Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine

Year 2019, Volume: 47 Issue: 2, 203 - 208, 18.09.2019

İnci Selin Doğan , Hasan Erdinç Sellitepe , Bahittin Kahveci

https://doi.org/10.15671/hjbc.623792

Abstract

I
n this study, the reactions of the 1-adamantyl amine with 4 different ester ethoxycarbonyl hydrazone derivatives were
studied. At first, iminoester hydrochloride derivatives were synthesized according to the Pinner method. Then they
were reacted with ethyl carbazate to synthesize ester ethoxycarbonyl hydrazone derivative compounds. In the last step,
3-substituted-4-adamantyl-1,2,4-triazol-5-one derivatives were aimed to synthesize, the ester ethoxycarbonyl hydrazone
compounds were heated in an oil bath dry to dry with 1-adamantyl amine. It has been observed, however, that the ring is
not closed according to IR and ¹H-NMR analysis and the ethyl N-(adamantylcarbamoyl)alkylcarbohydrazonoate derivative
compounds were synthesized as stabile and original compounds. The structures of the synthesized compounds were elucidated by spectroscopic methods using IR, ¹H-NMR, 13C-NMR spectra and LC/MS analysis.

Keywords

1-adamantyl amine, ester ethoxycarbonyl hydrazone, , iminoester hydrochlorides, Pinner method

Supporting Institution

TUBİTAK

Project Number

1919B011603783

Thanks

This study has been supported by Tübitak 2209A Project No. 1919B011603783 Support Program for Domestic Research Projects of University Students.

