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Journal articles on the topic 'Benzimidazolone'

Author: Grafiati

Published: 4 June 2021

Last updated: 15 February 2022

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1

Ahmad, Iftikhar, Shahid Hameed, Helmut Duddeck, Sigurd Lenzen, Ingo Rustenbeck, and Roshan Ahmad. "N-Arylsulfonyl-benzimidazolones as Potential Hypoglycemic Agents." Zeitschrift für Naturforschung B 57, no. 3 (2002): 349–54. http://dx.doi.org/10.1515/znb-2002-0315.

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Abstract1,3-Bis(arylsulfonyl)-benzimidazolones 1a-d were synthesized by reacting benzimidazolones with arenesulfonyl chlorides in the presence of NaOH. Mono(arylsulfonyl)-benzimidazolone derivatives 5a-c were prepared from benzimidazolone by protecting one of the Natoms with a tert-butoxycarbonyl group followed by arylsulfonylation and deprotection in acidic medium. The antidiabetic activity of three compounds 1a, 1c and 5a has been determined.

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2

Dombroski, Mark A., Michael A. Letavic, Kim F. McClure, et al. "Benzimidazolone p38 inhibitors." Bioorganic & Medicinal Chemistry Letters 14, no. 4 (2004): 919–23. http://dx.doi.org/10.1016/j.bmcl.2003.12.023.

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3

Amari, Mohamed, Mokhtar Fodili, Bellara Nedjar-Kolli, AlgÉrie Pascal Hoffmann, and Jacques PÉriÉ. "Reactivity studies on 4-aminopyrones: Access to benzimidazole and benzimidazolone derivatives." Journal of Heterocyclic Chemistry 39, no. 4 (2002): 811–16. http://dx.doi.org/10.1002/jhet.5570390429.

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4

Szadowski, Jerzy, and Zbigniew Niewiadomski. "Deaggregation of benzimidazolone azo dyes." Dyes and Pigments 33, no. 2 (1997): 97–105. http://dx.doi.org/10.1016/s0143-7208(96)00040-x.

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5

Yi, Wen Bin, Fang Luan, Jian Min Xiu, Lv Qi Jiang, and Chun Cai. "Triphosgene as a Safe and Environment-Friendly Carbonylation Reagent for the Preparation of 2-Benzimidazolone." Advanced Materials Research 955-959 (June 2014): 651–55. http://dx.doi.org/10.4028/www.scientific.net/amr.955-959.651.

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2-Benzimidazolone and their derivatives which have a wide range of biological and pharmaceutical activity are important intermediates for organic synthesis. Reported synthetic methods mostly involved unfriendly materials like phosgene, dimethyl carbonate and urea. This paper developed a novel method for the synthesis of 2-benzimidazolone by the reaction of o-phenylendiamine with triphosgene (BTC) instead of phosgene. BTC is a safer solid and easier to handle compared to phosgene. BTC can greatly reduce risks to both human health and the environment.

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6

Macho, Vendelín, Milan Králik, and Eva Bojsová. "Intramolecular Reductive Carbonylation of o-Nitroaniline by Carbon Monoxide to 2(3H)-Benzimidazolone." Collection of Czechoslovak Chemical Communications 62, no. 2 (1997): 325–30. http://dx.doi.org/10.1135/cccc19970325.

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o-Nitroaniline reacts with carbon monoxide under pressure in the presence of solvents (e.g. dioxane, tetrahydrofuran, N,N-dimethylformamide) and a catalytic system (sulfur or a low molecular sulfur compound - a basic medium - and optionally a vanadium(V) compound) at 370-445 K to give 2(3H)-benzimidazolone by intramolecular reductive carbonylation. Similarly to intermolecular carbonylation of nitroaromatic compounds also in the title reaction the efficiency of the sulfur component decreases in the order: COS > H2S >> CS2 > S. The promotor action of NH4VO3 and V2O5 is, however, less

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7

Amari, Mohamed, Mokhtar Fodili, Bellara Nedjar-Kolli, Pascal Hoffmann, and Jacques Perie. "ChemInform Abstract: Reactivity Studies on 4-Aminopyrones: Access to Benzimidazole and Benzimidazolone Derivatives." ChemInform 33, no. 52 (2010): no. http://dx.doi.org/10.1002/chin.200252119.

