880-13-7

Upstream product

• 3724-65-0 2-butenoic acid 
• 108-98-5 thiophenol 
• 38160-59-7 3-(phenylthio)butanal 
• 625-68-3 3-chlorobutyric acid 
• 3068-88-0 4-methyloxetan-2-one 
• 100-59-4 phenylmagnesium chloride 
• 29943-38-2 2-methoxycarbonyl-1-methylethyl phenyl sulfide 
• 10544-63-5 ethyl crotonate 
• 107-93-7 (E)-but-2-enoic acid 

Downstream Products

• 826-86-8 2-methyl-1-thiochroman-4-one 
• 851231-61-3 3-benzenesulfonyl-N-benzyloxy-butyramide 
• 851228-23-4 N-benzyloxy-3-phenylsulfanyl-butyramide 
• 16808-50-7 2-methyl-1-thiochroman-4-one 1,1-dioxide 

Relevant academic research and scientific papers

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).

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.

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.

Chiral discrimination of β-telluride carboxylic acids by NMR spectroscopy

In this work, the nuclei (1H and 125Te) for NMR spectroscopy and enantiopure compounds as chiral solvent agents (CSAs) and chiral derivatisation agents (CDAs) were evaluated under different conditions. The structure of β-telluride carboxylic acids was also modified to observe the effect on anisochrony.

Fluoride ion-catalyzed conjugate addition for easy synthesis of 3-sulfanylpropionic acid from thiol and α,β-unsaturated carboxylic acid

3-Sulfanylpropionic acids are obtained in excellent yields by proceeding through a simple, mild, and efficient procedure utilizing tetrabutylammonium fluoride (TBAF) as catalyst.

Iodine catalyzed conjugate addition of mercaptans to α,β- unsaturated carboxylic acids under solvent-free condition

We have described herein molecular iodine catalyzed Michael addition of thiol to α,β-unsaturated carboxylic acids. This environmentally benign catalytic system (iodine) used under mild and solvent-free conditions to achieve the corresponding adducts in excellent yield.

A structure-taste study of arylsulfonyl(cyclo)alkanecarboxylic acids

A number of sweeteners contain a sulfonyl group. In our current search for new glucophores several new compounds containing such group were obtained. A series of novel 1-phenylsulfonylcyklohexanecarboxylic acids and 2-arylsulfonylalkanecarboxylic acids was obtained and evaluated for their sweet taste quality. It has been found that methyl substituents are of the key importance for the activity of these compounds.

A mild, chemoselective oxidation of sulfides to sulfoxides using o-iodoxybenzoic acid and tetraethylammonium bromide as catalyst

A mild, selective, and high-yielding method for oxidation of sulfides to sulfoxides using IBX and tetraethylammonium bromide in a variety of solvents is described. The method offers the advantage of short reaction times, no over-oxidation to sulfones, and compatibility to a wide range of functional groups.

Hydroxamic acid derivatives as potent peptide deformylase inhibitors and antibacterial agents

Low-molecular-weight β-sulfonyl- and β-sulfinylhydroxamic acid derivatives have been synthesized and found to be potent inhibitors of Escherichia coli peptide deformylase (PDF). Most of the compounds synthesized and tested displayed antibacterial activities that cover several pathogens found in respiratory tract infections, including Chlamydia pneumoniae, Mycoplasma pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis. The potential of these compounds as antibacterial agents is discussed with respect to selectivity, intracellular concentrations in bacteria, and potential for resistance development.

Direct aromatic tert-butylation during the synthesis of thiochroman-4-ones

The synthesis of thiochroman-4-ones from thiophenols and 3-methylbut-2-enoic acid effected by methane sulphonic acid is accompanied by tert-butylation of the aromatic ring. 3-Arylthiobutanoic acids, available using β-butyrolactone, are efficiently cyclised in the same manner.