7152-24-1Relevant articles and documents
Synthesis of novel amides with antiradical capacity from 2-mercaptobenzimidazole and cinnamic acids: Evaluation through donor-acceptor maps and QSAR
Benicio, Fernando Obledo,Gami?o, José Antonio Valcárcel,Hernández, Carlos Eduardo Macías,Martínez, Francisco J. Martínez,Martínez, María Teresa Sumaya,Ramos-Organillo, ángel,Rodríguez, Omar Alejandro Ramos,Sánchez, Juan Pablo Mojica,Sandoval, Zeferino Gómez
, (2020/08/03)
The structures of thioethers I-III and the new amidic compounds 1(a-f)-3(a-f) derived from 2-mercaptobenzimidazole (MBZ) and cinnamic acids were confirmed by NMR and elemental analysis. Antioxidant activity was evaluated by 1,1-diphenyl-2-picrylhydrazyl (DPPH●) radical scavenging assay and 2,2-azinobis (3-ethyl benzothiazoline-6-sulfonic acid) ABTS●+ radical cation decolorization method. Besides, donor-acceptor maps (DAM) and electrophilicity were calculated using DFT/B3LYP method with a 6-311G(d,p) basis set. MBZ, I-III and (1a-3a) compounds showed higher activity in vitro antioxidant assays, confirming with in silico studies that they are the best candidates. The findings found in antiradical activity suggest that these compounds could be promising in the development of new antitumor and antimicrobial agents. QSAR Molecular properties and topological descriptors of the synthesized compounds 1(a-f)-3(a-f) were calculated. The QSAR model indicates that the size and molecular shape are relevant for the antiradical activity for this family of compounds.
Metal-Free Aminomethylation of Aromatic Sulfones Promoted by Eosin Y
Thierry, Thibault,Pfund, Emmanuel,Lequeux, Thierry
supporting information, p. 14826 - 14830 (2021/10/01)
A metal-free α-aminomethylation of heteroaryls promoted by eosin Y under green light irradiation is reported. A large variety of α-trimethylsilylamines as precursor of α-aminomethyl radical species were engaged to functionalize sulfonyl-heteroaryls following a Homolytic Aromatic Substitution (HAS) pathway. This method has provided a range of α-aminoheteroaryl compounds including a functionalized natural product. The mechanism of this late-stage functionalization of aryls was investigated and suggests the formation of a sulfonyl radical intermediate over a reductive quenching cycle.
Design, synthesis, and antitumor activity of PLGA nanoparticles incorporating a discovered benzimidazole derivative as EZH2 inhibitor
Elkot, Hoda A.,Ragab, Ibrahim,Saleh, Noha M.,Amin, Mohamed N.,Al-Rashood, Sara T.,El-Messery, Shahenda M.,Hassan, Ghada S.
, (2021/05/31)
Purpose: Targeting enhancer of zeste homolog 2 (EZH2) can represent a hopeful strategy for oncotherapy. Also, the use of PLGA-based nanoparticles as a novel and rate-controlling carrier system was of our concern. Methods: Benzimidazole derivatives were synthesized, and their structures were clarified. In vitro antitumor activity was evaluated. Then, a modeling study was performed to investigate the ability of the most active compounds to recognize EZH2 active sites. Compound 30 (Drug) was selected to conduct pre-formulation studies and then it was incorporated into polymeric PLGA nanoparticles (NPs). NPs were then fully characterized to select an optimized formula (NP4) that subjected to further evaluation regarding antitumor activity and protein expression levels of EZH2 and EpCAM. Results: The results showed the antitumor activity of some synthesized derivatives. Docking outcomes demonstrated that Compound 30 was able to identify EZH2 active sites. NP4 exhibited promising findings and proved to keep the antitumor activity of Compound 30. HEPG-2 was the most sensitive for both Drug and NP4. Protein analysis indicated that Drug and NP4 had targeted EZH2 and the downstream signaling pathway leading to the decline of EpCAM expression. Conclusions: Targeting EZH2 by Compound 30 has potential use in the treatment of cancer especially hepatocellular carcinoma.
Methylenation for Aldehydes and Ketones Using 1-Methylbenzimidazol-2-yl Methyl Sulfone
Ando, Kaori,Oguchi, Mai,Kobayashi, Takahisa,Asano, Haruka,Uchida, Nariaki
, p. 9936 - 9943 (2020/09/04)
The methylenation reagent 1-methylbenzimidazol-2-yl methyl sulfone 2 reacts with various aldehydes and ketones in the presence of t-BuOK (room temperature, 1 h) in dimethylformamide to give the corresponding terminal alkenes generally in high yields. For sensitive substrates, the reaction is better carried out at low temperature using sodium hexamethyldisilazide in 1,2-dimethoxyethane. The byproduct is easily removed from the products, and the reaction conditions are mild and practical. Reagent 2 can be easily prepared from commercially available 2-mercaptobenzimidazole 5 in 95% yield without any expensive reagents.
