Quinolone analogs 14: Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds

Yoshihisa Kurasawa, Kiminari Yoshida, Naoki Yamazaki, Kenji Sasaki, Yoshito Zamami, Zhao Min, Atsumi Togi, Hideyuki Ito, Eisuke Kaji, Haruhiko Fukaya

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Abstract

The 4-quinolone-2-carbohydrazide 6a was converted into 1-aryl-3-(4- quinolon-2-yl)ureas 5a, 5b, 5c, 5d, 5e, 1-aryl-3-(4-quinolon-2-yl)imidazolidine- 2,4-diones 9a,9b, and N-(4-quinolon-2-yl)carbamates 10a,10b via 4-quinolone-2-carbonylazide 7a. The 4-methoxyquinoline-2-carbohydrazide 6b was also transformed into 1-aryl-3-(4-methoxyquinolin-2-yl)ureas 11a, 11b, 11c, 11d, 1-aryl-3-(4-methoxyquinolin-2-yl)imidazolidine-2,4-diones 12a,12b, and N-(4-methoxyquinolin-2-yl)carbamates 13a,13b via 4-methoxyquinoline-2- carbonylazide 7b. Some of the 1-aryl-3-(4-quinolon-2-yl)ureas 5a, 5b, 5c, 5d, 5e showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein IC50 was 0.93 to 4.00 μM.

Original languageEnglish
JournalJournal of Heterocyclic Chemistry
Volume51
Issue numberSUPPL. 1
DOIs
Publication statusPublished - 2014

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ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Kurasawa, Y., Yoshida, K., Yamazaki, N., Sasaki, K., Zamami, Y., Min, Z., Togi, A., Ito, H., Kaji, E., & Fukaya, H. (2014). Quinolone analogs 14: Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds. Journal of Heterocyclic Chemistry, 51(SUPPL. 1). https://doi.org/10.1002/jhet.1813