13739-36-1

Usage

Uses

Used in Organic Synthesis:
3-[(4-METHOXYPHENYL)THIO]PROPANOIC ACID is used as a reagent for the synthesis of various organic compounds. Its unique structure allows for the formation of new chemical bonds and the creation of diverse molecules, which can be further utilized in the development of pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Research:
3-[(4-METHOXYPHENYL)THIO]PROPANOIC ACID is used as an intermediate in the development of new drugs. Its presence in the molecular structure of potential drug candidates can contribute to their pharmacological properties, such as binding affinity, selectivity, and bioavailability. Researchers in the pharmaceutical industry often explore the use of such compounds to design and optimize new therapeutic agents.
Used in Medicinal Chemistry:
3-[(4-METHOXYPHENYL)THIO]PROPANOIC ACID is used as a subject of interest in medicinal chemistry due to its potential biological activity. The presence of the thioether group and the 4-methoxyphenyl ring in its structure may confer specific interactions with biological targets, such as enzymes, receptors, or other proteins. This can lead to the discovery of new lead compounds or the optimization of existing drug candidates for improved therapeutic efficacy and safety.

InChI:InChI=1/C10H12O3S/c1-13-8-2-4-9(5-3-8)14-7-6-10(11)12/h2-5H,6-7H2,1H3,(H,11,12)

Upstream product

• 590-92-1 3-Bromopropionic acid 
• 696-63-9 4-Methoxybenzenethiol 
• 19488-09-6 sodium 4-methoxyphenylthiolate 
• 16987-03-4 sodium 3-chloroproanoate 
• 79-10-7 acrylic acid 
• 696-62-8 para-iodoanisole 
• 107-96-0 3-mercaptopropionic acid 
• 107-94-8 chloropropionic acid 
• 102236-72-6 2-cyanoethyl p-methoxyphenyl sulfide 

Downstream Products

• 108127-47-5 6-hydroxy-thiochroman-4-one 
• 13735-11-0 6-methoxy-2,3-dihydro-4H-thiochromen-4-one 
• 91062-23-6 3-p-methoxybenzenesulfonyl propionic acid 
• 110333-12-5 3-(4-Methoxyphenylsulfinyl)propanoic Acid 
• 1315306-66-1 3-(4-chlorophenyl)-6'-methoxy-spiro[oxirane-2,3'-thiochroman]-4'-one 
• 145903-32-8 7-methoxy-3,4-dihydrobenzo[f][1,4]thiazepin-5(2H)-one 
• 927871-76-9 S107 
• 145903-31-7 7-methoxy-2,3,4,5-tetrahydrobenzo[f][1,4]thiazepine 

Relevant academic research and scientific papers

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 of Novel Pterocarpen Analogues via [3?+?2] Coupling-Elimination Cascade of α,α-Dicyanoolefins with Quinone Monoimines

By employing triethylamine as a catalyst, [3?+?2] coupling-elimination cascade of α,α-dicyanoolefins with quinone monoimines was realized. The reactions afforded various novel pterocarpen analogues with generally moderate yields (up to 75%). In addition, a plausible reaction mechanism was proposed.

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.

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.

STORE OVERLOAD-INDUCED CALCIUM RELEASE INHIBITORS AND METHODS FOR PRODUCING AND USING THE SAME

The present invention provides compounds having store overload-induced Ca2+ release (SOICR) inhibitory activity and methods for producing and using the same. In particular, compounds of the invention is of the formula: R1-X1-L-X2-R2, wherein R1, X1, L, X2, and R2 are those defined herein.

Novel carvedilol analogues that suppress store-overload-induced Ca 2+ release

Carvedilol is a uniquely effective drug for the treatment of cardiac arrhythmias in patients with heart failure. This activity is in part because of its ability to inhibit store-overload-induced calcium release (SOICR) through the RyR2 channel. We describe the synthesis, characterization, and bioassay of ca. 100 compounds based on the carvedilol motif to identify features that correlate with and optimize SOICR inhibition. A single-cell bioassay was employed on the basis of the RyR2-R4496C mutant HEK-293 cell line in which calcium release from the endoplasmic reticulum through the defective channel was measured. IC50 values for SOICR inhibition were thus obtained. The compounds investigated contained modifications to the three principal subunits of carvedilol, including the carbazole and catechol moieties, as well as the linker chain containing the β-amino alcohol functionality. The SAR results indicate that significant alterations are tolerated in each of the three subunits.

Synthesis and pharmacological evaluation of novel bisindolylalkanes analogues

In an effort to develop potent anti-cancer chemopreventive agents that act on topoisomerase II, a novel series of bisindolylalkanes analogues such as 3,3′-(thiochroman-4,4-diyl)bis(1H-indole) are synthesized. Structures of all compounds are elucidated by 1H NMR, 13C NMR and HRMS. Anti-proliferative activities for all of these compounds are investigated by the method of MTT assay on 7 human cancer lines. Most of them showed antitumor activities in vitro, the half maximal inhibitory concentration (IC50) value is 7.798 μg/mL of 3a against MCF7. Compound 3a showed comparable topoisomerase II inhibitory activity to etoposide (VP-16) at 100 μM concentration. The rest of the compounds also showed varying degree topoisomerase II inhibitory activity.

Synthesis and biochemical evaluation of thiochromanone thiosemicarbazone analogues as inhibitors of cathepsin L

A series of 36 thiosemicarbazone analogues containing the thiochromanone molecular scaffold functionalized primarily at the C-6 position were prepared by chemical synthesis and evaluated as inhibitors of cathepsins L and B. The most promising inhibitors f

Design and synthesis of α,β-epoxyketones as new anticancer agents

As epoxy functional group has high anticancer activity, α,β-epoxyketones were designed and synthesized as new anticancer agents, and their structures were confirmed by UV, 1H NMR, IR, MS technigeces and elemental analysis. Their in vitro anticancer activities were evaluated by MTT method and the results showed that the compound 4c exhibited good activity with IC50 of 17.8, 22.0 and 24.1 μg/mL against A-549, Hela and HepG2 cells, respectively. The dose of LD50 of the mice by intragastric administration was 1864.4 mg/kg. Therefore, the α,β-epoxyketones could potentially provide as new anticancer agents. A series of α,β-epoxyketones were synthesized in a four steps reaction and tested for their anticancer activities.