Skip to main content
Log in

Synthesis and antiproliferative activity of novel aminoalkylated flavones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Naturally occurring 5-hydroxy-4',7-dimethoxyflavone (acacetin-7-O-methyl ether) was synthesized through dehydrogenation, glycoside hydrolysis, and selective O-methylation, using naringin as starting material. Two series of sixteen novel aminoalkylated flavones were synthesized from 5-hydroxy-4',7-dimethoxyflavone. Furthermore, antiproliferative activity of the compounds was evaluated in vitro on a panel of three human cancer cell lines (HeLa, HCC1954, and SK-OV-3) using Cell Counting Kit-8 assay. The result showed that most of the synthetic compounds exhibited moderate to potent antiproliferative activities against the three human cancer cell lines with IC50 values of 6.95–64.50 μΜ.

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) Verma, A. K.; Pratap, R. Tetrahedron 2012, 68, 8523. (b) Li, S.; Pan, M. H.; Lai, C. S.; Lo, C. Y.; Dushenkov, S.; Ho, C. T. Bioorg. Med. Chem. 2007, 15, 3381. (c) Liu, H. R.; Huang, X. Q.; Lou, D. H.; Liu, X. J.; Liu, W. K.; Wang, Q. A. Bioorg. Med. Chem. Lett. 2014, 24, 4749. (d) Soltesova-Prnova, M.; Milackova, I.; Stefek, M. Chem. Pap. 2016, 70, 1439.

  2. (a) Zhao, J.; Pawar, R. S.; Ali Z.; Kham, I. A. J. Nat. Prod. 2007, 70, 289. (b) Kou, L. Q.; Cheng, X. L. Zhang, Z. T. J. Chem. Crystallogr. 2008, 38, 21.

  3. (a) Kuo, Y. J.; Hwang, S. Y.; Wu, M. D.; Liao, C. C.; Liang, Y. H.; Kuo, Y. H.; Ho, H. O. Chem. Pharm. Bull. 2008, 56, 585. (b) Mori, A.; Nishino, C.; Enoki, N.; Tawata, S. Phytochemistry 1988, 27, 1017. (c) Wongsrikaew, N.; Kim, H.; Vichitphan, K.; Cho, S. K.; Han, J. J. Korean Soc. Appl. Biol. Chem. 2012, 55, 813.

  4. (d) Manthey, J. A.; Grohmann, K.; Guthrie, N. Curr. Med. Chem. 2001, 8, 135. (b) Kesarkar, S.; Bhandage, A.; Deshmukh, S.; Abhyankar, M. J. Pharm. Res. 2009, 2, 1148. (a) Li, X.; Chen, G. L.; Zhang, X. J.; Zhang, Q.; Zheng, S. L.; Wang, G. D.; Chen, Q. H. Bioorg. Med. Chem. Lett. 2016, 26, 4241. (b) Yuan, J.; Wong, I.; Jiang, T.; Wang, S. W.; Liu, T.; Wen, B. J.; Chow, L. M.; Wan, S. B. Eur. J. Med. Chem. 2012, 54, 413. (c) Amrutha, K.; Pandurangan, N. J.; Shaji, S. K.; Sunilkumar, D.; Subhalakshmi, K.; Rajakrishna, L.; Banerji, A. Bioorg. Med. Chem. Lett. 2014, 24, 4735.

  5. (a) Kovaleva, K. S.; Yarovaya, O. I.; Shernyukov, A. V.; Zarubaev, V. V.; Shtro, A. A.; Orshanskaya, Y. R.; Salakhutdinov, N. F. Chem. Heterocycl. Compd. 2017, 53, 364. [Khim. Geterotsikl. Soedin. 2017, 53, 364.] (b) Zhang, S.; Ma, J.; Bao, Y.; Yang, P.; Zhou, L.; Li, K.; Sun, X. Bioorg. Med. Chem. 2008, 16, 7127. (c) Bonesi, M.; Tundis, R.; Deguin, B.; Loizzo, M. R.; Menichini, F.; Tillequin, F.; Menichini, F. Bioorg. Med. Chem. Lett. 2008, 18, 5431. (d) Lozinskii, O. A.; Shokol, T. V.; Khilya, V. P. Chem. Heterocycl. Compd. 2011, 47, 1055. [Khim. Geterotsikl. Soedin. 2011, 1283.] (e) Liu, C. Y.; Dong, L. P.; Wang, S. C.; Wang, Q. A. Mol. Diversity 2015, 19, 737. (f) Voskoboynik, O. Y.; Kolomoets, O. S.; Berest, G. G.; Nosulenko, I. S.; Martynenko, Y. V.; Kovalenko, S. I. Chem. Heterocycl. Compd. 2017, 53, 256. [Khim. Geterotsikl. Soedin. 2017, 53, 256.]

  6. (a) Singh, S.; Ahmad, A.; Raghuvanshi, D. S.; Hasanain, M.; Agarwal, K. A.; Dubey, V.; Fatima, K.; Alam, S.; Sarkar, J.; Luqman, S.; Khman, F.; Tandon, S.; Gupta, A. Bioorg. Med. Chem. Lett. 2016, 26, 5322. (b) Yang, Z. M.; Huang, J.; Qin, J. K.; Dai, Z. K.; Lan, W. L.; Su, G. F.; Tang, H.; Yang, F. Eur. J. Med. Chem. 2014, 85, 487. (c) Fu, W.; Wang, J.; Yu, L.; Zhao, L.; Lu, N.; You, Q.; Guo, Q.; Li, Z. Bioorg. Med. Chem. Lett. 2012, 22, 1118.

  7. (a) Nguyen, V. S.; Dong, L. P.; Wang, S. C.; Wang, Q. A. Eur. J. Org. Chem. 2015, 10, 2297. (b) Nguyen, V. S.; Shi, L.; Luan, F. J.; Wang, Q. A. Acta. Biochim. Pol. 2015, 62, 547. (c) Nguyen, V. S.; Shi, L.; Wang, S. C.; Wang, Q. A. Anti-Cancer. Agent. Med. Chem. 2017, 17, 137.

  8. Wu, Z.; Cai, S. L.; Fan, W. J.; Wang, Q. A. Chinese J. Org. Chem. 2012, 32, 1296.

    Article  CAS  Google Scholar 

  9. Xuan, L. N.; Wang, P.; Zhang, K.; Shi, Y. P.; Liu, Y. M.; Zhu, T.; Cheng, B. Q. Med. Chem. Res. 2015, 24, 543.

    Article  CAS  Google Scholar 

Download references

We thank the National Natural Science Foundation of China (NO.J1210040) and Education Department of Hubei Province Science and Technology Research Project of China (NO.Q20162803) for the financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Qiuan Wang.

Additional information

Supplementary information file containing analytical data characterizing the synthesized compounds and doseresponse curves is available at the journal website http://link.springer.com/journal/10593.

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(8), 871–875

Electronic supplementary material

ESM 1

(PDF 2666 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Yan, L., Liu, H., Wang, Q. et al. Synthesis and antiproliferative activity of novel aminoalkylated flavones. Chem Heterocycl Comp 53, 871–875 (2017). https://doi.org/10.1007/s10593-017-2132-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-017-2132-7

Keywords

Navigation