Skip to main content
SpringerLink
Log in

Synthesis and biological evaluation of 2-(3-aminophenyl)-benzothiazoles as antiproliferative and apoptosis-inducing agents

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

A series of new 2-(3-aminophenyl)-benzothiazole derivatives were synthesized and evaluated for their in vitro antiproliferative activity against various human cancer cell lines including A549, HeLa, HepG2, MCF-7, MV4-11, and DB. Among the tested compounds, N-[3-(benzo[d]thiazol-2-yl)phenyl]nicotinamide displayed significantly improved antiproliferative activity toward A549 and MV4-11 cells with IC50 values of 5.42 ± 1.33 and 7.51 ± 0.98 μM, respectively, much stronger than the hit 3-(benzo[d]thiazol-2-yl)-N-(4-bromobenzyl)aniline. Furthermore, flow cytometric analysis indicated that N-[3-(benzo[d]thiazol-2-yl)phenyl]nicotinamide induced A549 cell apoptosis with cell cycle arrest at G1 phase in a concentration-dependent manner.

Graphical abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Jemal A, Bray F, Center MM, Ferlay J, Ward E, Forman D (2011) CA Cancer J Clin 61:69

    Article  Google Scholar 

  2. GBD 2015 Disease and Injury Incidence and Prevalence Collaborators (2016) Lancet 388:1545

    Article  Google Scholar 

  3. World Cancer Report (2014) World Health Organization. Accessed 3 Mar 2018

  4. Zhang J, Yang F, Qiao Z, Zhu M, Zhou H (2016) Bioorg Med Chem Lett 26:5797

    Article  CAS  Google Scholar 

  5. Tantawy MA, Nafie MS, Elmegeed GA, Ali IAI (2017) Bioorg Chem 73:128

    Article  CAS  Google Scholar 

  6. Rai A, Singh AK, Raj V, Saha S (2018) Mini Rev Med Chem 18:42

    CAS  PubMed  Google Scholar 

  7. Akhtar MJ, Yar MS, Khan AA, Ali Z, Haider MR (2017) Mini Rev Med Chem 17:1602

    Article  CAS  Google Scholar 

  8. Rouf A, Tanyeli C (2015) Eur J Med Chem 97:911

    Article  CAS  Google Scholar 

  9. Mei WW, Ji SS, Xiao W, Wang XD, Jiang CS, Ma WQ, Zhang HY, Gong JX, Guo YW (2017) Monatsh Chem 148:1807

    Article  CAS  Google Scholar 

  10. Thakkar SS, Thakor P, Ray A, Doshi H, Thakkar VR (2017) Bioorg Med Chem 25:5396

    Article  CAS  Google Scholar 

  11. Bhat M, Belagali SL (2018) Future Med Chem 10:71

    Article  CAS  Google Scholar 

  12. Cindrić M, Jambon S, Harej A, Depauw S, David-Cordonnier MH, Kraljević Pavelić S, Karminski-Zamola G, Hranjec M (2017) Eur J Med Chem 136:468

    Article  Google Scholar 

  13. Al-Harthy T, Zoghaib WM, Stoll R (2018) Monatsh Chem 149:645

    Article  CAS  Google Scholar 

  14. Kamal A, Syed MA, Mohammed SM (2015) Expert Opin Ther Pat 25:335

    Article  CAS  Google Scholar 

  15. Capuyo R, Calabrò ML, Micale N, Schimmer AD, Ali M, Zappalà M, Grasso S (2015) Med Chem Res 21:2644

    Article  Google Scholar 

  16. Hutchinson I, Chua MS, Browne HL, Trapani V, Bradshaw TD, Westwell AD, Stevens MF (2001) J Med Chem 44:1446

    Article  CAS  Google Scholar 

  17. Zhang Y, Chakraborty M, Cerda-Smith CG, Bratton RN, Maurer NE, Senser EM, Novak M (2013) J Org Chem 78:6992

    Article  CAS  Google Scholar 

  18. Chhabra M, Sinha S, Banerjee S, Paira P (2016) Bioorg Med Chem Lett 26:213

    Article  CAS  Google Scholar 

  19. Ehlert J, Herz T, Krauss R, Kubbutat M, Lang M, Saeb W, Schaechtele C, Tasler S, Totzke F, Zirrgiebel U (2007) 2-Arylbenzothiazole analogs as kinase inhibitors and their preparation, pharmaceutical compositions and use in the treatment of kinase-mediated diseases. US patent 20070021446 ((2007) Chem Abstr 146:184430)

  20. Ehlert J, Herz T, Krauss R, Kubbutat M, Martin L, Saeb W, Schaechtele C, Tasler S, Totzke F, Zirrgiebel U (2007) Preparation of 2-heteroarylaminophenylbenzothiazoles as anticancer drugs. European patent EP 1746096 A1 ((2007) Chem Abstr 146:184428)

  21. Asahara H (2017) Proc Eng 174:1046

    Article  CAS  Google Scholar 

  22. Mosmann T (1983) J Immunol Methods 65:55

    Article  CAS  Google Scholar 

  23. Wang J, Sánchez-Roselló M, Aceña JL, del Pozo C, Sorochinsky AE, Fustero S, Soloshonok VA, Liu H (2014) Chem Rev 114:2432

    Article  CAS  Google Scholar 

  24. Shankaraiaha N, Nekkantia S, Brahmab UR, Kumara NP, Deshpandea N, Prasannaa D, Senwara KR, Lakshmib UJ (2017) Bioorg Med Chem 25:4805

    Article  Google Scholar 

  25. Wade AR, Pawar HR, Biware MV, Chikate RC (2015) Green Chem 17:3879

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research work was financially supported by the National Natural Science Foundation of China (No. 21672082), Shandong Key Development Project (No. 2016GSF201209), the Young Taishan Scholars Program (No. tsqn20161037), Natural Science Foundation of Shandong Province (Nos. ZR2017BH038, JQ201721), Shandong Talents Team Cultivation Plan of University Preponderant Discipline (No. 10027), and the Brazilian Government Agencies FAP/DF and CNPq.

Author information

Author notes

  1. Juan Zhang, Zhi-Qiang Cheng, and Jia-Li Song contributed equally to this work.

Authors and Affiliations

  1. School of Biological Science and Technology, University of Jinan, Jinan, 250022, China

    Juan Zhang, Zhi-Qiang Cheng, Jia-Li Song, Hong-Rui Tao, Kongkai Zhu, Cheng-Shi Jiang & Hua Zhang

  2. Faculty of Ceilandia, University of Brasília, Brasília, 72220275, Brazil

    Juan Zhang & Luis Alexandre Muehlmann

Authors
  1. Juan Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zhi-Qiang Cheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Jia-Li Song
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hong-Rui Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Kongkai Zhu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Luis Alexandre Muehlmann
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Cheng-Shi Jiang
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Hua Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Cheng-Shi Jiang or Hua Zhang.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2686 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Zhang, J., Cheng, ZQ., Song, JL. et al. Synthesis and biological evaluation of 2-(3-aminophenyl)-benzothiazoles as antiproliferative and apoptosis-inducing agents. Monatsh Chem 149, 2093–2102 (2018). https://doi.org/10.1007/s00706-018-2274-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-018-2274-z

Keywords

Search

Navigation