1609583-49-4

Upstream product

• 108-98-5 thiophenol 
• 103844-28-6 2-(4-chlorophenyl)-6-methylimidazolo[1,2-a]pyridine 
• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 99-91-2 para-chloroacetophenone 
• 591-50-4 iodobenzene 
• 98-09-9 benzenesulfonyl chloride 
• 98-80-6 phenylboronic acid 
• 536-38-9 4-chlorobenzoylmethyl bromide 

Relevant academic research and scientific papers

Synthesis of imidazol[1,2-α]pyridine thioethers via using sulfur powder and halides as reactants

Structure containing the C[sbnd]S bond exist widely in nature, drugs and chemical materials. Here, a novel sulfenylation protocol employing an aryl or alkyl halide and odorless and cheap S as reagents was developed, generating regioselective alkyl-S- and Ar-S-substituted imidazol[1,2-α]pyridine derivatives in good yields under relatively environmentally friendly and mild conditions. This protocol enriches current thioether-producing methods, making up for the shortcomings of previous sulfenylation methods which can only make MeS- and ArS-substituted imidazol[1,2-α]pyridine derivatives.

Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles

We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.

One-pot synthesis of imidazo[1,2-α]pyridine thioethers using imidazo[1,2-α]pyridines, arylsulfonyl chlorides and hydrazine

A one-pot reaction of making RS-substituted imidazo[1,2-α]pyridine derivatives by directly using aryl or alkylsulfonyl chloride and hydrazine was developed, selectively giving good yields of the expected products. Compared with previously reported methods

One-Pot Three-Component Synthesis of Alkylthio-/Arylthio- Substituted Imidazo[1,2-a]pyridine Derivatives via C(sp2)–H Functionalization

Sulfenylation is an important transformation to generate C?S bonds in organic synthesis. Here, two three-component synthetic protocols have been developed by using imidazo[1,2-a]pyridine, inorganic, odorless S8 and alcohols or arylboronic acids

Cu-catalyzed sulfenylation of imidazol[1,2-: A] pyridine via C-H functionalization using a combination of Na2S2O3 and halides

A novel copper-catalysed sulfenylation method by using the inorganic salt Na2S2O3 and alkyl halides (Cl, Br, I) or iodobenzene homologues is described. The reactions proceeded smoothly, giving regioselective 2-phenylimidazo[1,2-a]pyridine thioether derivatives in good yields via a C-H functionalization process. More importantly, this method has extended the existing methods by offering a better method which can make both alkyl and aryl thioether derivatives under one set of reaction conditions.

N-chlorosuccinimide-promoted regioselective sulfenylation of imidazoheterocycles at room temperature

Regioselective sulfenylation of imidazoheterocycles with thiophenols at room temperature is reported. Sulfenylation is promoted by N-chlorosuccinimide under metal-free conditions with a broad range of substrate scopes.