18527-12-3

Usage

Uses

Used in Pharmaceutical Industry:
2-(4-CHLOROPHENYLTHIO)PROPANOIC ACID is used as a nonsteroidal anti-inflammatory drug (NSAID) for its capacity to inhibit the production of prostaglandins, which are responsible for pain and inflammation. It serves to relieve pain, reduce inflammation, and lower fever, providing symptomatic relief for various conditions characterized by these symptoms.
However, it is important to note that 2-(4-CHLOROPHENYLTHIO)PROPANOIC ACID, like other NSAIDs, can have side effects such as stomach ulcers, cardiovascular complications, and kidney problems. Therefore, its use should be approached with caution and under the supervision of a healthcare professional to ensure safe and effective treatment.

InChI:InChI=1/C9H9ClO2S/c1-6(9(11)12)13-8-4-2-7(10)3-5-8/h2-6H,1H3,(H,11,12)/p-1/t6-/m1/s1

Upstream product

• 106-54-7 p-Chlorothiophenol 
• 535-11-5 Ethyl 2-bromopropionate 
• 18518-85-9 ethyl 2-((4-chlorophenyl)thio)propanoate 
• 598-72-1 2-Bromopropionic acid 

Downstream Products

• 186458-40-2 3-(4-Chloro-phenylsulfanyl)-5-(2,2-diethoxy-ethyl)-3-methyl-dihydro-furan-2-one 
• 176021-32-2 (+)-(R)-2-(4-Chlorothiophenoxy)propanoic acid 
• 176021-33-3 (S)-2-(4-chlorophenylthio)propanoic acid 
• 18739-80-5 α-(p-Chlor-phenylsulfonyl)-propionsaeure-propylester 
• 98070-15-6 1,3-dihydroxy-3-methyl-2-butanone 
• 1312997-40-2 C₃₀H₂₃ClO₂S 
• 186505-63-5 (Z)-3-(2-{4-[(4-chlorophenyl)sulfanyl]-4-methyl-5-oxotetrahydrofuran-2-yl}ethylidene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one 
• 186505-71-5 (E)-3-(2-{4-[(4-chlorophenyl)sulfanyl]-4-methyl-5-oxotetrahydrofuran-2-yl}ethylidene)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one 
• 186458-36-6 3-(2-{4-[(4-chlorophenyl)sulfanyl]-4-methyl-5-oxotetrahydrofuran-2-yl}-1-hydroxyethyl)-3,3a,4,8b-tetrahydro-2H-indeno[1,2-b]furan-2-one 
• 186458-34-4 {4-[(4-chlorophenyl)sulfanyl]-4-methyl-5-oxotetrahydrofuran-2-yl}acetaldehyde 
• 103247-65-0 2-<(4-Chlorphenyl)thio>-propansaeuremethylester 
• 76161-45-0 α-((4-Chlorophenyl)thio)propanoyl chloride 
• 36304-06-0 t-Butyl-α-(4-chlorphenylmercapto)-propionat 
• 18739-78-1 α-(p-Chlor-phenylmercapto)-propionsaeure-n-propylester 

Relevant academic research and scientific papers

Enantioselective Synthesis of α-Thiocarboxylic Acids by Nitrilase Biocatalysed Dynamic Kinetic Resolution of α-Thionitriles

The enantioselective synthesis of α-thiocarboxylic acids by biocatalytic dynamic kinetic resolution (DKR) of nitrile precursors exploiting nitrilase enzymes is described. A panel of 35 nitrilase biocatalysts were screened and enzymes Nit27 and Nit34 were found to catalyse the DKR of racemic α-thionitriles under mild conditions, affording the corresponding carboxylic acids with high conversions and good-to-excellent ee. The ammonia produced in situ during the biocatalytic transformation favours the racemization of the nitrile enantiomers and, in turn, the DKR without the need of any external additive base.

Nonenzymatic dynamic kinetic resolution of α-(arylthio)- and α-(alkylthio)alkanoic acids

Dynamic solution: The title acids undergo dynamic kinetic resolution during an enantioselective esterification catalyzed by (S)-homobenzotetramisole ((S)-HBTM; see scheme). This method extends the scope of the carboxylic acid derivatives that are amenable to the nonenzymatic version of this transformation. Copyright

Kinetic resolution of α-substituted alkanoic acids promoted by homobenzotetramisole

A new method for catalytic nonenzymatic kinetic resolution of α-substituted alkanoic acids has been developed, which relies on their activation with DCC followed by enantioselective alcoholysis of the intermediate symm-anhydrides in the presence of the amidine-based catalyst homobenzotetramisole (HBTM). Moderate to excellent selectivity factors (s=5-96) have been obtained in the case of several classes of substrates, namely, α-aryl-, α-aryloxy/alkoxy-, α-halo-, α-azido-, and α-phthalimido-alkanoic acids. Under similar conditions, α-(arylthio/alkylthio)-alkanoic acids undergo dynamic kinetic resolution providing corresponding esters in up to 92 % ee and up to 93 % yield. Copyright

2-(4-R-Phenoxy/phenylthio)alkanoic esters of l-lupinine

Considering the great pharmacological interest in phenoxy/phenylthioalkanoic esters of open-chain or cyclic aminoalcohols, a set of ten such esters of lupinine was prepared. Initially, their ability to displace [3H]QNB from rat brain preparation was investigated. With the exception of two, all the prepared esters exhibited good affinity to muscarinic receptors (on a non-selective basis), with pKi in the range 6.67-7.68.

Differential eudismic ratios in the antagonism of human platelet function by phenoxy- and thiophenoxyacetic acids

The antilipidemic drug clofibric acid (CPIB) exhibits antiplatelet effects. In order to examine the role of enantioselectivity and hydrophobicity, the mono(desmethyl) enantiomers of 2-(4-chlorophenoxy)propanoic acid (CPPA), related butanoate homologs, 2-(

Presynaptic cholinergic modulators as potent cognition enhancers and analgesic drugs. 2. 2-Phenoxy-, 2-(phenylthio)-, and 2-(phenylamino)alkanoic acid esters

Further modifications of the leads ((R)-(+)-hyoscyamine and (p- chlorophenyl)propionic acid α-tropanyl ester), which show analgesic and nootropic activities as a consequence of increased central presynaptic ACh release, are reported. 2-Phenoxy- and 2-(phenylthio)alkanoic acid esters showed the best results. Several members of these classes possess analgesic properties which are comparable to that of morphine and at the same time are able to reverse dicyclomine-induced amnesia. Confirmation was found that the mechanism of action is due to an increase in ACh release at central muscarinic synapses and that both auto- and heteroreceptors controlling ACh release are very likely involved. According to the results obtained with (R)- (+)-hyoscyamine, analgesic activity is stereochemistry dependent, since the R-(+)-enantiomers are always more efficacious than the corresponding S-(-)- ones. On the basis of their potency and acute toxicity, compounds (±)-28 (SM21) and (±)-42 (SM32) were selected for further study.