O-methyl-N-(4-methylbenzyl)hydroxylamine | 330685-48-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: O-methyl-N-(4-methylbenzyl)hydroxylamine
• 英文别名: O-Methyl-N-(4-methyl-benzyl)-hydroxylamine；n-(4-Methylbenzyl)-o-methyl-hydroxylamine；N-methoxy-1-(4-methylphenyl)methanamine
• CAS: 330685-48-8
• 化学式: C₉H₁₃NO
• mdl: MFCD21100680
• 分子量: 151.208
• InChiKey: BNRQWGXEMCSRMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  21.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  D-葡萄糖 、 O-methyl-N-(4-methylbenzyl)hydroxylamine 以 甲醇 、 氯仿 、 溶剂黄146 为溶剂， 反应 48.0h， 以71%的产率得到O-methyl-N-(4-methylbenzyl)-N-(β-D-glucopyranosyl)hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019
• 作为产物：
  描述：

  4-methylbenzaldehyde-O-methyl oxime 在 盐酸 、 吡啶硼烷 作用下， 以 乙醇 、 水 为溶剂， 以3.29 g的产率得到O-methyl-N-(4-methylbenzyl)hydroxylamine
  参考文献：
  名称：

  Synthesis and biological evaluation of RON-neoglycosides as tumor cytotoxins

  摘要：

  Cardenolides such as digitoxin have been shown to inhibit cancer cell growth, to reduce cancer metastasis, and to induce apoptosis in tumor cells. Among the most potent digitoxin-based cytotoxins identified to date are MeON-neoglycosides generated via oxyamine neoglycosylation. Here, we report our studies of oxyamine neoglycosylation aimed at facilitating the elucidation of linkage-diversified digitoxin neoglycoside structure-activity relationships. We identified conditions suitable for the convenient synthesis of digitoxin neoglycosides and found that sugar structure, rather than RON-glycosidic linkage, exerts the strongest influence on neoglycoside yield and stereochemistry. We synthesized a library of digitoxin neoglycosides and assessed their cytotoxicity against eight human cancer cell lines. Consistent with previous findings, our data show that the structure of RON-neoglycosidic linkages influences both the potency and selectivity of digitoxin neoglycosides. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.09.019

文献信息

• HIV Integrase inhibitors
  申请人：——

  公开号：US20030176495A1

  公开（公告）日：2003-09-18

  The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the following formula, or a tautomer of said compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof: 1 wherein R 1 , R 2 and B 1 are as defined herein.

  本发明涉及抑制HIV整合酶，以及通过给予以下化合物、该化合物的互变异构体、或其药学上可接受的盐、溶剂化合物或前药来治疗艾滋病或ARC的方法：1其中R1、R2和B1如本文所定义。
• [EN] PROCESS FOR PREPARING PEPTIDE DEFORMYLASE INHIBITORS<br/>[FR] PROCÉDÉS DE PRÉPARATION D'INHIBITEURS DE LA PEPTIDE DÉFORMYLASE
  申请人：GLAXOSMITHKLINE IP NO 2 LTD

  公开号：WO2014141181A1

  公开（公告）日：2014-09-18

  The present invention relates to processes for making 2-(alkyl)-3-[2-(5-fluoro-4-pyrimidinyl) hydrazino]-3-oxopropyl}hydroxyformamide compounds of Formula (I), or pharmaceutically acceptable salts thereof and corresponding intermediates thereof, where such compounds are useful in the inhibition of bacterial peptide deformylase (PDF) activity and in treatment methods for bacterial infections.

  本发明涉及制备Formula(I)中的2-(烷基)-3-[2-(5-氟-4-嘧啶基)肼基]-3-氧代丙基}羟基甲酰胺化合物或其药用可接受的盐及相应的中间体的方法，其中这些化合物在抑制细菌肽变形酶（PDF）活性和治疗细菌感染的方法中具有用途。
• HIV integrase inhibitors
  申请人：Bristol-Myers Squibb Company

  公开号：US06777440B2

  公开（公告）日：2004-08-17

  The present invention relates to the inhibition of HIV integrase, and to the treatment of AIDS or ARC by administering compounds of the following formula, or a tautomer of said compound, or a pharmaceutically acceptable salt, solvate or prodrug thereof: wherein R1, R2 and B1 are as defined herein.

  本发明涉及抑制HIV整合酶以及通过给予以下式的化合物、其互变异构体或其药学上可接受的盐、溶剂或前药来治疗艾滋病或ARC的方法：其中R1，R2和B1如此定义。
• Synthesis, Structure, and Binding of Some 2-Imidazolines to Rat Brain Alfa-1 and Alfa-2-Adrenergic Receptors
  作者：F. Saczewski、E. Kobierska、T. Debowski、S. Charakchiewa-Minol、M. Mokrosz、M. Gdaniec、E. Nowak

  DOI：10.1002/1521-4184(200012)333:12<425::aid-ardp425>3.0.co;2-a

  日期：2000.12

  A series of novel 2-[(2-aminophenyl)imino]imidazolinium salts 3a-d and N-benzyl-N-(4,5-dihydro-imidazol-2-yl)-O-methylhydroxylamine hydrochloride 7a-c were prepared and their structure was determined by IR and NMR spectroscopic data as well as X-ray analysis of the imidazolinium azide salt 3e. Binding evaluation for both alpha 1- and alpha 2-adrenergic receptors in rat brain preparations of these compounds and the previously described alpha-hydroxy-2-aryliminoimidazolines 11a-d, N-(4,5-dihydroimidazol-2-yl)-1,3-2-oxodihydrobenzimidazoles 12a-b, 2-amino-N-(4,5-dihydroimidazol-2-yl)-benzimidazoles 13a-b, and N-(4,5-dihydroimidazol-2-yl)-indoles 14a-b was performed. Among the compounds tested, 2-[(2-amino-4,5-dichlorophenyl)imino]imidazolinium chloride 3c showed highest binding affinity to alpha 2-adrenoreceptors (Ki = 30 nM).
• US6777440B2
  申请人：——

  公开号：US6777440B2

  公开（公告）日：2004-08-17