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8

Gu, Xinming, Zhipeng Wang, Honghua Wang, Guangyuan Zhou, and Yanmin Zhou. "Synthesis of thermally robust benzimidazolone-based wholly aromatic polyketones." RSC Advances 11, no. 10 (2021): 5444–50. http://dx.doi.org/10.1039/d0ra09831k.

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9

Szadowski, J., and Z. Niewiadomski. "Reactive dyes containing a benzimidazolone residue." Coloration Technology 115, no. 10 (1999): 374–77. http://dx.doi.org/10.1111/j.1478-4408.1999.tb00291.x.

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10

Szadowski, J., and Z. Niewiadomski. "Reactive dyes containing a benzimidazolone residue." Coloration Technology 115, no. 12 (1999): 374–77. http://dx.doi.org/10.1111/j.1478-4408.1999.tb00296.x.

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11

Theberge, Cory R., Rodney A. Bednar, Ian M. Bell, et al. "Potent benzimidazolone-based CGRP receptor antagonists." Bioorganic & Medicinal Chemistry Letters 18, no. 23 (2008): 6122–25. http://dx.doi.org/10.1016/j.bmcl.2008.10.019.

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12

Makeiff, D. A., J. –Y Cho, N. Godbert, et al. "Supramolecular gels from alkylated benzimidazolone derivatives." Journal of Molecular Liquids 339 (October 2021): 116723. http://dx.doi.org/10.1016/j.molliq.2021.116723.

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13

Bouayad, Kaoutar, Youssef Kandri Rodi, Youness Ouzidan, El Mokhtar Essassi, Mohamed Saadi, and Lahcen El Ammari. "Crystal structure of 5-chloro-1,3-bis[2-(2-oxo-1,3-oxazolidin-3-yl)ethyl]-1H-benzimidazol-2(3H)-one." Acta Crystallographica Section E Crystallographic Communications 71, no. 10 (2015): o735—o736. http://dx.doi.org/10.1107/s2056989015016102.

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In the title compound, C17H19ClN4O5, the benzimidazole fused-ring system is essentially planar, the maximum deviation from the mean plane being 0.06 (1) Å. Both oxazolidine rings are nearly planar, the maximum deviations from the mean planes are 0.071 (13) and 0.070 (10) Å. The dihedral angle between the mean planes of the oxazolidine rings is 69.9 (7)°. The benzimidazole mean plane makes the dihedral angles of 43.9 (6) and 45.6 (6)° with the two oxazolidine rings. In the crystal, the molecules are linked together by weak C—H...O hydrogen bonds building zigzag tapes running along thecaxis. The

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14

Kim, Song Hyuk, Jae Hwan Kim, Seok Won Yang, Won-Ki Lee, Young Eup Jin, and Seong Soo Park. "A Study on Synthesis and Crystallization of a Benzimidazolone Pigment." Applied Chemistry for Engineering 26, no. 2 (2015): 159–64. http://dx.doi.org/10.14478/ace.2015.1001.

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15

Izevbekhai, Oisaemi Uduagele, Wilson Mugera Gitari, Nikita Tawanda Tavengwa, Wasiu Babatunde Ayinde, and Rabelani Mudzielwana. "Synthesis and evaluation of the oil removal potential of 3-bromo-benzimidazolone polymer grafted silica gel." RSC Advances 11, no. 19 (2021): 11356–63. http://dx.doi.org/10.1039/d0ra10848k.

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This work reports the synthesis of 3-bromo-benzimidazolone using melt condensation, its polymerization and functionalization on silica which was extracted from diatomaceous earth in our previous work.

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16

Tomović, Katarina, Jelena Mrmošanin, Denitsa Yancheva, Anelia Mavrova, and Andrija Šmelcerović. "In vitro antioxidant properties of 2-imino-benzimidazole and 1,3-thiazolo[3,2-a]benzimidazolone derivatives." Acta Facultatis Medicae Naissensis 37, no. 4 (2020): 381–86. http://dx.doi.org/10.5937/afmnai37-27103.

