SYNTHESIS OF AZATHIA-ANALOGS OF PLATELET-ACTIVATING-FACTOR CONTAINING A METHIONINOL BACKBONE

被引:5
作者
ZEIDLER, JM [1 ]
ZIMMERMANN, W [1 ]
ROTH, HJ [1 ]
机构
[1] UNIV TUBINGEN,INST PHARMAZEUT,AUF MORGENSTELLE 8,W-7400 TUBINGEN 1,GERMANY
关键词
PHOSPHOLIPID SYNTHESIS; PLATELET ACTIVATING FACTOR ANALOGS; AZATHIA-ANALOGS; ETHER LIPIDS; CHIRAL SULFUR COMPOUND;
D O I
10.1016/0009-3084(90)90100-6
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The synthesis of azathia-analogues of the platelet activating factor containing a methioninol backbone is reported. The preparation starts with acylating methionine ethyl ester-HCl with palmitoyl chloride to form the amide linkage. Following ester reduction the phosphocholine part is introduced via 2-chloro-2-oxo-1,3,2-dioxaphospholane and subsequent ring opening with trimethylamine under pressure. Two related compounds, the sulfoxide and the sulfone, are obtained by oxidation with 3-chloroperbencoic acid. In addition the sulfoxide derivative is prepared starting with d- and l-methionine ethyl ester-HCl.
引用
收藏
页码:175 / 183
页数:9
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