Synthesis and antidiabetic evaluation of benzimidazole-tethered 1,2,3-triazoles
Deswal, Laxmi,Verma, Vikas,Kumar, Devinder,Kaushik, Chander?P.,Kumar, Ashwani,Deswal, Yogesh,Punia, Suman
, (2020/07/04)
Some novel benzimidazole-tethered 1,2,3-triazole derivatives (4a–r) were synthesized by a click reaction between 2-substituted 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazole and in situ azide. The structures of the synthesized compounds were confirmed by spectroscopic studies (one- and two-dimensional nuclear magnetic resonance, Fourier transform infrared, and high-resolution mass spectra). The synthesized compounds were evaluated for their antidiabetic activity. Compounds 4a–r exhibited a good-to-moderate α-amylase and α-glucosidase inhibitory activity, with IC50 values ranging from 0.0410 to 0.0916 μmol/ml and 0.0146 to 0.0732 μmol/ml, respectively. Compounds 4e, 4g, and 4n were found to be most active. Furthermore, the binding conformation of the most active compounds was ascertained by docking studies.
S-Benzimidazolyl (SBiz) Imidates as a Platform for Oligosaccharide Synthesis via Active-Latent, Armed-Disarmed, Selective, and Orthogonal Activations
Hasty, Scott J.,Bandara, Mithila D.,Rath, Nigam P.,Demchenko, Alexei V.
, p. 1904 - 1911 (2017/03/01)
This article describes the development of S-benzimidazolyl (SBiz) imidates as versatile building blocks for oligosaccharide synthesis. The SBiz imidates have been originally developed as a new platform for active-latent glycosylations. This article expands upon the utility of these compounds. The application to practically all common concepts for the expeditious oligosaccharide synthesis including selective, chemoselective, and orthogonal strategies is demonstrated. The strategy development was made possible thanks to our enhanced understanding of the reaction mechanism and the modes by which SBiz imidates interact with various promoters of glycosylation.
An environmentally benign and selective electrochemical oxidation of sulfides and thiols in a continuous-flow microreactor
Laudadio, Gabriele,Straathof, Natan J. W.,Lanting, Menno D.,Knoops, Benny,Hessel, Volker,No?l, Timothy
supporting information, p. 4061 - 4066 (2017/09/07)
A practical and environmentally benign electrochemical oxidation of thioethers and thiols in a commercially-available continuous-flow microreactor is presented. Water is used as the source of oxygen to enable the oxidation process. The oxidation reaction utilizes the same reagents in all scenarios and the selectivity is solely governed by the applied potential. The procedure exhibits a broad scope and good functional group compatibility providing access to various sulfoxides (15 examples), sulfones (15 examples) and disulfides (6 examples). The use of continuous flow allows the optimal reaction parameters (e.g. residence time, applied voltage) to be rapidly assessed, to avoid mass- and heat-transfer limitations and to scale the electrochemistry.
Highly efficient tandem syntheses of unsymmetrically substituted isomeric S,N-disubstituted-2-mercaptobenzimidazoles
Rao, S. Srinivas,Reddy, Ch Venkata Ramana,Dubey
, p. 829 - 832 (2015/06/30)
Highly efficient tandem syntheses of unsymmetrically substituted isomeric S,N-disubstituted-2-mercaptobenzimidazoles have been developed. The structures of 6a-d and isomeric compounds 9a-d have been synthesized from 2-mercaptobenzimidazole using tandem synthesis. The structures of 6a-d and isomeric compounds 9a-d have been established by spectral and analytical data, and by unambiguous syntheses.
Cyanuric chloride as promoter for the oxidation of sulfides and deoxygenation of sulfoxides
Bahrami, Kiumars,Khodaei, Mohammad M.,Sohrabnezhad, Samira
experimental part, p. 6420 - 6423 (2011/12/21)
This Letter discusses the use of cyanuric chloride as an efficient promoter for the chemoselective oxidation of sulfides to the corresponding sulfones in the presence of H2O2 as the terminal oxidant. Sulfoxides were also found to undergo deoxygenation to sulfides with cyanuric chloride and potassium iodide system. The reaction is broad in scope and easy to perform.
Ionic liquids - Promoted S-methylation of thiols utilizing dimethyl carbonate
Xie, Jiangang,Wu, Chengyao,Christopher, Branford White,Quan, Jing,Zhu, Limin
experimental part, p. 31 - 37 (2011/04/22)
Convenient and efficient S-methylation of mercaptans or thiophenols occurs with dimethyl carbonate (DMC) in room temperature ionic liquids (RTILs) [Bmim]Cl. [Bmim]Cl can be recycled in four subsequent runs with only a gradual decrease in activity. A possible mechanism of this transformation is also discussed. Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