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Antioxidant properties of 2-[2-imino-5-nitro-3-(2-oxo-2-phenylethyl)-2,3-dihydro-1H-benzimidazol1-yl]-1-phenylethanone (compound 1) and 2-(4-fluorobenzylidene)-6-(phenylcarbonyl)[1,3]thiazolo[3,2a]benzimidazol-3(2H)-one (compound 2) were evaluated in vitro. Compounds 1 and 2 did not show significant radical scavenging activity. It has been suggested that antioxidant strategies should not be based on direct scavengers but rather on the potentiation of endogenous antioxidant defenses, or on the reduction of the sources of reactive species. Although a direct scavenging mechanism is missing, the a

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17

Benali, B., Z. Lazar, K. Elblidi, et al. "Solvatochromic effect on photophysical properties of benzimidazolone." Journal of Molecular Liquids 128, no. 1-3 (2006): 42–45. http://dx.doi.org/10.1016/j.molliq.2005.02.004.

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18

Nale, Deepak B., and Bhalchandra M. Bhanage. "Copper-catalyzed efficient synthesis of a 2-benzimidazolone scaffold from 2-nitroaniline and dimethyl carbonate via a hydrosilylation reaction." Green Chemistry 17, no. 4 (2015): 2480–86. http://dx.doi.org/10.1039/c4gc02408g.

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This work reports a copper-catalyzed novel protocol for the tandem synthesis of 2-benzimidazolone derivatives from dimethyl carbonate (DMC) and various 2-nitroanilines by using polymethylhydrosiloxane (PMHS) as an inexpensive, stable and environmentally benign reducing agent.

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19

Basu, Priyanka, Tusar Kanto Dey, Sk Riyajuddin, Surajit Biswas, Kaushik Ghosh, and Sk Manirul Islam. "Synthesis of benzimidazolones via CO2 fixation and N-phenyl formamides using formic acid in presence of zinc embedded polymer complex." New Journal of Chemistry 44, no. 29 (2020): 12680–91. http://dx.doi.org/10.1039/d0nj01363c.

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A merrifield supported heterogeneous zinc catalyst [Zn(Meri-Ald-Py)] was synthesized and applied for benzimidazolone synthesis through the fixation of carbon dioxide (CO<sub>2</sub>) and for different N-formylated products synthesis under mild reaction conditions.

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20

van de Streek, Jacco, Jürgen Brüning, Svetlana N. Ivashevskaya, et al. "Structures of six industrial benzimidazolone pigments from laboratory powder diffraction data." Acta Crystallographica Section B Structural Science 65, no. 2 (2009): 200–211. http://dx.doi.org/10.1107/s0108768108041529.

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The crystal structures of six industrially produced benzimidazolone pigments [Pigment Orange 36 (β phase), Pigment Orange 62, Pigment Yellow 151, Pigment Yellow 154 (α phase), Pigment Yellow 181 (β phase) and Pigment Yellow 194] were determined from laboratory X-ray powder diffraction data by means of real-space methods using the programs DASH and MRIA, respectively. Subsequent Rietveld refinements were carried out with TOPAS. The crystal phases correspond to those produced industrially. Additionally, the crystal structures of the non-commercial compound `BIRZIL' (a chloro derivative of Pigmen

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21

Rode, MA, BK Karale, and SS Rindhe. "Synthesis and biological activities of some benzimidazolone derivatives." Indian Journal of Pharmaceutical Sciences 77, no. 2 (2015): 230. http://dx.doi.org/10.4103/0250-474x.156619.

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22

Finley, Don R., Michael G. Bell, Anthony G. Borel та ін. "Potent benzimidazolone based human β3-adrenergic receptor agonists". Bioorganic & Medicinal Chemistry Letters 16, № 21 (2006): 5691–94. http://dx.doi.org/10.1016/j.bmcl.2006.08.010.

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23

Devor, D. C., A. K. Singh, R. A. Frizzell, and R. J. Bridges. "Modulation of Cl- secretion by benzimidazolones. I. Direct activation of a Ca(2+)-dependent K+ channel." American Journal of Physiology-Lung Cellular and Molecular Physiology 271, no. 5 (1996): L775—L784. http://dx.doi.org/10.1152/ajplung.1996.271.5.l775.

