34966-50-2Relevant articles and documents
Tris(pentafluorophenyl)borane-Catalyzed Oxygen Insertion Reaction of α-Diazoesters (α-Diazoamides) with Dimethyl Sulfoxide
Gao, Wen-Xia,Liu, Miao-Chang,Wu, Hua-Yue,Wu, Xiao-Yang,Zhou, Yun-Bing
supporting information, (2022/01/19)
A tris(pentafluorophenyl)borane-catalyzed oxidation reaction of α-diazoesters (α-diazo amides) with dimethyl sulfoxide has been developed. The reaction proceeds under metal free conditions to afford a series α-ketoesters and α-ketoamides. The synthetic utility of this protocol is demonstrated through synthetic transformations and scaled-up synthesis. (Figure presented.).
Preparation method of alpha-ketoester compound
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Paragraph 0110-0113, (2021/04/21)
The invention discloses a preparation method of an alpha-ketone ester compound. The method specifically comprises the following operation steps: adding raw materials alpha-diazo ester and an organic photocatalyst into a reaction flask, then adding an organic solvent, and reacting for 2-12 hours in air at room temperature under the irradiation of a visible light lamp; after the reaction is monitored by thin-layer chromatography (TLC), stopping the reaction, and extracting a reaction solution by using ethyl acetate; concentrating the extracting solution under reduced pressure to obtain a crude product, and performing column chromatography separation on the crude product to obtain the alpha-diazonium ester compound. According to the preparation method, clean visible light is used as reaction energy, cheap organic dye is used as a photocatalyst, air is used as a green oxidizing agent and an oxygen source, and the preparation method has the advantages of simplicity and convenience in operation, no metal residue and mild reaction conditions.
Design, synthesis and evaluation of novel diaryl-1,5-diazoles derivatives bearing morpholine as potent dual COX-2/5-LOX inhibitors and antitumor agents
Li, Zhang,Wang, Zhong-Chang,Li, Xin,Abbas, Muhammad,Wu, Song-Yu,Ren, Shen-Zhen,Liu, Qi-Xing,Liu, Yi,Chen, Peng-Wen,Duan, Yong-Tao,Lv, Peng-Cheng,Zhu, Hai-Liang
, p. 168 - 184 (2019/03/17)
In this paper, 41 hybrid compounds containing diaryl-1,5-diazole and morpholine structures acting as dual COX-2/5-LOX inhibitors have been designed, synthesized and biologically evaluated. Most of them showed potent antiproliferative activities and COX-2/5-LOX inhibitory in vitro. Among them, compound A33 displayed the most potency against cancer cell lines (IC50 = 6.43–10.97 μM for F10, HeLa, A549 and MCF-7 cells), lower toxicity to non-cancer cells than celecoxib (A33: IC50 = 194.01 μM vs. celecoxib: IC50 = 97.87 μM for 293T cells), and excellent inhibitory activities on COX-2 (IC50 = 0.17 μM) and 5-LOX (IC50 = 0.68 μM). Meanwhile, the molecular modeling study was performed to position compound A33 into COX-2 and 5-LOX active sites to determine the probable binding models. Mechanistic studies demonstrated that compound A33 could block cell cycle in G2 phase and subsequently induced apoptosis of F10 cells. Furthermore, compound A33 could significantly inhibit tumor growth in F10-xenograft mouse model, and pharmacokinetic study of compound A33 indicated that it showed better stability in vivo. In general, compound A33 could be a promising candidate for cancer therapy.