1-(2-羟基-5-丙氧基苯基)乙酮 | 288074-68-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 1-(2-羟基-5-丙氧基苯基)乙酮
• 英文名称: 2-hydroxy-5-propoxyacetophenone
• 英文别名: 1-(5-propoxy-2-hydroxyphenyl)ethan-1-one；1-(2-hydroxy-5-propoxyphenyl)ethanone
• CAS: 288074-68-0
• 化学式: C₁₁H₁₄O₃
• mdl: MFCD20483723
• 分子量: 194.23
• InChiKey: PSKYLWRFWHJACM-UHFFFAOYSA-N

物化性质

• 沸点：
  302.7±22.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.363
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(2-羟基-5-丙氧基苯基)乙酮 在 sodium chlorite 、 草酰氯 、 氨基磺酸 、 N,N-二甲基甲酰胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 反应 1.75h， 生成 Methyl 4-oxo-6-propoxychromene-3-carboxylate
  参考文献：
  名称：

  Structure−Activity Relationships of a Novel Class of Endothelin-A Receptor Antagonists and Discovery of Potent and Selective Receptor Antagonist, 2-(Benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3- carboxylic Acid (S-1255). 1. Study on Structure−Activity Relationships and Basic Structure Crucial for ET_A Antagonism

  摘要：

  A novel series of endothelin-A (ETA) selective receptor antagonists having a 2H-chromene skeleton are described. A lead compound, 2-(benzo[1,3]dioxol-5-yl)-2H-chromene-3-carboxylic acid (3), was found by modifications of our own angiotensin II antagonist. A structure-activity relationship (SAR) study of 3 reveals that the structural requirements essential for potent and selective ETA receptor binding affinity are the m,p-methylenedioxyphenyl, carboxyl, and isopropoxy groups at the 2-, 3-, and 6-positions, respectively, on the (R)-2H-chromene skeleton. The substituent at the 4-position is also important for improving the activity, and various hydrophobic functional groups of 6-9 Angstrom such as liner, branched, and cyclic aliphatic groups, unsubstituted and substituted aryl groups, and even halogen atoms were acceptable. These results suggest that (R)-2-(benzo[1,3]dioxol-5-yl)-6-isopropoxy-2H-chromene-3-carboxylic acid, formula 108, is the crucial basic structure to be recognized by the ETA receptor. The most potent compound is (R)-48 (S-1255), which binds to the ETA receptor with an IC50 value of 0.19 nM and is 630-fold selective for the ETA receptor than for the ETB receptor. This compound has 55% oral bioavailability in rats. On the basis of the SAR, the roles of each substituent in the receptor binding are discussed.

  DOI：

  10.1021/jm010382z
• 作为产物：
  描述：

  1-碘代丙烷 、 2,5-二羟基苯乙酮 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 30.0h， 生成 1-(2-羟基-5-丙氧基苯基)乙酮
  参考文献：
  名称：

  2-carbamide-4-phenylthiazole derivatives, preparation thereof and therapeutic use thereof

  摘要：

  该披露涉及通式（I）的2-氨基甲酰胺-4-苯基噻唑衍生物。该披露还涉及含有通式（I）化合物的药物组合物，以及制备通式（I）化合物的方法和使用方法。

  公开号：

  US20070179126A1

文献信息

• Synthetic Utility and Mechanistic Implications of the Fries Rearrangement of Hydroquinone Diesters in Boron Trifluoride Complexes
  作者：Jessica L. Boyer、Jodie E. Krum、Michael C. Myers、Aleem N. Fazal、Carl T. Wigal

  DOI：10.1021/jo000412q

  日期：2000.7.1

  trifluoride etherate complexes results in acetylhydroquinone derivatives. This procedure represents a one-step synthesis of acetylhydroquinone derivatives, important building blocks for a variety of synthetic applications.

