Synthesis and biological activity of the D-3-deoxy-3-fluoro and D-3-chloro-3-deoxy analogues of phosphatidylinositol

doi:10.1021/JO00084A010

Paper

Synthesis and biological activity of the D-3-deoxy-3-fluoro and D-3-chloro-3-deoxy analogues of phosphatidylinositol

Published Mar 1, 1994 · A. Kozikowski, G. Powis, A. Fauq

Journal of Organic Chemistry

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Abstract

The naturally occurring inositol derivative, L-quebrachitol (1), serves as starting material for the synthesis of D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol (4, 28). Their transformation into the title compounds 22 and 40 (abbreviated as FPI and CPI, respectively) is accomplished by benzylation of all hydroxyl groups but OH-1 to which the phosphatidic acid side chain is subsequently attached using the phosphoramidite protocol, and hydrogenolytic deprotection. Compounds 4 and 28, as reported earlier, exhibit moderate and high selectivity, respectively, in the growth inhibition of υ-sis transformed vs wild type murine NIH 3T3 cells if myo-inositol is agent but are inactive in the presence of physiological inositol levels. On the other hand, FPI possesses a nearly 2 orders of magnitude higher activity but no selectivity both in the absence or presence of myo-inositol. CPI is inactive as is the simplified analogue 24 of FPI in which the phosphatidic acid moiety has been replaced by an octadecyl group

Study Snapshot

D-3-deoxy-3-fluoro- and D-3-chloro-3-deoxy-myo-inositol exhibit moderate and high selectivity in growth inhibition of -sis transformed vs wild type murine NIH 3T3 cells, respectively, but are inactive in the

PopulationOlder adults (50-71 years)

Sample size24

MethodsObservational

OutcomesBody Mass Index projections

ResultsSocial networks mitigate obesity in older groups.

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Paper

Synthesis and biological activity of the D-3-deoxy-3-fluoro and D-3-chloro-3-deoxy analogues of phosphatidylinositol

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References

Citations

Optimized synthesis of phosphatidylserine

The optimized synthesis of phosphatidylserine using imidazolium chloride enables large-scale production of saturated fatty acids, with a one-pot multicomponent reaction and imidazolium chloride as a suitable substitute for tetrazole.

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Hydrogen iodide effectively deprotects multifunctional inositols, allowing for the synthesis of various chiro-inositols with different properties.

d-2-Deoxy-2-fluoro-chiro-inositol—a new member of the deoxy fluoro inositol family

A new synthetic route has been developed for d-2-deoxy-2-fluoro-chiro-inositol, using inversions of the C-1 and C-5 configuration of l-quebrachitol and one-pot epimerization procedures.

Highly-functionalised difluorinated (hydroxymethyl)conduritol analogues via the Diels-Alder reactions of a difluorinated dienophile.

Difluorinated dienophiles can be used to synthesize highly-functionalized (hydroxymethyl)conduritol analogues by undergoing Diels-Alder reactions with oxa[2.2.1]bicycloheptenes and palladium-cataly

Synthesis and biological activity of 3-hydroxy(phosphono)methyl-bearing phosphatidylinositol ether lipid analogues

Two 3-hydroxy(phosphono)methyl-bearing phosphatidylinositol ether lipid analogues inhibit Akt and PI3-K, and inhibit the growth of HT-29 human colon cancer cells and MCF-7 human breast cancer cells.