227803-35-2

Usage

Uses

Used in Pharmaceutical Research and Development:
5-CHLORO-3-(PHENYLTHIO)-INDOLE is used as a drug target for the development of new therapeutic agents for various diseases. Its unique chemical structure allows it to interact with specific biological targets, making it a promising candidate for drug discovery.
Used in Synthesis of Biologically Active Molecules:
5-CHLORO-3-(PHENYLTHIO)-INDOLE serves as a building block in the synthesis of various biologically active molecules. Its versatile chemical properties enable it to be incorporated into a wide range of compounds with potential therapeutic applications.
Used in Medicinal Chemistry:
5-CHLORO-3-(PHENYLTHIO)-INDOLE is utilized in medicinal chemistry for the design and optimization of new drug candidates. Its unique structural features make it a valuable tool for the development of innovative therapeutic agents.
Used in Drug Discovery:
5-CHLORO-3-(PHENYLTHIO)-INDOLE plays a role in drug discovery by providing a foundation for the identification and development of new pharmaceutical compounds. Its potential as a drug target and its use in the synthesis of biologically active molecules make it an important component in the drug development process.

InChI:InChI=1/C14H10ClNS/c15-10-6-7-13-12(8-10)14(9-16-13)17-11-4-2-1-3-5-11/h1-9,16H

Upstream product

• 17422-32-1 5-chloro-1H-indole 
• 108-98-5 thiophenol 
• 64605-36-3 5-chloro-2-amino-α-chloroacetophenone 
• 106-47-8 4-chloro-aniline 
• 894095-04-6 ketimine of 5-chloro-2-amino-α-chloroacetophenone 
• 512-35-6 benzenesulfonic anhydride 
• 1859-03-6 ethyl benzenesulfinate 
• 193140-32-8 5-chloro-2-nitrocinnamaldehyde 
• 873-55-2 sodium benzenesulfonate 
• 882-33-7 diphenyldisulfane 

Downstream Products

• 227803-36-3 5-chloro-2-(phenylsulfanyl)-1H-indole 

Relevant academic research and scientific papers

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

NH4I/1,10-phenanthroline catalyzed direct sulfenylation of N-heteroarenes with ethyl arylsulfinates

An efficient synthesis of N-heterocyclic aryl sulfides via NH4I/1,10-phenanthroline-catalyzed direct sulfenylation reactions was reported. In this reaction, heteroarenes such as indoles, and pyrroles serve as nucleophiles by installing a arylthio group at the C3 and C2 position of heterocycles, respectively. With readily accessible and free of unpleasant odor ethyl arylsulfinates as sulfur reagents, the metal-free-catalyzed direct sulfenylation of N-heteroarenes has been developed. 3-Arylthio-indoles and 2-arylthio-pyrroles derivatives were obtained in moderate to excellent yields, even on gram scale. The reaction was general for a broad scope of substrates and demonstrated good tolerance to a variety of functional groups.

Domino C?S/C?N Bond Formation Using Well-Defined Copper-Phosphine Complex Catalyst: Divergent Approach to 3-Sulfenylated Indoles

A protocol was developed for the synthesis of 3-thioindoles in good-to-excellent yields involving sulfenylation between 2-nitrocinnamaldehydes and various thiols using a well-defined copper(I)-phosphine complex catalyst. This unconventional divergent approach involves in situ generation of indoles via domino C?S/C?N bond formation initiated by sulfa-Michael addition followed by intramolecular N-heteroannulation. This protocol shows good chemoselectivity and broad substrate scope. To briefly demonstrate the value of this approach, 2-benzoyl-3-sulfenylated indoles were prepared from commercially available 2-nitrochalcones and thiols. (Figure presented.).

Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3

Herein, we report a greener protocol for the synthesis of 3-Se/S-indoles and imidazo[1,2-a]pyridines through direct C(sp2)?H bond chalcogenation of heteroarenes with half molar equivalents of different dichalcogenides, using KIO3 as a non-toxic, easy-to-handle catalyst and a stoichiometric amount of glycerol. The reaction features are high yields, based on atom economy, easy performance on gram-scale, metal- and solvent-free conditions as well as applicability to different types of N-heteroarenes.

Synergistic Cooperative Effect of Sodium borohydride-Iodine Towards Cascade C?N and C?S/Se Bond Formation: One-pot Regioselective Synthesis of 3-Sulfenyl/selenyl Indoles and Mechanistic Insight

In this work, a new strategy to synthesize 3-sulfenyl/selenyl indole is reported wherein LC?MS reveals a novel insight into synergistic cooperative effect of NaBH4-I2 which allows cascade C?N and C?S/C?Se bond formations via reduction-nucleophilic cyclization-chalcogenylation, three steps in one-pot, towards regioselective synthesis of diverse 3-chalcogenyl indoles including 5-bromo-3-[(3,4,5-trimethoxyphenyl)thio]-1H-indole, a known lead anticancer compound, directly from 2-amino-phenacylchlorides and thiophenols or disulfides/diselenides in aqueous dioxane under transition-metal-free condition. (Figure presented.).

Combined experimental/theoretical study on d-glucosamine promoted regioselective sulfenylation of indoles catalyzed by copper

A combined experimental/theoretical investigation on the d-glucosamine promoted sulfenylation of indoles at the C3 position with sodium sulfinates catalyzed by copper is presented. The C3-sulfenylation of indoles shows good functional-group tolerance and yields. The 3-I-indole was identified as a crucial intermediate in the catalytic cycle. The catalytic role of [Cu(DMSO)2]2+ was addressed using quantum chemical calculations. In the interaction of [Cu(DMSO)2]2+ with indole, the [Cu(DMSO)2]2+ complex abstracts a hydrogen from the C3 of indole. The electronic origin for selective C-H bond activation of indole was revealed.

Cooperative catalysis by bovine serum albumin-iodine towards cascade oxidative coupling-C(sp2)-H sulfenylation of indoles/hydroxyaryls with thiophenols on water

Cooperative cascade catalysis by bovine serum albumin (BSA)-iodine allows for the first time the performance of C(sp2)-H sulfenylation of indole from readily available thiophenol (-SH bond) via in situ generation/cleavage of disulfide (S-S bond

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.

Iodine-promoted selective 3-selanylation and 3-sulfenylation of indoles with dichalcogenides under mild conditions

A simple method was developed for the synthesis of 3-chalcogen indoles via iodine-promoted direct 3-selanyl- and 3-sulfenylation of indoles with dichalcogenides. The reaction was carried out smoothly in EtOH under air at room temperature, selectively givi

Iodine-catalyzed regioselective sulfenylation of indoles with sodium sulfinates

An iodine-catalyzed sulfenylation of free indoles with sodium sulfinates is described. The reaction selectively afforded 3-arylthioindoles in good to high yields in anisole under metal-free conditions. Functional groups such as halogens were well tolerated under the optimized reaction conditions.