2-bromo-N-(2-hydroxyphenyl)acetamide | 708262-58-2

• 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: 2-bromo-N-(2-hydroxyphenyl)acetamide
• CAS: 708262-58-2
• 化学式: C₈H₈BrNO₂
• 分子量: 230.061
• InChiKey: MFVLSYUAKKBHFY-UHFFFAOYSA-N

物化性质

• 沸点：
  389.2±27.0 °C(Predicted)
• 密度：
  1.715±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  49.3
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-bromo-N-(2-hydroxyphenyl)acetamide 在 sodium hydride 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 2-(3-氧代-1,4-苯并恶嗪-4-基)乙酸乙酯
  参考文献：
  名称：

  Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators

  摘要：

  With the aim of discovering new molecules with K+-channel activating properties, we have synthesized derivatives of cromakalim (CRK), an important molecule which shows specific affinity towards K+ channels, by replacing the benzopyrane ring of this reference compound with a 1,4-benzoxazine moiety. A different number of substituents showing a good discrimination between hydrophobic and electronic properties have been inserted at the 6-position of the 1,4-benzoxazine ring. We describe here the synthesis and discuss the solid state conformation of these new molecules. When tested on rat aorta ring precontracted with phenylephrine, two compounds (2c and 2d) showed a concentration-dependent relaxation similar to that measured for cromakalim but less potent than this reference drug. (C) Elsevier, Paris.

  DOI：

  10.1016/s0223-5234(99)80020-8
• 作为产物：
  描述：

  溴乙酰溴 、 2-氨基苯酚 在 sodium carbonate 作用下， 以 氯仿 为溶剂， 反应 3.0h， 生成 2-bromo-N-(2-hydroxyphenyl)acetamide
  参考文献：
  名称：

  新的1，4-苯并恶嗪衍生物钾通道开放剂的合成及其血管舒张活性。

  摘要：

  作为寻找新的钾通道开放剂的一部分，描述了衍生自克罗马卡林的苯并吡喃骨架的新的1,4-苯并恶嗪衍生物的合成和血管舒张活性。几种新的1,4-苯并恶嗪衍生物具有明显的血管舒张活性，其总体药理行为类似于CRK（1f，1i，2d，2e，2f和2i）。

  DOI：

  10.1016/s0968-0896(02)00091-3

文献信息

• [EN] INHIBITORS OF α-AMINO-β-CARBOXYMUCONIC ACID SEMIALDEHYDE DECARBOXYLASE<br/>[FR] INHIBITEURS DE LA SEMIALDÉHYDE DÉCARBOXYLASE DE L'ACIDE ALPHA-AMINO-BÊTA-CARBOXYMUCONIQUE
  申请人：TES PHARMA S R L

  公开号：WO2016030534A1

  公开（公告）日：2016-03-03

  The present disclosure discloses compounds capable of modulating the activity of α-amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.

  本公开揭示了能够调节α-氨基-β-羧基黄酮酸半醛脱羧酶（ACMSD）活性的化合物，这些化合物对于预防和/或治疗与NAD+生物合成缺陷相关的疾病和紊乱非常有用，例如代谢紊乱、神经退行性疾病、慢性炎症性疾病、肾脏疾病以及与衰老相关的疾病。本申请还揭示了包含所述化合物的药物组合物以及将这些化合物用作药物的用途。
• Synthesis, Characterization and Pharmacological Evaluation of N-Substituted Derivatives of 5-(4-Nitrophenyl)-1,3,4-oxadiazole-2yl-2"-sulphanyl Acetamide
  作者：Samreen Gul、Aziz-Ur-Rehman、Muhammad Athar Abbasi、Khadija Nafeesa、Abdul Malik、Muhammad Ashraf、Tayaba Ismail、Irshad Ahmad

  DOI：10.14233/ajchem.2013.14333

  日期：——

  A series of new N-substituted 5-(4-nitrophenyl)-1,3,4-oxadiazole-2-yl-2"-sulphanyl acetamides was synthesized and enzyme inhibiting activity was screened for all these chemical entities. Structural characterization of all these compounds was made by IR, EI-MS and 1H NMR. All derivatives demonstrated different extent of activity for lipoxygenase (LOX), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE). Compounds 6j exhibited excellent lipoxygenase inhibitory potential but against acetylcholinesterase the inhibitory potential is not appreciable and it is inactive against butyrylcholinesterase. Similarly compound 6e have good inhibitory potential against lipoxygenase with IC50 value 50.41 ± 0.12 μM while for acetylcholinesterase IC50 value is 174.21 ± 0.11 μM and 6e does not show any inhibitory potential for butyrylcholinesterase. Compound 6o showed good inhibition against acetylcholinesterase and butyrylcholinesterase but for lipoxygenase its inhibitory activity is the least.

