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Synthesis and Selected Properties of Novel Metal Complexes with Bis-Azomethine Based on 7-Hydroxy-4-methyl-8-formylcoumarin and 1,3-Diaminopropan-2-ol

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Abstract

Condensation of 7-hydroxy-4-methyl-8-formylcoumarin with 1,3-diaminopropan-2-ol has afforded a novel bis-azomethine, and its metal chelates with copper(II), nickel(II), and zinc(II) have been obtained. Structure and properties of the prepared compound have been studied by spectral and quantum-chemical methods.

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References

  1. Krause, M., Rouleau, A., Stark, H., Luger, P., Lipp, R., Garbarg, M., Schwartz, J.-C., and Schunack, W., J. Med. Chem., 1995, vol. 38, no. 20, p. 4070. https://doi.org/10.1021/jm00020a022

    Article  CAS  PubMed  Google Scholar 

  2. Hui, M.B.V., Lien, E.J., and Trousdale, M.D., Antivir. Res, 1994, vol. 24, no. 4, p. 261. https://doi.org/10.1016/0166-3542(94)90074-4

    Article  CAS  PubMed  Google Scholar 

  3. Lewinski, J., Zachara, J., Justyniak, I., and Dranka, M., Coord. Chem. Rev, 2005, vol. 249, nos. 11–12, p. 1185. https://doi.org/10.1016/j.ccr.2004.11.013

    Article  CAS  Google Scholar 

  4. Kleij, A.W., Chem. Eur. J., 2008, vol. 14, no. 34, p. 10520. https://doi.org/10.1002/chem.200801149

    Article  CAS  PubMed  Google Scholar 

  5. Garnovskii, A.D., Nivorozhkin, A.L., and Minkin, V.I., Coord. Chem. Rev., 1993, vol. 126, nos. 1–2, p. 1. https://doi.org/10.1016/0010-8545(93)85032-Y

    Article  CAS  Google Scholar 

  6. Garnovskii, A.D., Burlov, A.S., Vasil’chenko, I.S., Garnovskii, D.A., Uraev, A.I., and Sennikova, E.V., Russ. J. Coord. Chem., 2010, vol. 36, no. 2, p. 81. https://doi.org/10.1134/S1070328410020016

    Article  CAS  Google Scholar 

  7. Chattopadhyay, A., Meier, M., Ivaninskii, S., Burkhard, P., Speroni, F., Campanini, B., Bettati, S., Mozzarelli, A., Rabeh, W.M., Li, L., and Cook, P.F., Biochem., 2007, vol. 46, no. 28, p. 8315. https://doi.org/10.1021/bi602603c

    Article  CAS  Google Scholar 

  8. Montagner, C., de Souza, S.M., Groposo, C., Delle Monache, F., Smania, E.F.A., and Smania, A., Jr., Z. Naturforsch. (C), 2008, vol. 63, nos. 1–2, p. 21. https://doi.org/10.1515/znc-2008-1-205

    Article  CAS  Google Scholar 

  9. Minkin, V.I., Tsukanov, A.V., Dubonosov, A.D., and Bren, V.A., J. Mol. Struct., 2011, vol. 998, nos. 1–3, p. 179. https://doi.org/10.1016/j.molstruc.2011.05.029

    Article  CAS  Google Scholar 

  10. Uzhinov, B.M. and Khimich, M.N., Russ. Chem. Rev., 2011, vol. 80, no. 6, p. 553. https://doi.org/10.1070/RC2011v080n06ABEH004144

    Article  CAS  Google Scholar 

  11. Ohshima, A., Momotake, A., and Arai, T., J. Photochem. Photobiol. (A), 2004, vol. 162, nos. 2–3, p. 473. https://doi.org/10.1016/S1010-6030(03)00388-5

    Article  CAS  Google Scholar 

  12. Harada, J., Uekusa, H., and Ohashi, Y., J. Am. Chem. Soc., 1999, vol. 121, no. 24, p. 5809. https://doi.org/10.1021/ja9842969

