1-(2-ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol | 174689-38-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 四氢化萘
• 英文名称: 1-(2-ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol
• 英文别名: 3-(2-ethylphenoxy)-1[(1S)-1,2,3,4-tetrahydronaphth-1-ylamino]-(2S)-2-propanol；SR 59230A；SR59230A；RU-0084642；SR-59230A free base；(2S)-1-(2-ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]amino]propan-2-ol
• CAS: 174689-38-4
• 化学式: C₂₁H₂₇NO₂
• 分子量: 325.451
• InChiKey: VFDHMSXXELYMRW-ICSRJNTNSA-N

物化性质

• 沸点：
  519.6±50.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  41.5
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  草酸 、 1-(2-ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol 以 异丙醇 为溶剂， 以84.9%的产率得到3-(2-乙基苯氧基)-1-((1S)-1,2,3,4-四-氢萘-1-基氨基)-(2S)-2-丙醇草酸盐
  参考文献：
  名称：

  Synthesis of all of the stereoisomers of β3-adrenoceptor antagonist SR 59230 based on the spontaneous resolution of 3-(2-ethylphenoxy)propane-1,2-diol

  摘要：

  Racemic 3-(2-ethylphenoxy)propane-1,2-diol 2 has been effectively resolved into (S)- and (R)-enantiomers by a preferential crystallization procedure. Non-racemic diols 2, obtained via a Mitsunobu reaction, have been converted into the non-racemic 1,2-epoxy-3-(2-ethylphenoxy)propanes (S)- and (R)-5 and then into non-racemic 3-(2-ethylphenoxy)-1(1,2,3,4-tetrahydronaphth-1-ylamino)-2-propanols 1. The characteristics of all four stereoisomers, (S,S)-1 (SR 59230), (R,R)-1 (SR 59483), (R,S)-1 and (S,R)-1 (SR 59231) and their hydrogen oxalates with a 1:1 composition have been presented. The crystalline oxalates (S,S)-1 center dot C2H2O4 (SR 59230A) and (R,S)-1 center dot 0.5C(2)H(2)O(4) were studied by single crystal X-ray diffraction. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.05.001
• 作为产物：
  描述：

  乙基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 反应 108.17h， 生成 1-(2-ethylphenoxy)-3-[[(1S)-1,2,3,4-tetrahydro-1-naphthalenyl]amino]-(2S)-2-propanol
  参考文献：
  名称：

  一组新型 β-肾上腺素能受体配体的合理设计、合成和药理学评估能够评估结构-活性关系

  摘要：

  在过去十年中，能够调节 β-肾上腺素能信号的分子的生物医学应用变得越来越有吸引力，表明 β-肾上腺素能受体 (β-ARs) 是包括癌症在内的多种治疗干预的关键靶点。尽管在 β-AR 药物发现方面取得了成功，但鉴定可用作三种 β-AR 亚型药理学研究中的选择性化学工具的 β-AR 配体或用于药物开发的先导化合物仍然是一项极具挑战性的任务。这主要是由于 β-AR 作为 G 蛋白偶联受体的内在可塑性，以及对功能性受体亚型选择性、组织特异性和最小脱靶效应的要求。为了深入了解三种 β-AR 亚型的构效关系，MC ) 是基于 SR59230A 的芳氧基丙醇胺支架设计的。对它们在受体活性和非活性状态下的预测结合模式及其药理学特征的比较分析揭示了控制它们作为激动剂或拮抗剂活性的关键结构元素，此外还有关于介导一种受体亚型选择性的取代基的线索其他。我们预计这些结果将促进选择性 β-AR 药物的开发工作。

  DOI：

  10.1016/j.ejmech.2022.114961

文献信息

• Methods and materials for determining pain sensibility and predicting and treating related disorders
  申请人：The University of North Carolina At Chapel Hill

  公开号：EP2484780A1

  公开（公告）日：2012-08-08

  Methods of treating somatosensory disorders and modulating production of proinflammatory cytokines by administering to a subject an effective amount of a COMT modulator, ADRB2 modulator, ADRB3 modulator or combinations thereof are provided. Methods of predicting effective pharmacological therapies for a subject afflicted with a somatosensory disorder by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided. Methods of determining pain responses or pain perception and predicting susceptibility of a subject to develop related disorders, such as somatosensory disorders and somatization, by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided.

