The reaction of thiolates with 2,3-dibromo-1-propanol revisited: Application to the synthesis of bis(fattyalkylthio)propanols

Chemistry and Physics of Lipids

Volumn 101, Issue 2, 1999, Pages 215-222

  Gernon, Michael D ^a   Turcotte, Joseph G ^a   Notter, Robert H ^b   Wu, Min ^a   Lear, Yvonne ^c   Snelgrove, Jennifer L ^c   Schwan, Adrian L ^c  

^a UNIVERSITY OF RHODE ISLAND   (United States)

^b UNIVERSITY OF ROCHESTER   (United States)

^c UNIVERSITY OF GUELPH   (Canada)

Author keywords

Di thio phospholipid analogs; Fattyalkylthio propanols; Lung surfactants

Indexed keywords

2,3 DIBROMOPROPANOL; DIPALMITOYLPHOSPHATIDYLCHOLINE; GLYCEROPHOSPHOLIPID; LUNG SURFACTANT; PHOSPHATIDYLCHOLINE; PHOSPHOLIPID; PROPANOL; THIOL; UNCLASSIFIED DRUG;

CHROMATOGRAPHY; CONFERENCE PAPER; CONTROLLED STUDY; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

MAGNETIC RESONANCE SPECTROSCOPY; MODELS, CHEMICAL; PROPANOLS; SULFHYDRYL COMPOUNDS;

EID: 0032791263     PISSN: 00093084     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0009-3084(99)00048-1     Document Type: Conference Paper

References (16)

1. E.P. Adams, F.P. Doyle, D.L. Hatt et al., 1960. Antituberculous sulphur compounds. Part I. New mercapto-derviatives of alkanols, sulphides and hydroxy-sulphides. J. Chem. Soc. 2649-2659.
2. Fisher G.H., Schultz H.P. Quinoxaline studies. XXI. 1,4-Bis(p-toluenesulfonyl)-2-hydroxymethyl-1,2,3,4-tetrahydroquinoxaline. J. Org. Chem. 39:1974;631-635.
3. Ganong B.R., Bell R.M. Synthesis of cell-permeant diacylglycerol analogs for structure-function analysis of protein kinase C and other enzymes. Methods Enzymol. 141:1987;313-320.
4. Ganong B.R., Loomis C.R., Hannun Y.A., Bell R.M. Specificity and mechanism of protein kinase c activation by sn-1,2-diacylglycerols. Proc. Natl. Acad. Sci. USA. 83:1986;1184-1188.
5. 2. J. Lipid Res. 24:1983;1532-1537.
6. Jinbo Y., Taguchi M., Inoue Y. et al. Synthesis and antibacterial activity of a new series of tetracyclic pyridone carboxylic acids 2. J. Med. Chem. 36:1993;3148-3153.
7. N.S. Johary, L.N. Owen, 1955. Dithiols. Part XVII. S-Benzyl derivatives of 2:3-dimercaptopropanol and 1:3-dimercaptopropan-2-ol. J. Chem. Soc. 1302-1307.
8. I. Murata, K. Nakasuji, 1975. 5H-1,4-dithiepin and its anion. A lack of aromaticity in the 1,4-dithiepinide ion. Tetrahedron Lett. 1895-1899.
9. Notter R.H., Wang Z. Pulmonary surfactant: physical chemistry, physiology, and replacement. Rev. Chem. Eng. 13:1997;1-118. and references therein.
10. Ong C.W., Chou Y.M., Wang J.N. Novel rearrangements of 2,3-dimercapto-1-propanol derivatives: formation of dialkyl sulfide, dialkyl disulfide and 1,2,3,-tris(alkylthio)propane. J. Org. Chem. 61:1996;8244-8247.
11. 2-=1,3-bis(2-mercaptophenylthio)-2-propoanol (2-)). Inorg. Chim. Acta. 237:1995;137-141.
12. L.A. Stocken, 1947. 2:3-Dimercaptopropanol ("British Anti-Lewisite") and related compounds. J. Chem. Soc. 592-595.
13. Turcotte J.G., Sacco A.M., Steim J., Tabak S.A., Notter R.H. Chemical synthesis and surface properties of a dipalmitoyl phosphatidylcholine analog. Biochim. Biophys. Acta. 488:1977;235-248.
14. Turcotte J.G., Lin W.H., Pivarnik P.E. et al. Chemical synthesis and surface activity of lung surfactant phospholipid analogs. II. Racemic N-substituted diether phosphonolipids. Biochim. Biophys. Acta. 1084:1991;1-12.
15. Turcotte J.G., Lin W.H., Pivarnik P.E. et al. Chemical synthesis and surface activity of lung surfactant phospholipid analogs. III. Chiral N-substituted ether-amide phosphonolipids. Chem. Phys. Lipids. 58:1991;81-95.
16. Walsh J.P., Fahrner L., Bell R.M. sn-1,2-Diacylglycerol kinase of Escherichia coli. J. Biol. Chem. 265:1990;4374-4381.