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Monatshefte für Chemie - Chemical Monthly

, Volume 149, Issue 11, pp 2093–2102 | Cite as

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

  • Juan Zhang
  • Zhi-Qiang Cheng
  • Jia-Li Song
  • Hong-Rui Tao
  • Kongkai Zhu
  • Luis Alexandre Muehlmann
  • Cheng-Shi Jiang
  • Hua Zhang
Original Paper

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

Keywords

Heterocycles Cytotoxicity Antitumor agents Cell cycle arrest Structure–activity relationships 

Notes

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.

Supplementary material

706_2018_2274_MOESM1_ESM.doc (2.6 mb)
Supplementary material 1 (DOC 2686 kb)

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Copyright information

© Springer-Verlag GmbH Austria, part of Springer Nature 2018

Authors and Affiliations

  1. 1.School of Biological Science and TechnologyUniversity of JinanJinanChina
  2. 2.Faculty of CeilandiaUniversity of BrasíliaBrasíliaBrazil

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