13519-75-0Relevant articles and documents
Evidence for a hydrogen abstraction mechanism in P450-catalyzed N-dealkylations
Bhakta, Mehul,Hollenberg, Paul F.,Wimalasena, Kandatege
, p. 265 - 267 (2005)
The experimental evidence presented in this manuscript suggest against the widely accepted single electron/proton transfer mechanism for P450 catalyzed N-dealkylations and provides strong support for a hydrogen atom abstraction mechanism.
Novel hybrid conjugates with dual estrogen receptor α degradation and histone deacetylase inhibitory activities for breast cancer therapy
Zhao, Chenxi,Tang, Chu,Li, Changhao,Ning, Wentao,Hu, Zhiye,Xin, Lilan,Zhou, Hai-Bing,Huang, Jian
, (2021/05/10)
Hormone therapy targeting estrogen receptors is widely used clinically for the treatment of breast cancer, such as tamoxifen, but most of them are partial agonists, which can cause serious side effects after long-term use. The use of selective estrogen receptor down-regulators (SERDs) may be an effective alternative to breast cancer therapy by directly degrading ERα protein to shut down ERα signaling. However, the solely clinically used SERD fulvestrant, is low orally bioavailable and requires intravenous injection, which severely limits its clinical application. On the other hand, double- or multi-target conjugates, which are able to synergize antitumor activity by different pathways, thus may enhance therapeutic effect in comparison with single targeted therapy. In this study, we designed and synthesized a series of novel dual-functional conjugates targeting both ERα degradation and histone deacetylase inhibiton by combining a privileged SERD skeleton 7-oxabicyclo[2.2.1]heptane sulfonamide (OBHSA) with a histone deacetylase inhibitor side chain. We found that substituents on both the sulfonamide nitrogen and phenyl group of OBHSA unit had significant effect on biological activities. Among them, conjugate 16i with N-methyl and naphthyl groups exhibited potent antiproliferative activity against MCF-7 cells, and excellent ERα degradation activity and HDACs inhibitory ability. A further molecular docking study indicated the interaction patterns of these conjugates with ERα, which may provide guidance to design novel SERDs or PROTAC-like SERDs for breast cancer therapy.
Highly Active Ni Nanoparticles on N-doped Mesoporous Carbon with Tunable Selectivity for the One-Pot Transfer Hydroalkylation of Nitroarenes with EtOH in the Absence of H2
Tao, Yuewen,Nie, Yunqing,Hu, Haitao,Wang, Ke,Chen, Yi,Nie, Renfeng,Wang, Jianshe,Lu, Tianliang,Zhang, Yongsheng,Xu, Chunbao Charles
, p. 4243 - 4250 (2021/08/20)
Cost-effective and environmentally friendly conversion of nitroarenes into value-added products is desirable but still challenging. In this work, highly dispersed Ni nanoparticles (NPs) supported on N-doped mesoporous carbon (Ni/NC-x) were synthesized via novel ion exchange-pyrolysis strategy. Their catalytic performance was investigated for one-pot transfer hydroalkylation of nitrobenzene (NB) with EtOH in absence of H2. Interestingly, the catalytic performance could be easily manipulated by tuning the morphology and electronic state of Ni NPs via varying the pyrolysis temperature. It was found that the Ni/NC-650 achieved 100 % nitrobenzene conversion and approx. 90 % selectivity of N,N-diethyl aniline at 240 °C for 5 h, more active than those of homogeneous catalysts or supported Ni catalysts prepared by impregnation (Ni/NC-650-IM, Ni/SiO2). This can be ascribed to the higher dispersion and better reducibility as well as richer surface basicity of the catalyst. More interestingly, the Ni/NC-650 catalyst achieved complete conversion of various nitroarenes, yielding imines, secondary amines, or tertiary amines selectively by simply controlling the reaction temperature at 180, 200 and 240 °C, respectively. The one-pot hydrogen-free process with non-noble metal catalysts, as demonstrated in this work, shows great promise for selective conversion of nitroarenes with ethanol to various anilines at industrial scale, from an economic, environmental, and safety viewpoint.
Diethylsilane as a Powerful Reagent in Au Nanoparticle-Catalyzed Reductive Transformations
Louka, Anastasia,Kidonakis, Marios,Saridakis, Iakovos,Zantioti-Chatzouda, Elisavet-Maria,Stratakis, Manolis
, p. 3508 - 3514 (2020/06/02)
Diethylsilane (Et2SiH2), a simple and readily available dihydrosilane, that exhibits superior reactivity, as compared to monohydrosilanes, in a series of reductive transformations catalyzed by recyclable and reusable Au nanoparticles (1 mol-%) supported on TiO2. It reduces aldehydes or ketones almost instantaneously at ambient conditions. It can be used in a one pot rapid reductive amination procedure, in which premixing of aldehyde and amine is required prior to the addition of the reducing agent and the catalyst, even in a protic solvent. An unprecedented method for the synthesis of N-arylisoindolines is also shown in the reductive amination between o-phthalaldehyde and anilines. In this transformation, it is proposed that the intermediate N,2-diphenylisoindolin-1-imines are reduced stepwise to the isoindolines. Finally, Et2SiH2 readily reduces amides into amines in excellent yields and shorter reaction times relative to previously known analogous nano Au(0)-catalyzed protocols.
