21547-79-5

Upstream product

• 70-11-1 α-bromoacetophenone 
• 134469-07-1 Benzimidazol-2-thiol 
• 98-86-2 acetophenone 
• 174621-79-5 3-aminothiazolo[3,2-a]benzimidazole-2-carbonitrile 
• 95-54-5 1,2-diamino-benzene 
• 42574-08-3 O-Isopropyl-S-phenacyldithiocarbonat 
• 583-39-1 2,3-dihydrobenzimidazol-2-thione 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 

Downstream Products

• 1202709-16-7 3-(1H-benzimidazol-2-ylthio)-2-phenylquinoline-4-carboxylic acid 
• 1241899-71-7 2-(1H-benzo[d]imidazol-2-ylsulfonyl)-1-phenylethanone 
• 1339905-59-7 C₁₆H₁₆N₂O₃S 
• 176103-68-7 2-(1-methylbenzimidazol-2-ylsulfanyl)-1-phenylethanone 

Relevant academic research and scientific papers

A facile one pot synthesis of thiazolo[3,2-: A] benzimidazole and pyran fused polyheterocyclic scaffolds

An efficient synthesis of dihydro-4H-benzo[4,5]imidazo[2,1-b]pyrano[2,3-d]thiazole by a multicomponent route starting from 2-((1H-benzo[d]imidazol-2-yl)thio)-1-phenylethan-1-one, an aromatic aldehyde and malononitrile is described. This protocol features

Solvation models in the reaction between phenacyl bromide and 2-mercaptobenzimidazole

The reaction between phenacyl bromide and 2-mercaptobenzimidazole has been studied in 12 different protic and aprotic solvents. The kinetic study shows that the reaction is second-order with first-order dependence each on (phenacyl bromide) and (2-mercapt

Zinc oxide catalyzed solvent-free mechanochemical route for C-S bond construction: A sustainable process

A zinc oxide catalyzed solvent-free mechanochemical process has been developed for the rapid construction of C-S bonds by using a nucleophilic substitution reaction (SN2 mechanism) that involves a variety of thiols and phenacyl/ benzyl/alkyl bromides. Notable advantages of this method in-clude its broad substrate scope, clean reaction profile, safety, scalability, high product yields at ambient conditions, and the recyclability of the catalyst. Furthermore, the prepared compounds are valuable building blocks for the synthesis of various biologically active molecules.

A convenient route to benzimidazole fused chiral heterocyclic bases

An efficient synthetic protocol has been developed to obtain new chiral heterocyclic bases pyrrolo-benzimidazoles (DHP-Bz) and thiazolo-benzimidazoles (DHT-Bz). Notable characteristic of both series of the fused heterocycle is the presence of a chiral cen

Synthesis, crystal study, and anti-proliferative activity of some 2-benzimidazolylthioacetophenones towards triple-negative breast cancer MDA-MB-468 cells as apoptosis-inducing agents

On account of its poor prognosis and deficiency of therapeutic stratifications, triple negative breast cancer continues to form the causative platform of an incommensurate number of breast cancer deaths. Aiming at the development of potent anticancer agents as a continuum of our previous efforts, a novel series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a–w was synthesized and evaluated for its anti-proliferative activity towards triple negative breast cancer (TNBC) MDA-MB-468 cells. Compound 5k was the most active analog against MDA-MB-468 (IC50 = 19.90 ± 1.37 μM), with 2.1-fold increased activity compared to 5-fluorouracil (IC50 = 41.26 ± 3.77 μM). Compound 5k was able to induce apoptosis in MDA-MB-468, as evidenced by the marked boosting in the percentage of florecsein isothiocyanate annexin V (Annexin V–FITC)-positive apoptotic cells (upper right (UR) + lower right (LR)) by 2.8-fold in comparison to control accompanied by significant increase in the proportion of cells at pre-G1 (the first gap phase) by 8.13-fold in the cell-cycle analysis. Moreover, a quantitative structure activity relationship (QSAR) model was established to investigate the structural requirements orchestrating the anti-proliferative activity. Finally, we established a theoretical kinetic study.

Synthesis of N-alkylated-2-(1,3-diphenyl-1H-pyrazol-4-ylsulfanyl)-1H-benzimidazoles by Vilsmeir-Haack reaction and by condensation with DMF-DMA

2-(1H-Benzimidazol-2-ylsulfanyl)-1-phenylethanone 3 on condensation with phenyl hydrazine under acidic conditions gives the corresponding hydrazone derivative which when subjected to Vilsmeir Hack formylation followed by alkylation under phase transfer ca

2-((Benzimidazol-2-yl)thio)-1-arylethan-1-ones: Synthesis, crystal study and cancer stem cells CD133 targeting potential

In order to develop a potent anti-tumor agent that can target both cancer stem cells and the bulk of tumor cells, a series of 2-((benzimidazol-2-yl)thio)-1-arylethan-1-ones 5a-o was synthesized. All compounds were evaluated for their anti-proliferative activity towards colon HT-29 cancer cell line. In addition, their inhibitory effect against cell surface expression of CD133, a potent cancer stem cells (CSCs) marker, in the same cells was evaluated by flow cytometry at 10 μM. Compound 5l emerged as the most active anti-proliferative analog against HT-29 (IC50 Combining double low line 18.83 ± 1.37 μM), that almost equipotent as 5-fluorouracil (IC50 Combining double low line 15.83 ± 1.63 μM) with 50.11 ± 4.05% inhibition effect on CD133 expression, suggested dual targeted effect. Also, compounds 5h, 5j, 5k and 5m-o inhibited the expression of CD133 with more than 50%. The SAR study pointed out the significance of substitution of the pendent phenyl group with lipophilic electron-donating groups or replacing it by 2-thienyl or 2-furyl groups.

Synthesis and regiospecific methylation of new benzimidazolyl β-ketosulfones and β-hydroxysulfones

Condensation of 2-mercaptobenzimidazoles la-e with a-bromoacetylbenzene 2 resulting in benzimidazolyl P-ketosulfides 3a-e followed by oxidation with hydrogen peroxide giving β-ketosulfones 7a-e and subsequent reduction with sodium borohydride yielding β-h

The Eschenmoser coupling reaction under continuous-flow conditions

The Eschenmoser coupling is a useful carbon-carbon bond forming reaction which has been used in various different synthesis strategies. The reaction proceeds smoothly if S-alkylated ternary thioamides or thiolactames are used. In the case of S-alkylated s

Synthesis of difluorinated β-ketosulfones and novel gem-difluoromethylsulfone-containing heterocycles as fluorinated building blocks

A series of new heterocyclic β-ketosulfides was prepared by the reaction of the corresponding heterocyclic thiols with α-bromoacetophenone and its derivatives. Oxidation of the products using m-CPBA gave the corresponding heterocyclic β-ketosulfones, whic