3176-70-3

Usage

Uses

Used in Organic Synthesis:
1H-Benzimidazole-2-methanethiol, alpha-methyl-(9CI) is used as a building block in organic synthesis for the creation of various organic compounds. Its unique structure and properties allow for the development of new molecules with potential applications in various fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 1H-Benzimidazole-2-methanethiol, alpha-methyl-(9CI) is utilized in drug development. Its specific properties and reactivity make it a promising candidate for the synthesis of new drugs with potential therapeutic effects.
Used as a Reagent in Chemical Reactions:
1H-Benzimidazole-2-methanethiol, alpha-methyl-(9CI) also serves as a reagent in various chemical reactions. Its presence can facilitate or enhance the reaction process, leading to the formation of desired products with improved efficiency and selectivity.

InChI:InChI=1/C9H10N2S/c1-6(12)9-10-7-4-2-3-5-8(7)11-9/h2-6,12H,1H3,(H,10,11)

Upstream product

• 17617-05-9 pyridin-3-yl-methanethiol 
• 79-42-5 2-mercaptopropanoic acid 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 19275-82-2 2-(1-chloroethyl)-1H-benzo[d]imidazole 
• 95-54-5 1,2-diamino-benzene 

Downstream Products

• 74460-36-9 4-[1-(1H-Benzoimidazol-2-yl)-ethylsulfanyl]-4-phenyl-butan-2-one 
• 74460-47-2 2-(1H-Benzoimidazol-2-yl)-2,3-dimethyl-5-phenyl-tetrahydro-thiophen-3-ol 

Relevant academic research and scientific papers

The design and synthesis of potent benzimidazole derivatives via scaffold hybridization and evaluating their antiproliferative and proapoptotic activity against breast and lung cancer cell lines

One of the current approaches used in drug discovery and development is the synthesis of novel small compounds from existing structural motifs via molecular hybridization. In the current study, a new series of benzimidazo[1,5-a]imidazole, benzimidazo[1,2-c]thiazole, benzimidazotriazine, and benzimidazo[1,2-c]quinazoline scaffolds was synthesized via C-H cycloamination, using a metal-free synthetic pathway, as potent antiproliferative antiangiogenic molecules against breast (MCF-7) and lung (A549) cancer cell lines. The expansion of the benzimidazole scaffold with heterocyclic rings resulted in a tridentate cyclic system that occupied the ATP-binding site and neighboring hydrophobic pocket, eliciting promising affinity and selectivity toward VEGFR2 through extra H-bonding and completely occupying the entrance region. Molecular docking studies demonstrated that most of the designed compounds bind VEGFR-2 adopting a DFG-in conformation, where the benzimidazole scaffold occupied the hinge region, the central aromatic ring occupied hydrophobic region I adjacent to the hinge region, and the hydrogen bond donor/acceptor bound to the hydrogen-bond-rich region. In comparison to lenvatinib, which had a docking score of-12.47 kJ mol-1 and a Glide E-model value of-132.68 kcal mol-1, compound 17 had a decent docking score of-8.95 kJ mol-1 and a Glide E-model value of-92.17 kcal mol-1. The designed molecules exhibited promising in situ cytotoxic activities, with IC50 values ranging from 9.2 to 42.3 μM against MCF-7 and A549, comparable to 5-fluorouracil (which has IC50 values of 10.32 and 5.8 μM against MCF-7 and A549, respectively); they also showed selective in vitro inhibitory activity against VEGFR2 when compared with other designed kinases, with compound 17 showing an IC50 value (23 nM) as good as that of sorafenib (30 nM). Flow cytometry and cell cycle assays revealed that apoptotic cell death induction occurred in the A549 cell line through the activation of certain caspases and the tumor suppressor P53 and through repressing the generation of BAX and PUMA. Furthermore, the proposed compounds exhibited physicochemical and pharmacokinetics properties within the acceptable range for human usage, as anticipated by an in silico ADME study, making them lead molecules for developing new forms of medication.

Studies on synthesis of unsymmetrical 2,2′-bisbenzimidazole sulphides of pharmacological interest

Condensation of 2-(α-chloroethyl)benzimidazole 1 with benzimidazole-2-thiol 2 gives 2-(α-thioethyl-2′-benzimidazolyl)- benzimidazole 3. The latter can also be prepared by the reaction of 2-(α-thioethyl)benzimidazoie 4 with 2-chlorobenzimidazole 5. Alternatively, 3 can also be synthesized by the independent condensation of o-phenylenediamine 7 respectively with 2-(s-α-ethyl-o-ethyldithio- carbonate)benzimidazole 6 and with 2-(α-thiopropionic acid) benzimidazole 8. The structures of all the compounds synthesized have been established on the basis of their spectroscopic data.

Synthesis and structural features of new cyclofunctionalized benzimidazoles

The synthesis of new tricyclic derivatives having sulfur-containing six or seven-membered rings fused to the > edge of benzimidazole system, is reported. The stereochemical characteristics of thiazino- and thiazepinobenzimidazoles (4-7) are described

ACTIVITE ESTEROLYTIQUE DE COMPOSES ASSOCIANT UNE FONCTION THIOL ET UNE BASE HETEROCYCLIQUE. EXEMPLES DE PROCESSUS BIFONCTIONNEL

The synthesis of 19 compounds associating a thiol function and a basic heterocycle (i.e. benzimidazole, pyridine, thiazole) is described.Their esterolytic activity towards para nitrophenyl acetate (PNPA) is compared with that of simple monofunctional thiols.The influence of the substituents and of the nature of the basic heterocycle shows that the apparition of a cooperative effect depends both on the relative pKa values (thiol and heterocyclic) and on the possibility of proton exchange via the heterocyclic moiety.Examples of bifonctional process are reported in the case of benzimidazolylmethanethiol compounds, due to a basic assistancce on the neutral form of the thiol function.