Synthesis and Structural Characterization of some 3-oxapentane Podand Derivatives
Main Article Content
Abstract
A series of eight 3-oxapentane podand derivatives was successfully prepared based on the croton condensation reaction from 1,5-bis(aryl)-1,5-dithia-3-dioxadecane and 1,5-bis(aryl)-1,3,5-trioxadecane with bezaldehyde or acetophenone derivatives in acidic condition. These synthesized derivatives have structure of acyclic crown rings inserted by polyether or polythiaether chain and vinyl ketone chain conjugated with aryl group. Therefore, they are important sources for host-guest chemistry. They can wrap around a central alkali metal cations as well as organic cations and anions or even molecules to make interesting ion pair receptors. Structure of new podands was determined by spectral analyses including IR, 1H NMR, MS spectrocopies.
Keywords:
3-oxapentane podand, 1,5-dithia-3-oxapentane, 1,3,5-trioxapentane, the croton condensation reaction, acyclic crown.
References
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2. Swinburne, A. N., & Steed, J. W. “Podand. Supramolecular chemistry: From molecules to nanomaterials”. John Wiley & Sons, Vol. 3: Molecular Recognition, 2012, 1001 – 1043.
3. Nabeshima, T., Inaba, T., Furukawa, N. “Transition metal induced selective alkaline metal ion transport by asynthethic ionophore with double recognition sites for metals”. Tetrahedron Letters, 1987, 28(49), 6211 – 6214.
4. Tatsuya, N., Tadashi, I., Takahiro, S., Naomichi, F. “A novel type of pseudocryptand for simultaneous recognition of heavy and alkali metals”. Tetrahedron Letters, 1990, 31(27), 3919 – 3922.
5. Nabeshima, T., Inaba, T., Furukawa, N., Ohshima, S., Hosoya, T., Yano, Y. “Selective recognition for heavy and transition metals by novel polyethers bearing bipyridines, and molecular chirality of pseudocrown structure in the Cu(I) complex”. Tetrahedron Letters, 1990, 31(45), 6543 – 6546.
6. V.A.Popova, I.V. Podgornaya, I. Ya. Postovskii, N.N. Frolova (1976), “Synthesis and tuberculostatic activity of certain new derivatives of macrocyclic polyethers”, Pharmaceutical Chemistry Journal, Vol. 10(6), pp. 66-68.
7. V.A.Popova, I.V. Podgornaya, V.G. Lundina, L.I. Kurnikova, A.I. Tarasov (1987), “Acyl derivatives of N,N’-Diaminodibenzo-18-crown-6 ether, their complexing and catalytic properties”, Russian Chemical Bulletin, No.11, pp. 2544-2547.
8. Pham Thi Thanh Tam, Do Thao Thuyen, Nguyen Manh Linh, Nguyen Tien Dat, Tran Thach Van, Le Thi Huyen, Tran Thi Thanh Van, Le Tuan Anh. Synthesis and transformation of novel dibenzothipodand derivatives.// VNU Journal of Science: Natural Sciences and Technology. – 2020. – Vol. 36. – № 4. – P. 82 – 89.
9. A. N. Levov, V. M. Strokina, Le Tuan Anh, A. I. Komarova, A. T. Soldatenkov, V. N. Khrustalev. Mendeleev Commun. 2006, 16(1), 35.
10. A. N. Levov, V. M. Strokina, A. I. Komarova, Le Tuan Anh, A. T. Soldatenkov. Chemistry of Heterocyclic Compounds, 2006, 42 (1), 125.
11. H. H. Truong, T. A. Le, A. T. Soldatenkov, N. I. Golovtsov, S. A. Soldatenkov. Chemistry of Heterocyclic Compounds, 2012, 47 (10), 1317 - 1318.
12. 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., 2019, 29, 375–377.
13. 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., 2019, 55(7), 654–659.
14. Linh M. Nguyen, Hieu H. Truong, Victor N. Khrustalev, Sang T. Truong, Dat T. Nguyen, Van T. T. Tran, Son T. Mai, Van T. Tran, Anh T. Le. “Synthesis and biological evaluation of novel phane-structured diazacrowns containing γ-piperidone and pyridine rings”. Mendeleev Commun., 2020, 6, 753 – 755.
15. H. H. Truong, A. T. Soldatenkov, A.T. Le, H. T. To, S. A. Soldatova. Chemistry of Heterocyclic Compounds, 2012, 47 (10), 1315 - 1316.
16. T. A. Le, H. H. Truong, T. T. P. Nguyen, T. N. Dao, H. T. To, T. H. Pham, A. T. Soldatenkov. Mendeleev Commun. 2015, 25, 224 – 225.
17. Thanh Tam Pham Thi, Thao Thuyen Do, Tien Dat Nguyen, Van Boi Luu, Elena I. Polyakova, Thanh Van Tran Thi, Tuan Anh Le. Synthesis of the first dibenzo-4,12-dithio-8-azacrownophanes containing γ-arylpiridine subunit.// Chemistry of Heterocyclic Compounds. – 2020. – Vol.56. – № 9. – P. 1234 - 1236.
18. Fedorova O. W., Rusinov G. L., Mordovskoi G. G., Zueva M. N., Kravchenko M. A., Ovtschinnikova I. G., Chupakhin O. N (1997), “Synthesis and tuberculostatic activity of podands with fluoroquinolone fragments”, Pharmaceutical Chemistry Journal, Vol. 31(7), pp.21-23.
19. Fedorova O. W., Mordovskoi G. G., Rusinov G. L., Ovtschinnikova I. G., Zueva M. N., Kravchenko M. A., Chupakhin O. N (1998), “Synthesis and in vitro tuberculostatic activity of podands containing semicarbazide or thiosemicarbazide fragments”, Pharmaceutical Chemistry Journal, 1998, 32(2), 64 – 66.
20. Le, T.A., Dao, T.N., Le, A.T., Tran, T.T.V., Truong, H.H., Nguyen, V.T., Nguyen, T.T.P., Soldatenkov, A.T., Kotsuba V.E., Dang, T.T.A. “Novel podands containing N-arylthiosemicarbazide moiety”. Макрогетероциклы / Macroheterocycles 2017 10(2) 243-246.
21. Filimonov, D. A., Lagunin, A. A., Gloriozova, T. A., Rudik, A. V., Druzhilovskii, D. S., Pogodin, P. V. & Poroikov, V. V. (2014). Chem. Heterocyc. Compd, 50 (3), 444–457.
22. Potemkin, V. A., Grishina, M. A., Fedorova, O. V., Rusinov, G. L., Ovchinnikova, I. G., Ishmetova, R. I. “Theoretical Investigation of the Antituberculous Activity of Membranotropic Podands”. Pharmaceutical Chemistry Journal, 2003. 37(9), 468 – 472.
23. Fedorova, O. V., Mordovskoi, G. G., Rusinov, G. L., Zueva, M. N., Ovchinnikova, I. G. “Search for compounds possessing turbeculostatic activity among synthetic ionophors — podands". Pharmaceutical Chemistry Journal, 1996, 30(10), 611 – 612.
24. Vlietinck A. J., “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.
25. Vanden Bergher D. A., 17. Vlietinck A. J., “Screening methods for Antibacterial and Ativiral Agent from Higher Plants, Methods in Plant biochemistry”. Academic Press., USA, V. 6, 1991.
26. Mckane L., Kandel J., Microbiology, McGraw-Hill, INC., 1996.