6310-27-6

Usage

Uses

Used in Pharmaceutical Industry:
3-[(4-Chlorophenyl)sulfanyl]propanoic acid is utilized as a key intermediate in the synthesis of various drugs. Its unique structure allows for the development of pharmaceutical compounds with specific therapeutic properties, contributing to the advancement of medicinal chemistry.
Used in Agrochemical Industry:
In the agrochemical sector, 3-[(4-Chlorophenyl)sulfanyl]propanoic acid serves as a precursor for the production of pesticides. Its chemical reactivity enables the creation of effective pest control agents, helping to protect crops and ensure agricultural productivity.
Used in Specialty Chemicals Production:
3-[(4-Chlorophenyl)sulfanyl]propanoic acid is also employed in the manufacturing of specialty chemicals. Its versatile chemical properties make it suitable for a range of applications, including the development of new materials and compounds with unique characteristics.
Used in Research and Development:
3-[(4-CHLOROPHENYL)SULFANYL]PROPANOIC ACID is frequently used in research settings to explore its chemical properties and potential applications. It serves as a valuable tool for scientists and researchers working in the fields of organic synthesis, medicinal chemistry, and materials science, facilitating the discovery of new chemical reactions and the development of innovative products.

InChI:InChI=1/C9H9ClO2S/c10-7-1-3-8(4-2-7)13-6-5-9(11)12/h1-4H,5-6H2,(H,11,12)/p-1

Upstream product

• 16987-03-4 sodium 3-chloroproanoate 
• 18803-44-6 sodium p-chlorothiophenolate 
• 107-94-8 chloropropionic acid 
• 106-54-7 p-Chlorothiophenol 
• 79-10-7 acrylic acid 
• 57-57-8 β-Propiolactone 
• 5307-86-8 3-(4-chlorophenylsulfanyl)propionitrile 
• 590-92-1 3-Bromopropionic acid 

Downstream Products

• 13735-12-1 6-chlorothiochroman-4-one 
• 1315306-61-6 6'-chloro-3-(4-chlorophenyl)spiro[oxirane-2,3'-thiochroman]-4'-one 
• 54949-15-4 4,6-Dichloro-2H-thiochromene-3-carbaldehyde 
• 1438433-21-6 (E)-3-[[(2-aminophenyl)amino]methylene]-6-chloro-2,3-dihydro-4H-1-benzothiopyran-4-one 
• 1438433-20-5 (E)-6-chloro-2,3-dihydro-3-[(phenylamino)methylene]-4H-1-benzothiopyran-4-one 
• 1421435-03-1 2-[2-(6-chlorothiochroman-4-ylidene)hydrazinyl]-5-phenylthiazole 
• 90562-46-2 3-[(4-chlorophenyl)thio]propanamide 
• 67141-35-9 3-<4-Chlor-phenylmercapto>-propionsaeure-chlorid 
• 108129-97-1 <2-Carboxy-aethyl>--sulfoxid 
• 90396-00-2 p-chlorophenylsulfonylpropionic acid 

Relevant academic research and scientific papers

Pharmacological inhibition of syntenin PDZ2 domain impairs breast cancer cell activities and exosome loading with syndecan and EpCAM cargo

Exosomes support cell-to-cell communication in physiology and disease, including cancer. We currently lack tools, such as small chemicals, capable of modifying exosome composition and activity in a specific manner. Building on our previous understanding o

Fragment-based drug design targeting syntenin PDZ2 domain involved in exosomal release and tumour spread

Syntenin stimulates exosome production and its expression is upregulated in many cancers and implicated in the spread of metastatic tumor. These effects are supported by syntenin PDZ domains interacting with syndecans. We therefore aimed to develop, throu

Synthesis of benzothiazonine by rhodium-catalyzed denitrogenative transannulation of 1-sulfonyl-1,2,3-triazole and thiochromone

A facile synthesis of multi-functionalized benzothiazonine was achieved by the rhodium-catalyzed denitrogenative annulation of 1-sulfonyl-1,2,3-triazole and thiochromone. In view of the excellent atom economy, broad substrate scope and easy availability of starting materials, the protocol provided an efficient strategy for the construction of mediumN,S-heterocycles.

Synthesis method of 2,3-dihydrothiochromene-4-one and derivative thereof

The invention discloses a synthesis method of 2,3-dihydrothiochromene-4-one and a derivative thereof. The synthesis method is characterized in that a substituted and unsubstituted aromatic thiophenolcompound is used as a raw material, and reacts with acrylic acid to generate corresponding aromatic thiopropionic acid, and cyclizing is performed under the action of concentrated sulfuric acid to obtain the corresponding 2,3-dihydrothiochromene-4-one and the derivative thereof. According to the invention, the raw materials use acrylic acid and concentrated sulfuric acid, so that the raw materialsare easy to obtain, the cost is low, and the feeding is easy; and the post-treatment only needs acidification, extraction, washing and solvent evaporation, so that the method is simple in post-treatment, high in yield, low in cost and suitable for industrial production.

