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

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

Uses

Used in Pharmaceutical Industry:
(2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide is used as a potential enzyme inhibitor for targeting biological processes related to the central nervous system and hormone regulation. Its application in this industry is driven by the need for new therapeutic agents that can effectively modulate enzyme activity and potentially treat diseases or conditions associated with these systems.
Used in Research and Development:
In the field of research and development, (2S)-1-[(2S)-2-Amino-3-(3H-imidazol-4-yl)propanoyl]pyrrolidine-2-carboxamide serves as a valuable compound for studying the pharmacological and physiological effects of enzyme inhibition. Its unique structure and potential inhibitory properties make it an interesting subject for further investigation, with the aim of uncovering its full potential in the development of new therapeutic agents.

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

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

Downstream Products

• 63836-94-2 Blc-His-Pro-NH2 
• 57818-01-6 Kpc-His-Pro-NH₂ 
• 4257-92-5 cyclo(His-Pro) 
• 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.

Histidyl peptide derivatives

Novel peptide derivatives of the following formula STR1 wherein each symbol is as defined in the specification, pharmaceutically acceptable acid addition salts thereof and analogous copounds thereof. Since the derivatives and their pharmaceutically acceptable acid addition salts of the present invention possess stronger actions on central nervous system (e.g. antagonistic action against hypothermia, locomotor stimulant action, signal reflex stimulant action), they are of use as a therapeutic medicament for central nervous disorders such as impaired consciousness, depression, hypomnesia, the like in association association with schizophrenia, melancholia, senile dementia, sequelae of cerebrovascular disorders, head trauma, epilepsy and spinocerebellar degeneracy.

4-Substituted-2-azetidinone compound, process of producing the compounds, and medicaments containing the compounds

A novel 4-substituted-2-azetidinone compound shown by the general formula STR1 and salts thereof. The compounds of this invention have a strong CNS activity and are useful for improving a disturbance of consciousness in schizophrenia, a head injury, etc., or improving hypobulia, memory loss, etc.