174422-14-1Relevant articles and documents
Fast and efficient method for the synthesis of 2-arylbenzimidazoles using MCM-41-SO3H
Mahdavinia, Gholam Hossein,Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Sepehrian, Hamid
experimental part, p. 33 - 37 (2012/07/28)
Nanosized MCM-41-SO3H material based on ordered mesoporous silica gel with covalently attached sulfonic acid groups was synthesized and used as acid catalyst for green synthesis of 2-substituted benzimidazole derivatives. Echofriendly protocol, short reaction times, easy and quick isolation of the products, and excellent yields are the main advantages of this procedure. Copyright by Walter de Gruyter.
Novel clarithromycin analogs with C-4′′ 2-arylbenzimidazolyl bishydrazide side chain: Synthesis and antibacterial evaluation
Qi, Yunkun,Ma, Ruixin,Li, Xin,Hu, Yue,Ma, Siti,Cong, Chao,Ma, Xiaodong,Cui, Wenping,Ma, Shutao
experimental part, p. 966 - 971 (2012/07/01)
A series of novel 4′′-O-2-arylbenzimidazolyl derivatives of clarithromycin were synthesized and evaluated. These 4′′-O-2- arylbenzimidazolyl derivatives demonstrated excellent activity against erythromycin-susceptible strains and showed remarkably improved activity against erythromycin-resistant strains compared with the references. In particular, compound 7c, which possesses the terminal 2-(2-methoxyphenyl)benzimidazolyl group on the C-4′′ bishydrazide side chain, not only presented the most potent activity against erythromycin-susceptible Streptococcus pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923, exhibiting 4-fold and 4-fold higher efficacy than the parent clarithromycin, but also displayed the highest activity against erythromycin-resistant Streptococcus pneumoniae expressing the mef gene and the erm gene, which was 133-fold and 32-fold better than clarithromycin or azithromycin, respectively.
Microwave-assisted multi-component reaction in water leading to highly regioselective formation of benzo[f]azulen-1-ones
Wang, Shu-Liang,Cheng, Chuang,Wu, Fei-Yue,Jiang, Bo,Shi, Feng,Tu, Shu-Jiang,Rajale, Trideep,Li, Guigen
scheme or table, p. 4485 - 4493 (2011/07/08)
Microwave-assisted three-component reaction has been established for the regioselective synthesis of benzo[f]azulen-1-ones. The reaction was performed in aqueous media under microwave irradiation by using readily available and inexpensive starting materials. A total of 38 examples were examined to show a broad substrate scope and good overall yields (70-89%). The present new synthesis shows attractive green chemistry characteristics, such as the use of water as reaction media, concise one-pot conditions, short reaction periods (7-24 min), easy work-up/purification, and reduced waste production without the use of any strong acids or metal promoters.
Aqueous 1M glucose solution as a novel and fully green reaction medium and catalyst for the oxidant-free synthesis of 2-arylbenzimidazoles
Rostamizadeh, Shahnaz,Aryan, Reza,Ghaieni, Hamid Reza
experimental part, p. 1794 - 1804 (2011/06/24)
The reaction of various o-phenylenediamines and substituted benzaldehydes was carried out in 1M glucose solution as reaction medium and catalyst under one-pot oxidantfree conditions. The desired products were obtained at 60 °C with good to excellent yields, and the reaction was performed chemoselectively without formation of 1,2-disubstituted benzimidazoles. No need for any extra oxidant, simple workup, and use of carbohydrates as fully green promoters are some advantages of the present work.
Synthesis and antibacterial activity of novel 4″-O-benzimidazolyl clarithromycin derivatives
Cong, Chao,Wang, Haiyang,Hu, Yue,Liu, Chen,Ma, Siti,Li, Xin,Cao, Jichao,Ma, Shutao
supporting information; experimental part, p. 3105 - 3111 (2011/07/08)
Novel 4″-O-benzimidazolyl clarithromycin derivatives were designed, synthesized and evaluated for their in vitro antibacterial activities. These benzimidazolyl derivatives exhibited excellent activity against erythromycin-susceptible strains better than the references, and some of them showed greatly improved activity against erythromycin-resistant strains. Compounds 16 and 17, which have the terminal 2-(4-methylphenyl)benzimidazolyl and 2-(2-methoxyphenyl)benzimidazolyl groups on the C-4″ bishydrazide side chains, were the most active against erythromycin-resistant Staphylococcus pneumoniae expressing the erm gene and the mef gene. In addition, compound 17 exhibited the highest activity against erythromycin-susceptible S. pneumoniae ATCC49619 and Staphylococcus aureus ATCC25923 as well. It is worth noting that the 4″-O-(2-aryl)benzimidazolyl derivatives show higher activity against erythromycin-susceptible and erythromycin-resistant strains than the 4″-O-(2-alkyl)benzimidazolyl derivatives.
Solvent-free chemoselective synthesis of some novel substituted 2-arylbenzimidazoles using amino acid-based prolinium nitrate ionic liquid as catalyst
Rostamizadeh, Shahnaz,Aryan, Reza,Ghaieni, Hamid Reza,Amani, Ali Mohammad
scheme or table, p. 74 - 78 (2009/05/07)
A simple and eco-friendly protocol for the synthesis of substituted 2-arylbenzimidazoles is described. In this process, 2-arylbenzimidazoles were prepared in the presence of a newly introduced ionic liquid prolinium nitrate [Pro]NO3 as catalyst, under solvent-free condition. This process was performed under mild condition without using any oxidant with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct. The ionic liquid can be recovered easily and reused.
Very fast and efficient synthesis of some novel substituted 2-arylbenzimidazoles in water using ZrOCl2?nH2O on montmorillonite K10 as catalyst
Rostamizadeh, Shahnaz,Amani, Ali Mohammad,Aryan, Reza,Ghaieni, Hamid Reza,Norouzi, Leila
experimental part, p. 547 - 552 (2010/06/16)
A simple and eco-friendly protocol for the synthesis of some novel substituted 2-arylbenzimidazoles was developed. In this process, these compounds were prepared in water as the solvent using ZrOCl2?nH 2O supported on montmorillonite K10 as an efficient water tolerating Lewis acid. The reaction was performed under mild conditions with good to excellent yields and remarkable chemoselectivity in the absence of any byproduct.
SYNTHESIS OF 1,2-DISUBSTITUTED BENZIMIDAZOLE-5(6)-CARBOXAMIDES AND EVALUATION OF THEIR ANTIMICROBIAL ACTIVITY
Goeker, Hakan,Tebrizli, Emin,Abbasoglu, Ufuk
, p. 53 - 58 (2007/10/03)
A series of 14,N'-(N,N-dialkylaminoethyl)-benzimidazole-5(6) or 5-carboxamides (1-14), having several substituents on the azole and benzene nuclei, were prepared and evalueted in vitro for antimicrobial activity.The precursor bezimidazolecarboxylic acids (15-27) were prepared via oxidative condensation of diaminobenzoic acids and several aldehydes with cupric ion.Compounds 11-14 were prepared by selective regioisomer synthesis.All carboxamides were prepared from the corresponding acids and N,N-dialkylethylenediamine.Antibacterial and antifungal activities were determined as MICs values.Of the synthesized compounds 1-10, 6 and 10 were found to be most favourable.In order to clarify the effect of the substituents at N1 on antimicrobial activity, 12 was prepared by p-chlorobenzyl substitution of compound 6, and increased activity was shown.Compounds 13 and 14, which were prepared by replacement with more bulky alkyl groups on the tert-N atom than 12, gave the best results.
