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 journalArticle

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,?-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 languageEnglish
Pages (from-to)1957-1961
Number of pages5
JournalJournal of Medicinal Chemistry
Volume46
Issue number10
DOIs
Publication statusPublished - 8 May 2003

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Peroxides
Antimalarials
Hydrogen Peroxide
Carbonyl compounds
Cyclization
Alcohols

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Kim, H. S., Begum, K., Ogura, N., Wataya, Y., Nonami, Y., Ito, T., ... McCullough, K. J. (2003). Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes. Journal of Medicinal Chemistry, 46(10), 1957-1961. https://doi.org/10.1021/jm020387b
Kim, Hye Sook ; Begum, Khurshida ; Ogura, Naoki ; Wataya, Yusuke ; Nonami, Yuji ; Ito, Toyonari ; Masuyama, Araki ; Nojima, Masatomo ; McCullough, Kevin J. / Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes. In: Journal of Medicinal Chemistry. 2003 ; Vol. 46, No. 10. pp. 1957-1961.
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Kim, HS, Begum, K, Ogura, N, Wataya, Y, Nonami, Y, Ito, T, Masuyama, A, Nojima, M & McCullough, KJ 2003, 'Antimalarial activity of novel 1,2,5,6-tetraoxacycloalkanes and 1,2,5-trioxacycloalkanes', Journal of Medicinal Chemistry, vol. 46, no. 10, pp. 1957-1961. https://doi.org/10.1021/jm020387b

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 journalArticle

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AU - Kim, Hye Sook

AU - Begum, Khurshida

AU - Ogura, Naoki

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,?-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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