102-51-2Relevant articles and documents
Quantitative structure-activity relationships on 5-substituted terbenzimidazoles as topoisomerase I poisons and antitumor agents
Kim, Jung Sun,Sun, Qun,Yu, Chiang,Liu, Angela,Liu, Leroy F.,Lavoie, Edmond J.
, p. 163 - 172 (1998)
Several 5-substituted terbenzimidazoles were synthesized and evaluated as mammalian topoisomerase I poisons and for cytotoxicity against a human lymphoblastoma cell line, RPMI-8402. No correlation was observed between topoisomerase I poisoning activity and the Hansch π value or the σ(meta) and σ(para) values associated with each substituent. These data suggest that electronic effects and relative lipophilicity of substituents at the 5-position of these terbenzimidazoles do not have a significant effect upon intrinsic topoisomerase I poisoning activity. There was, however, a good correlation between the relative π values for the various subtituents evaluated and cytotoxic activity. Experimentally determined log P values did not correlate well with either cytotoxicity or π values. Capacity factors (log k') as determined by high pressure liquid chromatography did correlate well with the π values of varied substituents and cytotoxicity. These data indicate that the relative lipophilic activity of substituents at the 5-position of these terbenzimidazoles can strongly influence relative cytotoxic activity.
Synthesis and vasorelaxant evaluation of novel 7-methoxyl-2,3-disubstituted-quinoxaline derivatives
Gao, Wen-Cong,Li, Xun,Ma, Xin,Pang, Pan-Pan,Peng, Li-Chun,Yang, Liang,Zheng, Chang-Bo
, (2021)
An array of novel 7-methoxyl-2,3-disubstituted quinoxaline derivatives was designed, synthesized and their potential antihypertensive activities were examined, in an attempt to discover potent small molecules with vasorelaxant effects. The vasoactivities of these compounds on vascular tone, as well as underlying mechanisms were hereby explored. Results showed that five compounds (7s, 7t, 7v, 7w, 7γ) could induce endothelium-independent relaxation in high extracellular K+- and phenylephrine-precontracted C57 mice aortic rings. These five compounds, unlike other commonly used vasodilators, could slowly but effectively inhibit vasoconstriction.
The Discovery of Quinoxaline-Based Metathesis Catalysts from Synthesis of Grazoprevir (MK-5172)
Williams, Michael J.,Kong, Jongrock,Chung, Cheol K.,Brunskill, Andrew,Campeau, Louis-Charles,McLaughlin, Mark
, p. 1952 - 1955 (2016)
Olefin metathesis (OM) is a reliable and practical synthetic methodology for challenging carbon-carbon bond formations. While existing catalysts can effect many of these transformations, the synthesis and development of new catalysts is essential to increase the application breadth of OM and to achieve improved catalyst activity. The unexpected initial discovery of a novel olefin metathesis catalyst derived from synthetic efforts toward the HCV therapeutic agent grazoprevir (MK-5172) is described. This initial finding has evolved into a class of tunable, shelf-stable ruthenium OM catalysts that are easily prepared and exhibit unique catalytic activity.
Synthesis and application of novel styryl dyes derived from 1,4-diethyl-1,2,3,4-tetrahydro-6-methoxyquinoxaline
Satam, Vijay,Rajule, Rajkumar,Bendre, Samir,Bineesh, Purushotthaman,Kanetkar, Vinod
, p. 221 - 225 (2009)
The novel 1,4-diethyl-1,2,3,4-tetrahydro-7-methoxyquinoxalin-6- carboxaldehyde was synthesized, characterized, and condensed with suitably substituted active methylene compounds by classical Knoe- venagel condensation reaction to obtain novel monostyryl dyes 8a-8e and a bis-styryl dye 8f. These novel styryl dyes have hue varying from orange to violet. The dyes were applied to polyester fibers. The spectral and thermal characteristics of the dyes and fastness properties of the dyed polyester fabric were investigated.
Kinetic study on the anelation of heterocycles. 1. Quinoxalinone derivatives synthesized by Hinsberg reaction
Abasolo,Gaozza,Fernandez
, p. 1771 - 1775 (1987)
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Expedient synthesis of electronically modified luciferins for bioluminescence imaging
McCutcheon, David C.,Paley, Miranda A.,Steinhardt, Rachel C.,Prescher, Jennifer A.
, p. 7604 - 7607 (2012)
Bioluminescence imaging with luciferase enzymes requires access to light-emitting, small-molecule luciferins. Here, we describe a rapid method to synthesize d-luciferin, the substrate for firefly luciferase (Fluc), along with a novel set of electronically modified analogues. Our procedure utilizes a relatively rare, but synthetically useful dithiazolium reagent to generate heteroaromatic scaffolds in a divergent fashion. Two of the luciferin analogues produced with this approach emit light with Fluc in vitro and in live cells. Collectively, our work increases the number of substrates that can be used for bioluminescence imaging and provides a general strategy for synthesizing new collections of luciferins.
Methanol as the C1source: Redox coupling of nitrobenzenes and alcohols for the synthesis of benzimidazoles
An, Jie,Lai, Zemin,Li, Hengzhao,Peng, Mengqi,Sun, Yanhao,Yan, Zihan,Yang, Ruoyan,Zhang, Yuntong
supporting information, p. 748 - 753 (2022/02/02)
We present an operationally simple redox coupling for the synthesis of N-1 substituted benzimidazoles using feedstock building block 2-nitroaniline derivatives as the precursors and methanol as the C1 source. Higher atom, step, and redox economies and exc
Method for continuous-flow synthesis of 2-sulfydryl-5-methoxybenzimidazole
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Paragraph 0034-0038; 0042-044; 0047-0049; 0052-0054; 0057, (2021/07/17)
The invention belongs to the technical field of organic synthesis, and particularly relates to a method for continuous-flow synthesis of 2-sulfydryl-5-methoxybenzimidazole. The method comprises the following reaction steps in a continuous flow reactor: (1) subjecting 2-nitro-4-methoxyaniline to reacting with a reducing agent under the action of a catalyst to obtain a reaction solution containing 4-methoxy o-phenylenediamine; and (2) enabling the reaction solution containing the 4-methoxy o-phenylenediamine to react with carbon disulfide so as to generate the 2-sulfydryl-5-methoxybenzimidazole. According to the production process improved by a continuous flow technology in the invention, reaction time is greatly shortened, operation is simple and convenient, production efficiency is improved, and the yield and the purity of the obtained product are very high. Therefore, the method disclosed by the invention has a very good application prospect in the synthesis of 2-sulfydryl-5-methoxybenzimidazole.
