Design, Synthesis, and Functional Evaluation of 1, 5-Disubstituted Tetrazoles as Monoamine Neurotransmitter Reuptake Inhibitors |
Paudel, Suresh
(College of Pharmacy, Chonnam National University)
Wang, Shuji (College of Pharmacy, Chonnam National University) Kim, Eunae (College of Pharmacy, Chosun University) Kundu, Dooti (College of Pharmacy, Chonnam National University) Min, Xiao (College of Pharmacy, Chonnam National University) Shin, Chan Young (Department of Pharmacology and Department of Advanced Translational Medicine, School of Medicine, Konkuk University) Kim, Kyeong-Man (College of Pharmacy, Chonnam National University) |
1 | Kulkarni, S. K. and Dhir, A. (2009) Current investigational drugs for major depression. Expert Opin. Investig. Drugs 18, 767-788. DOI |
2 | Le Bourdonnec, B., Meulon, E., Yous, S., Goossens, J. F., Houssin, R. and Henichart, J. P. (2000) Synthesis and pharmacological evaluation of new pyrazolidine-3, 5-diones as AT(1) angiotensin II receptor antagonists. J. Med. Chem. 43, 2685-2697. DOI |
3 | Kim, K. M., Valenzano, K. J., Robinson, S. R., Yao, W. D., Barak, L. S. and Caron, M. G. (2001) Differential regulation of the dopamine D2 and D3 receptors by G protein-coupled receptor kinases and betaarrestins. J. Biol. Chem. 276, 37409-37414. DOI |
4 | Maier, J. A., Martinez, C., Kasavajhala, K., Wickstrom, L., Hauser, K. E. and Simmerling, C. (2015) ff14SB: improving the accuracy of protein side chain and backbone parameters from ff99SB. J. Chem. Theory Comput. 11, 3696-3713. DOI |
5 | Abraham, M. J., Murtola, T., Schulz, R., Pall, S., Smith, J. C., Hess, B. and Lindahl, E. (2015) GROMACS: high performance molecular simulations through multi-level parallelism from laptops to supercomputers. SoftwareX 1-2, 19-25. DOI |
6 | Gao, Y. L., Zhao, G. L., Liu, W., Shao, H., Wang, Y. L., Xu, W. R., Tang, L. D. and Wang, J. W. (2010) Design, synthesis and in vivo hypoglycemic activity of tetrazole-bearing N-glycosides as SGLT2 inhibitors. Indian. J. Chem. 49B, 1499-1508. |
7 | John, E. O., Kirchmeier, R. L. and Shreeve, J. M. (1989) Reactions of 5-(perfluoroalkyl)tetrazolates with cyanogen, nitrosyl, and cyanuric chlorides. Inorg. Chem. 28, 4629-4633. DOI |
8 | Jorgensen, W. L., Chandrasekhar, J. and Madura, J. D. (1983) Comparison of simple potential functions for simulating liquid water. J. Chem. Phys. 79, 926. DOI |
9 | Masson, J., Sagne, C., Hamon, M. and El Mestikawy, S. (1999) Neurotransmitter transporters in the central nervous system. Pharmacol. Rev. 51, 439-464. |
10 | Laskowski, R. A. and Swindells, M. B. (2011) LigPlot+: multiple ligand-protein interaction diagrams for drug discovery. J. Chem. Inf. Model. 51, 2778-2786. DOI |
11 | Singh, H., Chawla, A. S., Kapoor, V. K., Paul, D. and Malhotra, R. K. (1980) Medicinal chemistry of tetrazoles. Prog. Med. Chem. 17, 151-183. DOI |
12 | Yu, S. S., Lefkowitz, R. J. and Hausdorff, W. P. (1993) Beta-adrenergic receptor sequestration. A potential mechanism of receptor resensitization. J. Biol. Chem. 268, 337-341. DOI |
13 | Subbaiah, M. A. M. (2018) Triple reuptake inhibitors as potential therapeutics for depression and other disorders: design paradigm and developmental challenges. J. Med. Chem. 61, 2133-2165. DOI |
14 | Klapotke, T. M., Stierstorfer, J. and Weber, B. (2009) New energetic materials: synthesis and characterization of copper 5-nitriminotetrazolates. Inorg. Chim. Acta 362, 2311-2320. DOI |
15 | Prins, J., Olivier, B. and Korte, S. M. (2011) Triple reuptake inhibitors for treating subtypes of major depressive disorder: the monoamine hypothesis revisited. Expert Opin. Investig. Drugs 20, 1107-1130. DOI |
16 | Waterhouse, A., Bertoni, M., Bienert, S., Studer, G., Tauriello, G., Gumienny, R., Heer, F. T., de Beer, T. A. P., Rempfer, C., Bordoli, L., Lepore, R. and Schwede, T. (2018) SWISS-MODEL: homology modelling of protein structures and complexes. Nucleic Acids Res. 46, W296-W303. DOI |