    Article  CAS  Google Scholar 

  13. Garnovskii, A.D. and Vasil’chenko, I.S., Russ. Chem. Rev., 2005, vol. 74, no. 3, p. 193. https://doi.org/10.1070/RC2005v074n03ABEH001164

    Article  CAS  Google Scholar 

  14. Garnovskii, A.D., Koord. Khim., 1992, vol. 18, no. 7, p. 675.

    CAS  Google Scholar 

  15. Vigato, P.A. and Tamburini, S., Coord. Chem. Rev., 2004, vol. 248, nos. 17–20, p. 1717. https://doi.org/10.1016/j.cct.2003.09.003

    Article  CAS  Google Scholar 

  16. Minbaev, B.U., Shiffovy osnovaniya (Shiff Bases), Alma-Ata: Nauka, 1989.

    Google Scholar 

  17. Lewinski, J., Zachara, J., Justyniak, I., and Dranka M., Coord. Chem. Rev, 2005, vol. 249, p. 1185. https://doi.org/10.1016/j.ccr.2004.11.013

    Article  CAS  Google Scholar 

  18. Garnovskii, A.D., Koord. Khim., 1993, vol. 19, no. 5, p. 394.

    CAS  Google Scholar 

  19. Kogan, V.A., Lukov, V.V., and Shcherbakov, I.N., Russ. J. Coord. Chem., 2010, vol. 36, no. 6, p. 401. https://doi.org/10.1134/S1070328410060011

    Article  CAS  Google Scholar 

  20. Cozzi, P.G., Chem. Soc. Rev., 2004, vol. 33, p. 410. https://doi.org/10.1039/B307853C

    Article  CAS  PubMed  Google Scholar 

  21. Popov, L.D., Tupolova, Yu.P., Lukov, V.V., Shcherbakov, I.N., Burlov, A.S., Levchenkov, S.I., Kogan, V.A., Lyssenko, K.A., and Ivannikova, E.V., Inorg. Chim. Acta, 2009, vol. 362, p. 1673. https://doi.org/10.1016/j.ica2008.08.012

    Article  CAS  Google Scholar 

  22. Popov, L.D., Levchenkov, S.I., Shcherbakov, I.N., Lukov, V.V., Suponitsky, K.Yu., and Kogan, V.A., Inorg. Chem. Commun., 2012, vol. 17, p. 1. https://doi.org/10.1016/j.inoche.2011.11.020

    Article  CAS  Google Scholar 

  23. Tupolova, Yu.P., Shcherbakov, I.N., Popov, L.D., Levchenkov, S.I., Askalepova, O.I., Mishchenko, A.V., Lukov, V.V., and Kogan, V.A., Russ. J. Gen. Chem., 2010, vol. 80, no. 11, p. 2329. https://doi.org/10.1134/S1070363210110174

    Article  CAS  Google Scholar 

  24. Levchenkov, S.I., Popov, L.D., Tupolova, Yu.P., Morozov, A.N., Raspopova, E.A., Starikova, Z.A., and Shcherbakov, I.N., Russ. J. Coord. Chem., 2017, vol. 43, no. 10, p. 630. https://doi.org/10.1134/S1070328417100049

    Article  CAS  Google Scholar 

  25. Shcherbakov, I.N., Levchenkov, S.I., Popov, L.D., Aleksandrov, G.G., Etmetchenko, L.N., and Kogan, V.A., Russ. J. Coord. Chem., 2015, vol. 41, no. 2, p. 69. https://doi.org/10.1134/S1070328415020098

    Article  CAS  Google Scholar 

  26. Lin, W., Long, L., and Tan, W., Chem. Commun., 2010, vol. 46, no. 9, p. 1503. https://doi.org/10.1039/B922478E

    Article  CAS  Google Scholar 

  27. Park, S., Kwon, J.E., Kim, S.H., Seo, J., Chung, K., Park S-Y., Jang D-J., Medina, B.M., Gierschner, J., and Park, S.Y., J. Am. Chem. Soc, 2009, vol. 131, no. 39, p. 14043. https://doi.org/10.1021/ja902533f