Development of conjugate addition of lithium dialkylcuprates to thiochromones: Synthesis of 2-alkylthiochroman-4-ones and additional synthetic applications

Lithium dialkylcuprates undergo conjugate addition to thiochromones to afford 2-alkylthiochroman-4-ones in good yields. This approach provide an efficient and general synthetic approach to privileged sulfur-containing structural motifs and valuable precursors for many pharmaceuticals, starting from common substrates-thiochromones. Good yields of 2-alkyl-substituted thiochroman-4-ones are attained with lithium dialkylcuprates, lithium alkylcyanocuprates or substoichiometric amount of copper salts. The use of commercially available inexpensive alkyllithium reagents will expedite the synthesis of a large library of 2-alkyl substituted thiochroman-4-ones for additional synthetic applications.

Cu-Catalyzed Conjugate Addition of Grignard Reagents to Thiochromones: An Enantioselective Pathway for Accessing 2-Alkylthiochromanones

The enantioselective incorporation of alkyl groups in thiochromones was realized for the first time by a Cu/(R, S)-PPF-P t Bu 2 -catalyzed conjugate addition of Grignard reagents to thiochromones. With this method, a series of 2-methylthiochromanones were obtained in good yields (up to 96% yield) with moderate-to-good ee values (up to 87% ee). The established method expedites the synthesis of a large library of chiral thiochromanones for further synthetic applications and biological studies.

Design, synthesis, and biological evaluation of 4-chloro-2H-thiochromenes featuring nitrogen-containing side chains as potent antifungal agents

A series of 4-chloro-2H-thiochromenes featuring nitrogen-containing side chains were designed, synthesized and tested in vitro for their antifungal activities. The results of preliminary antifungal tests showed that most target compounds exhibited good inhibitory activities against Candida albicans, Cryptococcus neoformans, Candida tropicalis. Notably, compounds 10e and 10y showed most potent activity in vitro against a variety of fungal pathogens with low MICs. Meanwhile, low cytotoxicity on mammalian cells has been observed for compounds 10e and 10y in the tested concentrations by the MTT assay. Therefore, the 4-chloro-2H-thiochromenes with nitrogen-containing groups provide new lead structures in the search for novel antifungal agents.

Microwave-assisted synthesis of novel bisspiropyrrolidine thiochromanone derivatives and antifungal activity

Background: Multicomponent Reactions are being widely used in the synthesis of heterocyclic compounds. Spiroheterocyclic compounds also have various physiological activities such as anti-tumor and antifungal, and they are important in drug discovery. In order to find novel spiroheterocyclic compounds having potential antifungal activity, we found a fast and efficient approach to the synthesis of novel 4′-phenyldispiro[indoline-3,2′-pyrrolidine-3′,3″-thiochromane]-2,4″-dione, and the antifungal activity of the novel spiroheterocyclic compounds were tested. Methods: A variety of different substituents of 3-arylidene-thiochroman-4-one (1mmol) with isatin (1mmol) and different substituted amino acids (sarcosine, proline, leucine, glycine, phenylglycine, alanine, phenylalanine, glutamic acid or arginine, 1mmol) were mixed in [Bmim]Cl (2mL) and then gave microwave irradiation. After the reaction have finished, the reaction system was added in 10mL water, and a lot of white precipitation was obtained and filtrated. The pure objects were recrystallization by mixture of ethanol and water. The antifungal activity was determined by consecutive double dilution method. Results: Microwave irradiation dramatically decreases reaction time from hours to minutes for this multicomponent reaction, and the yields were also slightly increased. Neutral and acidic amino acids can successfully occur 1, 3-dipolar cycloaddition reactions but basic amino acids such as arginine can not. The solvent - [Bmim]Cl can be recycled to reuse after treatment. Compounds 6c and 6d have good inhibition than fluconazole for the two invasive fungi (C.n. and M.r.) and some compounds show moderate inhibition activities for tested fungi. Conclusion: A microwave-enhanced, fast, and efficient three-component reaction in [Bmim]Cl for generation of series novel 4′-phenyldispiro[indoline-3,2′-pyrrolidine-3′,3″-thiochromane]-2,4″-dione compounds has been developed. Among these compounds, several show better anti-invasive fungal activity than fluconazole and some show moderate inhibiton activity.

Rh-Catalyzed Conjugate Addition of Arylzinc Chlorides to Thiochromones: A Highly Enantioselective Pathway for Accessing Chiral Thioflavanones

A highly efficient asymmetric synthesis of chiral thioflavanones is developed via conjugate addition of arylzinc reagents to thiochromones using Rh(COD)Cl2/(R)-3,4,5-MeO-MeOBIPHEP catalyst. This method overcomes catalyst poisoning and substrate inertness and affords a series of chiral thioflavanones (2-arylthiochroman-4-ones) in good yields (up to 91% yield) with excellent ee values (up to 97% ee). The established asymmetric synthesis paves the way for further pharmaceutical studies.

Ionic liquid catalyzed synthesis of 2-(indole-3-yl)-thiochroman-4-ones and their novel antifungal activities

2-(Indole-3-yl)-thiochroman-4-ones were synthesized via ionic liquid and tested for in vitro antifungal activity. The contribution of ionic liquid to Michael addition reaction is significant. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Most of these compounds showed better antifungal activity than fluconazole. The results suggest that 2-(indole-3-yl)-thiochroman-4-ones would be efficient antifungal agents.