2002 Fiscal Year Final Research Report Summary
Synthesis and Biological Activity of Macrocyclic Peroxides
| Project/Area Number |
13650904
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| Research Category |
Grant-in-Aid for Scientific Research (C)
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| Allocation Type | Single-year Grants |
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| Section | 一般 |
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| Research Field |
有機工業化学
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| Research Institution | Osaka University |
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Principal Investigator |
NOJIMA Masatomo Osaka University Graduate School of Engineering, Professor, 大学院・工学研究科, 教授 (80029181)
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| Project Period (FY) |
2001 – 2002
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| Keywords | Macrocyclic Peroxides / Unsaturated Hvdroperoxides / BCIH-promoted Cyclization / Ozonation / Antimalarial Agents |
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| Research Abstract |
Since malaria parasites are rapidly developing resistance to the most commonly used chemo-tnerapeutic alkaloidal drugs, the antimalarial properties of nonalkaloidal compounds such as artemisinin have attracted considerable attention. Based on our original methodologies for the synthesis of medium-sized cyclic peroxides, we tried to develop new synthetic methods of macrocyclic peroxides. The key starting material is unsaturated hydroperoxides, which could be prepared by the mono-alkylation of 1, 1 -bishydroperoxides or selective oxidation of one of the double bonds of dienes. Bis(syn-collidine)iodine(l) hexafluorophosphate-promoted cyclization of the derived unsaturated hydroperoxides was found to give the corresponding 11- to 20-membered cyclic peroxides in excellent yields. Alternatively, ozonolyses of unsaturated hydroperoxides in trifluoroethanol gave the hydroperoxysubstituted cyclic peroxides including the 13-membred one, derived from intramolecular capture of the carbonyl oxide moiety by the hydroperoxy group. We are now investigating the biological activities of these macrocyclic peroxides.
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Research Products
(12 results)
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[Publications] Hye-Sook Kim, Yukiko Nagai, Kanako Ono, Khurshida Begum, Yusuke Wataya, Yoshiaki Hamada, Kaoru Tsuchiya, Araki Masuyama, Masatomo Nojima, and Kevin J. McCullough: "Synthesis and Antimakarial Activity of Novel Medium-Sized 1,2,4,5-Tetraoxacycloalkanes"Journal of Medicinal Chemistry. 44 (14). 2357-2361 (2001)
Description
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