O-(3-甲基苄基)羟胺 | 5555-50-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: O-(3-甲基苄基)羟胺
• 英文名称: O-(3-methylbenzyl)hydroxylamine
• 英文别名: O-[(3-methylphenyl)methyl]hydroxylamine
• CAS: 5555-50-0
• 化学式: C₈H₁₁NO
• 分子量: 137.181
• InChiKey: CMKJWNXXUNBWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  10
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  35.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  O-(3-甲基苄基)羟胺 在 碳酸氢钠 、 一水合肼 作用下， 以 乙醇 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-(3-Methyl-benzyloxy)-4,5-dihydro-1H-imidazole-2-thiol
  参考文献：
  名称：

  1-Benzyloxy-4,5-dihydro-1H-imidazol-2-yl-amines, a novel class of NR1/2B subtype selective NMDA receptor antagonists

  摘要：

  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. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00713-3
• 作为产物：
  描述：

  3-甲基苄基氯 生成 O-(3-甲基苄基)羟胺
  参考文献：
  名称：

  羟胺衍生物的合成具有降胆固醇的活性。

  摘要：

  DOI：

  10.1021/jm00316a012

文献信息

• Transformation of masked benzyl alcohols to o-aminobenzaldehydes through C–H activation: a facile approach to quinazolines
  作者：Xiaolan Chen、Jian Han、Yan Zhu、Chunchen Yuan、Jingyu Zhang、Yingsheng Zhao

  DOI：10.1039/c6cc05560e

  日期：——

  Direct Transformation of directing group to important synthetic units would provide a high atom efficiency synthetic approach in synthetic chemistry. Herein, a convenient protocol in synthesis of o-aminobenzaldehyde and benzoxazole...

  指导基团直接转化为重要的合成单元将为合成化学提供一种高原子效率的合成方法。此处是合成邻氨基苯甲醛和苯并恶唑的便捷方法...
• IDO Inhibitors
  申请人：Mautino Mario

  公开号：US20110053941A1

  公开（公告）日：2011-03-03

  Presently provided are methods for (a) modulating an activity of indoleamine 2,3-dioxygenase comprising contacting an indoleamine 2,3-dioxygenase with a modulation effective amount of a compound as described in one of the aspects described herein; (b) treating indoleamine 2,3-dioxygenase (IDO) mediated immunosuppression in a subject in need thereof, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (c) treating a medical conditions that benefit from the inhibition of enzymatic activity of indoleamine-2,3-dioxygenase comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; (d) enhancing the effectiveness of an anti-cancer treatment comprising administering an anti-cancer agent and a compound as described in one of the aspects described herein; (e) treating tumor-specific immunosuppression associated with cancer comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount of a compound as described in one of the aspects described herein; and (f) treating immunosuppression associated with an infectious disease, e.g., HIV-I infection, comprising administering an effective indoleamine 2,3-dioxygenase inhibiting amount a compound as described in one of the aspects described herein.

  目前提供以下方法：(a) 通过接触本文中描述的化合物的调节有效量与吲哚胺2,3-二氧化酶相互作用，从而调节吲哚胺2,3-二氧化酶的活性；(b) 治疗需要吲哚胺2,3-二氧化酶(IDO)介导的免疫抑制的患者，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(c) 治疗需要抑制吲哚胺-2,3-二氧化酶酶活性的医疗状况，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(d) 增强抗癌治疗的有效性，包括给予抗癌剂和本文中描述的化合物；(e) 治疗与癌症相关的肿瘤特异性免疫抑制，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量；(f) 治疗与传染病相关的免疫抑制，例如HIV-1感染，包括给予本文中描述的化合物的有效吲哚胺2,3-二氧化酶抑制剂量。
• NON-STEROIDAL COMPOUNDS
  申请人：Stewart Alastair

  公开号：US20120046255A1

  公开（公告）日：2012-02-23

  The present invention relates to non-steroidal compounds useful in the treatment of inflammatory conditions and pharmaceutical compositions comprising them. A representative example of these compounds is

  本发明涉及非甾体化合物，可用于治疗炎症状况，以及包含它们的制药组合物。这些化合物的代表性例子是：
• Palladium(II)-Catalyzed Remote <i>meta</i>-C–H Functionalization of Arenes Enabled by Multitasking Oxyamides as the Linker
  作者：Yue-Lu Zhu、Qiu-Xue Sun、Jin-Shuo Feng、You-Dong Shao、Jiao Chen

  DOI：10.1021/acs.orglett.3c01101

  日期：2023.6.23

  A palladium-catalyzed olefination of meta-C–H bonds in arenes containing oxyamides using a nitrile template as the directing group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groups such as benzyloxyamides and olefin substrates. The desired products were obtained in good yields. This approach enabled the modification of natural products and

  已经建立了使用腈模板作为导向基团在含有草酰胺的芳烃中进行间位-C-H键的钯催化烯化反应。该方法表现出高间位选择性并耐受不同的官能团，例如苄氧基酰胺和烯烃底物。以良好的收率获得了所需的产物。这种方法能够对天然产物和药物进行修饰，并且也适用于克级。此外，通过选择性裂解酰胺键或O-N键，可以轻松去除定向模板，以获得间位官能化的羟胺和苯甲醇。所提出的方法对于新药的设计具有巨大的潜力。
• O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1
  作者：William P. Malachowski、Maria Winters、James B. DuHadaway、Ariel Lewis-Ballester、Shorouk Badir、Jenny Wai、Maisha Rahman、Eesha Sheikh、Judith M. LaLonde、Syun-Ru Yeh、George C. Prendergast、Alexander J. Muller

  DOI：10.1016/j.ejmech.2015.12.028

  日期：2016.1

  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. (C) 2015 Elsevier Masson SAS. All rights reserved.