1-[(氨基氧基)甲基]-4-氟苯盐酸盐 | 51572-89-5

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物
• 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]-4-氟苯盐酸盐
• 中文别名: O-[(4-氟苯基)甲基]羟胺盐酸盐
• 英文名称: O-(4-fluorobenzyl)hydroxylamine hydrochloride
• 英文别名: O-[(4-fluorophenyl)methyl]hydroxylamine;hydrochloride
• CAS: 51572-89-5
• 化学式: C₇H₈FNO*ClH
• 分子量: 177.606
• InChiKey: YZNDOVGYWWHJBB-UHFFFAOYSA-N

物化性质

• 熔点：
  225-235°

计算性质

• 辛醇/水分配系数(LogP)：
  1.64
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  35.2
• 氢给体数：
  2
• 氢受体数：
  3

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922199090
• 包装等级：
  III
• 危险类别：
  4.1
• 危险性防范说明：
  P240,P210,P264,P280,P370+P378,P337+P313
• 危险品运输编号：
  1325
• 危险性描述：
  H228,H315,H319

反应信息

• 作为反应物：
  描述：

  1-[(氨基氧基)甲基]-4-氟苯盐酸盐 在 四(三苯基膦)钯 、 sodium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 甲苯 为溶剂， 反应 36.0h， 生成 (E)-N-[(4-fluorophenyl)methoxy]-1-[2-(4-methylsulfanylphenyl)cyclopenten-1-yl]methanimine
  参考文献：
  名称：

  (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](arylmethyloxy)amines. Methyleneaminoxymethyl (MAOM) analogues of diarylcyclopentenyl cyclooxygenase-2 inhibitors: synthesis and biological properties

  摘要：

  The (E)-[2-(4-Methylsulphonylphenyl)-1-cyclopentenyl-1-methyliden](methyloxy)amine (5) and (arylmethyloxy)amines (6-12) were designed in order to verify the effects on the biological properties of the substitution of an aryl of selective diarylcyclopentenyl cyclooxygenase-2 (COX-2) inhibitors. of type 3 with a methyleneaminoxymethyl moiety (MAOMM). Compounds 5-12 were tested in vitro for their inhibitory activity towards COX-1 and COX-2 by measuring prostaglandin E2 (PGE2) production in U937 cell lines and activated J774.2 macrophages, respectively. The compound with the highest in vitro activity towards COX-2 (9) was also assayed in vivo for its antiinflammatory activity by means of the carrageenan-induced paw edema test in rats. Some of the new compounds showed an appreciable in vitro COX-2 inhibitory activity, with IC50 values in the muM (6,7,9,10,11) range. Compound 9 also exhibited an appreciable in vivo activity (29% inhibition at a dose of 30 mg kg(-1)) when administered intraperitoneally. The structural parameters of 9 were determined by X-ray crystallographic analysis. (C) 2002 Editions scientifiques et medicales Elsevier SAS. All rights reserved.

  DOI：

  10.1016/s0223-5234(02)01359-4
• 作为产物：
  描述：

  对氟苯甲醇 在 盐酸 、 偶氮二甲酸二异丙酯 、 一水合肼 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 3.5h， 生成 1-[(氨基氧基)甲基]-4-氟苯盐酸盐
  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

文献信息

• SUBSTITUTED 1-HYDROXY-PYRIDIN-2(1H)-ONES, AND METHODS OF MAKING AND USING SAME
  申请人：ARBUTUS BIOPHARMA CORPORATION

  公开号：US20190169128A1

  公开（公告）日：2019-06-06

  The present invention includes novel substituted 1-hydroxy-pyridin-2(1H)-ones, which can be used to treat or prevent hepatitis B virus (HBV) infections in a patient. In certain embodiments, the compounds and compositions of the invention inhibit HBV RNAse H activity.

  本发明涉及新型的取代1-羟基吡啶-2(1H)-酮，可用于治疗或预防患者体内的乙型肝炎病毒（HBV）感染。在某些实施方式中，本发明的化合物和组合物抑制HBV RNA酶H活性。
• Design, synthesis and evaluation of wound healing activity for β-sitosterols derivatives as potent Na+/K+-ATPase inhibitors
  作者：Shaoyu Cui、Hongli Jiang、Lei Chen、Jian Xu、Wenzhuo Sun、Haopeng Sun、Zijian Xie、Yunhui Xu、Fubai Yang、Wenyuan Liu、Feng Feng、Wei Qu

  DOI：10.1016/j.bioorg.2019.103150

  日期：2020.5

  demonstrated. Na+/K+-ATPase, more than a pump, its signal transduction function for involvement in cell growth regulation attracts widespread concern. The Na+/K+-ATPase/Src receptor complex can serve as a receptor involved in multiple signaling pathways including promoting wound healing pathways. To finding potent accelerating wound healing small molecular, we choose the high inhibitory activity of Na+/K+-ATPase

