14394-91-3Relevant academic research and scientific papers
Unexpected synthesis of novel 2-pyrone derivatives: crystal structures, Hirshfeld surface analysis and computational studies
Sebhaoui, Jihad,El Bakri, Youness,Lai, Chin-Hung,Karthikeyan, Subramani,Anouar, El Hassane,Mague, Joel T.,Essassi, El Mokhtar
, p. 4859 - 4877 (2021)
Here we report synthesis of three new compounds namely, 1-acetyl-1H-benzimidazolo-2(3H)-one (I), N-(5-acetyl-6-methyl-2-oxo-2H-pyran-4-yl)-N-(2-acetamidophenyl)acetamide (II) and N-(2-acetamidophenyl)-N-2-oxo-2H-pyran-4-yl)acetamide (III) have been synthe
A novel application of heterocyclic compounds for biosensors based on NAD, FAD, and PQQ dependent oxidoreductases
Laurinavicius, Valdas,Kurtinaitiene, Bogumila,Liauksminas, Virginijus,Puodziunaite, Benedikta,Janciene, Regina,Kosychova, Lidija,Meskys, Rolandas
, p. 1269 - 1281 (1999)
Various five-, six-, and seven-membered heterocyclic compounds containing two nitrogen atoms as well as quinoid substances were synthesized and investigated. Electrochemical oxidation-polymerization of these heterocycles on carbon and platinum electrodes was performed in aqueous medium. Electrochemically pre-treated carbon electrodes modified with these heterocyclic compounds and were used for the electro-catalytic oxidation of NADH and for the design of mediated glucose biosensors.
Live-Cell Protein Modification by Boronate-Assisted Hydroxamic Acid Catalysis
Adamson, Christopher,Kajino, Hidetoshi,Kanai, Motomu,Kawashima, Shigehiro A.,Yamatsugu, Kenzo
, p. 14976 - 14980 (2021/09/29)
Selective methods for introducing protein post-translational modifications (PTMs) within living cells have proven valuable for interrogating their biological function. In contrast to enzymatic methods, abiotic catalysis should offer access to diverse and new-to-nature PTMs. Herein, we report the boronate-assisted hydroxamic acid (BAHA) catalyst system, which comprises a protein ligand, a hydroxamic acid Lewis base, and a diol moiety. In concert with a boronic acid-bearing acyl donor, our catalyst leverages a local molarity effect to promote acyl transfer to a target lysine residue. Our catalyst system employs micromolar reagent concentrations and affords minimal off-target protein reactivity. Critically, BAHA is resistant to glutathione, a metabolite which has hampered many efforts toward abiotic chemistry within living cells. To showcase this methodology, we installed a variety of acyl groups inE. colidihydrofolate reductase expressed within human cells. Our results further establish the well-known boronic acid-diol complexation as abona fidebio-orthogonal reaction with applications in chemical biology and in-cell catalysis.
Selenium-Catalyzed Carbonylative Synthesis of 2-Benzimidazolones from 2-Nitroanilines with TFBen as the CO Source
Qi, Xinxin,Zhou, Rong,Peng, Jin-Bao,Ying, Jun,Wu, Xiao-Feng
supporting information, p. 5161 - 5164 (2019/01/25)
A selenium-catalyzed carbonylative reaction for the synthesis of 2-benzimidazolones from 2-nitroanilines has been developed. In this strategy, to avoid the usage of toxic CO gas, TFBen (benzene-1,3,5-triyl triformate) was used as a solid and stable CO precursor, and a variety of desired 2-benzimidazolones were produced in moderate to excellent yields.
Inhibitors of the salicylate synthase (Mbti) from Mycobacterium tuberculosis discovered by high-throughput screening
Vasan, Mahalakshmi,Neres, Joao,Williams, Jessica,Wilson, Daniel J.,Teitelbaum, Aaron M.,Remmel, Rory P.,Aldrich, Courtney C.
experimental part, p. 2079 - 2087 (2011/11/29)
A simple steady-state kinetic high-throughput assay was developed for the salicylate synthase MbtI from Mycobacterium tuberculosis, which catalyzes the first committed step of mycobactin biosynthesis. The mycobactins are small-molecule iron chelators produced by M. tuberculosis, and their biosynthesis has been identified as a promising target for the development of new antitubercular agents. The assay was miniaturized to a 384-well plate format and high-throughput screening was performed at the National Screening Laboratory for the Regional Centers of Excellence in Biodefense and Emerging Infectious Diseases (NSRB). Three classes of compounds were identified comprising the benzisothiazolones (class I), diarylsulfones (class II), and benzimidazole-2-thiones (class III). Each of these compound series was further pursued to investigate their biochemical mechanism and structure-activity relationships. Benzimidazole-2-thione 4 emerged as the most promising inhibitor owing to its potent reversible inhibition.
1,3-Dihydro-1,3-diacetyl-2H-benzimidazol-2-one: A new versatile and selective acetylating agent
Chung, In Hwa,Cha, Ki Suk,Seo, Jae Hong,Kim, Joong Hyup,Chung, Bong Young,Kim, Choong Sup
, p. 529 - 533 (2007/10/03)
1,3-Dihydro-1,3-diacetyl-2H-benzimidazol-2-one (4, DABI) was proven to be a versatile and selective acetylating agent for amines. Selectivity and reactivity are not only superior than those of other known acetylating agents, but also products could be easily separated with excellent yield.
Oxidations with Lead Tetraacetate. VI. Oxidations of Benzimidazoles, Benzoxazoles and Benzothiazoles
Cole, Edward R.,Crank, George,Sumantri
, p. 295 - 301 (2007/10/02)
Benzimidazole is slowly oxidized in the imidazole ring by lead tetraacetate to benzimidazol-2(3H)-one, 1-acetylbenzimidazol-2(3H)-one and N,N'-(o-phenylene)bisacetamide.With excess oxidant, oxidation also occurs in the benzene ring at C5.Benzoxazole is much more reactive and gives a variety of products formed by oxidation of both rings.Benzothiazole is the least reactive system and suffers only minimal oxidation at C2 of the thiazole ring.
