Synthesis of alkyl glycerophospholipids through 1-o-benzyl-2-o-methyl-rac-glycerol

作者: V. I. Shvets , A. N. Pinchuk , B. I. Mitsner

DOI: 10.1007/BF00766461

关键词:

摘要: l-O-Alkyl-2-O-methylglycero-3-phosphocholines are the synthetic analogs of natural alkyllysolecithins. They display high biological activity [13] and, especially importantly, selective cytotoxicity relative to tumor cells various etiologies. This property has been repeatedly confirmed both in experiments with cell cultures and experimental animals [3, 4, 6, ii, 15]. One most active (according literature data), l-O-octadecyl-2O-methyl-rac-glycero-3-phosphocholine (ET-18-OCH3) is undergoing clinical testing at present time [5, 6].

参考文章(10)
F. Paltauf, H. K. Mangold, Ether lipids : biochemical and biomedical aspects Academic Press. ,(1983)
Fred Snyder, Dennis R. Hoffman, Loren H. Hoffman, Cytotoxicity and metabolism of alkyl phospholipid analogues in neoplastic cells. Cancer Research. ,vol. 46, pp. 5803- 5809 ,(1986)
P. E. Verkade, J. D. van Roon, Über die αγ‐Benzylidenglycerole Recueil des Travaux Chimiques des Pays-Bas. ,vol. 61, pp. 831- 841 ,(2010) , 10.1002/RECL.19420611110
Chung Il Hong, Seung Ho An, David J. Buchheit, Alexander Nechaev, Alan J. Kirisits, Charles R. West, Wolfgang E. Berdel, Nucleoside conjugates. 7. Synthesis and antitumor activity of 1-beta-D-arabinofuranosylcytosine conjugates of ether lipids. Journal of Medicinal Chemistry. ,vol. 29, pp. 2038- 2044 ,(1986) , 10.1021/JM00160A041
Karen L. Meyer, Susan W. Schwendner, Raymond E. Counsell, Potential tumor or organ-imaging agents. 30. Radioiodinated phospholipid ethers. Journal of Medicinal Chemistry. ,vol. 32, pp. 2142- 2147 ,(1989) , 10.1021/JM00129A020
Wolfgang E. Berdel, Ulrich Fink, Johann Rastetter, Clinical phase I pilot study of the alkyl lysophospholipid derivative ET-18-OCH3 Lipids. ,vol. 22, pp. 967- 969 ,(1987) , 10.1007/BF02535566
Kirti Agarwal, Anu Bali, C.M. Gupta, Synthesis of carbamyl and ether analogs of phosphatidylcholines Chemistry and Physics of Lipids. ,vol. 36, pp. 169- 177 ,(1984) , 10.1016/0009-3084(84)90069-0
Harold S. Hill, Myron S. Whelen, Harold Hibbert, STUDIES ON THE REACTIONS RELATING TO CARBOHYDRATES AND POLYSACCHARIDES. XV. THE ISOMERIC BENZYLIDENE GLYCEROLS Journal of the American Chemical Society. ,vol. 50, pp. 2235- 2242 ,(1928) , 10.1021/JA01395A025
SUSUMU TSUSHIMA, YOSHIO YOSHIOKA, SEIICHI TANIDA, HIROAKI NOMURA, SHOSHICHI NOJIMA, MOTOO HOZUMI, Syntheses and antimicrobial activities of alkyl lysophospholipids. Chemical & Pharmaceutical Bulletin. ,vol. 30, pp. 3260- 3270 ,(1982) , 10.1248/CPB.30.3260
Bruce Fleming, Henry I. Bolker, Reductive Cleavage of Acetals and Ketals by Borane Canadian Journal of Chemistry. ,vol. 52, pp. 888- 893 ,(1974) , 10.1139/V74-143