13735-11-0

Usage

Uses

Used in Organic Synthesis:
6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a key intermediate in the synthesis of various organic compounds. Its unique structural features allow for the formation of new chemical bonds and the creation of novel molecules with potential applications in various industries.
Used in Medicinal Chemistry:
In the field of medicinal chemistry, 6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a building block for the development of new pharmaceutical compounds. Its structural properties may contribute to the design of innovative drugs with improved therapeutic effects and reduced side effects.
Used in Pharmaceutical Industry:
6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a starting material for the synthesis of pharmaceutical compounds with potential therapeutic applications. Its unique chemical structure may lead to the discovery of new drugs with novel mechanisms of action and improved efficacy in treating various diseases.
Used in Chemical Research:
6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a research compound in chemical laboratories to study its properties, reactivity, and potential applications. Its unique structure and potential biological activities make it an interesting subject for further investigation and development in the field of chemistry.
Used in Drug Development:
In the process of drug development, 6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a lead compound for the discovery of new therapeutic agents. Its structural features and potential biological activities may contribute to the development of innovative drugs with improved pharmacological properties and therapeutic benefits.
Used in Chemical Industries:
6-Methoxy-3,4-dihydro-2H-1-benzothiin-4-one is used as a specialty chemical in various chemical industries. Its unique properties and potential applications in organic synthesis and medicinal chemistry make it a valuable compound for the development of new products and technologies.

Upstream product

• 13739-36-1 β-(4-methoxyphenylmercapto)propionic acid 
• 696-63-9 4-Methoxybenzenethiol 
• 107-94-8 chloropropionic acid 
• 19488-09-6 sodium 4-methoxyphenylthiolate 

Downstream Products

• 130689-05-3 3-[1-Benzo[1,3]dioxol-5-yl-meth-(Z)-ylidene]-6-methoxy-thiochroman-4-one 
• 130689-04-2 6-Methoxy-3-[1-(4-methoxy-phenyl)-meth-(Z)-ylidene]-thiochroman-4-one 
• 115091-89-9 3,6-Dimethoxy-1-(4-methoxy-phenyl)-10H-9-thia-4-aza-phenanthrene-2-carbonitrile 
• 115091-90-2 1-Benzo[1,3]dioxol-5-yl-3,6-dimethoxy-10H-9-thia-4-aza-phenanthrene-2-carbonitrile 
• 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 
• 110766-87-5 7-methoxy-2,3-dihydro-5H-benzo[b][1,4]thiazepin-4-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 and biological evaluation of novel pyrazoline derivatives containing indole skeleton as anti-cancer agents targeting topoisomerase II

In order to develop potent anticaner agents, a novel series of 3-(1H-indol-3-yl)-2,3,3a,4-tetrahydrothiochromeno[4,3-c]pyrazole derivatives were synthesized. Structures of all compounds were confirmed. MTT assay has been employed to study antiproliferative activity of these compounds with four human cancer cell lines (MGC-803, Hela, MCF-7 and Bel-7404) and a normal cell line L929. Most of these compounds showed potential anticancer activity and low cytotoxicity on normal cell in vitro. 7d and 7f showed the best anticancer activity, whose IC50 value is 15.43 μM and 20.54 μM towards MGC-803, respectively. Most of them exhibited topoisomerase II selective inhibitory. Cleavage reaction assay and DNA unwinding assay showed that 7f was a nonintercalative Topo II catalytic inhibitor, which was consistent with the docking results. Laser scanning confocal microscopy system tracks the location of representative compounds 7d and 7f which can be abundantly entering the nucleus. In particular, the most potent compounds 7d and 7f were shown to be able to induce G2/M cell cycle arrest and apoptosis in MGC-803 cells.

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.

SUBSTITUTED SULFONE-CONTAINING TRICYCLIC COMPOUNDS AND USES THEREOF

The present invention relates to substituted sulfone-containing tricyclic compounds and analogues thereof which inhibit Bak-mediated apoptosis. The invention further relates to pharmaceutical compositions comprising a compound of the present invention and to methods of inhibiting a Bak-mediated apoptotic pathway and Bak-mediated apoptosis in a cell.

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.

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.