73385-89-4

Basic information

• Product Name: N-(tert-butoxycarbonyl)-4-nitro-3-phenyl-L-alanyl-L-prolinamide
• Synonyms: N-(tert-butoxycarbonyl)-4-nitro-3-phenyl-L-alanyl-L-prolinamide;N-[(1,1-Dimethylethoxy)carbonyl]-4-nitro-L-Phe-L-Pro-NH2
• CAS NO: 73385-89-4
• Molecular Formula: C₁₉H₂₆N₄O₆
• Molecular Weight: 406.43294
• EINECS: 277-422-9
• Mol File: 73385-89-4.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• Density: 1.27g/cm³
• Refractive Index: 1.566
• CAS DataBase Reference: N-(tert-butoxycarbonyl)-4-nitro-3-phenyl-L-alanyl-L-prolinamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-butoxycarbonyl)-4-nitro-3-phenyl-L-alanyl-L-prolinamide(73385-89-4)
• EPA Substance Registry System: N-(tert-butoxycarbonyl)-4-nitro-3-phenyl-L-alanyl-L-prolinamide(73385-89-4)

Safety Data

• Hazardous Substances Data: 73385-89-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C19H26N4O6/c1-11(21-12-8-6-5-7-9-12)16(24)14-13(23(27)28)10-20-15(14)17(25)22-18(26)29-19(2,3)4/h5-9,11,13-15,20-21H,10H2,1-4H3,(H,22,25,26)/t11-,13?,14?,15-/m0/s1

Upstream product

• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 42429-27-6 L-prolinamide hydrochloride 

Downstream Products

• 88331-07-1 L-4-nitrophenylalanyl-L-prolinamide hydrochloride 
• 113132-81-3 C₄₀H₅₄N₁₂O₁₂S₂*2ClH 
• 88331-08-2 N-(tert-butyloxycarbonyl)glycyl-L-4-nitrophenylalanyl-L-prolinamide 
• 88331-09-3 glycyl-L-4-nitrophenylalanyl-L-prolinamide hydrochloride 
• 94213-45-3 N-(tert-butyloxycarbonyl)-D-methionylglycyl-L-4-nitrophenylalanyl-L-prolinamide 
• 113132-78-8 (R)-4-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-4-({[(S)-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-butyric acid 
• 113132-70-0 D-methionylglycyl-L-4-nitrophenylalanyl-L-prolinamide hydrochloride 
• 113132-79-9 (R)-4-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-[(S)-2-guanidino-3-(4-hydroxy-phenyl)-propionylamino]-butyric acid 
• 73385-91-8 N-(tert-butyloxycarbonyl)-L-tyrosyl-D-methionylglycyl-L-4-nitrophenylalanyl-L-prolinamide 
• 88331-12-8 [(S)-1-[(R)-1-({[(S)-2-((S)-2-Carbamoyl-pyrrolidin-1-yl)-1-(4-nitro-benzyl)-2-oxo-ethylcarbamoyl]-methyl}-carbamoyl)-4-guanidino-butylcarbamoyl]-2-(4-hydroxy-phenyl)-ethyl]-carbamic acid tert-butyl ester 
• 88331-15-1 L-tyrosyl-D-methionylglycyl-L-4-nitrophenylalanyl-L-prolinamide hydrochloride 
• 88331-14-0 L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide diacetate 
• 88331-16-2 L-tyrosyl-D-S-methylmethionylglycyl-L-4-nitrophenylalanyl-L-prolinamide chloride hydrochloride 
• 88331-18-4 N¹-amidino-L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide diacetate 

Relevant articles and documents

Peripherally acting enkephalin analogues. 1. Polar pentapeptides

The design, synthesis, and biological activity of a series of highly polar enkephalin-related pentapeptides are reported. These analogues incorporate structural features that exclude them from the central nervous system and thereby restrict their action to peripherally located receptors. Hydrophilic analogues were obtained by introduction of polar D-amino acid residues at position 2 and, in certain cases, by conversion of the N-terminal amino group of the Tyr residue to a guanidino function. The peptides were synthesized by classical solution methods. All compounds demonstrated in vitro opioid activity in the GPI and all were shown to possess antinociceptive activity in chemically induced writhing models. The analgesic effects were shown to be predominantly peripherally mediated by antagonism of antinociception with the peripheral antagonist N-methylnalorphine. Comparative data obtained in writhing and hot-plate tests were also supportive of a peripheral mode of action. Compound 13a, L-tyrosyl-D-arginylglycyl-L-4-nitrophenylalanyl-L-prolinamide (BW 443C), was identified as having a favorable pharmacological profile, indicating a high level of peripheral selectivity, and worthy of further investigation.