2-羟基-4-甲氧基苯硼酸 | 1068155-43-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 中文名称: 2-羟基-4-甲氧基苯硼酸
• 英文名称: (2-hydroxy-4-methoxyphenyl)boronic acid
• 英文别名: 2-Hydroxy-4-methoxyphenylboronic acid
• CAS: 1068155-43-0
• 化学式: C₇H₉BO₄
• 分子量: 167.957
• InChiKey: SULLGJWNKYFKQU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.92
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 储存条件：
  存储条件：2-8°C，密封保存，置于干燥且惰性气体环境中。

反应信息

• 作为反应物：
  描述：

  2-羟基-4-甲氧基苯硼酸 、 6-bromo-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridine 在 potassium phosphate 、 tris-(dibenzylideneacetone)dipalladium(0) 、 4,5-双二苯基膦-9,9-二甲基氧杂蒽 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 以70%的产率得到5-methoxy-2-[3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl]-phenol
  参考文献：
  名称：

  3，6-二芳基-[1,2,4]三唑并[4,3-a]吡啶类似物作为新型有效的微管蛋白聚合抑制剂的合成及生物学评价。

  摘要：

  在我们以前的工作的基础上，设计，合成和评估了29种具有3,4,5-三甲氧基苯基的[1,2,4]三唑并[4,3-a]吡啶，作为微管蛋白聚合抑制剂。生物测定结果表明，某些化合物在纳摩尔范围内对HeLa细胞显示出优异的抗增殖作用，最有前途的衍生物7i的活性几乎与参考CA-4相当，并且效力比母体化合物高62倍。6的IC 50值为12 nM。重要的是，7i对正常人胚胎肾HEK-293细胞具有高选择性（IC 50  > 100μM）。进一步的机理研究表明7i显着阻止了G2 / M期的细胞周期，以剂量依赖的方式诱导了细胞凋亡，并破坏了微管网络。此外，活性最高的化合物7i有效抑制微管蛋白聚合，其值类似于CA-4（分别为3.4和4.2μM）。此外，分子对接分析表明7i很好地占据了微管蛋白的秋水仙碱结合口袋。本研究强调化合物7i是一种新型的潜在微管蛋白聚合抑制剂，值得进一步研究治疗癌症。

  DOI：

  10.1016/j.ejmech.2020.112625

文献信息

• Xantphos‐ligated palladium dithiolates: An unprecedented and convenient catalyst for the carbonylative Suzuki–Miyaura cross‐coupling reaction with high turnover number and turnover frequency
  作者：Vinayak V. Gaikwad、Pravin A. Mane、Sandip Dey、Bhalchandra M. Bhanage

  DOI：10.1002/aoc.5255

  日期：2020.1

  Suzuki–Miyaura cross‐coupling reaction have been synthesized. The catalysts were characterized by 1H‐nuclear magnetic resonance (NMR), CHNS (carbon, hydrogen, nitrogen, and sulfur) analysis, melting point analysis, and 31P‐NMR spectroscopy. Several sensitive functional groups (e.g., –NO2, –F, –Cl, –Br, –NH2, and –CN) on the aromatic ring were well tolerated in the carbonylative Suzuki–Miyaura coupling reaction

  已经合成了黄磷和二硫醇盐连接的大环钯配合物，作为羰基化Suzuki-Miyaura交叉偶联反应的有效和稳定的催化剂。通过1 H核磁共振（NMR），CHNS（碳，氢，氮和硫）分析，熔点分析和31 P-NMR光谱对催化剂进行表征。几个敏感的官能团（例如，-NO 2，-F，-Cl，-Br，-NH 2，和-CN）在芳环上被Suzuki-Miyaura羰基化偶联反应很好地耐受。与常规的均相钯前体相比，本发明的钯络合物产生更高的周转数（TON）和更高的周转频率（TOF）五倍。在10的范围内最大吨5到10 6和TOF在10范围4到10 5可通过的催化剂负载（10的非常低的量来产生-5 摩尔％）。
• [EN] UROLITHIN DERIVATIVES AND METHODS OF USE THEREOF<br/>[FR] DÉRIVÉS D'UROLITHINE ET LEURS PROCÉDÉS D'UTILISATION
  申请人：VANDRIA SA

  公开号：WO2022162471A1

  公开（公告）日：2022-08-04

  Disclosed are compounds, compositions, and methods useful for treating neuronal and mitochondrial diseases.

