1-[(氨基氧基)甲基]-3-(三氟甲基)苯 | 85661-08-1

• 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: 1-[(氨基氧基)甲基]-3-(三氟甲基)苯
• 英文名称: O-(3-(trifluoromethyl)benzyl)hydroxylamine
• 英文别名: O-(3-trifluoromethylbenzyl)hydroxylamine；O-(3-Trifluormethyl-benzyl)-hydroxylamin；O-[[3-(trifluoromethyl)phenyl]methyl]hydroxylamine
• CAS: 85661-08-1
• 化学式: C₈H₈F₃NO
• 分子量: 191.153
• InChiKey: NXIOZALQLKJKPW-UHFFFAOYSA-N

物化性质

• 沸点：
  231.9±40.0 °C(Predicted)
• 密度：
  1.280±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  13
• 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：
  5

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  1-[(氨基氧基)甲基]-3-(三氟甲基)苯 在 盐酸 作用下， 以 乙醚 为溶剂， 生成 间三氟甲基苄氧胺盐酸盐
  参考文献：
  名称：

  O-alkylhydroxylamines as rationally-designed mechanism-based inhibitors of indoleamine 2,3-dioxygenase-1

  摘要：

  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.

  DOI：

  10.1016/j.ejmech.2015.12.028
• 作为产物：
  描述：

  3-三氟甲基苯甲醇 在 N-羟基邻苯二甲酰亚胺 、 三苯基膦 、 偶氮二甲酸二乙酯 、 一水合肼 作用下， 以 四氢呋喃 为溶剂， 反应 3.58h， 生成 1-[(氨基氧基)甲基]-3-(三氟甲基)苯
  参考文献：
  名称：

  通过CH活化将苄醇转化为邻氨基苯甲醛：喹唑啉的一种简便方法

  摘要：

  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...

  DOI：

  10.1039/c6cc05560e

文献信息

• Synthesis of anthelmintically activeN-methylated amidoxime analogues of the cyclic octadepsipeptide PF1022A
  作者：Peter Jeschke、Achim Harder、Georg von Samson-Himmelstjerna、Winfried Etzel、Wolfgang Gau、Gerhard Thielking、Gerhard Bonse

  DOI：10.1002/ps.590

  日期：2002.12

  product PF1022A. In particular an improved efficacy against Haemonchus contortus Rudolphi and Trichostrongylus colubriformis Giles in sheep compared to the potent cyclic octadepsipeptide PF1022A and its mono-thionated derivative has been observed. Here we report on a specific modification at the N-methyl amide linkage by using the mono-thionated PF1022A, resulting in novel anthelmintically active backbone

  环状十八肽PF1022A的N-甲基化a胺肟类似物代表新型衍生物，具有体外抗旋毛虫欧文和巴西柔毛夜蛾活性，并具有抗小鼠和绵羊寄生线虫的活性。与天然产物PF1022A相比，它们中的一些在小鼠中表现出更好的抗Hymenolepis nana Siebold，Spterosa Schneider和Heligmosomoides polygyrus Dujardin活性。尤其是，与强效的环八肽肽PF1022A及其单亚硫代衍生物相比，已观察到对绵羊的弯曲变形金丝猴（Ruemonphi Rutorphi）和毛细线虫（Trichostrongylus colubriformis Giles）有改善的功效。在这里，我们报告了通过使用单亚硫代PF1022A在N-甲基酰胺键处的特定修饰，从而产生了PF 1022A的新型具有抗炎活性的骨架类似物。
• 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...
• Pyrazole-amides and -sulfonamides
  申请人：Atkinson N. Robert

  公开号：US20050049237A1

  公开（公告）日：2005-03-03

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子流来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了吡唑酰胺和磺酰胺，以及其组合物和方法，这些化合物、组合物和方法对于治疗中枢或外周神经系统疾病特别是疼痛和慢性疼痛非常有用，通过阻止与所述疾病的发作或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚基的通道中的离子流来治疗神经病理性或炎性疼痛。
• PYRAZOLE-AMIDES AND -SULFONAMIDES
  申请人：Atkinson N. Robert

  公开号：US20080064690A1

  公开（公告）日：2008-03-13

  Compounds, compositions and methods are provided which are useful in the treatment of diseases through the inhibition of sodium ion flux through voltage-dependent sodium channels. More particularly, the invention provides pyrazole-amides and -sulfonamides, compositions and methods that are useful in the treatment of central or peripheral nervous system disorders, particularly pain and chronic pain by blocking sodium channels associated with the onset or recurrance of the indicated conditions. The compounds, compositions and methods of the present invention are of particular use for treating neuropathic or inflammatory pain by the inhibition of ion flux through a channel that includes a PN3 subunit.

  本发明提供了一种通过抑制电压依赖性钠通道中的钠离子通量来治疗疾病的化合物、组合物和方法。更具体地，本发明提供了嘧唑酰胺和磺酰胺、组合物和方法，用于治疗中枢或外周神经系统障碍，特别是疼痛和慢性疼痛，通过阻断与指示条件的发生或复发有关的钠通道。本发明的化合物、组合物和方法特别适用于通过抑制包括PN3亚单位的通道中的离子通量来治疗神经病理性或炎症性疼痛。
• 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。