methyl 4-bromo-3-ethoxy-5-hydroxybenzoate | 149517-94-2

• 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: methyl 4-bromo-3-ethoxy-5-hydroxybenzoate
• 英文别名: methyl 4-bromo-5-ethoxy-3-hydroxybenzoate
• CAS: 149517-94-2
• 化学式: C₁₀H₁₁BrO₄
• 分子量: 275.099
• InChiKey: OQTGCHJQFQDETR-UHFFFAOYSA-N

物化性质

• 沸点：
  379.2±37.0 °C(Predicted)
• 密度：
  1.507±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl 4-bromo-3-ethoxy-5-hydroxybenzoate 在 氢氧化钾 、 硝酸 作用下， 以 硝基甲烷 、 乙醇 、 二氯甲烷 为溶剂， 反应 16.17h， 生成 4-bromo-5-ethoxy-3-hydroxy-2-nitrobenzoic acid
  参考文献：
  名称：

  Synthesis and QSAR of substituted 3-hydroxyanthranilic acid derivatives as inhibitors of 3-hydroxyanthranilic acid dioxygenase (3-HAO)

  摘要：

  DOI：

  10.1016/s0223-5234(99)00220-2
• 作为产物：
  描述：

  4-bromo-5-ethoxy-3-hydroxybenzoic acid 以 甲醇 、 氯仿 为溶剂， 生成 methyl 4-bromo-3-ethoxy-5-hydroxybenzoate
  参考文献：
  名称：

  3-Hydroxy anthranilic acid derivatives for inhibiting 3-hydroxy anthranilate oxygenase

  摘要：

  本发明涉及一般式I的3-羟基蒽醌酸的新颖衍生物，其制备方法，新型药物组合物以及用于抑制产生内源神经毒素喹啉酸QUIN的酶3-羟基蒽醌酸氧化酶3-HAO的用途。

  公开号：

  EP0530166A2

文献信息

• [EN] Btk INHIBITORS WITH IMPROVED DUAL SELECTIVITY<br/>[FR] INHIBITEUR DE BTK AYANT UNE DOUBLE SÉLECTIVITÉ AMÉLIORÉE
  申请人：BEIGENE LTD

  公开号：WO2019034009A1

  公开（公告）日：2019-02-21

  Disclosed herein is a tri-substituted phenyl Btk inhibitors with improved dual selectivity, a method and a composition for inhibiting Btk and treating disease associated with undesirable Btk activity (Btk-related diseases).

  本文披露了一种具有改进的双重选择性的三取代苯基Btk抑制剂，以及用于抑制Btk和治疗与不良Btk活性相关的疾病（Btk相关疾病）的方法和组合物。
• BTK inhibitors with improved dual selectivity
  申请人：BEIGENE, LTD.

  公开号：US11377449B2

  公开（公告）日：2022-07-05

  Disclosed herein is a tri-substituted phenyl Btk inhibitors with improved dual selectivity, a method and a composition for inhibiting Btk and treating disease associated with undesirable Btk activity (Btk-related diseases).

  本文公开了一种具有改进的双选择性的三取代苯基 Btk 抑制剂、一种用于抑制 Btk 和治疗与不良 Btk 活性有关的疾病（Btk 相关疾病）的方法和组合物。
• Structural Requirements for Factor Xa Inhibition by 3-Oxybenzamides with Neutral P1 Substituents:  Combining X-ray Crystallography, 3D-QSAR, and Tailored Scoring Functions
  作者：Hans Matter、David W. Will、Marc Nazaré,、Herman Schreuder、Volker Laux、Volkmar Wehner

  DOI：10.1021/jm049187l

  日期：2005.5.1

  The design, synthesis, and structure-activity relationship of 3-oxybenzamides as potent inhibitors of the coagulation protease factor Xa are described on the basis of X-ray structures, privileged structure motifs, and SAR information. A total of six X-ray structures of fXa/inhibitor complexes led us to identify the major protein-ligand interactions. The binding mode is characterized by a lipophilic dichlorophenyl substituent interacting with Tyr228 in the protease S1 pocket, while polar parts are accommodated in S4. This alignment in combination with docking allowed derivation of 3D-QSAR models and tailored scoring functions to rationalize biological affinity and provide guidelines for optimization. The resulting models showed good correlation coefficients and predictions of external test sets. Furthermore, they correspond to binding site topologies in terms of steric, electrostatic, and hydrophobic complementarity. Two approaches to derive tailored scoring functions combining binding site and ligand information led to predictive models with acceptable predictions of the external set. Good correlations to experimental affinities were obtained for both AFMoC (adaptation of fields for molecular comparison) and the novel TScore function. The SAR information from 3D-QSAR and tailored scoring functions agrees with all experimental data and provides guidelines and reasonable activity estimations for novel fXa inhibitors.
• Novel factor Xa inhibitors based on a benzoic acid scaffold and incorporating a neutral P1 ligand
  作者：Marc Nazaré、Hans Matter、Otmar Klingler、Fahad Al-Obeidi、Herman Schreuder、Gerhard Zoller、Jörg Czech、Martin Lorenz、Angela Dudda、Anusch Peyman、Hans Peter Nestler、Matthias Urmann、Armin Bauer、Volker Laux、Volkmar Wehner、David W. Will

  DOI：10.1016/j.bmcl.2004.03.059

  日期：2004.6

  A series of novel, highly potent, achiral factor Xa inhibitors based on a benzoic acid scaffold and containing a chlorophenethyl moiety directed towards the protease S1 pocket is described. A number of structural features, such as the requirements of the P1, P4 and ester-binding pocket ligands were explored with respect to inhibition of factor Xa. Compound 46 was found to be the most potent compound in a series of antithrombotic secondary assays. (C) 2004 Elsevier Ltd. All rights reserved.
• NEW COMPOUNDS
  申请人：Astra Aktiebolag

  公开号：EP0643686A1

  公开（公告）日：1995-03-22