15728-46-8Relevant academic research and scientific papers
Synthesis, characterization, antitumor, antibacterial and urease inhibitory activity of a small series of N-tosyl benzimidazoles
Rashid, Naghmana,Kiran, Almas,Ashraf, Zaman,Bhatti, Moazzam Hussain,Mirza, Bushra,Ismail, Hammad,Rafiq, Muhammad,Jasinski, Jerry P.
, p. 366 - 374 (2018/06/06)
Benzimidazole derivatives exhibited a broad range of biological activities, e.g., antimicrobial, antiviral, anthelmintic, anti-inflammatory, anticancer and as an anti-ulcer/proton pump inhibitor. Keeping in view the large number of reported drugs containing benzimidazole moiety on one hand and sulfonamide on the other hand, a small series of N-tosyl benzimidazoles (4a-e) have been synthesized. The present work describes the synthesis, characterization and bio-evaluation of five new N-tosyl benzimidazoles with the objective to develop new compounds with improved anticancer, antibacterial and urease inhibitory activities. The substituted 1,2-phenylenediamines in the first step were condensed with aliphatic carboxylic acids to synthesize the substituted benzimidazoles. In the second step the tosyl chloride was reacted with substituted benzimidazoles in basic conditions to afford the title N-tosyl benzimidazoles (4a-e). The screening for their antitumor activities was performed against Agrobacterium tumefaciens by following the potato disc tumor assay. The compound (4e) exhibited excellent antitumor activity with IC50 values 474.45μgml-1 compared to other synthesized compounds. Antibacterial activity results revealed that compounds 4d and 4e having methyl and ethyl substitution respectively at the imidazole ring showed excellent zone inhibition against both gram positive and gram negative strains. The urease inhibitory activity results showed that derivative 4e exhibited highest potential to inhibit the urease enzyme compared to all other derivatives. Based upon our investigation it is proposed that compound (4e) may serve as lead structure to design more potent biological active compounds having multitargets inhibition activities.
Synthesis of sulfonamides from azoles and sodium sulfinates at ambient temperature
Fu, Lili,Bao, Xiaodong,Li, Shanshan,Wang, Lingtian,Liu, Zhiguo,Chen, Wanzhi,Xia, Qinqin,Liang, Guang
, p. 2504 - 2511 (2017/04/03)
NBS or NIS mediated direct S[sbnd]N bond formation between azoles and sodium sulfinates is described. The reaction shows good substrate scope and tolerates a wide range of functionalities in both azoles and sodium sulfinate substrates. Pyrazoles are also suitable for this method, various 4-halopyrazoles derivatives were obtained by using N-halosuccinimide (NXS) as the halogen source.
Additive-free pd-catalyzed α-allylation of imine-containing heterocycles
Kljajic, Marko,Puschnig, Johannes G.,Weber, Hansj?rg,Breinbauer, Rolf
supporting information, p. 126 - 129 (2017/11/27)
An additive-free Pd-catalyzed α-allylation of different imino-group-ontaining heterocycles is reported. The activation of α-CH pronucleophiles (pKa (DMSO) > 25) occurs without the addition of strong bases or Lewis acids using only the Pd/Xantphos catalyst system. The reaction scope has been studied for various 5- and 6-membered nitrogen-containing heterocycles (yields up to 96%). Mechanistic investigations suggest an initial allylation of the imine-N followed by a Pd-catalyzed formal aza-Claisen rearrangement.
Preparation method of N-substituted sulfonamide derivative
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Paragraph 0094; 0095; 0096; 0097; 0098; 0099, (2016/10/08)
The invention discloses a preparation method of N-substituted sulfonamide derivative. The preparation method includes the following steps: taking NBS or NIS as an oxidizing agent; reacting an azole compound and sodium arylsulfinate in an organic solvent;
Hypervalent iodine-mediated synthesis of benzoxazoles and benzimidazoles via an oxidative rearrangement
Zhang, Xiaohui,Huang, Ruofeng,Marrot, Jér?me,Coeffard, Vincent,Xiong, Yan
, p. 700 - 708 (2015/02/02)
A Beckmann-type rearrangement of o-hydroxy and o-aminoaryl N-H ketimines has been developed to prepare benzoxazoles and N-Ts benzimidazoles, respectively. The ketimine derivatives were easily prepared by condensation of ammonia with the corresponding ketones and (diacetoxyiodo)benzene was found to act as an efficient oxidant to trigger the [1,2]-aryl migration towards the formation of the desired heterocycles. Depending on the substitution pattern, the results revealed another mechanistic pathway through which benzisoxazoles or 1H-indazoles could be formed. The Beckmann-type rearrangement strategy was applied to the synthesis of benzimidazole-containing biorelevant targets such as chlormidazole and clemizole.