    Article  CAS  PubMed  Google Scholar 

  28. Lin, W., Long, L., Feng, J., Wang, B., and Guo, C., Eur. J. Org. Chem., 2007, vol. 26, p. 4301. https://doi.org/10.1002/ejoc.200700475

    Article  CAS  Google Scholar 

  29. Li, H., Cai, L., Li, J., Hu, Y., Zhou, P., and Zhang, J., Dyes Pigmentent, 2011, vol. 91, no. 3, p. 309. https://doi.org/10.1016/j.dyepig.2011.05.011

    Article  CAS  Google Scholar 

  30. Laurin, P., Ferroud, D., Klich, M., Dupuis-Haelin, C., Mauvais, P., Lassaigne, P., Bonnefoy, A., and Musicki, B., Bioorg. Med. Chem. Lett., 1999, vol. 9, no. 14, p. 2079. https://doi.org/10.1016/S0960-894X(99)00329-7

    Article  CAS  PubMed  Google Scholar 

  31. Rehman, S.U., Chohan, Z.H., Gulnazl, F., and Supuran, C.T., J. Enz. Inhib. Med. Chem., 2005, vol. 20, no. 4, p. 333. https://doi.org/10.1080/14756360500141911

    Article  CAS  Google Scholar 

  32. Barachevsky, V.A., Karpov, R.E., Venediktova, O.V., Valova, T.V., Strokach, Yu.P., Miroshnikov, V.S., Chibisova, T.A., and Traven, V.F., Russ. Chem. Bull, 2005, vol. 54, no. 10, p. 2425. https://doi.org/10.1007/s11172-006-0132-3

    Article  CAS  Google Scholar 

  33. Zakhs, E.R., Martynova, V.P., and Efros, L.S., Teoreticheskie i prikladnye voprosy khimii geterotsiklov (Theoretical and Applied Issues of Heterocycle Chemistry), Riga: Zinatne, 1985.

    Google Scholar 

  34. Metelitsa, A.V., Knyazhansky, M.I., Ivanitsky, V.V., Nikolaeva, O.I., Palchkov, V.A., Panina, A.P., Shelepin, N.E., and Minkin, V.I., Mol. Cryst. Liq. Cryst., 1994, vol. 246, no. 1, p. 37. https://doi.org/10.1080/10587259408037784

    Article  CAS  Google Scholar 

  35. Traven’, V.F., Ivanov, I.V., Panov, A.V., Safronova, O.B., and Chibisova, T.A., Russ. Chem. Bull., 2008, vol. 57, no. 9, p. 1989. https://doi.org/10.1007/s11172-008-0267-5

    Article  CAS  Google Scholar 

  36. Bagihalli, G.B., Avaji, P.G., Badami, P.S., and Patil, S.A., J. Coord. Chem., 2008, vol. 61, no. 17, p. 2793. https://doi.org/10.1080/00958970801975109

    Article  CAS  Google Scholar 

  37. Yan, M-h., Li, T-r., and Yang, Z-y., Inorg. Chem. Commun., 2011, vol. 14, no. 3, p. 463. https://doi.org/10.1016/j.inoche.2010.12.027

    Article  CAS  Google Scholar 

  38. An, J-m., Yang, Z-y., Yan, M-h., and Li, T-r., J. Lumin., 2013, vol. 139, p. 79. https://doi.org/10.1016/j.jlumin.2013.02.019

    Article  CAS  Google Scholar 

  39. Xie, L., Chen, Y., Wu, W., Guo, H., Zhao, J., and Yu, X., Dyes Pigment., 2012, vol. 92, no. 3, p. 1361. https://doi.org/10.1016/j.dyepig.2011.09.023

    Article  CAS  Google Scholar 

  40. Kulkarni, A.D., Bagihalli, G.B., Patil, S.A., and Badami, P.S., J. Coord. Chem., 2009, vol. 21, no. 18, p. 3060. https://doi.org/10.1080/00958970902914569

