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

Research output: Contribution to journal › Article

2 Citations (Scopus)

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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Quinolones
Antimalarials
4-Quinolones
Hydantoins
Urea
Carbamates
Chloroquine
carbohydrazide

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Quinolone analogs 14 : Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds. / Kurasawa, Yoshihisa; Yoshida, Kiminari; Yamazaki, Naoki; Sasaki, Kenji; Zamami, Yoshito; Min, Zhao; Togi, Atsumi; Ito, Hideyuki; Kaji, Eisuke; Fukaya, Haruhiko.

In: Journal of Heterocyclic Chemistry, Vol. 51, No. SUPPL. 1, 2014.

Research output: Contribution to journal › Article

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, vol. 51, no. SUPPL. 1. https://doi.org/10.1002/jhet.1813
Kurasawa Y, Yoshida K, Yamazaki N, Sasaki K, Zamami Y, Min Z et al. Quinolone analogs 14: Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds. Journal of Heterocyclic Chemistry. 2014;51(SUPPL. 1). https://doi.org/10.1002/jhet.1813
Kurasawa, Yoshihisa ; Yoshida, Kiminari ; Yamazaki, Naoki ; Sasaki, Kenji ; Zamami, Yoshito ; Min, Zhao ; Togi, Atsumi ; Ito, Hideyuki ; Kaji, Eisuke ; Fukaya, Haruhiko. / Quinolone analogs 14 : Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds. In: Journal of Heterocyclic Chemistry. 2014 ; Vol. 51, No. SUPPL. 1.
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AU - Yoshida, Kiminari

AU - Yamazaki, Naoki

AU - Sasaki, Kenji

AU - Zamami, Yoshito

AU - Min, Zhao

AU - Togi, Atsumi

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AU - Fukaya, Haruhiko

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AB - 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.

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