Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals

Yuji Nonami, Takahiro Tokuyasu, Araki Masuyama, Masatomo Nojima, Kevin J. McCullough, Hye-Sook Kim, Yusuke Wataya

Research output: Contribution to journalArticle

24 Citations (Scopus)

Abstract

Treatment of unsaturated hydroperoxy peracetals with bis(sym- collidine)iodine(I) hexafluorophosphate affords a series of iodine-containing spiro-1,2,4,5-tetraoxacycloalkane derivatives in high yield. In addition, ozonolysis of unsaturated hydroperoxy peracetals in AcOH-CH2Cl2 also results in the formation of spiro-1,2,4,5-tetraoxacycloalkanes. Two of the new compounds, 3-methyl-3,methyldioxy-1,2,6,7-tetraoxaspiro[7.11]nonadecane and dimethyl-4-iodo-1,2,6,7-tetraoxaspiro[7.11]nonadecane, exhibit significant in vitro antimalarial activity against P. falciparum with EC50 values of ca. 10-7 M. (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)4681-4684
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number23
Publication statusPublished - Jun 12 2000
Externally publishedYes

Fingerprint

Antimalarials
Iodine
Crystal structure
Derivatives
1,2,6,7-tetraoxaspiro(7.11)nonadecane
gamma-collidine
In Vitro Techniques

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. / Nonami, Yuji; Tokuyasu, Takahiro; Masuyama, Araki; Nojima, Masatomo; McCullough, Kevin J.; Kim, Hye-Sook; Wataya, Yusuke.

In: Tetrahedron Letters, Vol. 41, No. 23, 12.06.2000, p. 4681-4684.

Research output: Contribution to journalArticle

Nonami, Y, Tokuyasu, T, Masuyama, A, Nojima, M, McCullough, KJ, Kim, H-S & Wataya, Y 2000, 'Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals', Tetrahedron Letters, vol. 41, no. 23, pp. 4681-4684.
Nonami, Yuji ; Tokuyasu, Takahiro ; Masuyama, Araki ; Nojima, Masatomo ; McCullough, Kevin J. ; Kim, Hye-Sook ; Wataya, Yusuke. / Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals. In: Tetrahedron Letters. 2000 ; Vol. 41, No. 23. pp. 4681-4684.
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AU - McCullough, Kevin J.

AU - Kim, Hye-Sook

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