5962-00-5

Usage

Uses

Used in Pharmaceutical Synthesis:
2,3-Dihydro-2-phenyl-4H-1-benzothiopyran-4-one is used as a key building block in the pharmaceutical industry for the synthesis of various drugs. Its unique structure and sulfur-containing nature contribute to the development of new therapeutic agents with improved efficacy and selectivity.
Used in Agrochemical Synthesis:
In the agrochemical industry, 2,3-Dihydro-2-phenyl-4H-1-benzothiopyran-4-one serves as a crucial intermediate in the production of pesticides and other agrochemicals. Its incorporation into these compounds can enhance their effectiveness in controlling pests and diseases, thereby improving crop yields and quality.
Used in Medicinal Chemistry Research:
DHBTP is utilized as a subject of interest in medicinal chemistry research. Its potential pharmacological properties make it a promising candidate for the development of new drugs and therapeutic agents. Researchers explore its interactions with biological targets and evaluate its efficacy in treating various diseases.
Used in Drug Discovery:
In the field of drug discovery, 2,3-Dihydro-2-phenyl-4H-1-benzothiopyran-4-one plays a significant role as a starting point for the design and development of novel pharmaceutical compounds. Its unique structural features and potential biological activities make it an attractive scaffold for the creation of new drugs with improved pharmacokinetic and pharmacodynamic profiles.

InChI:InChI=1/C15H12OS/c16-13-10-15(11-6-2-1-3-7-11)17-14-9-5-4-8-12(13)14/h1-9,15H,10H2

Upstream product

• 784-62-3 1-thioflavone 
• 61955-78-0 3-Phenyl-3-phenylthiopropionylchlorid 
• 393-52-2 2-Fluorobenzoyl chloride 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 100-52-7 benzaldehyde 
• 107921-63-1 (E)-1-(2-iodophenyl)-3-phenylprop-2-en-1-one 
• 140-89-6 potassium ethyl xanthogenate 
• 809272-08-0 C₁₅H₁₂OS 
• 108-98-5 thiophenol 
• 70030-52-3 S-phenyl thiocinnamate 
• 5425-50-3 3-phenyl-3-(phenylmercapto)propanoic acid 
• 491-39-4 thiochromen-4-one 
• 100-58-3 phenylmagnesium bromide 
• 40142-77-6 1-(2-(benzylthio)phenyl)ethan-1-one 

Downstream Products

• 78115-51-2 3-methylene-1-thiaflavone 
• 119656-90-5 2-Phenyl-3-[1-p-tolyl-meth-(Z)-ylidene]-thiochroman-4-one 
• 135922-93-9 3-[1-(4-Fluoro-phenyl)-meth-(Z)-ylidene]-2-phenyl-thiochroman-4-one 
• 135922-92-8 3-[1-(4-Chloro-phenyl)-meth-(Z)-ylidene]-2-phenyl-thiochroman-4-one 
• 140381-18-6 3-(3-Nitro-benzyl)-2-phenyl-thiochromen-4-one 
• 135922-96-2 3-(4-Nitro-benzyl)-2-phenyl-thiochromen-4-one 
• 147375-58-4 (Z)-3-benzylidene-1-thioflavanone 
• 135922-89-3 3-[1-(4-Hydroxy-phenyl)-meth-(Z)-ylidene]-2-phenyl-thiochroman-4-one 
• 135922-90-6 3-(4-methoxybenzylidene)thioflavanone 
• 140381-15-3 3-(2,4-Dichloro-benzyl)-2-phenyl-thiochromen-4-one 
• 135922-94-0 3-(4-bromobenzyl)-1-thioflavone 
• 135922-95-1 3-(4-cyanobenzyl)-1-thioflavone 
• 140381-17-5 3-(2-Bromo-benzyl)-2-phenyl-thiochromen-4-one 
• 140381-16-4 3-(3,4-Dichloro-benzyl)-2-phenyl-thiochromen-4-one 

Relevant academic research and scientific papers

Visible Light Mediated Photocatalyst Free C-S Cross Coupling: Domino Synthesis of Thiochromane Derivatives via Photoinduced Electron Transfer

An efficient visible light mediated photocatalyst free C-S cross-coupling reaction has been developed for the synthesis of thiochromane derivatives through photoinduced electron transfer (PET). This methodology was further utilized for the synthesis of thiochroman-4-ol through intermolecular three-component cross-coupling reaction. The reaction proceeds via C-S bond formation through EDA complex/thioester cleavage/inter-or intramolecular sulfa-Michael addition followed by aldol reaction sequence. The EDA complex formation between aryl iodides and xanthate has been substantiated using spectroscopic experiments and DFT calculations.

Conjugate addition of grignard reagents to thiochromones catalyzed by copper salts: A unified approach to both 2-alkylthiochroman-4-one and thioflavanone

Grignard reagents undergo conjugate addition to thiochromones catalyzed by copper salts to afford 2-substituted-thiochroman-4-ones, both 2-alkylthiochroman-4-ones and thioflavanones (2-arylthiochroman-4-ones), in good yields with trimethylsilyl chloride (TMSCl) as an additive. The best yields of 1,4-adducts can be attained with CuCN-2LiCl as the copper source. Excellent yields of 2-alkyl-substituted thiochroman-4-ones and thioflavanones (2-aryl substituted) are attained with a broad range of Grignard reagents. This approach works well with both alkyl and aromatic Grignard reagents, thus providing a unified synthetic approach to privileged 2-substituted thiochroman-4-ones and a potential valuable precursor for further synthetic applications towards many pharmaceutically active molecules. The use of commercially available and/or readily prepared Grignard reagents will expedite the synthesis of a large library of both 2-alkyl substituted thiochroman-4-ones and thioflavanones for additional synthetic applications.

