1609583-55-2Relevant academic research and scientific papers
Metal-free direct regioselective thiolation of imidazoheterocycles in water at room temperature
Kong, Dulin,Wang, Qinghe,Huang, Tiao,Liang, Min,Lin, Qiang,Wu, Mingshu
, p. 1457 - 1463 (2019)
A metal-free direct thiolation of imidazoheterocycles with various thiophenol in water at room temperature has been developed. In addition, the chemistry provides several advantages including mild condition, high yields, good functional group tolerance, g
Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles
Chitrakar, Ravi,Rawat, Deepa,Sistla, Ramakrishna,Subbarayappa, Adimurthy,Vadithe, Lakshma Nayak
, (2021/08/13)
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.
Direct, Metal-free C(sp2)?H Chalcogenation of Indoles and Imidazopyridines with Dichalcogenides Catalysed by KIO3
Rafique, Jamal,Saba, Sumbal,Franco, Marcelo S.,Bettanin, Luana,Schneider, Alex R.,Silva, Lais T.,Braga, Antonio L.
supporting information, p. 4173 - 4180 (2018/02/06)
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.
C3 Sulfenylation of N-Heteroarenes in Water under Catalyst-Free Conditions
Ravi, Chitrakar,Joshi, Abhisek,Adimurthy, Subbarayappa
supporting information, p. 3646 - 3651 (2017/07/22)
A method for the catalyst-free C–H sulfenylation of imidazo[1,2-a]pyridines by using sulfonothioates as an odorless thioarylated reagent in aqueous medium was developed. This protocol was used for a variety of substituted imidazo[1,2-a]pyridines with broad functional-group tolerance and was extended to the sulfenylation of indoles and imidazothiazoles. The sulfonothioates were activated exclusively in aqueous medium rather than in an organic solvent, and the feasibility of the process for scale-up studies was demonstrated.
Iodine-triphenylphosphine mediated sulfenylation of imidazoheterocycles with sodium sulfinates
Huang, Xuhu,Wang, Shucheng,Li, Bowen,Wang, Xin,Ge, Zemei,Li, Runtao
, p. 22654 - 22657 (2015/03/14)
An efficient approach to sulfenyl imidazoheterocycles has been developed via iodine-triphenylphosphine mediated direct sulfenylation of imidazoheterocycles with sodium sulfinates. The reactions proceed smoothly under transition-metal-free conditions with a broad range of substrate scope, giving the desired products in moderate to excellent yields. This journal is
N-chlorosuccinimide-promoted regioselective sulfenylation of imidazoheterocycles at room temperature
Ravi, Chitrakar,Chandra Mohan, Darapaneni,Adimurthy, Subbarayappa
supporting information, p. 2978 - 2981 (2014/06/23)
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.
