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Research Article

Synthesis and receptor dependent 4D-QSAR studies of 4,5-dihydro-1,3,4-oxadiazole derivatives targeting cannabinoid receptor

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Pages 175-190 | Received 01 Dec 2020, Accepted 18 Jan 2021, Published online: 23 Feb 2021

References

  • S. Munro, K.L. Thomas, and M. Abu-Shaar, Molecular characterization of a peripheral receptor for cannabinoids, Nature 365 (1993), pp. 61–65. doi:10.1038/365061a0.
  • L.A. Matsuda, S.J. Lolait, M.J. Brownstein, A.C. Young, and T.I. Bonner, Structure of a cannabinoid receptor and functional expression of the cloned cDNA, Nature 346 (1990), pp. 561–564. doi:10.1038/346561a0.
  • A.C. Howlett, F. Barth, T.I. Bonner, G. Cabral, P. Casellas, W.A. Devane, C.C. Felder, M. Herkenham, K. Mackie, B.R. Martin, R. Mechoulam, and R.G. Pertwee, International union of pharmacology. XXVII. classification of cannabinoid receptors, Pharmacol. Rev. 54 (2002), pp. 161–202. doi:10.1124/pr.54.2.161.
  • R.P. Picone and D.A. Kendall, Minireview: From the bench, toward the clinic: Therapeutic opportunities for cannabinoid receptor modulation, Mol. Endocrinol. 29 (2015), pp. 801–813. doi:10.1210/me.2015-1062.
  • A.M. Malfitano, S. Basu, K. Maresz, M. Bifulco, and B.N. Dittel, What we know and do not know about the cannabinoid receptor 2 (CB2), Semin. Immunol. 26 (2014), pp. 369–379. doi:10.1016/j.smim.2014.04.002.
  • X. Xu, Y. Liu, S. Huang, G. Liu, C. Xie, J. Zhou, W. Fan, Q. Li, Q. Wang, D. Zhong, and X. Miao, Overexpression of cannabinoid receptors CB1 and CB2 correlates with improved prognosis of patients with hepatocellular carcinoma, Cancer Genet. Cytogenet. 171 (2006), pp. 31–38. doi:10.1016/j.cancergencyto.2006.06.014.
  • Z. Qamri, A. Preet, M.W. Nasser, C.E. Bass, G. Leone, S.H. Barsky, and R.K. Ganju, Synthetic cannabinoid receptor agonists inhibit tumor growth and metastasis of breast cancer, Mol. Cancer Ther. 8 (2009), pp. 3117–3129. doi:10.1158/1535-7163.MCT-09-0448.
  • S. Sarfaraz, F. Afaq, V.M. Adhami, A. Malik, and H. Mukhtar, Cannabinoid receptor agonist-induced apoptosis of human prostate cancer cells LNCaP proceeds through sustained activation of ERK1/2 leading to G1 cell cycle arrest, J. Biol. Chem. 281 (2006), pp. 39480–39491. doi:10.1074/jbc.M603495200.
  • S. Sarfaraz, V.M. Adhami, D.N. Syed, F. Afaq, and H. Mukhtar, Cannabinoids for cancer treatment: Progress and promise, Cancer Res. 68 (2008), pp. 339–342. doi:10.1158/0008-5472.CAN-07-2785.
  • A. Preet, Z. Qamri, M.W. Nasser, A. Prasad, K. Shilo, X. Zou, J.E. Groopman, and R.K. Ganju, Cannabinoid receptors, CB1 and CB2, as novel targets for inhibition of non-small cell lung cancer growth and metastasis, Cancer Prev. Res. (Phila.) 4 (2011), pp. 65–75. doi:10.1158/1940-6207.CAPR-10-0181.
  • J. Shim and A.D. Mackerell, Computational ligand-based rational design: Role of conformational sampling and force fields in model development, Medchemcomm 2 (2011), pp. 356–370. doi:10.1039/c1md00044f.
  • J.B. Ghasemi, M. Salahinejad, and M.K. Rofouei, Review of the quantitative structure–activity relationship modelling methods on estimation of formation constants of macrocyclic compounds with different guest molecules, Supramol. Chem. 23 (2011), pp. 614–629. doi:10.1080/10610278.2011.581281.
  • A.J. Hopfinger, S. Wang, J.S. Tokarski, B. Jin, M.G. Albuquerque, J.P. Madhav, and C. Duraiswami, Construction of 3D-QSAR models using the 4D-QSAR analysis formalism, J. Am. Chem. Soc. 119 (1997), pp. 10509–10524. doi:10.1021/ja9718937.
  • H. Khalilullah, M.J. Ahsan, M. Hedaitullah, S. Khan, and B. Ahmed, 1,3,4-oxadiazole: A biologically active scaffold, Mini. Rev. Med. Chem. 12 (2012), pp. 789–801. doi:10.2174/138955712801264800.
  • A.S. Kiselyov, M.N. Semenova, N.B. Chernyshova, A. Leitao, A.V. Samet, K.A. Kislyi, M.M. Raihstat, T. Oprea, H. Lemcke, M. Lantow, D.G. Weiss, N.N. Ikizalp, S.A. Kuznetsov, and V.V. Semenov, Novel derivatives of 1,3,4-oxadiazoles are potent mitostatic agents featuring strong microtubule depolymerizing activity in the sea urchin embryo and cell culture assay, Eur. J. Med. Chem. 45 (2010), pp. 1683–1697. doi:10.1016/j.ejmech.2009.12.072.
