57334-90-4

Basic information

• Product Name: Benzamide,5-chloro-N-[2-[4-[[[(cyclohexylamino) carbonyl]amino]sulfonyl]phenyl]- ethyl]-2-hydroxy-
• CAS NO: 57334-90-4
• Molecular Weight: 479.985
• Mol File: 57334-90-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Benzamide,5-chloro-N-[2-[4-[[[(cyclohexylamino) carbonyl]amino]sulfonyl]phenyl]- ethyl]-2-hydroxy- (CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide,5-chloro-N-[2-[4-[[[(cyclohexylamino) carbonyl]amino]sulfonyl]phenyl]- ethyl]-2-hydroxy- (57334-90-4)
• EPA Substance Registry System: Benzamide,5-chloro-N-[2-[4-[[[(cyclohexylamino) carbonyl]amino]sulfonyl]phenyl]- ethyl]-2-hydroxy- (57334-90-4)

Safety Data

• Hazardous Substances Data: 57334-90-4(Hazardous Substances Data)

Upstream product

• 3173-53-3 Cyclohexyl isocyanate 
• 1734-62-9 2-acetoxy-5-chloro-benzoic acid 
• 321-14-2 5-chloro-2-hydroxybenzoic acid 
• 10238-21-8 Glibenclamid 

Relevant articles and documents

Synthesis and In Vivo Evaluation of [11C]Glyburide for Imaging Pancreatic &β-Cells

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Synthesis of fluorine-18 labeled sulfonureas as β-cell imaging agents

Tolbutamide (1) and glyburide (7) are hypoglycemic drugs used to stimulate insulin secretion in type 2 diabetic patients. We have synthesized their fluorine-18 labeled analogs, 1-[(4-[18F]fluorobenzenesulfonyl)]-3-butyl]urea (p-[18F]fluorotolbutamide, 3a) and N-{4-[β-(2-[18F]fluoroethoxybenzene carboxamido)ethyl]benzenesulfonyl}-N′-cyclohexylurea (2-[18F]fluoroethoxyglyburide, 6a) as β-cell imaging agents. Compound 3a was synthesized via two approaches: One-step synthesis via nucleophilic substitution of p-nitrotolbutamide (2) with K[18F]/Kryptofix 2.2.2 in either CH3CN or DMSO gave a complicated mixture; a two-step synthesis via preparation and reaction of 4-[18F]fluorobenzenesulfonamide with butyl isocyanate in the presence of either copper (I) chloride or borontrifluoride etherate complex in CH3CN followed by HPLC purification yielded compound 3a in an overall yield of 1-2% with a synthesis time of 120 minutes from EOB. Compound 6a was synthesized by alkylation of the corresponding hydroxy precursor (5) with [18F]fluoroethyl tosylate in DMSO at 1200C for 20 minutes followed by HPLC purification in an overall yield of 5-10% with a synthesis time of 100 minutes from EOB. The lipid/water partition coefficient of compounds 3a and 6a was 3.13±0.28, n=6 and 124.33±21.61, n=8, respectively. The feasibility of using these radiotraces as β-cell imaging agents is under evaluation.