  三氟化硼甲基和乙基醚化物配合物与对苯二酚二酯的反应可生成乙酰氢醌的单甲基和单乙基衍生物。使用位阻三氟化硼醚化物配合物会生成乙酰氢醌衍生物。该步骤代表一步合成乙酰氢醌衍生物，这是各种合成应用的重要组成部分。
• 2-carbamide-4-phenylthiazole derivatives, preparation thereof and therapeutic use thereof
  申请人：Casellas Pierre

  公开号：US20070179126A1

  公开（公告）日：2007-08-02

  The disclosure concerns 2-carbamide-4-phenylthiazole derivatives of general formula (I). The disclosure also concerns pharmaceutical compositions containing a compound of general formula (I) and to processes for preparing and methods of using compounds of general formula (I).

  该披露涉及通式（I）的2-氨基甲酰胺-4-苯基噻唑衍生物。该披露还涉及含有通式（I）化合物的药物组合物，以及制备通式（I）化合物的方法和使用方法。
• Effect of the Chromone Core Substitution of Dirchromone on the Resultant Biological Activities
  作者：Alexis St-Gelais、Jérôme Alsarraf、Jean Legault、Joanne Plourde、André Pichette

  DOI：10.1021/acs.jnatprod.1c00385

  日期：2021.11.26

  Dirchromone is a bioactive vinyl sulfoxide-bearing chromone first isolated from the shrub Dirca palustris. Altogether, 32 of its derivatives were prepared to assess the effect of substitution of its chromone core upon activities against cancer cell lines, Gram-positive bacteria, and fungi (such as Candida albicans). All compounds were synthesized following a synthetic strategy involving Pummerer and

  Dirchromone 是一种生物活性的带有乙烯基亚砜的色酮，首先从灌木Dirca palustris中分离出来。总共制备了 32 种衍生物来评估其色酮核心取代对癌细胞系、革兰氏阳性细菌和真菌（如白色念珠菌）活性的影响。）。所有化合物都是按照涉及 Pummerer 和软烯醇化 Baker-Venkataraman 重排的合成策略合成的。取代基位置的变化对测试的活性几乎没有影响。细胞毒性和抗菌作用之间没有相关性，表明不同的潜在作用机制。特别是羟基和氰化物取代基降低了细胞毒性，后者具有增强的抗菌活性。6-烷氧基二色酮的高级同系物也表现出逐渐出现的抗真菌活性。其他修饰对细胞毒性有中等影响，一些衍生物导致效力增加。这种行为突出了天然二色酮药效团对装饰的稳健性，从而为更精细的未来药物设计铺平了道路。
• 2-Acylamino-4-phenylthiazole derivatives, preparation thereof and therapeutic application thereof
  申请人：Carayon Pierre

  公开号：US20060135575A1

  公开（公告）日：2006-06-22

  The invention relates to 2-acylamino-4-phenylthiazole derivatives of general formula (I): pharmaceutically acceptable acid-addition salts thereof, hydrates or solvates of such derivatives or such pharmaceutically acceptable acid addition salts, intermediates thereto, processes for the preparation thereof, and therapeutic application thereof.

  该发明涉及一般式（I）的2-酰氨基-4-苯基噻唑衍生物：其药学上可接受的酸加盐、这些衍生物的水合物或溶剂合物，或这些药学上可接受的酸加盐，以及这些衍生物的中间体，其制备方法和治疗应用。
• 2-acylamino-4-phenylthiazole derivatives, preparation thereof and therapeutic application thereof
  申请人：Sanofi-Aventis

  公开号：US07504511B2

  公开（公告）日：2009-03-17

  The invention relates to 2-acylamino-4-phenylthiazole derivatives of general formula (I): pharmaceutically acceptable acid-addition salts thereof, hydrates or solvates of such derivatives or such pharmaceutically acceptable acid addition salts, intermediates thereto, processes for the preparation thereof, and therapeutic application thereof.

  本发明涉及一般式（I）的2-酰胺基-4-苯基噻唑衍生物：其药物可接受的酸加成盐，这种衍生物或这种药物可接受的酸加成盐的水合物或溶剂化合物，其中间体，其制备过程以及其治疗应用。