  提供了通过向受试者施用有效量的 COMT 调节剂、ADRB2 调节剂、ADRB3 调节剂或其组合来治疗躯体感觉障碍和调节促炎细胞因子产生的方法。还提供了通过确定受试者选自 COMT、ADRB2、ADRB3 及其组合组成的组的基因的基因型来预测患有躯体感觉障碍的受试者的有效药物疗法的方法。还提供了通过确定受试者选自 COMT、ADRB2、ADRB3 及其组合组成的组的基因的基因型来确定疼痛反应或疼痛感知以及预测受试者患相关疾病（如躯体感觉障碍和躯体化）的易感性的方法。
• Methods and materials for determining pain sensitivity and predicting and treating related disorders
  申请人：The University of North Carolina at Chapel Hill

  公开号：US11085081B2

  公开（公告）日：2021-08-10

  Methods of treating somatosensory disorders and modulating production of proinflammatory cytokines by administering to a subject an effective amount of a COMT modulator, ADRB2 modulator, ADRB3 modulator or combinations thereof are provided. Methods of predicting effective pharmacological therapies for a subject afflicted with a somatosensory disorder by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided. Methods of determining pain responses or pain perception and predicting susceptibility of a subject to develop related disorders, such as somatosensory disorders and somatization, by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided.

  提供了通过向受试者施用有效量的 COMT 调节剂、ADRB2 调节剂、ADRB3 调节剂或其组合来治疗躯体感觉障碍和调节促炎细胞因子产生的方法。还提供了通过确定受试者选自 COMT、ADRB2、ADRB3 及其组合组成的组的基因的基因型来预测患有躯体感觉障碍的受试者的有效药物疗法的方法。还提供了通过确定受试者选自 COMT、ADRB2、ADRB3 及其组合组成的组的基因的基因型来确定疼痛反应或疼痛感知以及预测受试者患相关疾病（如躯体感觉障碍和躯体化）的易感性的方法。
• METHODS AND MATERIALS FOR DETERMINING PAIN SENSITIVITY AND PREDICTING AND TREATING RELATED DISORDERS
  申请人：The University of North Carolina at Chapel Hill

  公开号：EP1782321A2

  公开（公告）日：2007-05-09
• Methods and Materials for Determining Pain Sensitivity and Predicting and Treating Related Disorders
  申请人：UNIVERSITY OF NORTH CAROLINA AT CHAPEL HILL

  公开号：US20130244233A1

  公开（公告）日：2013-09-19

  Methods of treating somatosensory disorders and modulating production of proinflammatory cytokines by administering to a subject an effective amount of a COMT modulator, ADRB2 modulator, ADRB3 modulator or combinations thereof are provided. Methods of predicting effective pharmacological therapies for a subject afflicted with a somatosensory disorder by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided. Methods of determining pain responses or pain perception and predicting susceptibility of a subject to develop related disorders, such as somatosensory disorders and somatization, by determining a genotype of the subject with regard to a gene selected from the group consisting of COMT, ADRB2, ADRB3, and combinations thereof are further provided.
• SIGMA-1 RECEPTOR AGONIST SYSTOLIC BLOOD PRESSURE THERAPY
  申请人：ANAVEX LIFE SCIENCES CORP.

  公开号：US20210186920A1

  公开（公告）日：2021-06-24

  A method for lowering systolic blood pressure in a patient exhibiting resistance to a antihypertensive therapy with one or more drugs, the method comprising administering to the patient ANAVEX®2-73 at a dose and frequency effective to provide a reduction of at least about 3 mmHg in one or more blood pressure parameters selected from trough sitting systolic, 24-hour ambulatory systolic, and maximum diurnal systolic blood pressures.