57359-76-9

Basic information

• Product Name: 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID
• Synonyms: 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID;(2R)-2-Acetylthio-3-phenylpropionic Acid;(aR)-α-(Acetylthio)benzenepropanoic Acid;(R)-2-Acetylthio-3-phenylpropionic Acid;D-2-Thioacetyl-3-phenylpropionic Acid;(aR)-a-(Acetylthio)benzenepropanoic Acid;(αR)-α-(Acetylthio)benzenepropanoic Acid
• CAS NO: 57359-76-9
• Molecular Formula: C₁₁H₁₂O₃S
• Molecular Weight: 224.28
• Product Categories: Chiral Reagents;Inhibitors;Intermediates;Sulfur & Selenium Compounds
• Mol File: 57359-76-9.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 358.93°C at 760 mmHg
• Flash Point: 170.875°C
• Appearance: /
• Density: 1.261g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.581
• CAS DataBase Reference: 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID(CAS DataBase Reference)
• NIST Chemistry Reference: 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID(57359-76-9)
• EPA Substance Registry System: 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID(57359-76-9)

Safety Data

• Hazardous Substances Data: 57359-76-9(Hazardous Substances Data)

Usage

Description

2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID is an organic compound with the molecular structure featuring a benzene ring, a propanoic acid chain, and a thioester functional group. It is characterized by its unique chemical properties, which make it a versatile compound for various applications in different industries.

Uses

Used in Pharmaceutical Industry:
2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID is used as an IMP-1 metallo-β-lactamase inhibitor for its ability to inhibit bacterial resistance to β-lactam antibiotics. This application is crucial in the development of new antibiotics to combat drug-resistant bacteria.
Used in Chemical Synthesis:
2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID serves as a key intermediate in the synthesis of various pharmaceuticals, agrochemicals, and other specialty chemicals. Its unique structure allows for further functionalization and modification to create a wide range of compounds with specific properties and applications.
Used in Research and Development:
As a compound with distinct chemical properties, 2(R)-ACETYLTHIO-BENZENEPROPANOIC ACID is utilized in research and development for studying its potential applications in various fields, including drug discovery, material science, and chemical engineering. Its unique structure and reactivity make it an interesting subject for scientific exploration and innovation.

InChI:InChI=1/C11H12O3S/c1-8(12)15-10(11(13)14)7-9-5-3-2-4-6-9/h2-6,10H,7H2,1H3,(H,13,14)/t10-/m1/s1

Upstream product

• 507-09-5 tiolacetic acid 
• 35016-63-8 (S)-2-bromo-3-phenylpropionic acid 
• 34832-35-4 sodium thioacetate 
• 20312-36-1 L-3-phenyllactic acid 
• 10387-40-3 potassium thioacetate 
• 63-91-2 L-phenylalanine 
• 7474-06-8 (S)-2-chloro-3-phenyl-propionic acid 
• 56827-86-2 cesium thioacetate 
• 496962-20-0 ethyl 2-acetylthio-3-benzenepropanoate 

Downstream Products

• 740059-56-7 (R)-2-((R)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid 
• 714191-99-8 (S)-2-((S)-1-Carboxy-2-phenyl-ethylsulfanyl)-3-phenyl-propionic acid 
• 177930-60-8 (2S,5R)-1-[2-((R)-2-Acetylsulfanyl-3-phenyl-propionylamino)-acetyl]-5-phenyl-pyrrolidine-2-carboxylic acid methyl ester 
• 84800-12-4 (R)-2-mercapto-3-phenylpropanoic acid 
• 736170-70-0 (2S)-3-tert-butoxy-2-[(2R)-2-mercapto-3-phenyl-propionylamino]-propionic acid tert-butyl ester 
• 736170-76-6 (2S)-3-tert-butoxy-2-{(2R)-2-[(2S)-2-tert-butoxy-carbonylamino-4-methylsulfanyl-butyrylsulfanyl]-3-phenyl-propionylamino}-propionic acid tert-butyl ester 
• 148382-99-4 [(S)-1-((R)-2-{(R)-1-[((S)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-methyl]-2-phenyl-ethylsulfanyl}-3-phenyl-propylcarbamoyl)-2-methyl-propyl]-carbamic acid benzyl ester 
• 148382-97-2 (R)-2-((R)-1-Carbamoyl-2-phenyl-ethylsulfanyl)-3-phenyl-propionamide 
• 84800-13-5 [14C]-(S)-3-phenyl-2-mercaptopropionic acid 

Relevant articles and documents

Evidence for α-lactone formation in the thioacetylation of some α-hydroxy acids with the aid of Mitsunobu-type reagent

(S)-Mandelic acid, (S)-lactic acid, and (S)-2-hydroxy-3-phenylpropionic acid react with thioacetic acid in the presence of the salt of diisopropyl azodicarboxylate and triphenylphosphine to give the α-(acetylthio)-substituted products. (S)-Mandelic acid r

Synthesis of optically pure (S)-2-acetylthio-3-benzenepropanoic acid via enzymatic resolution

A method of synthesizing optically pure (S)-2-acetylthio-3-benzenepropanoic acid has been developed and good to excellent enantiomeric excess achieved via enzymatic resolution.

Optimal recognition of neutral endopeptidase and angiotensin-converting enzyme active sites by mercaptoacyldipeptides as a means to design potent dual inhibitors

An interesting approach for the treatment of congestive heart failure and chronic hypertension could be to avoid the formation of angiotensin II by inhibiting angiotensin converting enzyme (ACE) and to protect atrial natriuretic factor by blocking neutral endopeptidase 24.11 (NEP). This is supported by recent results obtained with potent dual inhibitors of the two zinc metallopeptidases, such as RB 105, HSCH2CH(CH3)PhCONHCH(CH3)COOH (Fournie-Zaluski et al. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4072-4076), which reduces blood pressure in experimental models of hypertension, independently of the salt and renin angiotensin system status. In order to develop new dual inhibitors with improved affinities, long duration of action, and/or better bioavailabilities, various series of mercaptoacyldipeptides corresponding to the general formula HSCH(R1)CONHCH(R1')CON(R)CH(R2')COOH have been synthesized. The introduction of well-selected β-branched chains in positions R1 and R1', associated with a tyrosine or a cyclic amino acid in the C-terminal position, led to potent dual inhibitors of NEP and ACE such as 21 [N-[(2S)-2-mercapto- 3-methylbutanoyl]-Ile-Tyr] and 22 [N-[(2S)-2-mercapte-3-phenylpropanoyl]Ala- Pro] which have IC50 values in the nanomolar range for NEP and subnanomolar range for ACE. These compounds could have different modes of binding to the two peptidases. In NEP, the dual inhibitors seem to interact only with the S1' and S2' subsites, whereas additional interactions with the S1 binding subsite of ACE probably account for their subnanomolar inhibitory potencies for this enzyme. The localization of the Pro residue of 22 outside the NEP active site is supported by biochemical data using (Arg102,Glu)NEP and molecular modeling studies with thermolysin used as model of NEP. One hour after oral administration in mice of a single dose (2.7 x 10-5 mol/kg), 21 inhibited 80% and 36% of kidney NEP and lung ACE, respectively, while 22 inhibited 40% of kidney NEP and 56% of lung ACE.