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Literature DB >> 21132105

Microwave Assisted Synthesis of Sodium Sulfonates Precursors of Sulfonyl Chlorides and Fluorides.

Shakiru O Alapafuja¹, Spyros P Nikas, Vidyanand G Shukla, Ioannis Papanastasiou, Alexandros Makriyannis.

Abstract

We describe the use of a microwave reaction for the conversion of various bromides to sodium sulfonates that have been further elaborated to sulfonyl chlorides. This new approach leads to much improved yields and shorter reaction times. Representative sulfonyl chlorides serve as precursors for the respective sulfonyl fluorides that are potent inhibitors of the fatty acid amide hydrolase.

Entities: Chemical Disease Gene

Year: 2009 PMID： 21132105 PMCID： PMC2994267 DOI： 10.1016/j.tetlet.2009.09.167

Source DB: PubMed Journal: Tetrahedron Lett ISSN： 0040-4039 Impact factor: 2.415

19 in total

Review 1. The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

Authors: Didier M Lambert; Christopher J Fowler
Journal: J Med Chem Date: 2005-08-11 Impact factor: 7.446

2. The Synthesis of Sulfonyl Chlorides by Chlorination of Sulphur Compounds.

Authors: T B Johnson
Journal: Proc Natl Acad Sci U S A Date: 1939-09 Impact factor: 11.205

Review 3. Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules.

Authors: D L Boger; S J Henriksen; B F Cravatt
Journal: Curr Pharm Des Date: 1998-08 Impact factor: 3.116

4. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling.

Authors: Michael H Bracey; Michael A Hanson; Kim R Masuda; Raymond C Stevens; Benjamin F Cravatt
Journal: Science Date: 2002-11-29 Impact factor: 47.728

5. Molecular characterization of human and mouse fatty acid amide hydrolases.

Authors: D K Giang; B F Cravatt
Journal: Proc Natl Acad Sci U S A Date: 1997-03-18 Impact factor: 11.205

6. Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor.

Authors: D G Deutsch; S Lin; W A Hill; K L Morse; D Salehani; G Arreaza; R L Omeir; A Makriyannis
Journal: Biochem Biophys Res Commun Date: 1997-02-03 Impact factor: 3.575

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Authors: Benjamin F Cravatt; Aron H Lichtman
Journal: Curr Opin Chem Biol Date: 2003-08 Impact factor: 8.822

8. Covalent inhibitors of human monoacylglycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis.

Authors: Nikolai Zvonok; Lakshmipathi Pandarinathan; John Williams; Meghan Johnston; Ioannis Karageorgos; David R Janero; Srinivasan C Krishnan; Alexandros Makriyannis
Journal: Chem Biol Date: 2008-08-25

Microwave Assisted Synthesis of Sodium Sulfonates Precursors of Sulfonyl Chlorides and Fluorides.

Review 1. The endocannabinoid system: drug targets, lead compounds, and potential therapeutic applications.

2. The Synthesis of Sulfonyl Chlorides by Chlorination of Sulphur Compounds.

Review 3. Oleamide: an endogenous sleep-inducing lipid and prototypical member of a new class of biological signaling molecules.

4. Structural adaptations in a membrane enzyme that terminates endocannabinoid signaling.

5. Molecular characterization of human and mouse fatty acid amide hydrolases.

6. Fatty acid sulfonyl fluorides inhibit anandamide metabolism and bind to the cannabinoid receptor.

Review 7. Fatty acid amide hydrolase: an emerging therapeutic target in the endocannabinoid system.

8. Covalent inhibitors of human monoacylglycerol lipase: ligand-assisted characterization of the catalytic site by mass spectrometry and mutational analysis.

9. Arachidonylsulfonyl derivatives as cannabinoid CB1 receptor and fatty acid amide hydrolase inhibitors.

10. Endocannabinoid enhancement protects against kainic acid-induced seizures and associated brain damage.

1. Synthesis of aryl sulfonamides via palladium-catalyzed chlorosulfonylation of arylboronic acids.

2. Enantioselective synthesis of (10S)- and (10R)-methyl-anandamides.

3. Sulfonyl fluoride inhibitors of fatty acid amide hydrolase.