References

• 1. J. Warren, Drug discovery: lessons from evolution, Br. J. Clin. Pharmacol., 71 (2011) 497-503.
• 2. H.U. Daeniker, 1‐Hydrazinoadamantan, Helvetica Chimica Acta., 50 (1967) 2008-2010.
• 3. T.L. Thomas, M. Fedorchuk, B.V. Shetty, F.E. Anderson, Synthesis and activity of some 3-substituted 1,2,3,4-pseudooxatriazol-5-ones and their precursors and related compounds, J. Med. Chem., 13 (1970) 196-203.
• 4. M.G. Alves Galvão, M.A. Rocha Crispino Santos, A.J. Alves da Cunha, Amantadine and rimantadine for influenza A in children and the elderly, Cochrane Database Syst Rev., 21 (2014) CD002745.
• 5. K. Spilovska, F. Zemek, J. Korabecny, E. Nepovimova, O. Soukup, M. Windisch, K. Kuca, Adamantane - A lead structure for drugs in clinical practice, Curr. Med. Chem., 23 (2016) 3245-3266.
• 6. S.V. Krapivin, S.A. Sergeeva, I.S. Morozov, Comparative analysis of the effects of adapromine, midantane, and bromantane on bioelectrical activity of rat brain, Bull. Exp. Biol. Med. 125 (1998) 175-179.
• 7. R. Naik, H. Valentine, A. Hall, W.B. Mathews, J.C. Harris, C.S. Carter, R.F. Dannals, D.F. Wong, A.G. Horti, Development of a radioligand for imaging V1a vasopressin receptors with PET, Eur. J. Med. Chem., 139 (2017) 644-656.
• 8. M. Kamenova-Nacheva, M. Schröder, E Pasheva, I. Slavchev, V. Dimitrov, G. Momekov, R. Nikolova, B. Shivachev, I. Ugrinova, G.M. Dobrikov, Synthesis of ferrocenylmethylidene and arylidene substituted camphane based compounds as potential anticancer agents, New J. Chem., 41 (2017) 9103- 9112.
• 9. U. Kalita, S. Kaping, R. Nongkynrih, I. Boiss, L. Indira Singha, J. Narain Vishwakarma, Design, synthesis, structure elucidation, and biological activities of 3-(substituted amino)-1-(pyridin-4-yl)propenones and 5-isonicotinoyl1,2,3,4-tetrahydropyrimidine–adamantane hybrids, Monatshefte für Chemie., 148 (2017) 2155-2171.
• 10. A.N. Balaev, V.N. Osipov, K.A. Okhmanovich, E.A. Ruchko, M.A. Baryshnikova, D.S. Khachatryan, Pentapeptide analogs of somatostatin containing a thiazolidine fragment: synthesis and cytotoxic activity, Russian Chemical Bulletin., 65 (2016) 2948-2951.
• 11. Y. Shi, Y.H. Duan, Y.Y. Ji, Z.L. Wang, Y.R. Wu, H. Gunosewoyo, X.Y. Xie, J.Z. Chen, F. Yang, J. Li, J. Tang, X. Xie, L.F. Yu, Amidoalkylindoles as potent and selective cannabinoid type 2 receptor agonists with in vivo efficacy in a mouse model of multiple sclerosis, J. Med. Chem., 60 (2017) 7067-7083.
• 12. A. Quéméner, M. Maillasson, L. Arzel, B. Sicard, R. Vomiandry, E. Mortier, D. Dubreuil, Y. Jacques, J. Lebreton, M. MathéAllainmat, Discovery of a small-molecule inhibitor of interleukin 15: Pharmacophore-based virtual screening and hit optimization, J. Med. Chem., 60 (2017) 6249-6272.
• 13. E. Azzali, D. Machado, A. Kaushik, F. Vacondio, S. Flisi, C.S. Cabassi, G. Lamichhane, M. Viveiros, G. Costantino, M. Pieroni, Substituted N-phenyl-5-(2-(phenylamino)thiazol4-yl)isoxazole-3-carboxamides are valuable antitubercular candidates that evade innate efflux machinery, J. Med. Chem., 60 (2017) 7108-7122.
• 14. F.W.W. Hartrampf, D.M. Barber, K. Gottschling, P. Leippe, M. Hollmann, D. Trauner, Development of a photoswitchable antagonist of NMDA receptors, Tetrahedron, 73 (2017) 4905-4912.
• 15. L.H. Al-Wahaibi, H.M. Hassan, A.M. Abo-Kamar, H.A. Ghabbour, A.A. El-Emam, Adamantane-isothiourea hybrid derivatives: synthesis, characterization, in vitro antimicrobial, and in vivo hypoglycemic activities, Molecules, 22 (2017) 710.
• 16. M. Xiaodong, F.Z. Shenging, US Patent 2017. CN106432104A.
• 17. A.P. Kozikowski, O.K. Onajole, J. Stec, C. Dupont, A. Viljoen, M. Richard, T. Chaira, S. Lun, W. Bishai, V.S. Raj, D. Ordway, L. Kremer, Targeting mycolic acid transport by indole2-carboxamides for the treatment of mycobacterium abscessus infections, J. Med. Chem., 60 (2017) 5876-5888.
• 18. R.P. Moldovan, K. Hausmann, W. Deuther-Conrad, P. Brust, Development of highly affine and selective fluorinated cannabinoid type 2 receptor ligands, ACS Med. Chem. Lett., 8 (2017) 566-571.
• 19. P.F. Zhao, Z.Q. Liu, 2-Isocyano glucose used in Ugi fourcomponent reaction: An approach to enhance inhibitory effect against DNA oxidation, Eur. J. Med. Chem., 135 (2017) 458-466.
• 20. N. Karalı, A. Akdemir, F. Göktaş, P. Eraslan Elma, A. Angeli, M. Kızılırmak, C.T. Supuran, Novel sulfonamide-containing 2-indolinones that selectively inhibit tumor-associated alpha carbonic anhydrases, Bioorg. Med. Chem., 25 (2017) 3714-3718.
• 21. J. Jimenez, I. Chakraborty, A.M. Del Cid, P.K. Mascharak, Five- and six-coordinated silver(i) complexes derived from 2,6-(pyridyl)iminodiadamantanes: sustained release of bioactive silver toward bacterial eradication, Inorg. Chem., 56 (2017) 4784-4787.
• 22. Y. Hu, Y. Wang, F. Li, C. Ma, J. Wang, Design and expeditious synthesis of organosilanes as potent antivirals targeting multidrug-resistant influenza A viruses, Eur. J. Med. Chem., 135 (2017) 70-76.
• 23. A. İkizler, N. Demirbaş, A. Demirbaş, A.A. İkizler, A convenient synthesis of 4-amino 3,5-dialkyl-4H-1,2,4-triazoles, Polish J. Chem., 70 (1996) 1114-1120.
• 24. B. Kahveci, Synthesis of 4-amino-4,5-dihydro-1H-1,2,4- triazole-5-ones and their isatin-3-imine derivatives, Molecules,10 (2005) 376-382.
• 25. A. Pinner, F. Klein, Umwandlung der Nitrile in Imide, Berichte der deutschenchemischen Gesellschaft, 10 (1877) 1889- 1897.
• 26. 26. R. Roger, D.G. Neilson, The chemistry of imidates, Chem. Rev., 61 (1961) 179-211.
• 27. P. Sykes, A Guidebook to Mechanism in Organic Chemistry, John Wiley&Sons, New York, 1977.
• 28. R.W. Layer, The chemistry of imines, Chem. Rev. 63 (1963) 489-510.
• 29. R.M. Silverstein, Spectrometric identification of organic compounds, John Wiley&Sons, New York,1998.
• 30. E. Pretsch, T. Clerk, J. Seibl, W. Simon, Tables of spectral data for structure determination of organic compounds, Springer-Verlag, Berlin, 1983.
• 31. S.D. Zurabishvili, T.J. Bukia, M.O. Lomidze, M.V. Trapaidze, E.N. Elizbarashvili, S.A. Samsoniya, T.V. Doroshenko, U. Kazmaier, Preparation of 2-(1-adamantyl)-1H-benzimidazole and novel derivatives thereof, Chem. Heterocyclic Comp., 51 (2015) 139-145.