  • Z. Li, Z. Gu, K. Yin, R. Zhang, Q. Deng, and J. Xiang, Synthesis of substituted-phenyl-1,2,4-triazol-3-thione analogues with modified d-glucopyranosyl residues and their antiproliferative activities, Eur. J. Med. Chem. 44 (2009), pp. 4716–4720. doi:10.1016/j.ejmech.2009.05.030.
  • E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin, UCSF chimera–a visualization system for exploratory research and analysis, J. Comput. Chem. 25 (2004), pp. 1605–1612. doi:10.1002/jcc.20084.
  • D. Van Der Spoel, E. Lindahl, B. Hess, G. Groenhof, A.E. Mark, and H.J.C. Berendsen, Gromacs: Fast, flexible, and free, J. Comput. Chem. 26 (2005), pp. 1701–1718. doi:10.1002/jcc.20291.
  • T. Darden, D. York, and L. Pedersen, Particle mesh ewald: An N-log(N) method for ewald sums in large systems, J. Chem. Phys. 98 (1993), pp. 10089–10092. doi:10.1063/1.464397.
  • H.J.C. Berendsen, J.P.M. Postma, W.F.V. Gunsteren, A. Dinola, and J.R. Haak, Molecular dynamics with coupling to an external bath, J. Chem. Phys. 81 (1984), pp. 3684–3690. doi:10.1063/1.448118.
  • R. Patil and S. Sawant, Molecular dynamics guided receptor independent 4D QSAR studies of substituted coumarins as anticancer agents, Curr. Comput. Aided Drug Des. 11 (2015), pp. 39–50. doi:10.2174/1573409911666150617113933.
  • P. Gramatica, N. Chirico, E. Papa, S. Cassani, and S. Kovarich, QSARINS: A new software for the development, analysis, and validation of QSAR MLR models, J. Comput. Chem. 34 (2013), pp. 2121–2132. doi:10.1002/jcc.23361.
  • E.G. Barbosa, K.F.M. Pasqualoto, and M.M.C. Ferreira, The receptor-dependent LQTA-QSAR: Application to a set of trypanothione reductase inhibitors, J. Comput. Aided Mol. Des. 26 (2012), pp. 1055–1065. doi:10.1007/s10822-012-9598-2.
  • A. Golbraikh and A. Tropsha, Beware of q2!, J. Mol. Graph. Model. 20 (2002), pp. 269–276. doi:10.1016/S1093-3263(01)00123-1.
  • A. Golbraikh and A. Tropsha, Predictive QSAR modeling based on diversity sampling of experimental datasets for the training and test set selection, J. Comput. Aided Mol. Des. 16 (2002), pp. 357–369. doi:10.1023/A:1020869118689.
  • S. Lateef, S. Reddy Krishna Mohan, and S. Reddy Jayarama Reddy, Electroorganic synthesis of benzathine, Tetrahedron Lett. 48 (2007), pp. 77–80. doi:10.1016/j.tetlet.2006.11.008.
  • M. Ślusarczyk, W.M. De Borggraeve, G. Hoornaert, F. Deroose, and J.T.M. Linders, Synthesis and biological evaluation of methylene-bridged analogs of the potent cannabinoid receptor antagonist rimonabant, European J. Org. Chem. 2008 (2008), pp. 1350–1357. doi:10.1002/ejoc.200700960.
  • K. Rikimaru, T. Wakabayashi, H. Abe, H. Imoto, T. Maekawa, O. Ujikawa, K. Murase, T. Matsuo, M. Matsumoto, C. Nomura, H. Tsuge, N. Arimura, K. Kawakami, J. Sakamoto, M. Funami, C.D. Mol, G.P. Snell, K.A. Bragstad, B.C. Sang, D.R. Dougan, T. Tanaka, N. Katayama, Y. Horiguchi, and Y. Momose, A new class of non-thiazolidinedione, non-carboxylic-acid-based highly selective peroxisome proliferator-activated receptor (PPAR) γ agonists: Design and synthesis of benzylpyrazole acylsulfonamides, Biorg. Med. Chem. 20 (2012), pp. 714–733. doi:10.1016/j.bmc.2011.12.008.
  • R. Socher, C. Csongár, I. Müler, and G. Tomaschewski, Photochemie substituierter 1,3,4-Δ2-oxadiazolinen; synthese von 2,4,5-arylsubstituierten 1,3,4-Δ2-oxadiazolinen, Zeitschrift für Chemie 21 (1981), pp. 182–183. doi:10.1002/zfch.19810210505.
  • N. Chirico and P. Gramatica, Real external predictivity of QSAR models: How to evaluate it? Comparison of different validation criteria and proposal of using the concordance correlation coefficient, J. Chem. Inf. Model. 51 (2011), pp. 2320–2335. doi:10.1021/ci200211n.
  • J.B. Ghasemi, R. Safavi-Sohi, and E.G. Barbosa, 4D-LQTA-QSAR and docking study on potent gram-negative specific LPXC inhibitors: A comparison to CoMFA modeling, Mol. Divers. 16 (2012), pp. 203–213. doi:10.1007/s11030-011-9340-3.

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