13735-13-2

Usage

Chemical Properties

Orange solid

InChI:InChI=1/C9H7BrOS/c10-6-1-2-9-7(5-6)8(11)3-4-12-9/h1-2,5H,3-4H2

Upstream product

• 13735-04-1 3-(4-Bromophenylsulfanyl)propanoic Acid 
• 3528-17-4 2,3-dihydro-4H-[1]benzothiopyran-4-one 
• 13457-82-4 4-bromothiophenol sodium salt 
• 106-53-6 para-bromobenzenethiol 
• 7381-30-8 2,2,7,7-tetramethyl-3,6-dioxa-2,7-disilaoctane 

Downstream Products

• 112819-26-8 6-bromo-1,1-dioxothiochroman-4-one 
• 1256726-42-7 C₁₇H₁₆BrF₂NO₃S 
• 1256725-85-5 N-[2-(2,5-difluorophenoxy)ethyl]-6-(methylsulfonyl)-3,4-dihydro-2H-thiochromen-4-amine 1,1-dioxide hydrochloride 
• 1256725-91-3 4-{[2-(2,5-difluorophenoxy)ethyl]amino}-3,4-dihydro-2Hthiochromene-6-carboxamide 1,1-dioxide hydrochloride 
• 1256725-95-7 N⁴-[2-(2,5-difluorophenoxy)ethyl]-N⁶-methyl-3,4-dihydro-2H-thiochromene-4,6-diamine 1,1-dioxide hydrochloride 
• 244241-10-9 ethyl 4-<(4-(4-(1,1-dimethylethyl)phenyl)-(2H)-thiochromen-6-yl)ethynyl>benzoate 
• 188889-29-4 ethyl 4-<(4-trifluorosulfonyloxy-(2H)-thiochromen-6-yl)ethynyl>benzoate 
• 244241-08-5 ethyl 4-<(4-(4-ethylphenyl)-(2H)-thiochromen-6-yl)ethynyl>benzoate 

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 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.

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.

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.

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

INHIBITORS OF CYSTEINE PROTEASES AND METHODS OF USE THEREOF

The present invention relates to semicarbazone or thiosemicarbazone inhibitors of cysteine proteases and methods of using such compounds to prevent and treat protozoan infections such as trypanosomiasis, malaria and leishmaniasis. The compounds also find use in inhibiting cysteine proteases associated with carcinogenesis, including cathepsins B and L.

BENZOTHIAZOLE COMPOUNDS

The present invention relates to benzothiazole compounds that mimic the activity of BH3 only proteins and are capable of binding to and neutralizing pro survival Bcl 2 proteins. The invention also relates to the use of such compounds in the regulation of cell death or cell survival and the treatment and/or prophylaxis of diseases or conditions associated with the deregulation of cell death or cell survival.

Design, synthesis, and biochemical evaluation of novel cruzain inhibitors with potential application in the treatment of Chagas' disease

A series of compounds bearing tetrahydronaphthalene, benzophenone, propiophenone, and related rigid molecular skeletons functionalized with thiosemicarbazone or unsaturated carbonyl moieties were prepared by chemical synthesis and evaluated for their ability to inhibit the enzyme cruzain. As potential treatment agents for Chagas' disease, three compounds from the group demonstrate potent inhibition of cruzain with IC50 values of 17, 24, and 80 nM, respectively.