2-[3-氟-4-(三氟甲基)苯基]-4-甲基-5-羟基甲基噻唑 | 317319-27-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-[3-氟-4-(三氟甲基)苯基]-4-甲基-5-羟基甲基噻唑
• 英文名称: 5-hydroxymethyl-4-methyl-2-[3-fluoro-4-(trifluoromethyl)phenyl]thiazole
• 英文别名: (2-(3- fluoro-4-(trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methanol；(2-(3-Fluoro-4-(trifluoromethyl)phenyl)-4-methylthiazol-5-yl)methanol；[2-[3-fluoro-4-(trifluoromethyl)phenyl]-4-methyl-1,3-thiazol-5-yl]methanol
• CAS: 317319-27-0
• 化学式: C₁₂H₉F₄NOS
• 分子量: 291.269
• InChiKey: SSJKNJYBSHISNC-UHFFFAOYSA-N

物化性质

• 熔点：
  159-161
• 溶解度：
  可溶于氯仿（少许）、乙酸乙酯（少许）、甲醇（少许）

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  61.4
• 氢给体数：
  1
• 氢受体数：
  7

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2934100090

反应信息

• 作为反应物：
  描述：

  2-[3-氟-4-(三氟甲基)苯基]-4-甲基-5-羟基甲基噻唑 在 甲基磺酰氯 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到2-[3-氟-4-(三氟甲基)苯基]-4-甲基-5-氯甲基噻唑
  参考文献：
  名称：

  Novel selective small molecule agonists for peroxisome proliferator-activated receptor δ (PPARδ)—synthesis and biological activity

  摘要：

  We report the synthesis and biological activity of a new series of small molecule agonists of the human Peroxisome Proliferator-Activated Receptor delta (PPARdelta). Several hits were identified from our original libraries containing lipophilic carboxylic acids. Optimization of these hits by structure-guided design led to 7k (GW501516) and 71 (GW0742), which shows an EC50 Of 1.1 nM against PPARdelta with 1000-fold selectivity over the other human subtypes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00207-5
• 作为产物：
  描述：

  乙基2-[3-氟-(三氟甲基)苯基]-4-甲基-噻唑-5-羧酸酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 以87%的产率得到2-[3-氟-4-(三氟甲基)苯基]-4-甲基-5-羟基甲基噻唑
  参考文献：
  名称：

  Novel selective small molecule agonists for peroxisome proliferator-activated receptor δ (PPARδ)—synthesis and biological activity

  摘要：

  We report the synthesis and biological activity of a new series of small molecule agonists of the human Peroxisome Proliferator-Activated Receptor delta (PPARdelta). Several hits were identified from our original libraries containing lipophilic carboxylic acids. Optimization of these hits by structure-guided design led to 7k (GW501516) and 71 (GW0742), which shows an EC50 Of 1.1 nM against PPARdelta with 1000-fold selectivity over the other human subtypes. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00207-5

文献信息

• Thiazolyl-indole derivatives, their manufacture and use as pharmaceutical agents
  申请人：Ackermann Jean

  公开号：US20050004187A1

  公开（公告）日：2005-01-06

  This invention relates to compounds of the formula wherein one of R 6 , R 7 or R 8 is and all enantiomers and pharmaceutically acceptable salts and/or esters thereof as well as pharmaceutical compositions containing such compounds, to a process for their preparation and to their use for the treatment and/or prevention of diseases which are modulated by PPARδ and/or PPARα agonists.

  这项发明涉及以下式的化合物 其中R 6 、R 7 或R 8 中的一个是 以及所有的对映体和药学上可接受的盐和/或酯，以及含有这种化合物的药物组合物，以及它们的制备方法和它们用于治疗和/或预防由PPARδ和/或PPARα激动剂调节的疾病。
• Organophosphorus-Catalyzed Direct Dehydroxylative Thioetherification of Alcohols with Hypervalent Organosulfur Compounds
  作者：Gang Sun、Shi-Ping Zhan、Yi-Feng Zhao、Xingyi Du、Mao-Ying Shi、Jing Li、Haoliang Yuan、Xiaoan Wen、Hongbin Sun、Qing-Long Xu

  DOI：10.1021/acs.joc.3c02175

  日期：2024.1.19

  thioethers was disclosed, driven by PIII/PV═O redox cycling. In this work, one-step dehydroxylative thioetherification of alcohols was fulfilled with various hypervalent organosulfur compounds. This established strategy features an excellent functional group tolerance and broad substrate scope, especially inactivated alcohols. The scale-up reaction and further transformation of the product were also successful

  公开了一种由 P III /P V = O 氧化还原循环驱动的无金属和无硫醇的有机磷催化形成硫醚的方法。在这项工作中，利用各种高价有机硫化合物实现了醇的一步脱羟基硫醚化。这种既定策略具有出色的官能团耐受性和广泛的底物范围，尤其是灭活醇。产品的放大反应和进一步转化也取得了成功。此外，该方法提供了一种无保护基且步骤有效的合成过氧化物酶体增殖物激活受体激动剂的方法，该方法在治疗哺乳动物骨质疏松症方面表现出良好的潜力。
• Novel selective small molecule agonists for peroxisome proliferator-activated receptor δ (PPARδ)—synthesis and biological activity
  作者：Marcos L. Sznaidman、Curt D. Haffner、Patrick R. Maloney、Adam Fivush、Esther Chao、Donna Goreham、Michael L. Sierra、Christelle LeGrumelec、H.Eric Xu、Valerie G. Montana、Millard H. Lambert、Timothy M. Willson、William R. Oliver、Daniel D. Sternbach

  DOI：10.1016/s0960-894x(03)00207-5

  日期：2003.5

  We report the synthesis and biological activity of a new series of small molecule agonists of the human Peroxisome Proliferator-Activated Receptor delta (PPARdelta). Several hits were identified from our original libraries containing lipophilic carboxylic acids. Optimization of these hits by structure-guided design led to 7k (GW501516) and 71 (GW0742), which shows an EC50 Of 1.1 nM against PPARdelta with 1000-fold selectivity over the other human subtypes. (C) 2003 Elsevier Science Ltd. All rights reserved.
• INDOLYL DERIVATIVES SUBSTITUTED WITH A THIAZOLE RING AND THEIR USE AS PPAR MODULATORS
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP1644368A1

  公开（公告）日：2006-04-12
• US7235572B2
  申请人：——

  公开号：US7235572B2

  公开（公告）日：2007-06-26