Phenyliodine diacetate-mediated intramolecular C(sp2)-H amidation for 1,2-disubstituted benzimidazole synthesis under metal-free conditions
Maiti, Saikat,Mal, Prasenjit
, p. 1416 - 1424 (2015/08/04)
A transition metal-free, hypervalent iodine(III) reagent [phenyliodine diacetate (PIDA)]-mediated C(sp2)-H amidation in trifluoroethanol (TFE) has been developed. The intramolecular coupling methodology presented here provides a direct access t
Iodobenzene catalyzed C-H amination of N-substituted amidines using m-chloroperbenzoic acid
Alla, Santhosh Kumar,Kumar, Rapolu Kiran,Sadhu, Pradeep,Punniyamurthy, Tharmalingam
supporting information, p. 1334 - 1337 (2013/04/23)
The oxidative C-H amination of N″-aryl-N′-tosyl/N′- methylsulfonylamidines and N,N′-bis(aryl)amidines has been accomplished using iodobenzene as a catalyst to furnish 1,2-disubstituted benzimidazoles in the presence of mCPBA as a terminal oxidant at room temperature. The reaction is general, and the target products can be obtained in moderate to high yields.
Palladium-catalyzed intramolecular sulfonamidation/oxidation of imines: Access to multifunctional benzimidazoles
Fu, Shaomin,Jiang, Huanfeng,Deng, Yuanfu,Zeng, Wei
, p. 2795 - 2804 (2011/12/01)
O-Sulfonamidophenylimines undergo intramolecular sulfonamidation/oxidation to produce 1,2-disubstituted benzimidazoles upon treatment with palladium(II) chloride/(diacetoxyiodo)benzene and potassium carbonate at room temperature. The substituent scope at
Identification of inhibitors of NOD1-induced nuclear factor-κB activation
Khan, Pasha M.,Correa, Ricardo G.,Divlianska, Daniela B.,Peddibhotla, Satyamaheshwar,Sessions, E. Hampton,Magnuson, Gavin,Brown, Brock,Suyama, Eigo,Yuan, Hongbin,Mangravita-Novo, Arianna,Vicchiarelli, Michael,Su, Ying,Vasile, Stefan,Smith, Layton H.,Diaz, Paul W.,Reed, John C.,Roth, Gregory P.
supporting information; experimental part, p. 780 - 785 (2011/12/02)
NOD1 (nucleotide-binding oligomerization domain 1) protein is a member of the NLR (NACHT and leucine rich repeat domain containing proteins) protein family, which plays a key role in innate immunity as a sensor of specific microbial components derived from bacterial peptidoglycans and induction of inflammatory responses. Mutations in NOD proteins have been associated with various inflammatory diseases that affect NF-κB (nuclear factor κB) activity, a major signaling pathway involved in apoptosis, inflammation, and immune response. A luciferase-based reporter gene assay was utilized in a high-throughput screening program conducted under the NIH-sponsored Molecular Libraries Probe Production Center Network program to identify the active scaffolds. Herein, we report the chemical synthesis, structure-activity relationship studies, downstream counterscreens, secondary assay data, and pharmacological profiling of the 2-aminobenzimidazole lead (compound 1c, ML130) as a potent and selective inhibitor of NOD1-induced NF-κB activation.
Copper-catalyzed one-pot synthesis of substituted benzimidazoles
Jin, Hongwei,Xu, Xiaoliang,Gao, Jianrong,Zhong, Jianhua,Wang, Yanguang
supporting information; experimental part, p. 347 - 350 (2010/04/29)
A copper-catalyzed one-pot synthesis of functionalized benzimidazoles has been developed. The procedure combines the copper-catalyzed three-component cascade reaction of sulfonyl azides, alkynes and 2-bromoaniline and the copper-catalyzed intramolecular N-arylation of sulfon-amides in one sequence, which afforded the products in moderate to good yields.
