281191-43-3

Basic information

• Product Name: (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID
• Synonyms: (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID;(2S,1'S)-Cyclopropyl-(1-phenyl-ethylaMino)-acetic acid;(S)-2-Cyclopropyl-2-((S)-1-phenylethylamino)acetic acid
• CAS NO: 281191-43-3
• Molecular Formula: C₁₃H₁₇NO₂
• Molecular Weight: 219.29
• Mol File: 281191-43-3.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID(281191-43-3)
• EPA Substance Registry System: (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID(281191-43-3)

Safety Data

• Hazardous Substances Data: 281191-43-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID is used as a potential drug candidate for its unique structure and possible biological activity. Its chiral nature and specific configuration may offer advantages in the development of new medications.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, (2S,1''S)-2-CYCLOPROPYL-2-(1-PHENYLETHYLAMINO)ACETIC ACID serves as a valuable compound for further research and studies. Its exploration may reveal therapeutic potential, as well as any potential side effects, contributing to the advancement of drug discovery and development.

Upstream product

• 2627-86-3 (S)-1-phenyl-ethylamine 
• 1489-69-6 Cyclopropanecarboxaldehyde 
• 151-50-8 potassium cyanide 
• 281191-42-2 C₁₃H₁₆N₂ 

Downstream Products

• 1188407-23-9 (S)-2-cyclopropyl-2-[(S)-1-phenylethylamino]ethanol 
• 1188407-25-1 (S)-1-cyclopropyl-2-methoxy-N-[(S)-1-phenylethyl]ethanamine 
• 1188407-45-5 (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile 
• 1350712-33-2 (S)-1-cyclopropyl-2-methyl-1-((S)-1-phenyl-ethylamino)-propan-2-ol 
• 1350712-31-0 (S)-cyclopropyl-((S)-1-phenyl-ethylamino)-acetic acid methyl ester 
• 49606-99-7 (S)-2-amino-2-cyclopropylacetic acid 

Relevant articles and documents

SYNTHESIS METHOD FOR L-CYCLIC ALKYL AMINO ACID AND PHARMACEUTICAL COMPOSITION HAVING THEREOF

A synthesis method for L-cyclic alkyl amino acid and a pharmaceutical composition having the said amino acid are provide in the present disclosure provides. The synthesis method comprises: step A.) preparing a cyclic alkyl keto acid or a cyclic alkyl keto acid salt having Structural Formula (I) or Structural Formula (II), and step B.) mixing the cyclic alkyl keto acid or the cyclic alkyl keto acid salt with ammonium formate, a leucine dehydrogenase, a formate dehydrogenase and a coenzyme NAD+, and carrying out a reductive amination reaction to generate the L-cyclic alkyl amino acid, wherein the Structural Formula (I) is where n1≧1, m1≧0 and the M1 is H or a monovalent cation; the Structural Formula (II) is where n2≧0, m2≧0, the M2 is H or a monovalent cation, an amino acid sequence of the leucine dehydrogenase is SEQ ID No.1.

Development of an efficient synthesis of two CRF antagonists for the treatment of neurological disorders

BMS-764459 (1) and BMS-763534 (2) are CRF1 antagonists for the treatment of neurological disorders such as depression and anxiety. An efficient synthesis of 1 and 2 is described, which features an efficient palladium-catalyzed cyanation of a 5-chloropyraz

Pyrazinone Modulator of Corticotropin-Releasing Factor Receptor Activity

The invention relates to the compound (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-(6-(difluoromethoxy)-2,5-dimethylpyridin-3-ylamino)-5-oxo-4,5-dihydropyrazine-2-carbonitrile, pharmaceutical compositions of the compound, and methods of using the compound for the treatment of psychiatric disorders and neurological diseases including depression, anxiety related disorders, irritable bowel syndrome, addiction and negative aspects of drug and alcohol withdrawal, and other conditions associated with CRF.

A strategy to minimize reactive metabolite formation: Discovery of (S)-4-(1-cyclopropyl-2-methoxyethyl)-6-[6-(difluoromethoxy)-2, 5-dimethylpyridin-3-ylamino]-5-oxo-4,5-dihydropyrazine-2-carbonitrile as a potent, orally bioavailable corticotropin-releasing factor-1 receptor antagonist

Detailed metabolic characterization of 8, an earlier lead pyrazinone-based corticotropin-releasing factor-1 (CRF1) receptor antagonist, revealed that this compound formed significant levels of reactive metabolites, as measured by in vivo and in vitro biotransformation studies. This was of particular concern due to the body of evidence suggesting that reactive metabolites may be involved in idiosyncratic drug reactions. Further optimization of the structure-activity relationships and in vivo properties of pyrazinone-based CRF1 receptor antagonists and studies to assess the formation of reactive metabolites led to the discovery of 19e, a high affinity CRF1 receptor antagonist (IC50= 0.86 nM) wherein GSH adducts were estimated to be only 0.1% of the total amount of drug-related material excreted through bile and urine, indicating low levels of reactive metabolite formation in vivo. Anovel 6-(difluoromethoxy)-2,5-dimethylpyridin-3- amine group in 19e contributed to the potency and improved in vivo properties of this compound and related analogues. 19e had excellent pharmacokinetic properties in rats and dogs and showed efficacy in the defensive withdrawal model of anxiety in rats. The lowest efficacious dose was 1.8 mg/kg. The results of a two-week rat safety study with 19e indicated that this compound was well-tolerated.

COMPOUNDS AND COMPOSITIONS AS CATHEPSIN S INHIBITORS

The invention provides compounds, pharmaceutical compositions comprising such compounds and methods of using such compounds to treat or prevent diseases or disorders associated with the activity of Cathepsin S.