  合成了一系列新的 N-取代 5-(4-硝基苯基)-1,3,4-恶二唑-2-基-2"-磺酰乙酰胺，并对所有这些化学实体的酶抑制活性进行了筛选。通过红外光谱、电离质谱和 1H NMR 对所有这些化合物进行了结构表征。所有衍生物都对脂氧合酶（LOX）、乙酰胆碱酯酶（AChE）和丁酰胆碱酯酶（BChE）表现出不同程度的活性。化合物 6j 对脂氧合酶有很好的抑制潜力，但对乙酰胆碱酯酶的抑制潜力不明显，而且对丁酰胆碱酯酶没有活性。同样，化合物 6e 对脂氧合酶具有良好的抑制潜力，IC50 值为 50.41 ± 0.12 μM，而对乙酰胆碱酯酶的 IC50 值为 174.21 ± 0.11 μM，6e 对丁酰胆碱酯酶没有显示出任何抑制潜力。化合物 6o 对乙酰胆碱酯酶和丁酰胆碱酯酶有很好的抑制作用，但对脂氧合酶的抑制活性最低。
• Inhibitors of alpha-amino-beta-carboxymuconic acid semialdehyde decarboxylase
  申请人：TES Pharma S.r.l.

  公开号：US11254644B2

  公开（公告）日：2022-02-22

  The present disclosure discloses compounds capable of modulating the activity of α-amino-β-carboxymuconic acid semialdehyde decarboxylase (ACMSD), which are useful for the prevention and/or the treatment of diseases and disorders associated with defects in NAD+ biosynthesis, e.g., metabolic disorders, neurodegenerative diseases, chronic inflammatory diseases, kidney diseases, and diseases associated with ageing. The present application also discloses pharmaceutical compositions comprising said compounds and the use of such compounds as a medicament.

  本申请公开了能够调节α-氨基-β-羧基琥珀酸半醛脱羧酶（ACMSD）活性的化合物，这些化合物可用于预防和/或治疗与NAD+生物合成缺陷有关的疾病和紊乱，例如代谢紊乱、神经退行性疾病、慢性炎症性疾病、肾脏疾病以及与衰老有关的疾病。本申请还公开了包含所述化合物的药物组合物以及将此类化合物用作药物的方法。
• 10.1016/j.tet.2024.134132
  作者：Darifa, Addichi、Aziz, Ihammi、Saliha, Loughmari、Khalid, Abdelmouna、Mohamed, Ellouz、Mohammed, Chigr

  DOI：10.1016/j.tet.2024.134132

  日期：——

  Owing to the biological importance of 1,2,3-triazoles and benzoxazine-3(4H)-ones scaffolds, we have attempted to design and synthesize novel 1,2,3-traizoles linked to benzoxazin-3-one moiety. Indeed, a novel series of 1,4-disubstituted 1,2,3-triazoles containing 2H-1,4-benzoxazin-

  由于1,2,3-三唑和苯并恶嗪-3(4H)-酮支架的生物学重要性，我们尝试设计和合成与苯并恶嗪-3-酮部分连接的新型1,2,3-三唑。事实上，一系列新型 1,4-二取代 1,2,3-三唑含有 2H-1,4-苯并恶嗪-
• Structure−Activity Relationships in the Binding of Chemically Derivatized CD4 to gp120 from Human Immunodeficiency Virus
  作者：Hui Xie、Danny Ng、Sergey N. Savinov、Barna Dey、Peter D. Kwong、Richard Wyatt、Amos B. Smith、Wayne A. Hendrickson

  DOI：10.1021/jm070564e

  日期：2007.10.1

  The first step in HIV infection is the binding of the envelope glycoprotein gp120 to the host cell receptor CD4. An interfacial "Phe43 cavity" in gp120, adjacent to residue Phe43 of gp120-bound CD4, has been suggested as a potential target for therapeutic intervention. We designed a CD4 mutant (D1D2F43C) for site-specific coupling of compounds for screening against the cavity. Altogether, 81 cysteine-reactive compounds were designed, synthesized, and tested. Eight derivatives exceeded the affinity of native D1D2 for gp 120. Structure-activity relationships (SAR) for derivatized CD4 binding to gp 120 revealed significant plasticity of the Phe43 cavity and a narrow entrance. The primary contacts for compound recognition inside the cavity were found to be van der Waals interactions, whereas hydrophilic interactions were detected in the entrance. This first SAR on ligand binding to an interior cavity of gp 120 may provide a starting point for structure-based assembly of small molecules targeting gp120-CD4 interaction.