Investigation of Reaction of Some Ester Ethoxycarbonyl Hydrazones with 1-Adamantyl Amine
Yıl 2019,
Cilt: 47 Sayı: 2, 203 - 208, 18.09.2019
İnci Selin Doğan
,
Hasan Erdinç Sellitepe
,
Bahittin Kahveci
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
İnci Selin Doğan
,
Hasan Erdinç Sellitepe
,
Bahittin Kahveci
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.