602314-41-0Relevant articles and documents
Ultrasound accelerated synthesis of: O-alkylated hydroximides under solvent- A nd metal-free conditions
Jiang, Hongmei,Tang, Xiaoyue,Liu, Sihan,Wang, Lian,Shen, Haicheng,Yang, Jiankui,Wang, Huixian,Gui, Qing-Wen
, p. 10223 - 10227 (2019/12/26)
A novel, sustainable, environmentally friendly, high substrate scope, efficient, solvent-free and metal catalyst-free method for the cross-dehydrogenative coupling (CDC) reaction between N-hydroxyphthalimide (NHPI) and benzyl/ether compounds is described. This coupling reaction proceeds through ultrasound acceleration. Compared to conventional heating conditions, the use of ultrasound techniques not only improves the reaction efficiency and enhances the reaction rate but also minimizes the side reactions.
O-benzyl-N-(9-acridinyl)hydroxylamines
Johnson, Alyssa L.,Duncan, Nathan,Mosher, Michael D.
, p. 139 - 148 (2018/06/27)
A series of O-benzyl-N-(9-acridinyl)hydroxylamines was prepared, isolated, and evaluated for biological activity using both thermal denaturation and MTT assays. Changes in the thermal denaturation temperature of genomic calf-thymus DNA ranged from +6.6 °C to +20.2 °C. MTT assays on SNB-19 glioblastoma cells provided biological activity that ranged from 17.4 μM to 33.2 μM. Both evaluation methods of biological activity indicate that substitution of the benzyl group by either electron-withdrawing or electron-donating groups provides a measureable benefit in these assays. The two assays agreed on the magnitude of the interaction for each substitution pattern.
O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1
Malachowski, William P.,Winters, Maria,DuHadaway, James B.,Lewis-Ballester, Ariel,Badir, Shorouk,Wai, Jenny,Rahman, Maisha,Sheikh, Eesha,LaLonde, Judith M.,Yeh, Syun-Ru,Prendergast, George C.,Muller, Alexander J.
, p. 564 - 576 (2016/01/09)
Indoleamine 2,3-dioxygenase-1 (IDO1) is a promising therapeutic target for the treatment of cancer, chronic viral infections, and other diseases characterized by pathological immune suppression. Recently important advances have been made in understanding IDO1's catalytic mechanism. Although much remains to be discovered, there is strong evidence that the mechanism proceeds through a heme-iron bound alkylperoxy transition or intermediate state. Accordingly, we explored stable structural mimics of the alkylperoxy species and provide evidence that such structures do mimic the alkylperoxy transition or intermediate state. We discovered that O-benzylhydroxylamine, a commercially available compound, is a potent sub-micromolar inhibitor of IDO1. Structure-activity studies of over forty derivatives of O-benzylhydroxylamine led to further improvement in inhibitor potency, particularly with the addition of halogen atoms to the meta position of the aromatic ring. The most potent derivatives and the lead, O-benzylhydroxylamine, have high ligand efficiency values, which are considered an important criterion for successful drug development. Notably, two of the most potent compounds demonstrated nanomolar-level cell-based potency and limited toxicity. The combination of the simplicity of the structures of these compounds and their excellent cellular activity makes them quite attractive for biological exploration of IDO1 function and antitumor therapeutic applications.
NBu4NI-catalyzed intermolecular C-O cross-coupling reactions: Synthesis of alkyloxyamines
Lv, Yunhe,Sun, Kai,Wang, Tingting,Li, Gang,Pu, Weiya,Chai, Nannan,Shen, Huihui,Wu, Yingtao
, p. 72142 - 72145 (2015/09/08)
A practical and simple nBu4NI-catalyzed C-O bond formation for the synthesis of alkyloxyamines was achieved under metal-free conditions. The reaction is applicable to the coupling of a range of benzylic and allylic hydrocarbons with N-hydroxyphthalimide and is tolerant of various functional groups. The reaction mechanism was primarily investigated and a radical process was proposed.
Organocatalytic Radical Involved Oxidative Cross-Coupling of N-Hydroxyphthalimide with Benzylic and Allylic Hydrocarbons
Dian, Longyang,Wang, Sisi,Zhang-Negrerie, Daisy,Du, Yunfei
supporting information, p. 3836 - 3842 (2016/01/25)
The cross-coupling reaction between N-hydroxyphthalimide and various benzylic and allylic hydrocarbons was realized through an organocatalytic radical-mediated process involving C(sp3)-O bond formation using tert-butyl hydroperoxide (t-BuOOH) as an oxidant and tetra-n-butylammonium iodide [(n-Bu]4NI] as a catalyst, during which the phthalimide N-oxyl (PINO) radical and benzylic and allylic radicals were generated in situ and underwent the selective radical/radical cross-coupling reaction. This novel method provides a convenient metal-free approach to the synthesis of O-alkylated hydroxy imides under mild reaction conditions.
2-[(arylmethoxy)imino]imidazolidines with potential biological activities
Saczewski, Jaroslaw,Hudson, Alan L.,Rybczynska, Apolonia
experimental part, p. 671 - 680 (2010/07/04)
A series of 2-[(arylmethoxy)imino]imidazolidines was synthesized by reacting 2-chloro-4,5-dihydroimidazole with corresponding O- arylmethylhydroxylamines and evaluated for their α1-, α2-adrenergic and imidazoline I1, I2 receptor binding affinities. The most potent 2-[(naphthalen-1-ylmethoxy)imino] imidazolidine showed a high selectivity and good affinity for the [ 3H]prazosin-labeled α1-adrenoceptors (Ki = 107 nM). Representative compounds of this series were also tested in vivo for possible circulatory effects in rats after intravenous administration.
1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists
Alanine, Alexander,Bourson, Anne,Buettelmann, Bernd,Gill, Ramanjit,Heitz, Marie-Paule,Mutel, Vincent,Pinard, Emmanuel,Trube, Gerhard,Wyler, Rene
, p. 3155 - 3159 (2007/10/03)
Screening of the Roche compound depository led to the identification of (1-benzyloxy-4,5-dihydro-1H-imidazol-2-yl)-butyl amine 4, a structurally novel NR1/2B subtype selective NMDA receptor antagonist. The structure-activity relationships developed in this series resulted in the discovery of a novel class of potent and selective NMDA receptor blockers displaying activity in vivo.
