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Convenient Synthesis and Anticancer Activity of Bis(aryl)alkanes and Bis(indolyl)methane Alkaloid Analogs

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Abstract

An efficient metal free high yield method of synthesis of bis(indolyl)methanes (BIMs) and bis(aryl)alkanes analogs in the presence of B(C6F5)3 by condensation of primary amines with pyruvates has been successfully developed. Some analogs of BIMs display good in vitro antitumor activity, screened by MTT assay. Compound 3b demonstrates the best anti-cancer activity against lung carcinoma cell A549 cells with IC50 of 4.52 µM.

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REFERENCES

  1. Sarva, S., Harinath, J.S., Sthanikam, S.P., Ethiraj, S., Vaithiyalingam, M., and Cirandur, S.R., Chin. Chem. Lett., 2016, vol. 27, p. 16. https://doi.org/10.1016/j.cclet.2015.08.012

    Article  CAS  Google Scholar 

  2. Grosso, C., Cardoso, A.L., Lemos, A., Varela, J., Rodrigues, M.J., Custodio, L., Barreira, L., and Melo, T., Eur. J. Med. Chem., 2015, vol. 93, p. 9. https://doi.org/10.1016/j.ejmech.2015.01.050

    Article  CAS  PubMed  Google Scholar 

  3. Veisi, H., Maleki, B., Eshbala, F.H., Masti, R., Ashrafib, S.S., and Baghayeri, M., RSC Adv., 2014, vol. 4, p. 30683. https://doi.org/10.1039/C4RA03194F

    Article  CAS  Google Scholar 

  4. Das, P.J., and Das, J., Tetrahedron Lett., 2012, vol. 53, p. 4718. https://doi.org/10.4236/gsc.2013.34A002

    Article  CAS  Google Scholar 

  5. Xiang, Z.W., Liu, Z.Q., Chen, X., Wu, Q., and Lin, X.F., Amino Acids, 2013, vol. 45, p. 937. https://doi.org/10.1007/s00726-013-1547-4

    Article  CAS  PubMed  Google Scholar 

  6. Stephan, D.W., Science, 2016, vol. 354, p. 1248. https://doi.org/10.1126/science.aaf7229

    Article  CAS  Google Scholar 

  7. Mahdi, T., and Stephan, D.W., J. Am. Chem. Soc., 2014, vol. 136, p. 15809. https://doi.org/10.1021/ja508829x

    Article  CAS  PubMed  Google Scholar 

  8. Li, W, Werner, T., Org. Lett., 2017, vol. 19, p. 2568. https://doi.org/10.1021/acs.orglett.7b00720

    Article  CAS  PubMed  Google Scholar 

  9. Kim, D.W., Joung, S., Kim, J.G., and Chang, S., Angew. Chem. Int. Ed., 2015, vol. 54, p. 14805. https://doi.org/10.1002/anie.201507863

    Article  CAS  Google Scholar 

  10. Ling, F., Xiao, L., Fang, L., Feng, C., Xie, Z., Lv, Y., and Zhong, W.H., Org. Biomol. Chem., 2018, vol. 16, p. 9274. https://doi.org/10.1039/C8OB02805B

    Article  CAS  PubMed  Google Scholar 

  11. Kumar, B.A. and Jagarlapudi, V.S.K., Russ. J. Gen. Chem., 2020, vol. 90, p.929. https://doi.org/10.1134/S1070363219120296

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

We thank Jiangsu Vocational College of Medicine (20186104) and Jiangsu Provincial Higher Education Natural Science Foundation (19KJB350010) for financial support.

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Correspondence to L. Xiao.

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Qi, L., Xiao, L. Convenient Synthesis and Anticancer Activity of Bis(aryl)alkanes and Bis(indolyl)methane Alkaloid Analogs. Russ J Gen Chem 90, 1974–1980 (2020). https://doi.org/10.1134/S1070363220100217

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  • DOI: https://doi.org/10.1134/S1070363220100217

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