55418-31-0Relevant academic research and scientific papers
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.
Transformation of masked benzyl alcohols to: O -aminobenzaldehydes through C-H activation: A facile approach to quinazolines
Chen, Xiaolan,Han, Jian,Zhu, Yan,Yuan, Chunchen,Zhang, Jingyu,Zhao, Yingsheng
supporting information, p. 10241 - 10244 (2016/10/22)
Direct transformation of a directing group to important synthetic units would provide a high atom efficiency synthetic approach in synthetic chemistry. Herein, a convenient protocol for the synthesis of o-aminobenzaldehyde and benzoxazole derivatives from benzyl alcohols has been developed by employing (N,N-dimethyl)oxamoyl amide as a directing group in a palladium-catalyzed intramolecular amination. Furthermore, the attached directing center may not only be transformed into the product, but may also be further applied to generate synthetically important quinazoline and quinoline units. Finally, a high atom efficiency one-pot, two-step approach to form quinazolines from benzyl alcohol derivatives has been achieved in good yields, thus demonstrating its high utility.
Design, synthesis and antifungal activities of novel pyrrole alkaloid analogs
Wang, Ming-Zhong,Xu, Han,Liu, Tuan-Wei,Feng, Qi,Yu, Shu-Jing,Wang, Su-Hua,Li, Zheng-Ming
experimental part, p. 1463 - 1472 (2011/05/04)
A series of novel analogs of pyrrole alkaloid were designed and synthesized by a facile method and their structures were characterized by 1H NMR, 13C NMR and high-resolution mass spectrometry (HRMS). The structure of compound 2a was identified by 2D NMR including heteronuclear multiple-quantum coherence (HMQC), heteronuclear multiple-bond correlation (HMBC) and H-H correlation spectrometry (H-H COSY) spectra. Their antifungal activities against five fungi were evaluated, and the results indicated that some of the title compounds showed moderate fungicidal activities in vitro against Alternaria solani, Cercospora arachidicola, Fusarium omysporum, Gibberella zeae and Physalospora piricola at the dosage of 50 μg mL -1. Compound 2a and 3a exhibited good activities against P. piricola at low dosage.
Synthesis and aldose reductase inhibitory activity of N-(arylsulfonyl)- and N-(aroyl)-N-(arylmethyloxy)glycines
Balsamo, A.,Belfiore, M. S.,Macchia, M.,Martini, C.,Nencetti, S.,et al.
, p. 787 - 794 (2007/10/02)
Some N-(arylsulfonyl)- C and N-(aroyl)-N-(arylmethyloxy)glycines D were synthesised and tested as aldose reductase inhibitors (ARIs).They are structurally related to the previously described ARIs of type A and B, from which they differ owing to the presen
