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

doi:10.1002/jhet.1813

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 language	English
Pages (from-to)	E241-E248
Journal	Journal of Heterocyclic Chemistry
Volume	51
Issue number	SUPPL. 1
DOIs	https://doi.org/10.1002/jhet.1813
Publication status	Published - Aug 2014

ASJC Scopus subject areas

Organic Chemistry

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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, 08.2014, p. E241-E248.

Research output: Contribution to journal › Article › peer-review

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

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.",

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

year = "2014",

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doi = "10.1002/jhet.1813",

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volume = "51",

pages = "E241--E248",

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T2 - Synthesis of antimalarial 1-aryl-3-(4-quinolon-2-yl) ureas and related compounds

AU - Kurasawa, Yoshihisa

AU - Yoshida, Kiminari

AU - Yamazaki, Naoki

AU - Sasaki, Kenji

AU - Zamami, Yoshito

AU - Min, Zhao

AU - Togi, Atsumi

AU - Ito, Hideyuki

AU - Kaji, Eisuke

AU - Fukaya, Haruhiko

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N2 - 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.

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

Abstract

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