260433-14-5

Basic information

• Product Name: N⁽¹⁾-Boc-N⁽⁴⁾-benzoyl-1,4-diaminobutane
• Synonyms: N⁽¹⁾-Boc-N⁽⁴⁾-benzoyl-1,4-diaminobutane
• CAS NO: 260433-14-5
• Molecular Weight: 292.378
• Mol File: 260433-14-5.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N⁽¹⁾-Boc-N⁽⁴⁾-benzoyl-1,4-diaminobutane(CAS DataBase Reference)
• NIST Chemistry Reference: N⁽¹⁾-Boc-N⁽⁴⁾-benzoyl-1,4-diaminobutane(260433-14-5)
• EPA Substance Registry System: N⁽¹⁾-Boc-N⁽⁴⁾-benzoyl-1,4-diaminobutane(260433-14-5)

Safety Data

• Hazardous Substances Data: 260433-14-5(Hazardous Substances Data)

Upstream product

• 33545-98-1 N-(4-aminobutyl)carbaminsaeure-(tert-butyl)ester-hydrochlorid 
• 98-88-4 benzoyl chloride 

Downstream Products

• 1335096-54-2 N⁽¹⁾-Boc-1,4-diaminobutane*TFA 
• 1335096-42-8 N⁽¹⁾-benzoyl-N⁽⁴⁾-(2-fluoro-1-iminoethyl)-1,4-diaminobutane*TFA 

Relevant articles and documents

The development of N-α-(2-carboxyl)benzoyl- N 5-(2-fluoro- 1-iminoethyl)- l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl) benzoyl-N5-(2-chloro-1-iminoethyl)-l-ornithine amide (o -Cl-amidine) as second generation protein arginine deiminase (PAD) inhibitors

Protein arginine deiminase (PAD) activity is upregulated in a number of human diseases, including rheumatoid arthritis, ulcerative colitis, and cancer. These enzymes, there are five in humans (PADs 1-4 and 6), regulate gene transcription, cellular differentiation, and the innate immune response. Building on our successful generation of F- and Cl-amidine, which irreversibly inhibit all of the PADs, a structure-activity relationship was performed to develop second generation compounds with improved potency and selectivity. Incorporation of a carboxylate ortho to the backbone amide resulted in the identification of N-α-(2-carboxyl)benzoyl-N5-(2-fluoro-1- iminoethyl)-l-ornithine amide (o-F-amidine) and N-α-(2-carboxyl)benzoyl- N5-(2-chloro-1-iminoethyl)-l-ornithine amide (o-Cl-amidine), as PAD inactivators with improved potency (up to 65-fold) and selectivity (up to 25-fold). Relative to F- and Cl-amidine, the compounds also show enhanced potency in cellulo. As such, these compounds will be versatile chemical probes of PAD function.