17 | Zhang, X. and Kim, K. M. (2017) Multifactorial regulation of G protein-coupled receptor endocytosis. Biomol. Ther. (Seoul) 25, 26-43. DOI |
18 | Trott, O. and Olson, A. J. (2010) AutoDock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization, and multithreading. J. Comput. Chem. 31, 455-461. DOI |
19 | Wang, K. H., Penmatsa, A. and Gouaux, E. (2015) Neurotransmitter and psychostimulant recognition by the dopamine transporter. Nature 521, 322-327. DOI |
20 | Xue, W., Wang, P., Tu, G., Yang, F., Zheng, G., Li, X., Li, X., Chen, Y., Yao, X. and Zhu, F. (2018) Computational identification of the binding mechanism of a triple reuptake inhibitor amitifadine for the treatment of major depressive disorder. Phys. Chem. Chem. Phys. 20, 6606-6616. DOI |
21 | El-Sayed, W. A., El-Kosy, S. M., Ali, O. M., Emselm, H. M. and Abdel-Rahman, A. A. (2012) Anticancer activity of new (tetrazol-5-yl)methylindole derivatives and their acyclic c-nucleoside analogs. Acta Pol. Pharm. 69, 669-677. |
22 | Vieira, E., Huwyler, J., Jolidon, S., Knoflach, F., Mutel, V. and Wichmann, J. (2005) 9H-Xanthene-9-carboxylic acid [1,2,4]oxadiazol3-yl- and (2H-tetrazol-5-yl)-amides as potent, orally available mGlu1 receptor enhancers. Bioorg. Med. Chem. Lett. 15, 4628-4631. DOI |
23 | Wagle, S., Adhikari, A. V. and Kumari, N. S. (2009) Synthesis of some new 4-styryltetrazolo[1,5-a]quinoxaline and 1-substituted4-styryl[1,2,4]triazolo[4,3-a]quinoxaline derivatives as potent anticonvulsants. Eur. J. Med. Chem. 44, 1135-1143. DOI |
24 | Wagner, D., Wellmer, F., Dilks, K., William, D., Smith, M. R., Kumar, P. P., Riechmann, J. L., Greenland, A. J. and Meyerowitz, E. M. (2004) Floral induction in tissue culture: a system for the analysis of LEAFY-dependent gene regulation. Plant J. 39, 273-282. DOI |
25 | Dhayanithi, V., Shafi Syed, S., Kumaran, K., Jai Sankar, K. R., Ragavan Venkat, R., Goud Kumar Sanath, P., Kumari Suchetha, N. and Pati Hari, N. (2011) Synthesis of selected 5-thio-substituted tetrazole derivatives and evaluation of their antibacterial and antifungal activities. J. Serb. Chem. Soc. 76, 165-175. DOI |
26 | Burger, A. (1991) Isosterism and bioisosterism in drug design. Prog. Drug Res. 37, 287-371. |
27 | Cho, D., Zheng, M., Min, C., Ma, L., Kurose, H., Park, J. H. and Kim, K. M. (2010) Agonist-induced endocytosis and receptor phosphorylation mediate resensitization of dopamine D(2) receptors. Mol. Endocrinol. 24, 574-586. DOI |
28 | Hess, B., Bekker, H., Berendsen, H. J. C. and Fraaije, J. G. E. M. (1997) LINCS: a linear constraint solver for molecular simulations. J. Comput. Chem. 18, 1463-1472. DOI |
29 | Coleman, J. A., Green, E. M. and Gouaux, E. (2016) X-ray structures and mechanism of the human serotonin transporter. Nature 532, 334-339. DOI |
30 | Dahlof, B., Devereux, R. B., Kjeldsen, S. E., Julius, S., Beevers, G., De Faire, U., Fyhrquist, F., Ibsen, H., Kristiansson, K., Lederballe-Pedersen, O., Lindholm, L. H., Nieminen, M. S., Omvik, P., Oparil, S. and Wedel, H.; LIFE Study Group (2002) Cardiovascular morbidity and mortality in the Losartan Intervention For Endpoint reduction in hypertension study (LIFE): a randomised trial against atenolol. Lancet 359, 995-1003. DOI |
31 | Herr, R. J. (2002) 5-Substituted-1H-tetrazoles as carboxylic acid isosteres: medicinal chemistry and synthetic methods. Bioorg. Med. Chem. 10, 3379-3393. DOI |
32 | Hirschfeld, R. M. (2000) History and evolution of the monoamine hypothesis of depression. J. Clin. Psychiatry 61 Suppl 6, 4-6. DOI |
33 | Holtzheimer, P. E., 3rd and Nemeroff, C. B. (2006) Advances in the treatment of depression. NeuroRx 3, 42-56. DOI |
34 | Hutchinson, D. W. and Naylor, M. (1985) The antiviral activity of tetrazole phosphonic acids and their analogues. Nucleic Acids Res. 13, 8519-8530. DOI |
