Quinolone analogues 15

Synthesis and antimalarial activity of 4-phenyl-1-(1-triazolylmethyl-4-quinolon-3-ylcarbonyl)semicarbazide 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 1-hydrazinocarbonylmethyl-4-quinolone-3-carboxylate (10) was converted into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acid (13), whose reaction with arylcarbaldehydes gave the 1-(4-arylmethyleneamino-1, 2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acids (5a, 5b, 5c, 5d, 5e, 5f, 5g). Compound 10 was also transformed into the 1-(4-amino-1,2,4-triazol-3- ylmethyl)-4-quinolone-3-carbohydrazide (15), whose reaction with phenyl isocyanate or phenyl isothiocyanate afforded the 4-phenyl-1-(1-triazolylmethyl- 4-quinolon-3-ylcarbonyl)semicarbazide (6a) or 4-phenyl-1-(1-triazolylmethyl-4- quinolon-3-ylcarbonyl)thiosemicarbazide (6b), respectively. Compounds 6a, 6b showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein their IC50 was 3.89 and 3.91 μM, respectively.

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

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4-Quinolones
Quinolones
Antimalarials
Chloroquine
4-quinolone-3-carboxylic acid
carbamylhydrazine

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Quinolone analogues 15 : Synthesis and antimalarial activity of 4-phenyl-1-(1-triazolylmethyl-4-quinolon-3-ylcarbonyl)semicarbazide 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 journalArticle

Kurasawa, Yoshihisa ; Yoshida, Kiminari ; Yamazaki, Naoki ; Sasaki, Kenji ; Zamami, Yoshito ; Min, Zhao ; Togi, Atsumi ; Ito, Hideyuki ; Kaji, Eisuke ; Fukaya, Haruhiko. / Quinolone analogues 15 : Synthesis and antimalarial activity of 4-phenyl-1-(1-triazolylmethyl-4-quinolon-3-ylcarbonyl)semicarbazide and related compounds. In: Journal of Heterocyclic Chemistry. 2014 ; Vol. 51, No. SUPPL. 1.
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abstract = "The 1-hydrazinocarbonylmethyl-4-quinolone-3-carboxylate (10) was converted into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acid (13), whose reaction with arylcarbaldehydes gave the 1-(4-arylmethyleneamino-1, 2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acids (5a, 5b, 5c, 5d, 5e, 5f, 5g). Compound 10 was also transformed into the 1-(4-amino-1,2,4-triazol-3- ylmethyl)-4-quinolone-3-carbohydrazide (15), whose reaction with phenyl isocyanate or phenyl isothiocyanate afforded the 4-phenyl-1-(1-triazolylmethyl- 4-quinolon-3-ylcarbonyl)semicarbazide (6a) or 4-phenyl-1-(1-triazolylmethyl-4- quinolon-3-ylcarbonyl)thiosemicarbazide (6b), respectively. Compounds 6a, 6b showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein their IC50 was 3.89 and 3.91 μM, respectively.",
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",
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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

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N2 - The 1-hydrazinocarbonylmethyl-4-quinolone-3-carboxylate (10) was converted into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acid (13), whose reaction with arylcarbaldehydes gave the 1-(4-arylmethyleneamino-1, 2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acids (5a, 5b, 5c, 5d, 5e, 5f, 5g). Compound 10 was also transformed into the 1-(4-amino-1,2,4-triazol-3- ylmethyl)-4-quinolone-3-carbohydrazide (15), whose reaction with phenyl isocyanate or phenyl isothiocyanate afforded the 4-phenyl-1-(1-triazolylmethyl- 4-quinolon-3-ylcarbonyl)semicarbazide (6a) or 4-phenyl-1-(1-triazolylmethyl-4- quinolon-3-ylcarbonyl)thiosemicarbazide (6b), respectively. Compounds 6a, 6b showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein their IC50 was 3.89 and 3.91 μM, respectively.

AB - The 1-hydrazinocarbonylmethyl-4-quinolone-3-carboxylate (10) was converted into the 1-(4-amino-1,2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acid (13), whose reaction with arylcarbaldehydes gave the 1-(4-arylmethyleneamino-1, 2,4-triazol-3-ylmethyl)-4-quinolone-3-carboxylic acids (5a, 5b, 5c, 5d, 5e, 5f, 5g). Compound 10 was also transformed into the 1-(4-amino-1,2,4-triazol-3- ylmethyl)-4-quinolone-3-carbohydrazide (15), whose reaction with phenyl isocyanate or phenyl isothiocyanate afforded the 4-phenyl-1-(1-triazolylmethyl- 4-quinolon-3-ylcarbonyl)semicarbazide (6a) or 4-phenyl-1-(1-triazolylmethyl-4- quinolon-3-ylcarbonyl)thiosemicarbazide (6b), respectively. Compounds 6a, 6b showed the in vitro antimalarial activity to chloroquine-resistant Plasmodium falciparum, wherein their IC50 was 3.89 and 3.91 μM, respectively.

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