51290-77-8Relevant articles and documents
Facile synthesis and antimicrobial properties of 2-(substituted- benzylsulfanyl)-1H-benzimidazoles
Kumar, Ramanatham Vinod,Gopal, Kotarkonda Raja,Seshu Kumar, Kotha V. S. R.
, p. 1405 - 1408 (2005)
A simple and convenient procedure for the preparation of 2-benzylthiobenzimidazoles by the reaction of 2-mercaptobenzimidazole and benzyl bromides in acetone/potassium carbonate condition has been reported and the compounds were screened for their potenti
Benzimidazole derivatives as novel inhibitors for the corrosion of mild steel in acidic solution: Experimental and theoretical studies
Zhang,Hou,Hou,Liu
, p. 413 - 427 (2019)
The inhibition effects of three kinds of benzimidazole derivatives (2-mercaptobenzimidazole (MBI), 2-thiobenzylbenzimidazole (TBBI) and 1-butyl-2-thiobenzylbenzimidazole (BTBBI)) on the corrosion of mild steel in 1 M HCl solution were studied by weight loss and electrochemical measurements, and theoretical calculations. It is found that these compounds act as mixed type inhibitors with predominant cathodic effectiveness and exhibit high inhibition efficiencies with the order: BTBBI > TBBI > MBI. Molecular dynamics simulations reveal that these benzimidazole derivatives adsorb on Fe (1 1 0) surface in flat orientation. The theoretical calculations are in good accordance with the weight loss and electrochemical measurements.
Transition-metal-free synthesis of imidazobenzothiazines via domino C-S/C-N bond formation
Tu, Xingzhao,Zhou, Lihong,Li, Zhijie,Lei, Ning,Zeng, Qingle
, p. 1925 - 1931 (2014)
The carbon-heteroatom bond formation is an important research field. Transition-metal-free synthesis of medicinally important heterocycles avoids products of transition metal contamination, and thus it is an environmentally friendly and cost-saving proces
Expression, Purification, and Comparative Inhibition of Helicobacter pylori Urease by Regio‐Selectively Alkylated Benzimidazole 2‐Thione Derivatives
Amer, Mohamed R.,Eissa, Ibrahim H.,El Ashry, El Sayed H.,Elkaeed, Eslam B.,Elshobaky, Ahmed,Hafez, Elsayed E.,Khalid, Asaad,Metwaly, Ahmed M.,Mohammed, Salih Osman
, (2022/01/31)
The urease enzyme has been an important target for the discovery of effective pharmacological and agricultural products. Thirteen regio‐selectively alkylated benzimidazole‐2‐thione derivatives have been designed to carry the essential features of urease i
Design, synthesis, and evaluation of different scaffold derivatives against NS2B-NS3 protease of dengue virus
Ganji, Lata R.,Gandhi, Lekha,Musturi, Venkataramana,Kanyalkar, Meena A.
, p. 285 - 301 (2020/11/19)
The number of deaths or critical health issues is a threat in the infection caused by Dengue virus, which complicates the situation, as only symptomatic treatment is the current solution. In this regard we have targeted the dengue protease NS2B-NS3 that is responsible for the replication. The series was designed with the help of molecular modeling approach using docking protocols. The series comprised of different scaffolds viz. cinnamic acid analogs (CA1–CA11), chalcone (C1–C10) and their molecular hybrids (Lik1–Lik10), analogs of benzimidazole (BZ1-BZ5), mercaptobenzimidazole (BS1-BS4), and phenylsulfanylmethylbenzimidazole (PS1-PS4). Virtual screening of various natural phytoconstituents was employed to determine the interactions of designed analogs with the residues of catalytic triad in the active site of NS2B-NS3. We have further synthesized the selected leads. The synthesized analogs were evaluated for the cytotoxicity and NS2B-NS3 protease inhibition activity and compared with known anti-dengue natural phytoconstituent quercetin as the standard. CA2, BZ1, and BS2 were found to be more potent and efficacious than the standard quercetin as evident from the protease inhibition assay.
