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Synthesis, crystal structure, and ESR study of a novel phosphorylated lipophilic spin trap
Xu, YK; Chen, ZW; Sun, J; Liu, K; Chen, W; Shi, W; Wang, HM; Liu, Y
2002-11-01
Source PublicationJOURNAL OF ORGANIC CHEMISTRY
ISSN0022-3263
Volume67Issue:22Pages:7624-7630
AbstractIn this article, the synthesis of a novel alpha-phosphorus-containing spin trap DEPPEPO [2-(diethoxyphosphoryl)-2-phenethyl-3,4-dihydro-2H-pyrrole-1-oxide] and the evaluation of its ability to spintrap radicals, especially superoxide and hydroxyl radicals, are described. Single crystal X-ray structure analysis reveals that there exist a lot of intramolecular nonbonded attractive interactions in the molecule. The phenethyl group is located away from the diethoxyphosphoryl group and the nitronyl plane, and only one face of the nitronyl plane is sterically hindered by the oxygen attached to the phosphorus with a double bond. The latter feature is responsible for the stereoselection of the free radical additions on the nitronyl moiety. The ability of DEPPEPO to trap the active superoxide anion radical generated in the HX/XO system and the stability of their spin adduct were investigated with that for DEPMPO. The half-life of DEPPEPO is about 13.4 min, and as a result, the DEPPEPO seems to be a promising lipophilic spin trap, perhaps in both in vitro and in vivo ESR investigation. Because DEPPEPO is a solid compound, it is quite easy to purify by recrystallization and to store the compound even at room temperature. In addition, an obvious increase in lipophilicity for DEPPEPO was found as a contribution of 2-substituted phenethyl.
DOI10.1021/jo020126+
Indexed ByIC ; SCI
Language英语
WOS IDWOS:000178820200007
PublisherAMER CHEMICAL SOC
Citation statistics
Document Type期刊论文
Identifierhttp://ir.iccas.ac.cn/handle/121111/78782
Collection中国科学院化学研究所
Corresponding AuthorLiu, Y
AffiliationChinese Acad Sci, Inst Chem, Ctr Mol Sci, State Key Lab Struct Chem Unstable & Stable Speci, Beijing 100080, Peoples R China
Recommended Citation
GB/T 7714
Xu, YK,Chen, ZW,Sun, J,et al. Synthesis, crystal structure, and ESR study of a novel phosphorylated lipophilic spin trap[J]. JOURNAL OF ORGANIC CHEMISTRY,2002,67(22):7624-7630.
APA Xu, YK.,Chen, ZW.,Sun, J.,Liu, K.,Chen, W.,...&Liu, Y.(2002).Synthesis, crystal structure, and ESR study of a novel phosphorylated lipophilic spin trap.JOURNAL OF ORGANIC CHEMISTRY,67(22),7624-7630.
MLA Xu, YK,et al."Synthesis, crystal structure, and ESR study of a novel phosphorylated lipophilic spin trap".JOURNAL OF ORGANIC CHEMISTRY 67.22(2002):7624-7630.
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