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

doi:10.1016/S0040-4039(00)00688-2

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 journal › Article › peer-review

28 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 language	English
Pages (from-to)	4681-4684
Number of pages	4
Journal	Tetrahedron Letters
Volume	41
Issue number	23
DOIs	https://doi.org/10.1016/S0040-4039(00)00688-2
Publication status	Published - Jun 12 2000
Externally published	Yes

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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@article{4d596aba5e024dad818cd2fc794c458e,

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

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.",

author = "Yuji Nonami and Takahiro Tokuyasu and Araki Masuyama and Masatomo Nojima and McCullough, {Kevin J.} and Kim, {Hye Sook} and Yusuke Wataya",

note = "Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas (10153238 and 10166211) from the Ministry of Education, Science, Culture and Sports of Japan.",

year = "2000",

month = jun,

day = "12",

doi = "10.1016/S0040-4039(00)00688-2",

language = "English",

volume = "41",

pages = "4681--4684",

journal = "Tetrahedron Letters",

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T1 - Synthesis, crystal structure and antimalarial activity of functionalized spiro-1,2,4,5-tetraoxacycloalkanes from unsaturated hydroperoxy peracetals

AU - Nonami, Yuji

AU - Tokuyasu, Takahiro

AU - Masuyama, Araki

AU - Nojima, Masatomo

AU - McCullough, Kevin J.

AU - Kim, Hye Sook

AU - Wataya, Yusuke

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Scientific Research on Priority Areas (10153238 and 10166211) from the Ministry of Education, Science, Culture and Sports of Japan.

PY - 2000/6/12

Y1 - 2000/6/12

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

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ER -

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

Abstract

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