21852-50-6Relevant articles and documents
Asakawa et al.
, p. 1057 (1976)
Synthesis of colchifulvin, a colchicine–griseofulvin hybrid
Marset, Azucena,Caprioglio, Diego,Torretta, Simone,Appendino, Giovanni,Minassi, Alberto
, p. 1540 - 1543 (2016)
Since the antimitotic agent colchicine (4) and the antifungal antibiotic griseofulvin (5) bind the same target (tubulin), we have explored the possibility of combining the potency of 4 and the low-toxicity of 5 into a hybrid [colchifulvin (6)], where the aromatic A-ring of 4 is bound to a dienone C-ring in a spiro fashion reminiscent of 5. To this purpose, the intramolecular oxidative cyclization of bibenzyl and stilbenoid precursors of spiro[4.5]decadienones was investigated, eventually taming the unexpected subtleties of the reaction. Disappointingly, rac-6 did not share the biological profile of the two inspiring lead structures.
Identification of Pyruvate Carboxylase as the Cellular Target of Natural Bibenzyls with Potent Anticancer Activity against Hepatocellular Carcinoma via Metabolic Reprogramming
Sheng, Yuwen,Chen, Yuwen,Zeng, Zhongqiu,Wu, Wenbi,Wang, Jing,Ma, Yuling,Lin, Yuan,Zhang, Jichao,Huang, Yulan,Li, Wenhua,Zhu, Qiyu,Wei, Xiao,Li, Suiyan,Wisanwattana, Wisanee,Li, Fu,Liu, Wanli,Suksamrarn, Apichart,Zhang, Guolin,Jiao, Wei,Wang, Fei
, p. 460 - 484 (2022/01/03)
Cancer cell proliferation in some organs often depends on conversion of pyruvate to oxaloacetate via pyruvate carboxylase (PC) for replenishing the tricarboxylic acid cycle to support biomass production. In this study, PC was identified as the cellular target of erianin using the photoaffinity labeling-click chemistry-based probe strategy. Erianin potently inhibited the enzymatic activity of PC, which mediated the anticancer effect of erianin in human hepatocellular carcinoma (HCC). Erianin modulated cancer-related gene expression and induced changes in metabolic intermediates. Moreover, erianin promotes mitochondrial oxidative stress and inhibits glycolysis, leading to insufficient energy required for cell proliferation. Analysis of 14 natural analogs of erianin showed that some compounds exhibited potent inhibitory effects on PC. These results suggest that PC is a cellular target of erianin and reveal the unrecognized function of PC in HCC tumorigenesis; erianin along with its analogs warrants further development as a novel therapeutic strategy for the treatment of HCC.
Synthesis method of 2-benzoxepin compound
-
, (2021/05/29)
The invention discloses a synthesis method of a 2-benzoxepin compound. The method comprises the following specific steps: under the protection of nitrogen, adding N-phenylseleno-phthalimide into a reactor, then adding anhydrous dichloromethane to dissolve the N-phenylseleno-phthalimide, then adding a 1-[(cinnamyl) methyl]-3, 4, 5-trimethoxybenzene compound, taking zinc chloride as a catalyst, reacting at room temperature, adding saturated sodium bicarbonate for quenching after the reaction is finished, extracting by dichloromethane, combining organic phases, drying by anhydrous magnesium sulfate, concentrating under reduced pressure, and performing silica gel rapid chromatographic purification by thin-layer chromatography silica gel to obtain the 2-benzoxepin compound. The method is simple in reaction operation, mild in reaction condition, relatively high in yield, environment-friendly and suitable for large-scale industrialized production.
Pd-catalyzed sp-sp3cross-coupling of benzyl bromides using lithium acetylides
Buter, Jeffrey,Doze, Anna M.,Feringa, Ben L.,Mondal, Anirban,Visser, Paco
supporting information, p. 7529 - 7532 (2021/08/05)
Organolithium-based cross-coupling reactions have emerged as an indispensable method to construct C-C bonds. These transformations have proven particularly useful for the direct and fast coupling of various organolithium reagents (sp, sp2, and sp3) with aromatic (pseudo) halides (sp2). Here we present an efficient method for the cross-coupling of benzyl bromides (sp3) with lithium acetylides (sp). The reaction proceeds within 10 min at room temperature and can be performed in the presence of organolithium-sensitive functional groups such as esters, nitriles, amides and boronic esters. The potential application of the methodology is demonstrated in the preparation of key intermediates used in pharmaceuticals, chemical biology and natural products.
