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DOI: 10.1055/a-2759-6905
Synthesis and Activity Evaluation of Gemcitabine Prodrugs with 4-(Boronic acid) benzoylamide Structure
Autoren
This research was funded by the General Project of the Education Department of Liaoning Province in 2023 (JYTMS20231789), Project of Doctoral Scientific Research Start-up Fund of Liaoning Institute of Science and Technology (2307B14) and Pharmaceutical cleaner production and industrialization innovation team of Liaoning Institute of Science and Technology (XKT202304).
Gefördert durch: Fund of Liaoning Institute of Science and Technology 2307B14
Gefördert durch: team of Liaoning Institute of Science and Technology XKT202304
Abstract
A convenient approach was developed for the syntheses of amide derivatives and novel gemcitabine prodrugs with 4-(boronic acid) benzoylamide structure. The amide compounds containing the phenylboronic acid structure were synthesized by a one-step reaction strategy using o-toluidine and 4-boronobenzoic acid as starting materials. Also, the pure product was quickly obtained through acid–base post-treatment. Moreover, the prodrugs of gemcitabine containing phenylboronic acid structure were rapidly synthesized by the microchannel continuous flow technology. Three of all the obtained targets were subjected to the antiproliferative activity test.
Keywords
Gemcitabine prodrug - 4-(Boronic acid) benzoylamide compounds - Amination reaction - Flow chemistry - Antitumor activity assayPublikationsverlauf
Eingereicht: 26. Oktober 2025
Angenommen nach Revision: 29. November 2025
Accepted Manuscript online:
29. November 2025
Artikel online veröffentlicht:
10. Dezember 2025
© 2025. Thieme. All rights reserved.
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References
- 1 Labroli MA, Dwyer MP, Shen R. et al. Tetrahedron Lett 2014; 55: 598-602
- 2 Ding Y. Chem Lett 2006; 35: 952-953
- 3 Peng YF, Guo J, Yang QX, Ling Y. Prog Pharm Sci 2018; 42: 544-550
- 4 Wickremsinhe E, Bao JQ, Smith R, Burton R, Dow S, Perkins E. Pharmaceutics 2013; 5: 261-276
- 5 Adema AD, Laan AC, Myhren F. et al. Int J Oncol 2010; 36: 285-294
- 6 Yamamoto N, Nokihara H, Yamada Y. et al. Cancer Chemother Pharmacol 2013; 71: 1645-1655
- 7 Sznaider F, Rojas AM, Stortz CA, Navarro DA. Carbohydr Polym 2020; 228: 115388
- 8 Zhu Y, Xue J, Chen W. et al. Controlled Release 2020; 322: 300-311
- 9 Peiró Cadahía J, Bondebjerg J, Hansen CA. et al. J Med Chem 2018; 61: 3503-3515
- 10 Atapalkar RS, Kulkarni AA. Chem Commun 2023; 59: 9231-9234
- 11 Zhang AY, Huang ZH, Du LH. et al. RSC Adv 2024; 14: 39560-39568
- 12 Chaudhary A, Girgis M, Prashad M. et al. Tetrahedron Lett 2003; 44: 5543-5546
- 13 Nedev H, Naharisoa H, Haertlé T. Tetrahedron Lett 1993; 34: 4201-4204
- 14 Kusukawa T, Matoba K, Hoshihara Y, Tanaka S, Nakajima A. Tetrahedron 2021; 96: 132373
- 15 Zhou S, Xin Y, Wang J, Wu C, Sun T. Org Process Res Dev 2021; 25: 1648-1657
- 16 de Carvalho BLC, Aguillon AR, Leão RAC, de Souza ROMA. Tetrahedron Lett 2021; 80: 153318
- 17 Zhang L, Jia G, Li Z. et al. Bioorg Chem 2025; 157: 108293
- 18 Ohara N, Das A, Mahato SK. et al. Chem Lett 2021; 50: 1722-1724
- 19 Qi H, Lu J, Li J. et al. J Pharm Sci 2016; 105: 2966-2973
- 20 Deshmukh M, Chao P, Kutscher HL, Gao D, Sinko PJ. J Med Chem 2010; 53: 1038-1047
- 21 Arastu-Kapur S, Anderl JL, Kraus M. et al. Clin Cancer Res 2011; 17: 2734-2743
- 22 Li T, Timmins HC, King T, Kiernan MC, Goldstein D, Park SB. HumOncol 2021; 38: 229-243
- 23 Song SM, Jeon J, Jang HR. et al. Nephrol Dial Transplant 2023; 38 (09) 2077-2085
- 24 Hadrup N, Frederiksen M, Sharma AK. Regul Toxicol Pharmacol 2021; 121: 104873
- 25 Li AC, Yu E, Ring SC, Chovan JP. Chem Res Toxicol 2013; 26: 608-615