Jump to content
 







Main menu
    


Navigation  


●Main page
 ●Contents
 ●Current events
 ●Random article
 ●About Wikipedia
 ●Contact us
 ●Donate
  



Contribute  


●Help
 ●Learn to edit
 ●Community portal
 ●Recent changes
 ●Upload file
  







Search  

































●Create account

●Log in
 









●Create account
 ● Log in
  



Pages for logged out editors learn more  


●Contributions
 ●Talk
  


















Contents

   



(Top)
  


1 Synthesis  




2 Further reading  




3 References  




4 External links  













Lisofylline






●Српски / srpski
 ●Srpskohrvatski / српскохрватски
  
Edit links
  








●Article
 ●Talk
  
















●Read
 ●Edit
 ●View history
  







Tools
    


Actions  


●Read
 ●Edit
 ●View history
  



General  


●What links here
 ●Related changes
 ●Upload file
 ●Special pages
 ●Permanent link
 ●Page information
 ●Cite this page
 ●Get shortened URL
 ●Download QR code
 ●Wikidata item
  



Print/export  


●Download as PDF
 ●Printable version
  



In other projects  


●Wikimedia Commons
  















Appearance
    

 





From Wikipedia, the free encyclopedia
  

Lisofylline
Skeletal formula of lisofylline
Space-filling model of the lisofylline molecule
Clinical data
Other names1-(5-Hydroxyhexyl)-3,7-dimethylxanthine (HDX)
Identifiers

  • 1-[(5R)-5-Hydroxyhexyl]-3,7-dimethyl-3,7-dihydro-1H-purine-2,6-dione

CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC13H20N4O3
Molar mass280.328 g·mol−1
3D model (JSmol)

  • O=C2N(c1ncn(c1C(=O)N2CCCC[C@H](O)C)C)C

  • InChI=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 checkY

  • Key:NSMXQKNUPPXBRG-SECBINFHSA-N checkY

 ☒NcheckY (what is this?)  (verify)

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 metaboliteofpentoxifylline.

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[edit]

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.

Lisofylline synthesis: U.S. patent 5,567,704NB[1][2][3][4][5][6][7]

For analogs see:[8]

Further reading[edit]

References[edit]

  1. ^ Matteson DS, Sadhu KM, Peterson ML (1986). "99% Chirally selective synthesis via pinanediol boronic esters: Insect pheromones, diols, and an amino alcohol". Journal of the American Chemical Society. 108 (4): 810. doi:10.1021/ja00264a039.
  • ^ Matteson DS, Ray R, Rocks RR, Tsai DJ (1980). "Directed chiral synthesis with pinanediol boronic esters". Journal of the American Chemical Society. 102 (25): 7590. doi:10.1021/ja00545a046.
  • ^ Matteson DS, Jesthi PK, Sadhu KM (1997). "Asymmetric synthesis of alkylarylcarbinols via reaction of a chiral pinanediol alkylboronic ester with arylmethyl chlorides". Tetrahedron: Asymmetry. 8 (23): 3843. doi:10.1016/S0957-4166(97)00565-X.
  • ^ Matteson DS, Jesthi PK, Sadhu KM (1984). "Synthesis and properties of pinanediol .alpha.-amido boronic esters". Organometallics. 3 (8): 1284. doi:10.1021/om00086a024.
  • ^ Matteson DS (1988). "Asymmetric synthesis with boronic esters". Accounts of Chemical Research. 21 (8): 294–300. doi:10.1021/ar00152a002.
  • ^ Matteson DS (October 2013). "Boronic esters in asymmetric synthesis". The Journal of Organic Chemistry. 78 (20): 10009–23. doi:10.1021/jo4013942. PMID 23875690.
  • ^ Scott HK, Aggarwal VK (November 2011). "Highly enantioselective synthesis of tertiary boronic esters and their stereospecific conversion to other functional groups and quaternary stereocentres". Chemistry: A European Journal. 17 (47): 13124–32. doi:10.1002/chem.201102581. PMID 22052475.
  • ^ Cui P, Macdonald TL, Chen M, Nadler JL (July 2006). "Synthesis and biological evaluation of lisofylline (LSF) analogs as a potential treatment for Type 1 diabetes". Bioorganic & Medicinal Chemistry Letters. 16 (13): 3401–5. doi:10.1016/j.bmcl.2006.04.036. PMID 16650991.

    • External links[edit]


    Retrieved from "https://en.wikipedia.org/w/index.php?title=Lisofylline&oldid=1188222764"
    Categories: 
    ●Anti-inflammatory agents
     ●Xanthines
     ●Anti-interleukin drugs
     Hidden categories: 
    ●Articles with short description
     ●Short description matches Wikidata
     ●Articles with changed CASNo identifier
     ●Chemical pages without DrugBank identifier
     ●Articles without KEGG source
     ●Drugs missing an ATC code
     ●Drugs with no legal status
     ●Drugboxes which contain changes to verified fields
      


    ●This page was last edited on 4 December 2023, at 01:35 (UTC).
    ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization.


    ●Privacy policy
    ●About Wikipedia
    ●Disclaimers
    ●Contact Wikipedia
    ●Code of Conduct
    ●Developers
    ●Statistics
    ●Cookie statement
    ●Mobile view


    Wikimedia Foundation
    Powered by MediaWiki