Quinolone analogs 11: Synthesis of novel 4‐quinolone‐3‐carbohydrazide derivatives with antimalarial activity |
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| Authors: | Yoshihisa Kurasawa Kiminari Yoshida Naoki Yamazaki Eisuke Kaji Kenji Sasaki Yoshito Zamami Yasuhiro Sakai Takatoshi Fujii Hideyuki Ito |
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| Affiliation: | 1. School of Pharmacy, Iwakli Meisei University, Iino, Chuodai, Iwaki‐shi, Fukushima 970‐8551, Japan;2. School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato‐ku, Tokyo 108‐8641, Japan;3. Graduate School of Medicine, Dentistory, and Pharmaceutical Sciences, Okayama University, Tsushimanaka, Okayama‐shi, Okayama 700‐8530, Japan |
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| Abstract: | The reaction of the 6‐substituted 1‐methyl‐4‐quinolone‐3‐carboxylates 10a , 10b with hydrazine hydrate gave the 3‐carbohydrazides 7a , 7b , respectively, whose reaction with 2‐, 3‐, and 4‐pyridinecarbaldehydes afforded the 3‐(N2‐pyridylmethylene)carbohydrazides 8a , 8b , 8c and 9a , 9b , 9c . 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. J. Heterocyclic Chem.,(2011). |
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