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Lisofylline

Chemical compound

Field	Value
Verifiedfields	changed
verifiedrevid	462092166
IUPAC_name	1-[(5R)-5-Hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione
image	lisofylline.svg
image_class	skin-invert-image
alt	Skeletal formula of lisofylline
image2	Lisofylline 3D spacefill.png
image_class2	bg-transparent
alt2	Space-filling model of the lisofylline molecule
pregnancy_AU
pregnancy_US
legal_AU
legal_CA
legal_UK
legal_US
CAS_number_Ref
CAS_number	100324-81-0
ATC_prefix
PubChem	501254
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID	438549
UNII_Ref
UNII	L1F2Q2X956
ChEBI	143527
ChEMBL_Ref
ChEMBL	1411
synonyms	1-(5-Hydroxyhexyl)-3,7-dimethylxanthine (HDX)
C	13	H=20	N=4	O=3
smiles	O=C2N(c1ncn(c1C(=O)N2CCCCC@HC)C)C
StdInChI_Ref
StdInChI	1S/C13H20N4O3/c1-9(18)6-4-5-7-17-12(19)10-11(14-8-15(10)2)16(3)13(17)20/h8-9,18H,4-7H2,1-3H3/t9-/m1/s1
StdInChIKey_Ref
StdInChIKey	NSMXQKNUPPXBRG-SECBINFHSA-N

| elimination_half-life =

Lisofylline (LSF) is a synthetic small molecule with novel anti-inflammatory properties. LSF can effectively prevent type 1 diabetes in preclinical models and improves the function and viability of isolated or transplanted pancreatic islets. It is a metabolite of pentoxifylline.

As well, LSF improves cellular mitochondrial function and blocks interleukin-12 (IL-12) signaling and STAT-4 activation in target cells and tissues. IL-12 and STAT-4 activation are important pathways linked to inflammation and autoimmune damage to insulin producing cells. Therefore, LSF and related analogs could provide a new therapeutic approach to prevent or reverse type 1 diabetes. LSF also directly reduces glucose-induced changes in human kidney cells suggesting that LSF and analogs have the potential to treat the complications associated with diabetes.

Synthesis

The R enantiomer of the pentoxyfylline analogue in which the ketone has been reduced to an alcohol shows enhanced activity as an inhibitor of acetyl CoA over the parent drug.

doi = 10.1002/chem.201102581 }}</ref>

For analogs see:

References

(1986). "99% Chirally selective synthesis via pinanediol boronic esters: Insect pheromones, diols, and an amino alcohol". Journal of the American Chemical Society.
(1980). "Directed chiral synthesis with pinanediol boronic esters". Journal of the American Chemical Society.
(1997). "Asymmetric synthesis of alkylarylcarbinols via reaction of a chiral pinanediol alkylboronic ester with arylmethyl chlorides". Tetrahedron: Asymmetry.
(1984). "Synthesis and properties of pinanediol .alpha.-amido boronic esters". Organometallics.
(1988). "Asymmetric synthesis with boronic esters". Accounts of Chemical Research.
(October 2013). "Boronic esters in asymmetric synthesis". The Journal of Organic Chemistry.
(November 2011). "Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres". Chemistry: A European Journal.
(July 2006). "Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes". Bioorganic & Medicinal Chemistry Letters.

Info: Wikipedia Source

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anti-inflammatory-agents xanthines anti-interleukin-drugs

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