Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes

Hye Sook Kim; Khurshida Begum; Naoki Ogura; Yusuke Wataya; Yuji Nonami; Toyonari Ito; Araki Masuyama; Masatomo Nojima; Kevin J. McCullough

doi:10.1021/jm020387b

Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes

Hye Sook Kim, Khurshida Begum, Naoki Ogura, Yusuke Wataya, Yuji Nonami, Toyonari Ito, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough

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

35 Citations (Scopus)

Abstract

Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide afforded 1,2-bishydroperoxide 3, which could be cycloalkylated on treatment with silver oxide and a 1,ω-diiodoalkane to provide the tricyclic peroxides 12. Trimethylsilylation of 3 followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 14 containing a 1,2,4,5-tetroxepane structure. Photooxygenation of 1 in the presence of either unsaturated hydroperoxides or unsaturated alcohols followed by bis(collidine)-iodine hexafluorophosphate promoted cyclization gave the corresponding cyclic peroxides 15-17. Several of these cyclic peroxides showed substantial antimalarial activity particularly in vitro.

Original language	English
Pages (from-to)	1957-1961
Number of pages	5
Journal	Journal of medicinal chemistry
Volume	46
Issue number	10
DOIs	https://doi.org/10.1021/jm020387b
Publication status	Published - May 8 2003

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes. / Kim, Hye Sook; Begum, Khurshida; Ogura, Naoki; Wataya, Yusuke; Nonami, Yuji; Ito, Toyonari; Masuyama, Araki; Nojima, Masatomo; McCullough, Kevin J.

In: Journal of medicinal chemistry, Vol. 46, No. 10, 08.05.2003, p. 1957-1961.

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

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abstract = "Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide afforded 1,2-bishydroperoxide 3, which could be cycloalkylated on treatment with silver oxide and a 1,ω-diiodoalkane to provide the tricyclic peroxides 12. Trimethylsilylation of 3 followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 14 containing a 1,2,4,5-tetroxepane structure. Photooxygenation of 1 in the presence of either unsaturated hydroperoxides or unsaturated alcohols followed by bis(collidine)-iodine hexafluorophosphate promoted cyclization gave the corresponding cyclic peroxides 15-17. Several of these cyclic peroxides showed substantial antimalarial activity particularly in vitro.",

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AU - Wataya, Yusuke

AU - Nonami, Yuji

AU - Ito, Toyonari

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - McCullough, Kevin J.

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AB - Photooxygenation of 2-phenylnorbornene 1 in the presence of 30% aqueous hydrogen peroxide afforded 1,2-bishydroperoxide 3, which could be cycloalkylated on treatment with silver oxide and a 1,ω-diiodoalkane to provide the tricyclic peroxides 12. Trimethylsilylation of 3 followed by TMSOTf-catalyzed cyclocondensation with carbonyl compounds led to the formation of the tricyclic peroxides 14 containing a 1,2,4,5-tetroxepane structure. Photooxygenation of 1 in the presence of either unsaturated hydroperoxides or unsaturated alcohols followed by bis(collidine)-iodine hexafluorophosphate promoted cyclization gave the corresponding cyclic peroxides 15-17. Several of these cyclic peroxides showed substantial antimalarial activity particularly in vitro.

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