21300-07-2Relevant academic research and scientific papers
SYNTHESIS, KINETICS OF THE FORMATION, AND PHYSICAL PROPERTIES OF 5-ALKOXYFURFURALS
Novikov, V. N.,Polyakov, V. E.
, p. 563 - 566 (1982)
The reaction of 5-bromofurfural with potassium alkoxides in an alcohol medium was studied, and 5-alkoxyfurfurals and the products of their condensation with m-nitroacetophenone were obtained.A mechanism for the alkoxylation is proposed on the basis of the kinetic data.
Identification of new 3-phenyl-1H-indole-2-carbohydrazide derivatives and their structure–activity relationships as potent tubulin inhibitors and anticancer agents: A combined in silico, in vitro and synthetic study
Saruengkhanphasit, Rungroj,Butkinaree, Chutikarn,Ornnork, Narittira,Lirdprapamongkol, Kriengsak,Niwetmarin, Worawat,Svasti, Jisnuson,Ruchirawat, Somsak,Eurtivong, Chatchakorn
supporting information, (2021/03/17)
Virtual screening of commercially available molecular entities by using CDRUG, structure-based virtual screening, and similarity identified eight new derivatives of 3-phenyl-1H-indole-2-carbohydrazide with anti-proliferative activities. The molecules were tested experimentally for inhibition of tubulin polymerisation, which revealed furan-3-ylmethylene-3-phenyl-1H-indole-2-carbohydrazide (27a) as the most potent candidate. Molecule 27a was able to induce G2/M phase arrest in A549 cell line, similar to other tubulin inhibitors. Synthetic modifications of 27a were focussed on small substitutions on the furan ring, halogenation at R1 position and alteration of furyl connectivity. Derivatives 27b, 27d and 27i exhibited the strongest tubulin inhibition activities and were comparable to 27a. Bromine substitution at R1 position showed most prominent anticancer activities; derivatives 27b-27d displayed the strongest activities against HuCCA-1 cell line and were more potent than doxorubicin and the parent molecule 27a with IC50 values 50 = 0.34 μM), while 27d displayed stronger activity against A549 cell line (IC50 = 0.43 μM) compared to doxorubicin and 27a. Fluorine substitutions at the R1 position tended to show more modest anti-tubulin and anticancer activities, and change of 2-furyl to 3-furyl was tolerable. The new derivatives, thiophenyl 26, displayed the strongest activity against A549 cell line (IC50 = 0.19 μM), while 1-phenylethylidene 21b and 21c exhibited more modest anticancer activities with unclear mechanisms of action; 26 and 21c demonstrated G2/M phase arrest, but showed weak tubulin inhibitory properties. Molecular docking suggests the series inhibit tubulin at the colchicine site, in agreement with the experimental findings. The calculated molecular descriptors indicated that the molecules obey Lipinski's rule which suggests the molecules are drug-like structures.
Transformations of levoglucosenone at the anhydroglucoside bond
Efremov
, p. 582 - 589 (2007/10/03)
The results are given of transformations of levoglucosenone at the anhydroglucoside bond in the presence of a catalyst of the acid type in an aqueous medium, in TFAA, and in lower aliphatic alcohols. Possibilities are shown of obtaining hydroxymethylfurfural and levulinic acid or their derivatives from levoglucosenone in high yields. Possible mechanisms of the reactions taking place are discussed on the basis of kinetic studies and investigations on the composition of the intermediate compounds.
Short and efficient synthesis of the antitumor heptenes melodienone and isomelodienone
Boukouvalas, John,Cheng, Yun-Xing
, p. 7025 - 7026 (2007/10/03)
The antitumor heptenes melodienone and isomelodienone were synthesized in 5 steps from 2-methoxyfuran (overall yield = 36 and 45% respectively) via oxidative ring-opening of a common methoxyfuran precursor.
Synhetic approaches to haplphytine. 2. Synthesis of 4-methylamino-1-(2-furanyl)-2-phenyl-2-(2-pivaloylamidophenyl)butan-1-one
Schwartz, David Aaron,Yates, Peter
, p. 1126 - 1131 (2007/10/02)
Approaches to the synthesis of compounds related to the 7-aryl-7-(3-(1-hydroxy-2-aminophenyl))-9-methylamino-5,6-dioxononanoic acid moiety (3) of the alkaloid haplophytine and its dihydrobromide are described.Treatment of the dianion of phenyl (o-pivaloyl