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We evaluated the effects of the novel benzimidazolone, 1-ethyl-2-benzimidazolinone (1-EBIO), on Cl- secretion across T84 monolayers. 1-EBIO stimulated a sustained Cl- secretory response at a half-maximal effective concentration of 490 microM. Charybdotoxin (CTX) inhibited the 1-EBIO-induced short-circuit current (Isc) with an inhibitory constant (Ki) of 3.6 nM, whereas 293B, an inhibitor of adenosine 3',5'-cyclic monophosphate-activated K+ channels, had no effect on the current induced by 1-EBIO. In contrast, CTX failed to inhibit the 293B-sensitive forskolin-induced Isc. The above results sug

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24

Caci, Emanuela, Chiara Folli, Olga Zegarra-Moran, et al. "CFTR activation in human bronchial epithelial cells by novel benzoflavone and benzimidazolone compounds." American Journal of Physiology-Lung Cellular and Molecular Physiology 285, no. 1 (2003): L180—L188. http://dx.doi.org/10.1152/ajplung.00351.2002.

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Activators of the CFTR Cl- channel may be useful for therapy of cystic fibrosis. Short-circuit current ( Isc) measurements were done on human bronchial epithelial cells to characterize the best flavone and benzimidazolone CFTR activators identified by lead-based combinatorial synthesis and high-throughput screening. The 7,8-benzoflavone UCcf-029 was a potent activator of Cl- transport, with activating potency (<1 μM) being much better than other flavones, such as apigenin. The benzimidazolone UCcf-853 gave similar Isc but with lower potency (5–20 μM). In combination, the effect induced by m

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25

Petrov, Ognyan I., Veneta B. Kalcheva, and Antonina Ts Antonova. "C-Formylation of Some 2(3H)-Benzazolones and 2H-1,4-Benzoxazin-3(4H)-one." Collection of Czechoslovak Chemical Communications 62, no. 3 (1997): 494–97. http://dx.doi.org/10.1135/cccc19970494.

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The C-formylation of 1,3-dimethyl-2(3H)-benzimidazolone and 4-methyl-2H-1,4-benzoxazin-3(4H)-one was performed using 1,1-dichloromethyl methyl ether at the Friedel-Crafts reaction conditions. The formylation of 3-methyl-2(3H)-benzoxa- and -thiazolone at the 6-position was carried out by modified Duff's method with hexamethylenetetramine in trifluoroacetic acid.

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26

Bakkali, Said, Abdelillah Benabida, and Mohammed Cherkaoui. "Tin electrodeposition from sulfate solution containing a benzimidazolone derivative." Mediterranean Journal of Chemistry 6, no. 2 (2016): 15–22. http://dx.doi.org/10.13171/mjc61/01611211149/bakkali.

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Tin electrodeposition in an acidic medium in the presence of N,N’-1,3-bis-[N-3-(6-deoxy-3-O-methylD-glucopyranose-6-yl)-2-oxobenzimidazol-1-yl)]-2-tetradecyloxypropane as an additive was investigated in this work. The adequate current density and the appropriate additive concentration were determined by gravimetric measurements. Chronopotentiometric curves showed that the presence of the additive caused an increase in the overpotential of tin reduction. The investigations by cyclic voltammetry technique revealed that, in the presence and in absence of the additive, there were two peaks, one in

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27

ABRAMOVA, N. D., L. V. ANDRIYANKOVA, A. G. MAL'KINA, and YU M. SKVORTSOV. "ChemInform Abstract: Cyanoacetylenes in the Reaction with 2-Benzimidazolone." ChemInform 25, no. 13 (2010): no. http://dx.doi.org/10.1002/chin.199413172.

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28

Benali, B., A. El Assyry, A. Boucetta, Z. Lazar, and B. Lakhrissi. "Thermal, structural, and conformational study of the benzimidazolone molecule." Research on Chemical Intermediates 41, no. 2 (2013): 821–30. http://dx.doi.org/10.1007/s11164-013-1234-9.

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29

Lütnant, Ines, Dirk Schepmann, and Bernhard Wünsch. "Benzimidazolone bioisosteres of potent GluN2B selective NMDA receptor antagonists." European Journal of Medicinal Chemistry 116 (June 2016): 136–46. http://dx.doi.org/10.1016/j.ejmech.2016.03.065.