    Article  CAS  Google Scholar 

  41. Chen, F., Liu, G., Shi, Y., Xi, P., Cheng, J., Hong, J., Shen, R., Yao, X., Bai, D., and Zeng, Z., Talanta, 2014, vol. 124, p. 139. https://doi.org/10.1016/j.talanta.2014.02.034

    Article  CAS  PubMed  Google Scholar 

  42. Levchenkov, S.I., Shcherbakov, I.N., Popov, L.D., Vlasenko, V.G., Suponitsky, K. Yu., Tsaturyan, A.A., Lukov, V.V., and Kogan, V.A., Russ. J. Coord. Chem., 2014, vol. 40, no. 8, p. 523. https://doi.org/10.1134/S1070328414080041

    Article  CAS  Google Scholar 

  43. Vlasenko, V.G., Uraev, A.I., Zubavichus, Ya. V., Chernyshov, A.A., Garnovskii, A.D., and Mamin, R.K., Bull. Russ. Acad. Sci. Phys., 2008, vol. 72. 4, p. 468. https://doi.org/10.3103/S1062873808040114

    Article  Google Scholar 

  44. Funke, H., Scheinhost, A.C., and Chukalina, M., Phys. Rev. (B), 2005, vol. 71, p. 094110. https://doi.org/10.1103/PhysRevB.71.094110

    Article  CAS  Google Scholar 

  45. Vlasenko, V.G., Popov, L.D., Shcherbakov, I.N., Lukov, V.V., Levchenkov, S.I., Pankov, I.V., Zubavichus, Ya. V., and Trigub, A.L., J. Struct. Chem., 2017, vol. 58, no. 6, p. 1226. https://doi.org/10.1134/S0022476617060221

    Article  CAS  Google Scholar 

  46. Parker, C.A., Photoluminescence of Solutions, Amsterdam: Elsevier, 1968.

    Google Scholar 

  47. Chernyshov, A.A., Veligzhanin, A.A., and Zubavichus, Ya. V., Nucl. Instr. Meth. Phys. Res. (A), 2009, vol. 603, p. 95. https://doi.org/10.1016/j.nima.2008.12.167

    Article  CAS  Google Scholar 

  48. Newville, M., J. Synchrotron Rad., 2001, vol. 8, p. 96. https://doi.org/10.1107/S0909049500016290

    Article  CAS  Google Scholar 

  49. Zabinski, S.I., Rehr, J.J., Ankudinov, A., and Alber, R.C., Phys. Rev. (B), 1995, vol. 52, p. 2995. https://doi.org/10.1103/PhysRevB.52.2995

    Article  Google Scholar 

  50. Becke, A.D., J. Chem. Phys., 1993, vol. 98, no. 7, p. 5648. https://doi.org/10.1063/1.464913

    Article  CAS  Google Scholar 

  51. Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., G. Scalmani, V.B., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., A.F. Izmaylov, Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Nakai, H., Vreven, T., Montgomery, J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., and Fox, D.J., Gaussian 09, Revision, A.02., 2009.

  52. Tomasi, J., Mennucci, B., and Cammi, R., Chem. Rev., 2005, vol. 105, no. 8, p. 2999. https://doi.org/10.1021/cr9904009

    Article  CAS  PubMed  Google Scholar 

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Funding

This study was supported by internal grant of Southern Federal University (no. VnGr-07/2017-29) and performed using the equipment of the Center for Collective Usage “Molecular Spectroscopy” of Southern Federal University.

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Correspondence to L. D. Popov.

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Russian Text © The Author(s), 2019, published in Zhurnal Obshchei Khimii, 2019, Vol. 89, No. 9, pp. 1394–1403.

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Popov, L.D., Borodkin, S.A., Revinskii, Y.V. et al. Synthesis and Selected Properties of Novel Metal Complexes with Bis-Azomethine Based on 7-Hydroxy-4-methyl-8-formylcoumarin and 1,3-Diaminopropan-2-ol. Russ J Gen Chem 89, 1800–1807 (2019). https://doi.org/10.1134/S1070363219090123

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