1159501-74-2

Basic information

• Product Name: (S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid
• Synonyms: N-(tert-Butoxycarbonyl)-3-(diethoxyphosphoryl)-D-alanine;(S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid
• CAS NO: 1159501-74-2
• Molecular Formula: C12H24NO9P
• Molecular Weight: 357.294021
• EINECS: -0
• Mol File: 1159501-74-2.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 467.5±40.0 °C(Predicted)
• Appearance: /
• Density: 1.201±0.06 g/cm3(Predicted)
• PKA: 3.48±0.10(Predicted)
• CAS DataBase Reference: (S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(1159501-74-2)
• EPA Substance Registry System: (S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid(1159501-74-2)

Safety Data

• Hazardous Substances Data: 1159501-74-2(Hazardous Substances Data)

Usage

Description

(S)-2-((tert-butoxycarbonyl)amino)-3-(diethoxyphosphoryl)propanoic acid is a unique chemical compound that is a derivative of the amino acid proline, featuring a phosphoryl group attached to its structure. (S)-2-((tert-butoxycarbonyl)aMino)-3-(diethoxyphosphoryl)propanoic acid is characterized by the presence of a tert-butoxycarbonyl group that acts as a protecting group for the amino function, and a diethoxyphosphoryl group that offers stability and structural support. Its distinctive structure and properties lend it a wide range of applications in the fields of organic chemistry and biochemistry.

Uses

Used in Organic Synthesis:
(S)-2-((tert-butoxycarbonyl)amino)-3-(diethoxyphosphoryl)propanoic acid is utilized as a key building block in organic synthesis, allowing for the creation of a variety of new compounds with potential applications across different industries.
Used in Pharmaceutical Research:
In the pharmaceutical industry, this compound serves as an important intermediate in drug development. Its unique structure allows it to be a versatile component in the design and synthesis of new pharmaceuticals, potentially leading to the discovery of novel treatments and therapies.
Used in Biochemical Studies:
Due to its structural features, (S)-2-((tert-butoxycarbonyl)amino)-3-(diethoxyphosphoryl)propanoic acid is also used in biochemical research. It can help scientists understand the interactions between different biomolecules and may contribute to the advancement of biochemistry and related fields.

Upstream product

• 170848-34-7 N-t-butoxycarbonyl-3-iodo-D-alanine methyl ester 

Relevant articles and documents

4-((R)-2-{[6-((S)-3-Methoxypyrrolidin-1-yl)-2-phenylpyrimidine-4-carbonyl]amino}-3-phosphonopropionyl)piperazine-1-carboxylic Acid Butyl Ester (ACT-246475) and Its Prodrug (ACT-281959), a Novel P2Y12 Receptor Antagonist with a Wider Therapeutic Window in the Rat Than Clopidogrel

Recent post hoc analyses of several clinical trials with P2Y12 antagonists showed the need for new molecules being fully efficacious as antiplatelet agents and having a reduced propensity to cause major bleeding. We have previously reported the discovery of the 2-phenylpyrimidine-4-carboxamide analogs as P2Y12 antagonists with nanomolar potency in the disease-relevant platelet aggregation assay in human plasma. Herein we present the optimization steps that led to the discovery of clinical candidate ACT-246475 (30d). The key step was the replacement of the carboxylic acid functionality by a phosphonic acid group which delivered the most potent molecules of the program. In addition, low in vivo clearance in rat and dog was achieved for the first time. Since the bioavailability of 30d was low in rat and dog, we developed the bis((isopropoxycarbonyl)oxy)methyl ester prodrug (ACT-281959, 45). Compound 30d showed efficacy in the rat ferric chloride thrombosis model when administered intravenously as parent or orally as its prodrug 45. Moreover, 30d displays a wider therapeutic window as compared to clopidogrel in the rat surgical blood loss model.

PHOSPHONIC ACID DERIVATES AND THEIR USE AS P2Y12 RECEPTOR ANTAGONISTS

The invention relates to 2-phenyl-pyrimidine derivatives containing a phosphonic acid motif and their use as P2Y12 receptor antagonists in the treatment and/or prevention of peripheral vascular, of visceral-, hepatic- and renal-vascular, of cardiovascular and of cerebrovascular diseases or conditions associated with platelet aggregation, including thrombosis in humans and other mammals. (I).