Skip to main content
Log in

Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Aminomethylation of aurones was studied by using anabasine. The reaction in the case of 6-hydroxyaurones was shown to selectively provide 7-aminomethyl-6-hydroxyaurones, while 5-aminomethyl-6-hydroxy-7-methylaurones could be obtained by transamination of 5-dimethylaminomethyl derivatives of 6-hydroxy-7-methylaurones in the presence of anabasine.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. (a) Tilyabaev, Z.; Dalimov, D. N.; Kushiev, Kh. Kh.; Gafurov, M. B.; Abduvakhabov, A. A. Chem. Nat. Compd. 1994, 30, 15. [Khim. Prirod. Soedin. 1994, 19.] (b) Rozengart, E. V.; Basova, N. E.; Suvorov, A. A. J. Evol. Biochem. Physiol. 2006, 42, 11. [Zh. Evol. Biokhim. i Fiziol. 2006, 42, 11.]

  2. (a) Nasirov, S. Kh.; Khazbievich, I. S. Pharmacology of Anabasis aphylla L. Alkaloids and Clinical Use of Anabasine Hydrochloride [in Russian]; Anichkov, S. V., Ed.; FAN: Tashkent, 1982. a Bhatti, B. S.; Strachan, J.-P.; Breining, S. R.; Miller, C. H.; Tahiri, P.; Crooks, P. A.; Deo, N.; Day, C. S.; Caldwell, W. S. J. Org. Chem. 2008, 73, 3497. b Lee, S. T.; Wildeboer, K.; Panter, K. E.; Kem, W. R.; Gardner, D. R.; Molyneux, R. J.; Chang, C.-W. T.; Soti, F.; Pfister, J. A. Neurotoxicol. Teratol. 2006, 28, 220. c Mastropaolo, J.; Rosse, R. B.; Deutsch, S. I. Behav. Brain Res. 2004, 153, 419. d Sarkar, T. K.; Basak, S.; Wainer, I.; Moaddel, R.; Yamaguchi, R.; Jozwiak, K.; Chen, H.-T.; Lin, C.-C. J. Med. Chem. 2004, 47, 6691.

  3. Anichkov, S.; Khromov-Borisov, N.; Zakharova, N.; Gaft, S.; Bekhtereva, É.; Rudenko, A. Pharm. Chem. J. 1976, 10, 1478. [Khim.-Farm. Zh. 1976, 10(11), 53.]

  4. Zhang, Y.; Liu, Y.-B.; Li, Y.; Ma, S.-G.; Li, L.; Qu, J.; Zhang, D.; Chen, X.-G.; Jiang, J.-D.; Yu, S.-S. J. Nat. Prod. 2013, 76, 1058.

    Article  CAS  PubMed  Google Scholar 

  5. (a) Kabdraisova, A. Z.; Faskhutdinov, M. F.; Yu, V. K.; Praliev, K. D.; Fomicheva, E. E.; Shin, S. N.; Berlin, K. D. Chem. Nat. Compd. 2007, 43, 437. [Khim. Prirod. Soedin. 2007, 360.] (b) Mavrov, M. V.; Zlotin, S. G. Russ. Chem. Bull., Int. Ed. 2007, 56, 1637. [Izv. Akad. Nauk, Ser. Khim. 2007, 1576.] (c) Mavrov, M. V.; Zlotin, S. G. Russ. Chem. Bull., Int. Ed. 2009, 58, 1921. [Izv. Akad. Nauk, Ser. Khim. 2009, 1860.]

  6. Tlegenov, R. T. Chemistry of Raw Materials of Plant Origin [in Russian], 2008, (1), 115.

  7. (a) Popova, A. V.; Bondarenko, S. P.; Frasinyuk, M. S. Chem. Heterocycl. Compd. 2016, 52, 592. [Khim. Geterotsikl. Soedin. 2016, 52, 592.] (b) Bondarenko, S. P.; Frasinyuk, M. S. Chem. Heterocycl. Compd. 2018, 54, 765. [Khim. Geterotsikl. Soedin. 2018, 54, 765.] (c) Popova, A. V.; Frasinyuk, M. S.; Bondarenko, S. P.; Zhang, W.; Xie, Y.; Martin, Z. M.; Cai, X.; Fiandalo, M. V.; Mohler, J. L.; Liu, C.; Watt, D. S.; Sviripa, V. M. Chem. Pap. 2018, 72, 2443.

  8. (a) Mughal, E. U.; Sadiq, A.; Murtaza, S.; Rafique, H.; Zafar, M. N.; Riaz, T.; Khan, B. A.; Hameed, A.; Khan, K. M. Bioorg. Med. Chem. 2017, 25, 100. (b) Liew, K.-F.; Chan, K.-L.; Lee, C.-Y. Eur. J. Med. Chem. 2015, 94, 195. (c) Lee, Y. H.; Shin, M. C.; Yun, Y. D.; Shin, S. Y.; Kim, J. M.; Seo, J. M.; Kim, N.-J.; Ryu, J. H.; Lee, Y. S. Bioorg. Med. Chem. 2015, 23, 231.

  9. Bondarenko, S. P.; Frasinyuk, M. S.; Mrug, G. P.; Vinogradova, V. I.; Khilya, V. P. Chem. Nat. Compd. 2018, 54, 1068. [Khim. Prirod. Soedin. 2018, 907.]

  10. Popova, A. V.; Bondarenko, S. P.; Podobii, E. V.; Frasinyuk, M. S.; Vinogradova, V. I. Chem. Nat. Compd. 2017, 53, 708. [Khim. Prirod. Soedin. 2017, 603.]

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Mykhaylo S. Frasinyuk.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(3), 212–216

Electronic supplementary material

ESM 1

(PDF 3917 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Popova, A.V., Bondarenko, S.P., Vinogradova, V.I. et al. Synthesis of anabasine-containing aminomethyl derivatives of 6-hydroxyaurones. Chem Heterocycl Comp 55, 212–216 (2019). https://doi.org/10.1007/s10593-019-02444-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-019-02444-2

Keywords

Navigation