(1R,2S)-2-amino-1-(4-(methylthio)phenyl)propan-1-ol hydrochloride | 1028459-36-0

• 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: (1R,2S)-2-amino-1-(4-(methylthio)phenyl)propan-1-ol hydrochloride
• 英文别名: (1R,2S)-2-amino-1-[4-(methylthio)phenyl]propan-1-ol hydrochloride；(1R,2S)-2-amino-1-(4-methylsulfanylphenyl)propan-1-ol;hydrochloride
• CAS: 1028459-36-0
• 化学式: C₁₀H₁₅NOS*ClH
• 分子量: 233.762
• InChiKey: YFAQJTUWUGDMOJ-YUWZRIFDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.21
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  71.6
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-5-碘-1H-吲唑 、 (1R,2S)-2-amino-1-(4-(methylthio)phenyl)propan-1-ol hydrochloride 在 copper(l) iodide 、 caesium carbonate 作用下， 反应 22.0h， 以72%的产率得到(1R,2S)-1-((1-(4-fluorophenyl)-1H-indazol-5-yl)oxy)-1-(4-(methylthio)phenyl)propan-2-amine
  参考文献：
  名称：

  Discovery of indazole ethers as novel, potent, non-steroidal glucocorticoid receptor modulators

  摘要：

  A structure-based design approach led to the identification of a novel class of indazole ether based, nonsteroidal glucocorticoid receptor (GR) modulators. Several examples were identified that displayed cell potency in the picomolar range, inhibiting LPS-induced TNF-alpha release by primary peripheral blood mononuclear cells (PBMCs). Additionally, an improved steroid hormone receptor binding selectivity profile, compared to classical steroidal GR agonists, was demonstrated. The indazole ether core tolerated a broad range of substituents allowing for modulation of the physiochemical parameters. A small subset of indazole ethers, with pharmacokinetic properties suitable for oral administration, was investigated in a rat antigen-induced joint inflammation model and demonstrated excellent anti-inflammatory efficacy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.052
• 作为产物：
  描述：

  tert-butyl (1R,2S)-1-hydroxy-1-(4-(methylthio)phenyl)propan-2-ylcarbamate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 反应 1.5h， 以98%的产率得到(1R,2S)-2-amino-1-(4-(methylthio)phenyl)propan-1-ol hydrochloride
  参考文献：
  名称：

  Discovery of indazole ethers as novel, potent, non-steroidal glucocorticoid receptor modulators

  摘要：

  A structure-based design approach led to the identification of a novel class of indazole ether based, nonsteroidal glucocorticoid receptor (GR) modulators. Several examples were identified that displayed cell potency in the picomolar range, inhibiting LPS-induced TNF-alpha release by primary peripheral blood mononuclear cells (PBMCs). Additionally, an improved steroid hormone receptor binding selectivity profile, compared to classical steroidal GR agonists, was demonstrated. The indazole ether core tolerated a broad range of substituents allowing for modulation of the physiochemical parameters. A small subset of indazole ethers, with pharmacokinetic properties suitable for oral administration, was investigated in a rat antigen-induced joint inflammation model and demonstrated excellent anti-inflammatory efficacy. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2016.10.052

文献信息

• Chemical compounds
  申请人：Berger Markus

  公开号：US20080207721A1

  公开（公告）日：2008-08-28

  Compounds of formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).

  化学式为（I）的化合物或其药学上可接受的盐、包含它们的组合物、制备它们的过程以及它们在医疗治疗中的应用（例如在温血动物中调节糖皮质激素受体）。
• CHEMICAL COMPOUNDS
  申请人：Berger Markus

  公开号：US20120065173A1

  公开（公告）日：2012-03-15

  Compounds of formula (I): or a pharmaceutically acceptable salt thereof; compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).

  式(I)的化合物或其药学上可接受的盐；包含它们的组合物；制备它们的过程以及它们在医疗治疗中的应用（例如调节温血动物的糖皮质激素受体）。
• Indazolyl sulphonamide derivatives useful as glucocorticoid modulators
  申请人：AstraZeneca AB

  公开号：US08030340B2

  公开（公告）日：2011-10-04

  Compounds of formula (I): or a pharmaceutically acceptable salt thereof, compositions comprising them, processes for preparing them and their use in medical therapy (for example modulating the glucocorticoid receptor in a warm blooded animal).

  化学式为(I)的化合物或其药学上可接受的盐，包括它们的组合物，制备它们的过程以及它们在医学治疗中的应用（例如在温血动物中调节糖皮质激素受体）。
• WO2008/63116
  申请人：——

  公开号：——

  公开（公告）日：——
• WO2008/76048
  申请人：——

  公开号：——

  公开（公告）日：——