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Synthesis and structure of functionalized podands containing 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring. Differently substituted dihydropyrimidine podands

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Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 3-oxobutanoate-containing polyethers with benzaldehyde and 5-aminotetrazole in the presence of polyphosphoric acid was used to synthesize podands containing two terminal tetrazolo[1,5-а]dihydropyrimidine groups. Byproducts were isolated and identified as podands containing different substituents – one 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring system and a free hydroxy group at the other terminus of the polyether chain. Analogous differently substituted podands, including one 3,4-dihydropyrimidine-2(1H)-thione moiety, were isolated from the reactions of 3-oxobutanoate-containing polyethers with benzaldehyde and thiourea.

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References

  1. Contreras, J.-M.; Sippl, W. In The Practice of Medicinal Chemistry; Wermuth, G., Ed.; Academic Press: London, 2008, p. 380.

  2. (a) Tomassoli, I.; Gündisch, D. Bioorg. Med. Chem. 2015, 23, 4375. (b) Da Silva, W. A. V.; Rodrigues, D. C.; de Oliveira, R. G.; Mendes, R. K. S.; Olegário, T. R.; Rocha, J. C.; Keesen, T. S. L.; Lima-Junior, C. G.; Vasconcellos, M. L. A. A. Bioorg. Med. Chem. Lett. 2016, 26, 4523.

  3. Zefirova, O. N.; Zefirov, N. S. Vestn. MGU, Ser. 2. Khimiya 2000, 41, 103.

  4. Klein, E.; DeBonis, S.; Thiede, B.; Skoufias, D. A.; Kozielski, F.; Lebeau, L. Bioorg. Med. Chem. 2007, 15, 6474.

    Article  CAS  Google Scholar 

  5. (a) Ovchinnikov, Yu. A.; Ivanov, V. E.; Shkrob, А. M. Membrane-active Complexing Agents [in Russian]; Nauka: Moscow, 1974. (b) Pressman, B. C. Ann. Rev. Biochem. 1976, 45, 501.

  6. (а) Danagulyan, G. G. Chem. J. Arm. 2017, 70, 113. a Łakomska, I.; Fandzloch, M. Coord. Chem. Rev. 2016, 327, 221.

  7. a Tsuda, N.; Mishina, T.; Obata, M.; Araki, K.; Inui, A.; Nakamura, T. JPS Patent 63101383. (b) Tsuda, Y.; Mishina, T.; Obata, M.; Araki, K.; Inui, J.; Nakamura, T. EU Patent 0217142.

  8. Rusinov, G. L.; Fedorova, O. V.; Zhidovinova, M. S.; Gorbunov, E. B.; Chupakhin, O. N.; Kravchenko, M. A.; Mordovskoi, G. G.; Ovshinnikova, I. G. RU patent 2360905.

  9. (a) Shipps, G. W.; Rosner, K. E.; Popovici-Muller, J.; Deng, Y.; Wang, T.; Curran, P. J. US Patent 7196111. (b) Fraley, M. E.; Hambaugh, S. R.; Rubino, R. S.; Hungate, R. W. US Patent 7262199. (c) Zhou, H.-B.; Sheng, S.; Compton, D. R.; Kim, Y.; Joachimiak, A.; Sharma, S.; Carlson, K. E.; Katzenellenbogen, B. S.; Nettles, K. W.; Greene, G. L.; Katzenellenbogen, J. A. J. Med. Chem. 2007, 50, 399.

  10. (a) Gein, V. L.; Panova, O. S.; Syropyatov, B. Ya.; Kovaleva, M. Yu. RU patent 2413730. (b) Mishunin, V. V. Thesis of Candidate of Chemical Sciences; Perm, 2011. (c) Сuconati, A.; Block, T. M.; Xu, X. US Patent 2009088397.

  11. (a) Orlov, V. D.; Desenko, S. M.; Pivnenko, N. S. Chem. Heterocycl. Compd. 1988, 24, 1233. [Khim. Geterotsikl. Soedin. 1988, 1489.] (b) Nussbaum, F. V.; Karthaus, D.; Anlauf, S.; Delbeck, M.; Li, V. M.-J.; Meibom, D.; Lustig, K. US Patent 2014038988.

  12. (a) Ghorbani-Vaghei, R.; Toghraei-Semiromi, Z.; Amiri, M.; Karimi-Nami, R. Mol. Diversity 2013, 17, 307. (b) Yao, C.; Lei, S.; Wang, C.; Yu, C.; Tu, S. J. Heterocycl. Chem. 2008, 45, 1609. (c) Gein, V. L.; Zamaraeva, Т. М.; Dmitriev, М. V.; Ovchinnikova, I. G.; Fedorova, О. V. Russ. J. Org. Chem. 2017, 53, 1090. [Zh. Org. Khim. 2017, 53, 1077.]. (d) Zeng, L.-Y.; Cai, C. J. Comb. Chem. 2010, 12, 35. (e) Dolshenko, A. V. Heterocycles 2017, 94, 1819.

  13. Zhidovinova, M. S.; Fedorova, O. V.; Rusinov, G. L.; Ovchinnikova, I. G. Mol. Diversity 2003, 6, 323.

    Article  CAS  Google Scholar 

  14. (a) Fedorova, О. V.; Filatova, Е. S.; Titova, Yu. А.; Kravchenko, М. А.; Medvinskiy, I. D.; Rusinov, G. L.; Charushin, V. N. Russ. Chem. Bull., Int. Ed. 2018, 67, 743. [Izv. Akad. Nauk, Ser. Khim. 2018, 743.] (b) Filatova, Е. S.; Fedorova, О. V.; Titova, Yu. А.; Slepukhin, P. А.; Kravchenko, М. А.; Skornyakov, S. N.; Rusinov, G. L.; Charushin, V. N. Russ. Chem. Bull., Int. Ed. 2016, 65, 1360. [Izv. Akad. Nauk, Ser. Khim. 2016, 1360.]

  15. Fedorova, О. V.; Ovchinnikova, I. G.; Kravchenko, М. А.; Skornyakov, S. N.; Rusinov, G. L.; Chupakhin, O. N.; Charushin, V. N. Chem. Heterocycl. Compd. 2014, 7, 946. [Khim. Geterotsikl. Soedin. 2014, 1027.]

  16. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

    Article  CAS  Google Scholar 

  17. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

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This work was performed with financial support from the Russian Science Foundation (project 15-13-00077-P).

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Correspondence to Elena S. Filatova.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(10), 971–976

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Filatova, E.S., Fedorova, O.V., Slepukhin, P.A. et al. Synthesis and structure of functionalized podands containing 4,7-dihydrotetrazolo[1,5-а]pyrimidine ring. Differently substituted dihydropyrimidine podands. Chem Heterocycl Comp 54, 971–976 (2018). https://doi.org/10.1007/s10593-018-2373-0

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