1014-23-9Relevant articles and documents
Cu-Catalyzed Oxidative-Reaction of Tosylmethylisocyanide and Benzyl Alcohols: Efficient Synthesis of 4-(tert-butylperoxy)-5-aryloxazol-2(3H)-ones and 5-Aryloxazol-2(5H)-ones
Sepahvand, Heshmatollah,Bazgir, Ayoob,Shaabani, Ahmad
, p. 2068 - 2075 (2020)
Herein, a novel copper-catalyzed reaction of tosylmethylisocyanide (TosMIC) with benzyl alcohols has been developed using tert-butyl hydroperoxide (TBHP) for the first time. The reaction involves the in-situ oxidation of benzyl alcohol to corresponding be
Discovery of a Potent Glutathione Peroxidase 4 Inhibitor as a Selective Ferroptosis Inducer
Xu, Congjun,Xiao, Zhanghong,Wang, Jing,Lai, Hualu,Zhang, Tao,Guan, Zilin,Xia, Meng,Chen, Meixu,Ren, Lingling,He, Yuanfeng,Gao, Yuqi,Zhao, Chunshun
, p. 13312 - 13326 (2021/09/28)
Potent and selective ferroptosis regulators promote an intensive understanding of the regulation and mechanisms underlying ferroptosis, which is highly associated with various diseases. In this study, through a stepwise structure optimization, a potent and selective ferroptosis inducer was developed targeting to inhibit glutathione peroxidase 4 (GPX4), and the structure-activity relationship (SAR) of these compounds was uncovered. Compound26aexhibited outstanding GPX4 inhibitory activity with a percent inhibition up to 71.7% at 1.0 μM compared to 45.9% of RSL-3. At the cellular level,26acould significantly induce lipid peroxide (LPO) increase and effectively induce ferroptosis with satisfactory selectivity (the value of 31.5). The morphological analysis confirmed the ferroptosis induced by26a. Furthermore,26asignificantly restrained tumor growth in a mouse 4T1 xenograft model without obvious toxicity.
Reaction Conditions for the Regiodivergent Direct Arylations at C2- or C5-Positions of Oxazoles using Phosphine-Free Palladium Catalysts
Shi, Xinzhe,Soulé, Jean-Fran?ois,Doucet, Henri
, p. 4748 - 4760 (2019/09/12)
Two sets of reaction conditions for the regiodivergent C2- or C5- direct arylations of oxazole are reported. In both cases, phosphine-free catalysts and inexpensive bases were employed allowing the access to the arylated oxazoles in moderate to high yields. Using Pd(OAc)2/KOAc as catalyst and base, regioselective C5-arylations were observed; whereas, using Pd(acac)2/Cs2CO3 system, the arylation occurred at the C2-position of oxazole. The higher reactivity of C5-H bond of oxazole as compared to the C2-H bond in the presence of Pd(OAc)2/KOAc system is consistent with a concerted metalation deprotonation mechanism; whereas the C2-arylation likely occurs via a simple base deprotonation of the oxazole C2-position. Then, from these C2- or C5-arylated oxazoles, a second palladium-catalyzed direct C?H bond arylation affords 2,5-diaryloxazoles with two different aryl groups. We also applied these sequential arylations to the straightforward synthesis of 2-arylphenanthro[9,10-d]oxazoles via three C?H bond functionalization steps. The Ru-catalyzed C?H arylation of the aryl unit of 2-aryloxazoles is also described. (Figure presented.).