  β-谷甾醇是一种常见的类固醇，可以在多种植物中鉴定出来，并且已证明它们在促进伤口愈合方面具有功效。Na + / K + -ATPase不仅仅是一种泵，其参与细胞生长调节的信号转导功能引起了广泛关注。Na + / K + -ATPase / Src受体复合物可作为参与多种信号途径（包括促进伤口愈合途径）的受体。为了找到有效的加速伤口愈合的小分子，我们选择了具有高抑制活性的Na + / K + -ATPase和无心脏毒性的天然化合物β-谷甾醇作为底物。设计，合成和评估了一系列β-谷甾醇衍生物，作为潜在的Na + / K + -ATPase抑制剂。其中，化合物31、47、49对Na + / K + -ATPase的抑制活性增强，IC50值分别为3.0μM，3.4μM，2.2μM，比β-谷甾醇的IC50 7.6μM更有效。特别地，化合物49可以诱导L929成纤维细胞中的细胞增殖，迁移和可溶性胶原蛋
• Design, synthesis and evaluation of oxime-functionalized nitrofuranylamides as novel antitubercular agents
  作者：Yi-Lei Fan、Jian-Bing Wu、Xing Ke、Zhong-Ping Huang

  DOI：10.1016/j.bmcl.2018.07.046

  日期：2018.10

  H37Rv and drug-resistant clinical isolates. Among them, two compounds 7a and 7b exhibited excellent activity against the three tested strains. Both of them were comparable to the first-line anti-TB agents INH and RIF against MTB H37Rv, and were far more potent than INH and RIF against MDR-TB 16833 and 16995 strains. Thus, both of them could act as leads for further optimization.

  设计，合成了一系列肟官能化的硝基呋喃酰胺，并评估了它们对MTB H37Rv和耐药临床分离株的体外抗分枝杆菌活性。其中，两种化合物7a和7b对三种测试菌株表现出优异的活性。它们两者均与针对MTB H37Rv的一线抗结核病药物INH和RIF相当，并且比针对MDR-TB 16833和16995菌株的INH和RIF更有力。因此，它们两者都可以作为进一步优化的线索。
• Vinylogous Aza‐Michael Addition of Urea Derivatives with <i>p</i> ‐Quinone Methides Followed by Oxidative Dearomative Cyclization: Approach to Spiroimidazolidinone Derivatives
  作者：Navpreet Kaur、Priyanka Singh、Prabal Banerjee

  DOI：10.1002/adsc.202100077

  日期：2021.6.8

  report an efficient protocol for the synthesis of spiro-imidazolidinone-cyclohexadienones from p-quinone methides (p-QMs) and dialkyloxy ureas under mild conditions. The strategy follows a two-step process involving an initial vinylogous conjugate addition of urea derivatives to p-QMs, followed by oxidative dearomative cyclization of open-chain product to the projected spiro-imidazolidinones. This protocol

  在此，我们报告了一种在温和条件下从对醌甲基化物 ( p- QMs) 和二烷氧基脲合成螺-咪唑烷酮-环己二烯酮的有效方案。该策略遵循两步过程，包括将脲衍生物初始与p- QMs 进行乙烯基共轭加成，然后将开链产物氧化脱芳环化成预期的螺-咪唑烷酮。该协议表现出良好的官能团耐受性，并提供了一种直接的方法来访问螺-咪唑烷酮-环己二烯酮。在后续化学中，我们已经展示了螺咪唑烷酮的脱苄基化作用，得到N-羟基环脲。
• Synthesis and antibacterial evaluation of (E)-1-(1H-indol-3-yl) ethanone O-benzyl oxime derivatives against MRSA and VRSA strains
  作者：Ravikumar Akunuri、Vaishnavi Veerareddy、Grace Kaul、Abdul Akhir、Tanveer Unnissa、Ramulu Parupalli、Y.V. Madhavi、Sidharth Chopra、Srinivas Nanduri

  DOI：10.1016/j.bioorg.2021.105288

  日期：2021.11

  attracted attention of researchers owing to their interesting biological properties. Current work details the synthesis of indole containing oxime ether derivatives and their evaluation for antimicrobial activity against a panel of bacterial and mycobacterial strains. Synthesized compounds demonstrated good to moderate activity against drug-resistant S. aureus including resistant to vancomycin. Among

  由多重耐药菌引起的感染已成为对人类健康的持续威胁。尽管目前有多种抗生素可用于治疗传染病，但仍有大量细菌菌株对其中的许多菌株产生了抗药性。其中，金黄色葡萄球菌引起的感染在成人和儿童人群中占主导地位。吲哚是一种突出的化学支架，存在于许多具有药理活性的天然产品和合成药物中。许多含肟醚的化合物由于其有趣的生物学特性而引起了研究人员的关注。目前的工作详细介绍了含吲哚肟醚衍生物的合成及其对一组细菌和分枝杆菌菌株的抗菌活性的评估。合成的化合物对耐药性金黄色葡萄球菌表现出良好到中等的活性，包括对万古霉素的耐药性。其中，发现化合物5h对金黄色葡萄球菌的敏感菌株以及 MRSA 和 VRSA 菌株具有强效活性具有1μMIC克/毫升和2-4μ克/毫升分别。此外，发现化合物5h对 Vero 细胞无毒，并表现出>40 的良好选择性指数。此外，5h、E -9a和E -9b对金黄色葡萄球菌具有良好的生物膜抑制作用。有了这