35 | Rajasekaran, A. and Thampi, P. P. (2004) Synthesis and analgesic evaluation of some 5-[beta-(10-phenothiazinyl)ethyl]-1-(acyl)-1,2,3,4-tetrazoles. Eur. J. Med. Chem. 39, 273-279. DOI |
36 | Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J. Immunol. Methods 65, 55-63. DOI |
37 | Paudel, S., Cao, Y., Guo, S., An, B., Kim, K. M. and Cheon, S. H. (2015) Design and synthesis of 4-benzylpiperidine carboxamides as dual serotonin and norepinephrine reuptake inhibitors. Bioorg. Med. Chem. 23, 6418-6426. DOI |
38 | Pegklidou, K., Koukoulitsa, C., Nicolaou, I. and Demopoulos, V. J. (2010) Design and synthesis of novel series of pyrrole based chemotypes and their evaluation as selective aldose reductase inhibitors. A case of bioisosterism between a carboxylic acid moiety and that of a tetrazole. Bioorg. Med. Chem. 18, 2107-2114. DOI |
39 | Sorensen, L., Andersen, J., Thomsen, M., Hansen, S. M., Zhao, X., Sandelin, A., Stromgaard, K. and Kristensen, A. S. (2012) Interaction of antidepressants with the serotonin and norepinephrine transporters: mutational studies of the S1 substrate binding pocket. J. Biol. Chem. 287, 43694-43707. DOI |
40 | Ichikawa, T., Kitazaki, T., Matsushita, Y., Hosono, H., Yamada, M., Mizuno, M. and Itoh, K. (2000) Optically active antifungal azoles. XI. An alternative synthetic route for 1-[(1R, 2R)-2-(2, 4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1, 2, 4-triazol-1-yl)propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456) and its analog. Chem. Pharm. Bull. 48, 1947-1953. DOI |
41 | ChemAxon (2014) MarvinSketch (version 6.2.2), calculation module developed by ChemAxon. Available from: http://www.chemaxon.com/products/marvin/marvinsketch/. |
42 | Paudel, S., Kim, E., Zhu, A., Acharya, S., Min, X., Cheon, S. H. and Kim, K. M. (2021) Structural requirements for modulating 4-benzylpiperidine carboxamides from serotonin/norepinephrine reuptake inhibitors to triple reuptake inhibitors. Biomol. Ther. (Seoul) 29, 392-398. DOI |
43 | Iversen, L. (2006) Neurotransmitter transporters and their impact on the development of psychopharmacology. Br. J. Pharmacol. 147 Suppl 1, S82-S88. DOI |
44 | Torres, G. E., Yao, W. D., Mohn, A. R., Quan, H., Kim, K. M., Levey, A. I., Staudinger, J. and Caron, M. G. (2001) Functional interaction between monoamine plasma membrane transporters and the synaptic PDZ domain-containing protein PICK1. Neuron 30, 121-134. DOI |
45 | Pettersen, E. F., Goddard, T. D., Huang, C. C., Couch, G. S., Greenblatt, D. M., Meng, E. C. and Ferrin, T. E. (2004) UCSF Chimera--a visualization system for exploratory research and analysis. J. Comput. Chem. 25, 1605-1612. DOI |
46 | Belmaker, R. H. and Agam, G. (2008) Major depressive disorder. N. Engl. J. Med. 358, 55-68. DOI |
47 | Martirosyan, A. O., Aleksanyan, M. V., Terzyan, S. S., Ter-Zakharyan, Y. Z., Agababyan, R. V., Karapetyan, A. A., Mndzhoyan, S. L. and Tamazyan, R. A. (2001) Synthesis and molecular and crystal structure of 1-(5-benzyl-2-tetrazolyl)-1-cyclopentanecarboxylic acid. penicillin and cephalosporins based on this acid. Pharm. Chem. J. 35, 169-171. DOI |
48 | Paudel, S., Acharya, S., Yoon, G., Kim, K. M. and Cheon, S. H. (2017a) Design, synthesis and in vitro activity of 1,4-disubstituted piperazines and piperidines as triple reuptake inhibitors. Bioorg. Med. Chem. 25, 2266-2276. DOI |
49 | Paudel, S., Min, X., Acharya, S., Khadka, D. B., Yoon, G., Kim, K. M. and Cheon, S. H. (2017b) Triple reuptake inhibitors: design, synthesis and structure-activity relationship of benzylpiperidinetetrazoles. Bioorg. Med. Chem. 25, 5278-5289. DOI |
50 | Sprenger, K. G., Jaeger, V. W. and Pfaendtner, J. (2015) The general AMBER force field (GAFF) can accurately predict thermodynamic and transport properties of many ionic liquids. J. Phys. Chem. B 119, 5882-5895. DOI |