66134-74-5

Basic information

• Product Name: hippuryl N-hydroxysuccinimide ester
• Synonyms: hippuryl N-hydroxysuccinimide ester
• CAS NO: 66134-74-5
• Molecular Formula: C₁₃H₁₂N₂O₅
• Molecular Weight: 276.24478
• Mol File: 66134-74-5.mol
• Article Data: 3

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.41g/cm³
• Refractive Index: 1.602
• PKA: 12.47±0.46(Predicted)
• CAS DataBase Reference: hippuryl N-hydroxysuccinimide ester(CAS DataBase Reference)
• NIST Chemistry Reference: hippuryl N-hydroxysuccinimide ester(66134-74-5)
• EPA Substance Registry System: hippuryl N-hydroxysuccinimide ester(66134-74-5)

Safety Data

• Hazardous Substances Data: 66134-74-5(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H12N2O5/c16-10-6-7-11(17)15(10)20-12(18)8-14-13(19)9-4-2-1-3-5-9/h1-5H,6-8H2,(H,14,19)

Upstream product

• 495-69-2 Hippuric Acid 
• 6066-82-6 1-hydroxy-pyrrolidine-2,5-dione 
• 65-85-0 benzoic acid 

Downstream Products

• 103818-50-4 N-benzoylglycylcyanamide 

Relevant articles and documents

Preparation of asymmetric urea derivatives that target prostate-specific membrane antigen for SPECT imaging

Prostate-specific membrane antigen (PSMA) has been identified as a diagnostic and therapeutic target for prostate cancer. (S)-2-[3-[(R)-1-Carboxy- 2-mercaptoethyl]ureido-pentanedioic acid (Cys-CO-Glu) were used to design novel PSMA targeting probes by nucleophilic conjugate addition between cysteine and maleimide based reagents. 3 ([123I]IGLCE) was synthesized by this strategy and showed high affinity for PSMA. Results of binding inhibition assays of these derivatives suggested the importance of an aromatic group and succinimide moiety for high affinity. [123I]3 was evaluated in vivo with PSMA positive LNCaP and PSMA negative PC-3 human prostate cancer xenograft bearing mice. [125I]3 accumulated in LNCaP tumors but not in PC-3 tumors, and the accumulation was inhibited by 2-(phosphonomethyl)pentanedioic acid (2-PMPA). Use of [123I]3 provided positive images of LNCaP tumors in single photon emission tomography scans. These results warrant further evaluation of [123I]3 and its derivatives as radiolabeled probes for the diagnosis of prostate cancer.

Acyl, N-Protected α-Aminoacyl, and Peptidyl Derivatives as Prodrug Forms of the Alcohol Deterrent Agent Cyanamide

Cyanamide , a potent aldehyde dehydrogenase (AlDH) inhibitor that is used therapeutically as an alcohol deterrent agent, is known to be rapidly metabolized and excreted in the urine as acetylcyanamide (1). On the basis of our observation that 1 is deacetylated to cyanamide in vivo, albeit very slightly, thereby serving as a precursor or prodrug form of the latter, several acyl derivatives of cyanamide were synthesized specifically as prodrugs, including benzoylcyanamide (2), pivaloylcyanamide (3), and 1-adamantoylcyanamide (4), as well as long- and medium-chain fatty acyl derivatives such as palmitoyl- (6), stearoyl- (7), and n-butyrylcyanamide (5). N-Protected α-aminoacyl and peptidyl derivatives of cyanamide were also synthesized, and these include N-carbobenzoxyglycyl- (10), hippuryl- (13), N-benzoyl-L-leucyl- (14), N-carbobenzoxyglycyl-L-leucyl- (18), N-carbobenzoxy-L-pyroglutamyl- (22), L-pyroglutamyl-L-leucyl- (19), and L-pyroglutamyl-L-phenylalanylcyanamide (20). All of these prodrugs of cyanamide raised ethanol-derived blood acetaldehyde levels in rats significantly over controls 3h after ip drug administration, and some of these were still capable of elevating blood acetaldehyde 16 h post drug administration. A selected group of cyanamide prodrugs were also evaluated by the oral route of administration and showed nearly equivalent activity as the ip route in elevating ethanol-derived blood acetaldehyde. These results suggest potential utility of these prodrugs as deterrent agents for the treatment of alcoholism.