33605-69-5

Basic information

• Product Name: (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide
• Synonyms: (2S)-1-[(2S)-2-amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carbo xamide;histidylprolineamide;L-histidyl-L-prolinamide;His-pro-amide;H-His-Pro-NH2;(S)-1-((S)-2-amino-3-(1H-imidazol-4-yl)propanoyl)pyrrolidine-2-carboxamide(WXG01683)
• CAS NO: 33605-69-5
• Molecular Formula: C₁₁H₁₇N₅O₂
• Molecular Weight: 251.28
• Mol File: 33605-69-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 678°Cat760mmHg
• Flash Point: 363.9°C
• Appearance: /
• Density: 1.378g/cm³
• Vapor Pressure: 3.06E-18mmHg at 25°C
• Refractive Index: 1.625
• PKA: 14.22±0.10(Predicted)
• CAS DataBase Reference: (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide(33605-69-5)
• EPA Substance Registry System: (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide(33605-69-5)

Safety Data

• Hazardous Substances Data: 33605-69-5(Hazardous Substances Data)

Usage

General Description

"(2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide" is a chemical compound with the molecular formula C12H18N6O2. It is a peptide derivative that contains an imidazole ring and a pyrrolidine ring within its structure. (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide is a potential inhibitor of enzymes involved in various biological processes, particularly those related to the central nervous system and hormone regulation. It may also have potential therapeutic applications in the treatment of certain diseases or conditions related to these systems. Further research and studies are needed to fully understand the pharmacological and physiological effects of this compound.

InChI:InChI=1/C11H17N5O2/c12-8(4-7-5-14-6-15-7)11(18)16-3-1-2-9(16)10(13)17/h5-6,8-9H,1-4,12H2,(H2,13,17)(H,14,15)/t8-,9-/m0/s1

Synthetic route

1-(Nα-benzyloxycarbonyl-histidyl)-proline amide (32990-93-5) → L-histidinyl-L-prolinamide (33605-69-5)

Conditions	Yield
With hydrogenchloride; hydrogen; palladium on activated charcoal In methanol

trifluoroacetate salt of L-histidyl-L-prolinamide (74528-30-6) → L-histidinyl-L-prolinamide (33605-69-5)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide at 0℃;

trans-L-hydroxy-proline (18610-59-8) + L-histidinyl-L-prolinamide (33605-69-5) → C16H24N6O4

Conditions	Yield
Stage #1: trans-L-hydroxy-proline With benzotriazol-1-ol; dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 20℃; for 6h; Stage #2: L-histidinyl-L-prolinamide In N,N-dimethyl-formamide at 5℃;	21%

Nα,Nca-di-tert-butyloxycarbonylglutamine (98115-14-1) + L-histidinyl-L-prolinamide (33605-69-5) → {(S)-4-tert-Butoxycarbonylamino-4-[(S)-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-1-(1H-imidazol-4-ylmethyl)-2-oxo-ethylcarbamoyl]-butyryl}-carbamic acid tert-butyl ester; compound with acetic acid

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate 1.) THF; 2.) DMF, water, 1 h; Yield given. Multistep reaction;

Nα,Nca-di-tert-butyloxycarbonyl-L-homoglutamine (108312-35-2) + L-histidinyl-L-prolinamide (33605-69-5) → {(S)-5-tert-Butoxycarbonylamino-5-[(S)-2-((S)-2-carbamoyl-pyrrolidin-1-yl)-1-(1H-imidazol-4-ylmethyl)-2-oxo-ethylcarbamoyl]-pentanoyl}-carbamic acid tert-butyl ester; compound with acetic acid

Conditions	Yield
With 4-methyl-morpholine; isobutyl chloroformate 1.9 THF; 2.) H2O, DMF, 1 h; Yield given. Multistep reaction;

(S)-4-oxo-azetidine-2-carboxylic acid (16404-94-7) + L-histidinyl-L-prolinamide (33605-69-5) → Nα-[((S)-4-oxo-2-azetidinyl)carbonyl]-L-histidyl-L-prolineamide (95729-65-0)

Conditions	Yield
Stage #1: (S)-4-oxo-azetidine-2-carboxylic acid With 2,3,4,5,6-pentafluorophenol; dicyclohexyl-carbodiimide In 1,4-dioxane; N,N-dimethyl-formamide at 0℃; for 3.5h; Stage #2: L-histidinyl-L-prolinamide In 1,4-dioxane; N,N-dimethyl-formamide at 0℃; for 2h;

Upstream product

• 32990-93-5 1-(N^α-benzyloxycarbonyl-histidyl)-proline amide 
• 74528-30-6 trifluoroacetate salt of L-histidyl-L-prolinamide 

Downstream Products

• 57818-01-6 Kpc-His-Pro-NH₂ 
• 4257-92-5 cyclo(His-Pro) 
• 63836-94-2 Blc-His-Pro-NH2 
• 95729-65-0 azetirelin 

Relevant articles and documents

Cyclic dipeptides and azetidinone compounds and their use in treating CNS injury and neurodegenerative disorders

The present invention provides 4-substituted-2-azetidinone compounds, bicyclic 2-5-diketopiperazine compounds, and pharmaceutical compositions thereof that are potent, safe and effective neuroprotective agents. Due to their strong central nervous system (CNS) activity, the compounds can be used to enhance memory and to treat a variety of neurological disorders. The compounds are particularly useful for treating neurological disorders caused by, or associated with, CNS trauma.

Synthesis of thyrotropin-releasing hormone-related peptides using N(α)-tert-butyloxycarbonly-ω-(N-tert- butyloxycarbonylcarbamoyl)-α-amino Acids(1))

-