Synthesis and Transformation of Novel Dibenzothipodand Derivatives
Main Article Content
Abstract
This study develops a new method of synthesizing podands containing thioether fragments 1.10-bis(2-formylphenyl)-1.10-dithia-4.7-dioxadecane and 1.10-bis(2-acetophenyl)-1.10-dithia-4.7-dioxadecane. The synthesized podands’ transformations were studied in acidic condition to obtain products of the croton condensation reaction having arylenone fragment. All the synthesized compounds’ bioactivities were predicted by PASS online programme in which podand (9) was evaluated for its antibiotic activity. The structure of the new podand was determined by IR, 1H NMR, MS spectrums.
Keywords:
Dibenzothiopodand, the croton condensation reaction, antibiotic activity, PASS online programme
References
[1] V.A.Popova, I.V. Podgornaya, I. Ya. Postovskii, N.N. Frolova, “Synthesis and tuberculostatic activity of certain new derivatives of macrocyclic polyethers”, Pharmaceutical Chemistry Journal 10(6) (1976) 66-68.
[2] V.A.Popova, I.V. Podgornaya, V.G. Lundina, L.I. Kurnikova, A.I. Tarasov, “Acyl derivatives of N,N’-Diaminodibenzo-18-crown-6 ether, their complexing and catalytic properties”, Russian Chemical Bulletin 11(1987) 2544-2547.
[3] V.A. Popova, Tsivadze, A. Yu., Podgornaya, I.V., Pyatova,E. N., Kopytin, A.V., Eganova, L. V. “Synthesis and properties of podands with 4-antipyryliminomethine groups”, Russian Chemical Bulletin 9 (1990) 2099-2102.
[4] I.G. Pervova, A.V. Zaіdman, I.N. Lipunov, P.A. Slepukhin. “X-Ray diffraction study of 1,5-Bis (2-formylphenoxy) pentane”. Crystallography Reports 55(2) (2010) 237–239.
[5] A.N. Levov, V.M. Strokina, Le Tuan Anh, A.I. Komarova, A.T. Soldatenkov, V.N. Khrustalev. Mendeleev Commun. 16(1) (2006) 35.
[6] A.T. Le, V.T.T. Tran, H.H. Truong, L.M. Nguyen, D.M. Luong, T.T. Do, D.T. Nguyen, N.T. Dao, D.T. Le, A.T. Soldatenkov, V.N. Khrustalev, Mendeleev Commun. 29 (2019) 375-377.
[7] T.N. Dao, H.H. Truong, V.B. Luu, A.T. Soldatenkov, N.M. Kolyadina, A.N. Kulakova, V.N. Khrustalev, A.T. Wodajo, H.Q. Nguyen, T.T.V. Tran, T.A. Le, Chem. Heterocycl. Compd., 55(7) (2019) 654–659.
[8] A.N. Levov, V.M. Strokina, A.I. Komarova, Le Tuan Anh, A.T. Soldatenkov. Chemistry of Heterocyclic Compounds 42 (1) (2006) 125.
[9] H.H. Truong, T.A. Le, A.T. Soldatenkov, N.I. Golovtsov, S. A. Soldatenkov. Chemistry of Heterocyclic Compounds 47 (10)(2012) 1317- 1318.
[10] H.H. Truong, A.T. Le, A. T. Soldatenkov, V.V. Kurilkin, V.N. Khrustalev. Acta Cryst., 2012, E68, 2848-2849.
[11] T.A. Le, H.H. Truong, T.T.P. Nguyen, T.N. Dao, H.T. To, T.H. Pham, A.T. Soldatenkov. Mendeleev Commun. 25 (2015) 224 – 225.
[12] H.H. Truong, A. T. Soldatenkov, A.T. Le, H. T. To, S. A. Soldatova. Chemistry of Heterocyclic Compounds 47 (10) (2012) 1315-1316.
[13] T.T. V. Tran, A.T. Le, H.H. Nguyen, H.H. Truong, A.T. Soldatenkov. Acta Cryst. E72 (2016) 663-666.
[14] O.W. Fedorova, G.L. Rusinov, G.G. Mordovskoi, M.N. Zueva, M.A. Kravchenko, I.G. Ovtschinnikova, O.N. Chupakhin, “Synthesis and tuberculostatic activity of podands with fluoroquinolone fragments”, Pharmaceutical Chemistry Journal 31(7)(1997) 21-23.
[15] O.W. Fedorova, G.G. Mordovskoi, G.L. Rusinov, I.G. Ovtschinnikova, M.N. Zueva, M.A. Kravchenko, O.N. Chupakhin, “Synthesis and in vitro tuberculostatic activity of podands containing semicarbazide or thiosemicarbazide fragments”, Pharmaceutical Chemistry Journal 32(2) (1998) 11-12.
[16] T.A. Le, T.N. Dao, A.T. Le, T.T.V. Tran, H.H. Truong, V.T. Nguyen, T.T.P. Nguyen, A.T. Soldatenkov, V.E. Kotsuba, T.T.A. Dang, “Novel Podands Containing N-Arylthiosemicarbazide Moiety”. Макрогетероциклы/Macroheterocycles 2017 10(2) 243-246.
[17] A.J. Vlietinck, “Screening methods for detection and evaluation of biological activities of plant preparation, Bioassay Methods in Natural Product reseach and Drug development”. Kluwer academic publishers, USA, 1998.
