A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum

Naoto Yamasaki; Ikumi Iwasaki; Kazu Sakumi; Rei Hokari; Aki Ishiyama; Masato Iwatsuki; Masataka Nakahara; Shuhei Higashibayashi; Takeshi Sugai; Hiroshi Imagawa; Miwa Kubo; Yoshiyasu Fukuyama; Satoshi Ōmura; Hirofumi Yamamoto

doi:10.1002/chem.202100032

A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum

Naoto Yamasaki, Ikumi Iwasaki, Kazu Sakumi, Rei Hokari, Aki Ishiyama, Masato Iwatsuki, Masataka Nakahara, Shuhei Higashibayashi, Takeshi Sugai, Hiroshi Imagawa, Miwa Kubo, Yoshiyasu Fukuyama, Satoshi Ōmura, Hirofumi Yamamoto

School of Pharmaceutical Sciences

Research output: Contribution to journal › Article › peer-review

1 Citation (Scopus)

Abstract

The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5-dichloro-2H-1,4-oxazin-2-one with 14 a as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine-resistant Plasmodium falciparum.

Original language	English
Pages (from-to)	5555-5563
Number of pages	9
Journal	Chemistry - A European Journal
Volume	27
Issue number	17
DOIs	https://doi.org/10.1002/chem.202100032
Publication status	Published - 2021 Mar 22

Keywords

Diels–Alder reactions
antimalarial drugs
dehydroantofine
density functional calculations
pi interactions

ASJC Scopus subject areas

Catalysis
Organic Chemistry

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10.1002/chem.202100032

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Yamasaki, N., Iwasaki, I., Sakumi, K., Hokari, R., Ishiyama, A., Iwatsuki, M., Nakahara, M., Higashibayashi, S., Sugai, T., Imagawa, H., Kubo, M., Fukuyama, Y., Ōmura, S., & Yamamoto, H. (2021). A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum. Chemistry - A European Journal, 27(17), 5555-5563. https://doi.org/10.1002/chem.202100032

Yamasaki, N, Iwasaki, I, Sakumi, K, Hokari, R, Ishiyama, A, Iwatsuki, M, Nakahara, M, Higashibayashi, S , Sugai, T, Imagawa, H, Kubo, M, Fukuyama, Y, Ōmura, S & Yamamoto, H 2021, 'A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum', Chemistry - A European Journal, vol. 27, no. 17, pp. 5555-5563. https://doi.org/10.1002/chem.202100032

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abstract = "The total synthesis of dehydroantofine was achieved by employing a novel, regioselective, azahetero Diels–Alder reaction of easily accessible 3,5-dichloro-2H-1,4-oxazin-2-one with 14 a as a key step. Furthermore, it is demonstrated that dehydroantofine is a promising candidate as a new antimalarial agent in a biological assay with chloroquine-resistant Plasmodium falciparum.",

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author = "Naoto Yamasaki and Ikumi Iwasaki and Kazu Sakumi and Rei Hokari and Aki Ishiyama and Masato Iwatsuki and Masataka Nakahara and Shuhei Higashibayashi and Takeshi Sugai and Hiroshi Imagawa and Miwa Kubo and Yoshiyasu Fukuyama and Satoshi Ōmura and Hirofumi Yamamoto",

note = "Funding Information: We are grateful to Dr. Yasuko Okamoto (analysis center at Tokushima Bunri University) for determining the HRMS results. Part of this study was financially supported by a Grant‐in‐Aid (no. 18K05365) from the MEXT (Ministry of Education, Culture, Sports, Science, and Technology) of the Japanese Government. Publisher Copyright: {\textcopyright} 2021 Wiley-VCH GmbH",

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AU - Iwasaki, Ikumi

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AU - Hokari, Rei

AU - Ishiyama, Aki

AU - Iwatsuki, Masato

AU - Nakahara, Masataka

AU - Higashibayashi, Shuhei

AU - Sugai, Takeshi

AU - Imagawa, Hiroshi

AU - Kubo, Miwa

AU - Fukuyama, Yoshiyasu

AU - Ōmura, Satoshi

AU - Yamamoto, Hirofumi

N1 - Funding Information: We are grateful to Dr. Yasuko Okamoto (analysis center at Tokushima Bunri University) for determining the HRMS results. Part of this study was financially supported by a Grant‐in‐Aid (no. 18K05365) from the MEXT (Ministry of Education, Culture, Sports, Science, and Technology) of the Japanese Government. Publisher Copyright: © 2021 Wiley-VCH GmbH

PY - 2021/3/22

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A Concise Total Synthesis of Dehydroantofine and Its Antimalarial Activity against Chloroquine-Resistant Plasmodium falciparum

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