dandan and B.C. Knollmann, Goodman & Gilman's The Pharmacological Basis of Therapeutics, McGraw-Hill, New York, edn 12 (2011).

J.M. Grohol, Top 25 Psychiatric Medication Prescriptions for 2011 Psych Central (2012); Available from: http://psychcentral.com/lib/2012/top-25-psyciatric-medication-prescriptions-for-2011.

Z. Zhou, J. Zhen, N.K. Karpowich, C.J. Law, M.E.A. Reith and D.N. Wang, Nat. Struct. Mol. Biol., 16, 652 (2009); doi:10.1038/nsmb.1602.

A. Uppal, P. Kothiyal and A. Singh, J. Heterocycl. Chem.; doi 10.1002/jhet.2203.

http://www.chemaxon.com/marvin/sketch/index.php Retrieved 1 January 2013.

Calculated based on the methodology available from: http://www.molinspiration.com/cgi-bin/properties Retrieved 9 January 2013.

Calculated based on the methodology available from: http://www.organic-chemistry.org/prog/peo/ Retrieved 15 January 2013.

K. Bhandari, V.L. Sharma, C.M. Singh, G. Shanker and H.K. Singh, J. Indian Chem., 39B, 468 (2000).

R.D. Porsolt, M. Le Pichon and M. Jalfre, Nature, 266, 730 (1977); doi:10.1038/266730a0.

L. Steru, R. Chermat, B. Thierry and P. Simon, Psychopharmacology, 85, 367 (1985); doi:10.1007/BF00428203.

C.S. Hall and E. L. Ballachey, Univ. Calif. Publ. Psych, 6, 1 (1932).

Test No. 423: Acute Oral Toxicity-Acute Toxic Class Method; OECD Guidelines for the Testing of Chemicals, pp. 1-14(14) (2010).

Z. Rogoz, G. Skuza and A. Kodzinska, Pol. J. Pharmacol., 56, 519 (2004).

Y. Kitamura, H. Araki, K. Shibata, Y. Gomita and Y. Tanizaki, Eur. J. Pharmacol., 481, 75 (2003); doi:10.1016/j.ejphar.2003.09.008.

Issue

Vol. 27 No. 1 (2015): Vol 27 Issue 1

Structure-Based Design, Synthesis and Antidepressant-Like Activity of Phenylthiazolyl-1H,2H,3H,4H-naphthalene Derivatives

Corresponding Author(s) : Anita Singh

Abstract

Keywords

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