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30

Menteşe, Emre, Okan Güven, Nedime Çalışkan, and Nimet Baltaş. "Synthesis and biological evaluation of benzimidazolone bridged triheterocyclic compounds." Journal of Heterocyclic Chemistry 58, no. 6 (2021): 1259–67. http://dx.doi.org/10.1002/jhet.4252.

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31

Devor, D. C., A. K. Singh, R. J. Bridges, and R. A. Frizzell. "Modulation of Cl- secretion by benzimidazolones. II. Coordinate regulation of apical GCl and basolateral GK." American Journal of Physiology-Lung Cellular and Molecular Physiology 271, no. 5 (1996): L785—L795. http://dx.doi.org/10.1152/ajplung.1996.271.5.l785.

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We previously demonstrated that the novel benzimidazolone, 1-ethyl-2-benzimidazolinone (1-EBIO), stimulates a sustained Cl- secretory response across T84 monolayers by opening a Ca(2+)-dependent basolateral K+ channel. In the present work, we evaluated the effects on Cl-secretion of other benzimidazolones, NS-004 and NS-1619, which have been shown to open cystic fibrosis transmembrane conductance regulator (CFTR) Cl- channels. In contrast to 1-EBIO, neither NS-004 nor NS-1619 stimulated a significant Cl- secretory current (Isc). Neither NS-004 nor NS-1619 increased Isc subsequent to forskolin

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32

Lazar, Z., B. Benali, K. Elblidi, et al. "Photophysical study of benzimidazolone and its derivative molecules in solution." Journal of Molecular Liquids 106, no. 1 (2003): 89–95. http://dx.doi.org/10.1016/s0167-7322(03)00023-0.

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33

Intagliata, Sebastiano, Walid F. Alsharif, Christophe Mesangeau та ін. "Benzimidazolone-based selective σ2 receptor ligands: Synthesis and pharmacological evaluation". European Journal of Medicinal Chemistry 165 (березень 2019): 250–57. http://dx.doi.org/10.1016/j.ejmech.2019.01.019.

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34

Lakhrissi, Brahim, Abdelhafid Benksim, Mohamed Massoui, et al. "Towards the synthesis of new benzimidazolone derivatives with surfactant properties." Carbohydrate Research 343, no. 3 (2008): 421–33. http://dx.doi.org/10.1016/j.carres.2007.11.028.

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35

Olesen, Søren-P., Ellen Munch, Peter Moldt, and Jørgen Drejer. "Selective activation of Ca2+ -dependent K+ channels by novel benzimidazolone." European Journal of Pharmacology 251, no. 1 (1994): 53–59. http://dx.doi.org/10.1016/0014-2999(94)90442-1.

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36

Omura, Hirofumi, Makoto Kawai, Akiko Shima, et al. "The SAR studies of novel CB2 selective agonists, benzimidazolone derivatives." Bioorganic & Medicinal Chemistry Letters 18, no. 11 (2008): 3310–14. http://dx.doi.org/10.1016/j.bmcl.2008.04.032.

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37

Tang, Bing Tao, Jin Jing Qiu, Yang Lin Luo, Shu Fen Zhang, and De Feng Zhao. "Yellow Reactive Dyes Containing Benzimidazolone Group for Low-Salt Dyeing of Cotton." Advanced Materials Research 968 (June 2014): 156–60. http://dx.doi.org/10.4028/www.scientific.net/amr.968.156.

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Yellow reactive dyes containing the benzimidazolone group were synthesized by a diazo-coupling process based on 5-aminobenzimidazolone and 2,4-diaminobenzenesulfonic acid. These reactive dyes were subsequently used for cotton dyeing. The structures of the dyes were confirmed by mass spectrometry, Fourier-transform infrared spectroscopy, and proton nuclear magnetic resonance spectroscopy. The dyes demonstrated satisfactory light stability when exposed to simulating light. The results of cotton dyeing showed that the exhaustion and fixation of dyes were reasonably effective and acceptable as ‘lo

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38

Rubinov, D. B., T. A. Zheldakova, I. L. Rubinova, and F. A. Lakhvich. "Synthesis of benzimidazolone derivatives based on 2-acylcyclohexane-1,3-diones alkoximes." Russian Journal of Organic Chemistry 44, no. 7 (2008): 1024–30. http://dx.doi.org/10.1134/s1070428008070130.

