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

Yıl 2019, Cilt: 47 Sayı: 2, 203 - 208, 18.09.2019
https://doi.org/10.15671/hjbc.623792

Öz

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.

Destekleyen Kurum

TUBİTAK

Proje Numarası

1919B011603783

Teşekkür

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

Kaynakça

  • 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.
Yıl 2019, Cilt: 47 Sayı: 2, 203 - 208, 18.09.2019
https://doi.org/10.15671/hjbc.623792

Öz

Proje Numarası

1919B011603783

Kaynakça

  • 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.
Toplam 31 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Bölüm Articles
Yazarlar

İnci Selin Doğan

Hasan Erdinç Sellitepe Bu kişi benim

Bahittin Kahveci Bu kişi benim

Proje Numarası 1919B011603783
Yayımlanma Tarihi 18 Eylül 2019
Kabul Tarihi 14 Şubat 2019
Yayımlandığı Sayı Yıl 2019 Cilt: 47 Sayı: 2

Kaynak Göster

APA Doğan, İ. S., Sellitepe, H. E., & Kahveci, B. (2019). Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine. Hacettepe Journal of Biology and Chemistry, 47(2), 203-208. https://doi.org/10.15671/hjbc.623792
AMA Doğan İS, Sellitepe HE, Kahveci B. Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine. HJBC. Eylül 2019;47(2):203-208. doi:10.15671/hjbc.623792
Chicago Doğan, İnci Selin, Hasan Erdinç Sellitepe, ve Bahittin Kahveci. “Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones With 1-Adamantyl Amine”. Hacettepe Journal of Biology and Chemistry 47, sy. 2 (Eylül 2019): 203-8. https://doi.org/10.15671/hjbc.623792.
EndNote Doğan İS, Sellitepe HE, Kahveci B (01 Eylül 2019) Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine. Hacettepe Journal of Biology and Chemistry 47 2 203–208.
IEEE İ. S. Doğan, H. E. Sellitepe, ve B. Kahveci, “Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine”, HJBC, c. 47, sy. 2, ss. 203–208, 2019, doi: 10.15671/hjbc.623792.
ISNAD Doğan, İnci Selin vd. “Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones With 1-Adamantyl Amine”. Hacettepe Journal of Biology and Chemistry 47/2 (Eylül 2019), 203-208. https://doi.org/10.15671/hjbc.623792.
JAMA Doğan İS, Sellitepe HE, Kahveci B. Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine. HJBC. 2019;47:203–208.
MLA Doğan, İnci Selin vd. “Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones With 1-Adamantyl Amine”. Hacettepe Journal of Biology and Chemistry, c. 47, sy. 2, 2019, ss. 203-8, doi:10.15671/hjbc.623792.
Vancouver Doğan İS, Sellitepe HE, Kahveci B. Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine. HJBC. 2019;47(2):203-8.

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