[18] D.A. Vanden Bergher, 17. A.J.Vlietinck, “Screening methods for Antibacterial and Ativiral Agent from Higher Plants, Methods in Plant biochemistry”. Academic Press., USA, V. 6, 1991.
[19] L. Mckane, J. Kandel, Microbiology, McGraw-Hill, INC., 1996.
[20] D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, A.V. Rudik, D.S. Druzhilovskii, P..V. Pogodin, V.V. Poroikov. Chem. Heterocyc. Compd 50 (3) (2014) 444–457.
[2] V.A.Popova, I.V. Podgornaya, V.G. Lundina, L.I. Kurnikova, A.I. Tarasov, “Acyl derivatives of N,N’-Diaminodibenzo-18-crown-6 ether, their complexing and catalytic properties”, Russian Chemical Bulletin 11(1987) 2544-2547.
[3] V.A. Popova, Tsivadze, A. Yu., Podgornaya, I.V., Pyatova,E. N., Kopytin, A.V., Eganova, L. V. “Synthesis and properties of podands with 4-antipyryliminomethine groups”, Russian Chemical Bulletin 9 (1990) 2099-2102.
[4] I.G. Pervova, A.V. Zaіdman, I.N. Lipunov, P.A. Slepukhin. “X-Ray diffraction study of 1,5-Bis (2-formylphenoxy) pentane”. Crystallography Reports 55(2) (2010) 237–239.
[5] A.N. Levov, V.M. Strokina, Le Tuan Anh, A.I. Komarova, A.T. Soldatenkov, V.N. Khrustalev. Mendeleev Commun. 16(1) (2006) 35.
[6] A.T. Le, V.T.T. Tran, H.H. Truong, L.M. Nguyen, D.M. Luong, T.T. Do, D.T. Nguyen, N.T. Dao, D.T. Le, A.T. Soldatenkov, V.N. Khrustalev, Mendeleev Commun. 29 (2019) 375-377.
[7] T.N. Dao, H.H. Truong, V.B. Luu, A.T. Soldatenkov, N.M. Kolyadina, A.N. Kulakova, V.N. Khrustalev, A.T. Wodajo, H.Q. Nguyen, T.T.V. Tran, T.A. Le, Chem. Heterocycl. Compd., 55(7) (2019) 654–659.
[8] A.N. Levov, V.M. Strokina, A.I. Komarova, Le Tuan Anh, A.T. Soldatenkov. Chemistry of Heterocyclic Compounds 42 (1) (2006) 125.
[9] H.H. Truong, T.A. Le, A.T. Soldatenkov, N.I. Golovtsov, S. A. Soldatenkov. Chemistry of Heterocyclic Compounds 47 (10)(2012) 1317- 1318.
[10] H.H. Truong, A.T. Le, A. T. Soldatenkov, V.V. Kurilkin, V.N. Khrustalev. Acta Cryst., 2012, E68, 2848-2849.
[11] T.A. Le, H.H. Truong, T.T.P. Nguyen, T.N. Dao, H.T. To, T.H. Pham, A.T. Soldatenkov. Mendeleev Commun. 25 (2015) 224 – 225.
[12] H.H. Truong, A. T. Soldatenkov, A.T. Le, H. T. To, S. A. Soldatova. Chemistry of Heterocyclic Compounds 47 (10) (2012) 1315-1316.
[13] T.T. V. Tran, A.T. Le, H.H. Nguyen, H.H. Truong, A.T. Soldatenkov. Acta Cryst. E72 (2016) 663-666.
[14] O.W. Fedorova, G.L. Rusinov, G.G. Mordovskoi, M.N. Zueva, M.A. Kravchenko, I.G. Ovtschinnikova, O.N. Chupakhin, “Synthesis and tuberculostatic activity of podands with fluoroquinolone fragments”, Pharmaceutical Chemistry Journal 31(7)(1997) 21-23.
[15] O.W. Fedorova, G.G. Mordovskoi, G.L. Rusinov, I.G. Ovtschinnikova, M.N. Zueva, M.A. Kravchenko, O.N. Chupakhin, “Synthesis and in vitro tuberculostatic activity of podands containing semicarbazide or thiosemicarbazide fragments”, Pharmaceutical Chemistry Journal 32(2) (1998) 11-12.
[16] T.A. Le, T.N. Dao, A.T. Le, T.T.V. Tran, H.H. Truong, V.T. Nguyen, T.T.P. Nguyen, A.T. Soldatenkov, V.E. Kotsuba, T.T.A. Dang, “Novel Podands Containing N-Arylthiosemicarbazide Moiety”. Макрогетероциклы/Macroheterocycles 2017 10(2) 243-246.
[17] A.J. Vlietinck, “Screening methods for detection and evaluation of biological activities of plant preparation, Bioassay Methods in Natural Product reseach and Drug development”. Kluwer academic publishers, USA, 1998.
[18] D.A. Vanden Bergher, 17. A.J.Vlietinck, “Screening methods for Antibacterial and Ativiral Agent from Higher Plants, Methods in Plant biochemistry”. Academic Press., USA, V. 6, 1991.
[19] L. Mckane, J. Kandel, Microbiology, McGraw-Hill, INC., 1996.
[20] D.A. Filimonov, A.A. Lagunin, T.A. Gloriozova, A.V. Rudik, D.S. Druzhilovskii, P..V. Pogodin, V.V. Poroikov. Chem. Heterocyc. Compd 50 (3) (2014) 444–457.