New chemical and biological aspects of artemisinin-Derived trioxane dimers

Gary H. Posner; John Northrop; Ik Hyeon Paik; Kristina Borstnik; Patrick Dolan; Thomas W. Kensler; Suji Xie; Theresa A. Shapiro

doi:10.1016/S0968-0896(01)00270-X

New chemical and biological aspects of artemisinin-Derived trioxane dimers

Gary H. Posner, John Northrop, Ik Hyeon Paik, Kristina Borstnik, Patrick Dolan, Thomas W. Kensler, Suji Xie, Theresa A. Shapiro

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

52 Scopus citations

Abstract

Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. ¹H spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dimers 5a and 5b, are promising for chemotherapy of both malaria and cancer.

Original language	English (US)
Pages (from-to)	227-232
Number of pages	6
Journal	Bioorganic and Medicinal Chemistry
Volume	10
Issue number	1
DOIs	https://doi.org/10.1016/S0968-0896(01)00270-X
State	Published - 2002

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/S0968-0896(01)00270-X

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title = "New chemical and biological aspects of artemisinin-Derived trioxane dimers",

abstract = "Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. 1H spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dimers 5a and 5b, are promising for chemotherapy of both malaria and cancer.",

author = "Posner, {Gary H.} and John Northrop and Paik, {Ik Hyeon} and Kristina Borstnik and Patrick Dolan and Kensler, {Thomas W.} and Suji Xie and Shapiro, {Theresa A.}",

note = "Funding Information: We thank the NIH (AI-34885, CA-44530, and RR-00052) and the Burroughs Wellcome Fund for generous financial support, the NCI′s Developmental and Therapeutics program for evaluation of these dimers, the Pfizer Pharmaceutical Co. for a summer research fellowship to J.N., and Dr. Paul O′Neill (Liverpool, UK) for helpful suggestions. ",

year = "2002",

doi = "10.1016/S0968-0896(01)00270-X",

language = "English (US)",

volume = "10",

pages = "227--232",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Limited",

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T1 - New chemical and biological aspects of artemisinin-Derived trioxane dimers

AU - Posner, Gary H.

AU - Northrop, John

AU - Paik, Ik Hyeon

AU - Borstnik, Kristina

AU - Dolan, Patrick

AU - Kensler, Thomas W.

AU - Xie, Suji

AU - Shapiro, Theresa A.

N1 - Funding Information: We thank the NIH (AI-34885, CA-44530, and RR-00052) and the Burroughs Wellcome Fund for generous financial support, the NCI′s Developmental and Therapeutics program for evaluation of these dimers, the Pfizer Pharmaceutical Co. for a summer research fellowship to J.N., and Dr. Paul O′Neill (Liverpool, UK) for helpful suggestions.

PY - 2002

Y1 - 2002

N2 - Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. 1H spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dimers 5a and 5b, are promising for chemotherapy of both malaria and cancer.

AB - Joining two 10-deoxoartemisinin trioxane units via a p-diacetylbenzene linker produces new C-10 non-acetal dimers 3b and 3c. 1H spectroscopy allows unambiguous assignment of the stereochemistry at C-10 in these dimers. Successful replacement of both carbonyl oxygen atoms in these diketone dimers by fluorine atoms produces new tetrafluorinated dimers 5a and 5b. Each dimer was evaluated in vitro for antimalarial, antiproliferative, and antitumor activities; ketone dimers 3b and 3c, more than fluorinated dimers 5a and 5b, are promising for chemotherapy of both malaria and cancer.

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JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 1

ER -

New chemical and biological aspects of artemisinin-Derived trioxane dimers

Abstract

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