Tandem Double-Cross-Coupling/Hydrothiolation Reaction of 2-Sulfenyl Benzimidazoles with Boronic Acids
Lopes, Alexandra Basilio,Choury, Mickael,Wagner, Patrick,Gulea, Mihaela
supporting information, p. 5943 - 5947 (2019/08/26)
A new tandem palladium-catalyzed reaction involving a Suzuki-Miyaura coupling, a desulfenylative coupling, and a hydrothiolation of a triple bond is reported. Notably, the desulfenylative coupling occurs without copper(I) assistance and the hydrothiolatio
New Strategy of the Synthesis of 3,4-Dihydropyrimido[1,2-a]benzimidazol-2(1H)-ones
Kharaneko
, p. 1363 - 1368 (2018/11/21)
A new procedure has been developed for preparative synthesis of 3,4-dihydropyrimido[1,2-a]-benzimidazol-2(1H)-ones by thermal intramolecular heterocyclization of 3-[2-(propylsulfanyl)- and 2-(benzylsulfanyl)-1H-benzimidazol-1-yl]propanehydrazides and 3-[2-(benzylsulfanyl)-1H-benzimidazol-1-yl]-propanamide.
One-Pot Synthesis of 2-Benzyl/2-Allyl-Substituted Thiobenzoazoles Using Transition-Metal-Free Conditions in Water
Zhang, Shi-Bo,Liu, Xing,Gao, Ming-Yuan,Dong, Zhi-Bing
, p. 14933 - 14941 (2019/01/04)
A transition-metal-free protocol for the one-pot synthesis of 2-benzyl/2-allyl-substituted thiobenzoazoles in water was developed. The cyclization of 2-aminothiophenols, 2-aminophenols, and 1,2-phenylenediamines with tetramethylthiuram disulfide (TMTD) gave mercapto benzoheterocycles, and the subsequent C-S coupling with benzyl or allyl halides furnished the desired products in good to excellent yields. This method features transition-metal-free conditions with water as a solvent, an easy performance, mild reaction conditions, a wide substrate scope, and good to excellent yields, thus paving an efficient and useful way to establish a library of potentially active drug molecules.
Zinc oxide catalyzed solvent-free mechanochemical route for C-S bond construction: A sustainable process
Md. Khaja Mohinuddin,Gangi Reddy
, p. 1207 - 1214 (2017/12/07)
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.
Synthesis of 2-Alkoxy/Thioalkoxy Benzo[d]imidazoles and 2-Thione Benzo[d]imidazoles via a Phase-Based, Chemoselective Reaction
Yoon, Hyo-Jeong,Yang, Seung-Ju,Gong, Young-Dae
, p. 738 - 747 (2017/12/18)
2-Alkoxy/thioalkoxy benzo-[d]-imidazole and 2-thione benzo-[d]-imidazole libraries were constructed in solution phase and on solid phase, respectively. The key step in this work is the phase-based chemoselective reaction of the 2-mercaptobenzo-[d]-imidazole intermediate with benzyl chloride (solution phase) and Merrifield resin (solid phase). In the solution-phase case, benzyl chloride reacted with the thiol group of 2-mercaptobenzo-[d]-imidazole, whereas in the solid-phase case, Merrifield resin was introduced at an internal amine group of benzo-[d]-imidazole. To afford the desired 2-alkoxy/thioalkoxy benzo-[d]-imidazole analogues, we used various alkyl halides, alcohols, and thiols in solution phase, and to obtain 2-thione benzo-[d]-imidazole derivatives on solid phase, we used diverse alkyl halides and boronic acids. Finally, to measure the drug potential to be orally active and the molecular diversity in three-dimensional (3D) space, we calculated physicochemical properties and displayed energy-minimized 3D structures. As a result, the libraries from solution phase and solid phase show distinct features in physicochemical properties and skeletal diversities in 3D space.
