Quinolone analogs 11: Synthesis of novel 4-quinolone-3-carbohydrazide derivatives with antimalarial activity

Yoshihisa Kurasawa; Kiminari Yoshida; Naoki Yamazaki; Eisuke Kaji; Kenji Sasaki; Yoshito Zamami; Yasuhiro Sakai; Takatoshi Fujii; Hideyuki Ito

doi:10.1002/jhet.774

Quinolone analogs 11: Synthesis of novel 4-quinolone-3-carbohydrazide derivatives with antimalarial activity

Yoshihisa Kurasawa, Kiminari Yoshida, Naoki Yamazaki, Eisuke Kaji, Kenji Sasaki, Yoshito Zamami, Yasuhiro Sakai, Takatoshi Fujii, Hideyuki Ito

Institute for Education and Student Services

Research output: Contribution to journal › Article

10 Citations (Scopus)

Abstract

The reaction of the 6-substituted 1-methyl-4-quinolone-3-carboxylates 10a,b with hydrazine hydrate gave the 3-carbohydrazides 7a,b, respectively, whose reaction with 2-, 3-, and 4-pyridinecarbaldehydes afforded the 3-(N ²-pyridylmethylene)carbohydrazides 8a-c and 9a-c. The Curtius rearrangement of compound 7b provided the N,N'-bis(4-quinolon-3-yl)urea 14 presumably via the 3-carboazide 11 and then 3-isocyanate 12. Compounds 7a, 8a, and 9a were found to possess antimalarial activity from the in vitro screening data.

Original language	English
Pages (from-to)	288-292
Number of pages	5
Journal	Journal of Heterocyclic Chemistry
Volume	49
Issue number	2
DOIs	https://doi.org/10.1002/jhet.774
Publication status	Published - Mar 1 2012

ASJC Scopus subject areas

Organic Chemistry

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Kurasawa, Y., Yoshida, K., Yamazaki, N., Kaji, E., Sasaki, K., Zamami, Y., Sakai, Y., Fujii, T., & Ito, H. (2012). Quinolone analogs 11: Synthesis of novel 4-quinolone-3-carbohydrazide derivatives with antimalarial activity. Journal of Heterocyclic Chemistry, 49(2), 288-292. https://doi.org/10.1002/jhet.774

Quinolone analogs 11 : Synthesis of novel 4-quinolone-3-carbohydrazide derivatives with antimalarial activity. / Kurasawa, Yoshihisa; Yoshida, Kiminari; Yamazaki, Naoki; Kaji, Eisuke; Sasaki, Kenji; Zamami, Yoshito; Sakai, Yasuhiro; Fujii, Takatoshi; Ito, Hideyuki.

In: Journal of Heterocyclic Chemistry, Vol. 49, No. 2, 01.03.2012, p. 288-292.

Research output: Contribution to journal › Article

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abstract = "The reaction of the 6-substituted 1-methyl-4-quinolone-3-carboxylates 10a,b with hydrazine hydrate gave the 3-carbohydrazides 7a,b, respectively, whose reaction with 2-, 3-, and 4-pyridinecarbaldehydes afforded the 3-(N 2-pyridylmethylene)carbohydrazides 8a-c and 9a-c. The Curtius rearrangement of compound 7b provided the N,N'-bis(4-quinolon-3-yl)urea 14 presumably via the 3-carboazide 11 and then 3-isocyanate 12. Compounds 7a, 8a, and 9a were found to possess antimalarial activity from the in vitro screening data.",

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AU - Kaji, Eisuke

AU - Sasaki, Kenji

AU - Zamami, Yoshito

AU - Sakai, Yasuhiro

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