  本发明涉及用于治疗神经元和线粒体疾病的化合物、组合物和方法。
• Finger-loop inhibitors of the HCV NS5b polymerase. Part 1: Discovery and optimization of novel 1,6- and 2,6-macrocyclic indole series
  作者：David McGowan、Sandrine Vendeville、Tse-I Lin、Abdellah Tahri、Lili Hu、Maxwell D. Cummings、Katie Amssoms、Jan Martin Berke、Maxime Canard、Erna Cleiren、Pascale Dehertogh、Stefaan Last、Els Fransen、Elisabeth Van Der Helm、Iris Van den Steen、Leen Vijgen、Marie-Claude Rouan、Gregory Fanning、Origène Nyanguile、Kristof Van Emelen、Kenneth Simmen、Pierre Raboisson

  DOI：10.1016/j.bmcl.2012.03.097

  日期：2012.7

  Novel conformationaly constrained 1,6- and 2,6-macrocyclic HCV NS5b polymerase inhibitors, in which either the nitrogen or the phenyl ring in the C2 position of the central indole core is tethered to an acylsulfamide acid bioisostere, have been designed and tested for their anti-HCV potency. This transformational route toward non-zwitterionic finger loop-directed inhibitors led to the discovery of derivatives with improved cell potency and pharmacokinetic profile. (C) 2012 Elsevier Ltd. All rights reserved.
• Discovery of <i>N</i>-(1-Ethylpropyl)-[3-methoxy-5-(2-methoxy-4-trifluoromethoxyphenyl)-6-methyl-pyrazin-2-yl]amine <b>59</b> (NGD 98−2): An Orally Active Corticotropin Releasing Factor-1 (CRF-1) Receptor Antagonist
  作者：Kevin J. Hodgetts、Ping Ge、Taeyoung Yoon、Stéphane De Lombaert、Robbin Brodbeck、Michael Gulianello、Andrzej Kieltyka、Raymond F. Horvath、John H. Kehne、James E. Krause、George D. Maynard、Diane Hoffman、Younglim Lee、Laurence Fung、Dario Doller

  DOI：10.1021/jm200365y

  日期：2011.6.23

  The design, synthesis, and structure-activity relationships of a novel series of pyrazines, acting as corticotropin releasing factor-1 (CRF-1) receptor antagonists, are described. Synthetic methodologies were developed to prepare a number of substituted pyrazine cores utilizing regioselective halogenation and chemoselective derivatization. Noteworthy, an efficient 5-step synthesis was developed for the lead compound 59 (NGD 98-2), which required no chromatography. Compound 59 was characterized as an orally bioavailable, brain penetrant, and highly selective CRF-1 receptor antagonist. Occupancy of rat brain CRF-1 receptors was quantified using ex vivo receptor occupancy assays, using both brain tissue homogenates as well as brain slices receptor autoradiography. Behaviorally, oral administration of 59 significantly antagonized CRF-induced locomotor activity at doses as low as 10 mg/kg and dose-dependently reduced the restraint stress-induced ACTH increases.
• THERAPEUTIC USES OF UROLITHIN DERIVATIVES
  申请人：[en]VANDRIA SA

  公开号：WO2024025953A2

  公开（公告）日：2024-02-01

  Disclosed are methods for treating a neuromuscular disorder, muscle disorder, heart disease, pulmonary fibrosis, liver disease, inflammatory bowel disease, or cancer. Also disclosed is a method of enhancing cancer immunotherapy.