21243-18-5

Usage

Uses

Used in Pharmaceutical Research and Drug Development:
6-Fluorothio-4-chromanone is used as a potential drug candidate in the field of medicinal chemistry due to its distinctive structural features and properties. Its ability to interact with biological targets and modulate various biological pathways makes it a valuable compound for the development of new therapeutic agents.
Used in Medicinal Chemistry as a Building Block:
6-Fluorothio-4-chromanone is also utilized as a building block for synthesizing other bioactive molecules. Its versatile chemical structure allows for the creation of novel compounds with potential applications in various therapeutic areas.
Further research into the properties and potential applications of 6-fluorothio-4-chromanone is necessary to fully understand its capabilities and limitations, as well as to explore its full potential in the pharmaceutical industry.

InChI:InChI=1/C9H7FOS/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-2,5H,3-4H2

Upstream product

• 79-37-8 oxalyl dichloride 
• 682760-24-3 3-p-fluorobenzenesulfonyl propionic acid 
• 68-12-2 N,N-dimethyl-formamide 
• 371-42-6 4-Fluorothiophenol 
• 107-94-8 chloropropionic acid 
• 3887-61-4 sodium 4-fluorophenylthiolate 
• 19543-85-2 3-(4-fluorophenylthio)propanoic acid 

Downstream Products

• 52831-35-3 Fluor-2-6H(I)benzothiopyrano<4,3-b>chinolin 
• 52831-37-5 Fluor-2-methyl-7 6H(1)benzothiopyrano<4,3-b>chinolin 
• 52831-44-4 Dihydro-6,13-fluor-2(I)benzothiopyrano<4,3-b>benzoindol 
• 52831-41-1 2-fluoro-6,13-dihydro-benzo[g]thiochromeno[4,3-b]indole 
• 1178529-19-5 C₂₄H₁₈FNO₂S 
• 1256726-32-5 N-[2-(2,5-difluorophenoxy)ethyl]-6-fluoro-3,4-dihydro-2H-thiochromen-4-amine 1,1-dioxide hydrochloride 
• 1438433-26-1 (E)-3-[[(2-aminophenyl)amino]methylene]-6-fluoro-2,3-dihydro-4H-1-benzothiopyran-4-one 
• 1438433-25-0 (E)-6-fluoro-2,3-dihydro-3-[(phenylamino)methylene]-4H-1-benzothiopyran-4-one 
• 1315306-72-9 6'-fluoro-3-(4-methoxyphenyl)spiro[oxirane-2,3'-thiochroman]-4'-one 
• 1315306-70-7 6'-fluoro-3-phenyl-spiro[oxirane-2,3'-thiochroman]-4'-one 
• 1315306-69-4 3-(4-chlorophenyl)-6'-fluoro-spiro[oxirane-2,3'-thiochroman]-4'-one 

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.

Pure organic room-temperature phosphorescent material based on thiochromanone derivative as well as preparation method and application of pure organic room-temperature phosphorescent material

The embodiment of the invention discloses a pure organic room-temperature phosphorescent material based on a thiochromanone derivative as well as a preparation method and application of the pure organic room-temperature phosphorescent material. The organi

Cu(I)-Catalyzed Enantioselective Alkynylation of Thiochromones

A highly efficient asymmetric synthesis of chiral thiochromanones is developed via Cu(I)/phosphoramidite catalyzed asymmetric alkynylation of thiochromones under mild reaction conditions. The catalyst system is tolerant of various thiochromone precursors and terminal alkynes. The established asymmetric transformation provides different enatiomeric-enriched thiochromanones with more molecular complexity and enables access to chiral thioflavanones, a subgroup of flavonoid by further functionalization.

Synthesis and anti cervical cancer activity of novel 5H-thiochromeno [4,3-d]pyrimidines

A series of novel 5H-Thiochromeno[4,3-d]pyrimidine derivatives were synthesized, purified and characterized by different spectroscopy techniques such as1H NMR,13C NMR, Mass and Elemental Analysis. The new compounds were evaluated for their anti-cervical cancer activity on Human Cervical Cell Line HeLa. They were found to be potent anti-cervical cancer agents with GI50 values less than 10 μg/mL with respect to positive control drug Adriamycin.

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.

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).

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.

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.