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

Institute for Education and Student Services

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 language	English
Journal	Journal of Heterocyclic Chemistry
Volume	51
Issue number	SUPPL. 1
DOIs	https://doi.org/10.1002/jhet.1813
Publication status	Published - 2014

Fingerprint

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

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

@article{13b3d67bbd38465085d9dd1e40d90575,

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",

doi = "10.1002/jhet.1813",

language = "English",

volume = "51",

journal = "Journal of Heterocyclic Chemistry",

issn = "0022-152X",

publisher = "Heterocorporation",

number = "SUPPL. 1",

}

TY - JOUR

T1 - Quinolone analogs 14

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

PY - 2014

Y1 - 2014

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.

UR - http://www.scopus.com/inward/record.url?scp=84907022311&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84907022311&partnerID=8YFLogxK

U2 - 10.1002/jhet.1813

DO - 10.1002/jhet.1813

M3 - Article

AN - SCOPUS:84907022311

VL - 51

JO - Journal of Heterocyclic Chemistry

JF - Journal of Heterocyclic Chemistry

SN - 0022-152X

IS - SUPPL. 1

ER -

Access to Document

10.1002/jhet.1813