1622221-68-4

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 1593-60-8 p-toluenesulfonylhydroxylamine 
• 4124-41-8 p-toluenesulfonylanhydride 
• 1858-86-2 Ethyl p-toluenesulfinate 
• 106-45-6 para-thiocresol 
• 1576-35-8 toluene-4-sulfonic acid hydrazide 
• 824-79-3 sodium 4-methylbenzenesulfinate 
• 98-59-9 p-toluenesulfonyl chloride 

Relevant academic research and scientific papers

New Inhibitors of Indoleamine 2,3-Dioxygenase 1: Molecular Modeling Studies, Synthesis, and Biological Evaluation

Indoleamine 2,3-dioxygenase 1 (IDO1) is an attractive target for anticancer therapy. Herein, we report a virtual screening study which led to the identification of compound 5 as a new IDO1 inhibitor. In order to improve the biological activity of the identified hit, arylthioindoles 6-30 were synthesized and tested. Among these, derivative 21 exhibited an IC50 value of 7 μM, being the most active compound of the series. Furthermore, compounds 5 and 21 induced a dose-dependent growth inhibition in IDO1 expressing cancer cell lines HTC116 and HT29. Three-dimensional quantitative structure-activity relationship studies were carried out in order to rationalize obtained results and suggest new chemical modifications.

Synergistic Effect of Squaric Acid in Bromine-Catalyzed Deoxygenation of Sulfonyl Derivatives: Mechanistic Investigations and Synthetic Applications in Electrophilic (Fluoroalkyl)sulfenylation

A method for electrophilic (fluoroalkyl)sulfenylation of nucleophiles by collaborative CTAB- and squaric acid-promoted deoxygenation of sulfonyl derivatives is reported. Mechanistic studies indicate that squaric acid dramatically decreased the energy barr

Iodine/Manganese Catalyzed Sulfenylation of Indole via Dehydrogenative Oxidative Coupling in Anisole

This protocol describes an iodine/manganese catalytic system for dehydrogenative oxidative coupling reaction of indoles with thiols in anisole. Particularly, the dual roles of anisole have been first demonstrated as a solvent and as a promoter via the formation of an oxonium ion intermediate to accelerate the generation of products. A series of sulfenylindoles are readily constructed under aerobic mild reaction conditions. In addition, the achievement for preparing anticancer and anti-AIDS drugs testifies the practicability of this approach. The mechanism studies disclose probable alternative pathways and a single-electron transfer process are involved in this transformation. (Figure presented.).

Preparation method of indole sulfide compound

The invention discloses a preparation method of an indole sulfide compound. The preparation method is conducted according to the following steps that a catalyst, an indole reactant, hydrazine hydrate,substituted phenyl sulfonyl chloride and a solvent are

Catalyst-free sulfenylation of indoles with sulfinic esters in ethanol

A novel catalyst-free method for the synthesis of structurally diverse indole thioethers in moderate to excellent yields has been developed. In this reaction, sulfinic esters serve as new sulfur electrophiles.

TBAI-mediated regioselective sulfenylation of indoles with sulfonyl chlorides in one pot

A versatile method for the synthesis of 3-sulfenylated indoles via TBAI promoted sulfenylation of indoles with sulfonyl chlorides in one pot has been presented. This system features highly regioselective, metal-free, easy operation, and shows a broad functional group tolerance leading to excellent yields. And this reaction could be easily conducted in 10 mmol scale with high effectivity. A plausible mechanism is proposed.

N-Hydroxy sulfonamides as new sulfenylating agents for the functionalization of aromatic compounds

An unprecedented use of N-hydroxy sulfonamides as sulfenylating agents has been established. In the presence of catalytic amounts of iodine and N-hydroxysuccinimide, N-hydroxy sulfonamides participated in sulfenylation with indoles, 7-azaindole, N-methyl pyrrole, and 2-naphthol to afford structurally diverse thioethers in moderate to excellent yields with very high regioselectivity.

Photocatalytic direct C-S bond formation: Facile access to 3-sulfenylindoles: Via metal-free C-3 sulfenylation of indoles with thiophenols

An efficient and convenient photocatalytic direct C-3 sulfenylation of indoles with thiophenols has been developed for the construction of 3-sulfenylations. This protocol employs thiophenols as the sulfenylating agents, inexpensive rose bengal as the photocatalyst, and shows mild conditions, readily available starting materials, high atom and step atom economy, and environmental advantages. The representative method provides a straightforward approach for C-S bond formation, and has potential applications in the chemical and pharmaceutical industries.

Preparation method for 3-sulfo-indoles compound

The invention relates to the technical field of organic synthesis and provides a preparation method for a 3-sulfo-indoles compound. The 3-sulfo-indoles compound is acquired through the substitution reaction of thiophenols compound and indoles compound under the photo-catalytic effect of photo-catalyst and organic solvent, wherein the photo-catalyst comprises one or more of eosin B, eosin Y and rose bengal. According to the preparation method provided by the invention, the reaction condition is mild, no alkali or oxidizing agent is required, no transition metal catalyst participates into the reaction, the adverse effect of the metal residue to the product performance is effectively avoided, the product performance is promoted, the product yield is increased to 70%, the multi-step synthesis of the reaction raw materials is not required and the technological process is simplified.

Copper-catalyzed aerobic oxidative N-S bond functionalization for C-S bond formation: Regio- and stereoselective synthesis of sulfones and thioethers

A regio- and stereoselective synthesis of sulfones and thioethers by means of CuI-catalyzed aerobic oxidative N-S bond cleavage of sulfonyl hydrazides, followed by cross-coupling reactions with alkenes and aromatic compounds to form the C-sp-2-S bond, is described herein. N2 and H2O are the byproducts of this transformation, thus offering an environmentally benign process with a wide range of potential applications in organic synthesis and medicinal chemistry. First cleave, then cross-couple: A direct Cu-catalyzed aerobic oxidative C-sp-2-H functionalization and C-S bond coupling reaction has been developed (see scheme). By slight modification of the additive, sulfonyl hydrazides could serve as sulfonation, sulfenation, or arylation reagents to undergo cross-coupling reactions with alkenes and (hetero)aromatic cycles, affording sulfones, thioethers, and biaryl compounds with high regio- and stereoselectivities (see scheme).