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39

Kochergin, Yu S., T. I. Grigorenko, M. A. Grigorenko, and D. P. Loiko. "Modification of epoxy polymers with epoxy thiirane derivative of benzimidazolone-2." Polymer Science. Series D 3, no. 2 (2010): 124–28. http://dx.doi.org/10.1134/s1995421210020103.

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40

Hammach, Abdelhakim, Antonio Barbosa, Faith Corbo Gaenzler, et al. "Discovery and design of benzimidazolone based inhibitors of p38 MAP kinase." Bioorganic & Medicinal Chemistry Letters 16, no. 24 (2006): 6316–20. http://dx.doi.org/10.1016/j.bmcl.2006.09.014.

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41

Baxter, Gordon S., and David E. Clarke. "Benzimidazolone derivatives act as 5-HT4 receptor ligands in rat oesophagus." European Journal of Pharmacology 212, no. 2-3 (1992): 225–29. http://dx.doi.org/10.1016/0014-2999(92)90333-y.

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42

Ivashevskaya, Svetlana N., Jacco van de Streek, Martin U. Schmidt, Jürgen Brüning, and Martin Ermrich. "Crystal structures of six industrial benzimidazolone pigments from X-ray powder data." Acta Crystallographica Section A Foundations of Crystallography 65, a1 (2009): s318. http://dx.doi.org/10.1107/s0108767309093234.

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43

Kumar, Surendra, Vineet Singh, and Meena Tiwari. "QSAR modeling of the inhibition of reverse transcriptase enzyme with benzimidazolone analogs." Medicinal Chemistry Research 20, no. 9 (2010): 1530–41. http://dx.doi.org/10.1007/s00044-010-9406-2.

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44

Zeng, Qingbei, Stuart B. Rosenblum, Zhaoxia Yang, et al. "Synthesis and SAR studies of benzimidazolone derivatives as histamine H3-receptor antagonists." Bioorganic & Medicinal Chemistry Letters 23, no. 21 (2013): 6001–3. http://dx.doi.org/10.1016/j.bmcl.2013.08.012.

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45

P., Schiantarelli, Bockaert J., Cesana R., et al. "The prokinetic properties of new benzimidazolone derivatives are related to 5-HT4 agonism." Pharmacological Research 22 (September 1990): 453. http://dx.doi.org/10.1016/s1043-6618(09)80459-3.

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46

Ohta, Shunsaku, Teruyuki Yuasa, Yoshihiro Narita, Ikuo Kawasaki, Eiji Minamii, and Masayuki Yamashita. "Synthesis and Application of Imidazole Derivatives. Synthesis of Pyrido[1,2-a]benzimidazolone Derivatives." HETEROCYCLES 32, no. 10 (1991): 1923. http://dx.doi.org/10.3987/com-91-5805.

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47

Pacios, Luis F., Zhor Lazar, and Bouziane Benali. "Theoretical study of molecular properties depending on the electron density of benzimidazolone derivatives." Journal of Molecular Structure: THEOCHEM 594, no. 1-2 (2002): 89–100. http://dx.doi.org/10.1016/s0166-1280(02)00368-8.

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48

Li, Dazhi, and Thierry Ollevier. "Synthesis of Imidazolidinone, Imidazolone, and Benzimidazolone Derivatives through Oxidation Using Copper and Air." Organic Letters 21, no. 10 (2019): 3572–75. http://dx.doi.org/10.1021/acs.orglett.9b00973.

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49

Gribkoff, V. K., G. Champigny, P. Barbry, S. I. Dworetzky, N. A. Meanwell, and M. Lazdunski. "The substituted benzimidazolone NS004 is an opener of the cystic fibrosis chloride channel." Journal of Biological Chemistry 269, no. 15 (1994): 10983–86. http://dx.doi.org/10.1016/s0021-9258(19)78079-x.

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50

Ellis, Keisha K., Burkhardt Wilke, Yuegang Zhang, and Steven T. Diver. "A New Method for the Synthesis of Imidazolidinone- and Benzimidazolone-Containing [2.2]Cyclophanes." Organic Letters 2, no. 24 (2000): 3785–88. http://dx.doi.org/10.1021/ol0064866.

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