Quinolone Analogs 14: Synthesis of Antimalarial 1‐Aryl‐3‐(4‐quinolon‐2‐yl)ureas and Related Compounds |
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| Authors: | Yoshihisa Kurasawa Kiminari Yoshida Naoki Yamazaki Kenji Sasaki Yoshito Zamami Zhao Min Atsumi Togi Hideyuki Ito Eisuke Kaji Haruhiko Fukaya |
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| Affiliation: | 1. School of Pharmacy, Iwaki Meisei University, Iino, Chuodai, Iwaki‐shi, Fukushima, Japan;2. Center for Faculty Development, Okayama University, Tsushimanaka, Okayama‐shi, Okayama, Japan;3. Graduate School of Medicine, Dentistry, and Pharmaceutical Sciences, Okayama University, Tsushimanaka, Okayama‐shi, Okayama, Japan;4. School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato‐ku, Tokyo, Japan;5. School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Horinouchi, Hachioji, Tokyo, Japan |
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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. |
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