Copper-Catalyzed One-Pot Synthesis of 2-Arylthiochromenones: An in Situ Recycle of Waste Byproduct as Useful Reagent

Copper-catalyzed one-pot synthesis of various 2-arylthiochromenones is developed using xanthate as an odorless sulfur source from easily acquirable 2′-halochalcones. This methodology demonstrates that the cross-coupled product thiochromanone synthesized from 2′-halochalcones (upstream reaction) is oxidized to thiochromenone (downstream reaction) in the same pot using waste byproduct (KI) of the first step as powerful oxidant molecular iodine (I2). This one-pot synthesis has been further extended for the synthesis of 3,3′-methylenebisthioflavone using dimethyl sulfoxide (DMSO) as solvent and methylene source.

Hydrazone derivatives enhance antileishmanial activity of thiochroman-4-ones

Cutaneous leishmaniasis (CL) is a neglected tropical disease, which causes severe skin lesions. Due to the lack of effective vaccines, and toxicity or reduced effectiveness of available drugs in addition to complex and prolonged treatments, there is an urgent need to develop alternatives for the treatment for CL with different mechanisms of action. In our effort to search for new promising hits against Leishmania parasites we prepared 18 acyl hydrazone derivatives of thiochroman-4-ones. Compounds were evaluated for their in vitro antileishmanial activity against the intracellular amastigote form of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Our results show that derivatization of the thiochroman-4-ones with acyl hydrazones significantly enhances the antileishmanial activity. Among the compounds tested semicarbazone and thiosemicarbazone derivatives of thioflavanone 19 and 20 displayed the highest antileishmanial activities, with EC50 values of 5.4 and 5.1 μM and low cytotoxicities (100.2 and 50.1 μM respectively), resulting in higher indexes of selectivity (IS).

A rapid entry into thioflavanones via conjugate additions of diarylcuprates to thiochromones

Thiochromone undergo conjugate addition reactions with arylcuprates to afford 2-substituted thioflavanones, providing an efficient synthetic approach to privileged sulfur-containing structural motifs and valuable precursor for many pharmaceuticals. Excellent yields of substituted thioflavanones are achieved with lithium diarylcuprates, lithium arylcyanocuprates and Grignard reagents with copper catalysis. This method provides a rapid entry to a variety of thioflavanones in excellent yields (up to 92%). The use of commercially available or easily prepared organometallic reagents will expedite the synthesis of a large library of thioflavanones for further synthetic applications and biological studies.

Synthesis and evaluation of thiochroman-4-one derivatives as potential leishmanicidal agents

The S-containing heterocyclic compounds benzothiopyrans or thiochromones stand out as having promising biological activities due to their structural relationship with chromones (benzopyrans), which are widely known as privileged scaffolds in medicinal chemistry. In this work, we report the synthesis of 35 thiochromone derivatives and the in vitro antileishmanial and cytotoxic activities. Compounds were tested against intracellular amastigotes of Leishmania panamensis and cytotoxic activity against human monocytes (U-937 ATCC CRL-1593.2). Compounds bearing a vinyl sulfone moiety, 4h, 4i, 4j, 4k, 4l and 4m, displayed the highest antileishmanial activity, with EC50 values lower than 10 μM and an index of selectivity over 100 for compounds 4j and 4l. When the double bond or the sulfone moiety was removed, the activity decreased. Our results show that thiochromones bearing a vinyl sulfone moiety are endowed with high antileishmanial activity and low cytotoxicity.

Copper-Catalyzed Domino Synthesis of 2-Arylthiochromanones through Concomitant C-S Bond Formations Using Xanthate as Sulfur Source

An efficient domino process for the synthesis of thioflavanones has been described using a copper catalyst without addition of any external ligand. A variety of thioflavanones have been synthesized from easily accessible 2′-iodochalcones or 2′-bromochalco

Practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides

A practical and versatile synthesis of thioflavones from 2-bromobenzoyl chlorides as potent drug candidates, including derivatives with chloro, methyl, or methoxy substituents on the condensed benzene ring was reported. 4,6-Pyrimidyl di(2-halobenzoates)were readily prepared by acylation of 2 equiv of 1 with 4,6-dihydroxypyrimidine in the presence of 2 equiv of triethylamine in methylene chloride at room temperature. After evaporating methylene chloride, the mixture was dissolved in anhydrous THF and triethylamine hydrochloride was filtered off. The condensed residue was purified by short pathway silica gel column chromatography or recrystallization in 75% EtOAc/n-hexane to give 2 in 85-94% yields. Successful synthesis of 2 equiv of 1-(2-bromophenyl)-3-(hetero)aryl-2-propyn-1-ones was accomplished by reacting 1 equiv of 2 with 2 equiv of (hetero)arylethynylmagnesium bromides. Benzothiopyran ring formation was achieved via the 1,4-addition of hydrosulfide anion and one-pot sequence of bromide substitution. The reaction worked well with electron-withdrawing substituents, such as 7-chloro groups, and electrondonating substituents, such as 7-methyland 6-methoxy groups, in the condensed benzene rings.

Synthesis of flavanones, azaflavanones, and thioflavanones catalyzed by PMA-SiO2 as a mild, efficient, and reusable catalyst

Cyclization of a variety of chalcones to flavanones catalyzed by 1 mol% phosphomolybdic acid (PMA) supported on silica as a mild, efficient, and reusable catalyst was carried out in high yields. PMA-SiO2 is an efficient, inexpensive, and green catalyst which gave high conversion yields and could be recycled up to three times without significant loss in activity. Springer-Verlag 2011.