5-iodo-2-(4-isopropoxyphenoxy)thiazole | 929118-52-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-iodo-2-(4-isopropoxyphenoxy)thiazole
• 英文别名: 5-iodo-2-(4-isopropoxyphenoxy)-1,3-thiazole；5-iodo-2-(4-propan-2-yloxyphenoxy)-1,3-thiazole
• CAS: 929118-52-5
• 化学式: C₁₂H₁₂INO₂S
• 分子量: 361.203
• InChiKey: WXLWOLWFKNXBLS-UHFFFAOYSA-N

物化性质

• 沸点：
  414.1±51.0 °C(Predicted)
• 密度：
  1.625±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  59.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-iodo-2-(4-isopropoxyphenoxy)thiazole 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 肼 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  The synthesis and structure–activity relationship studies of selective acetyl-CoA carboxylase inhibitors containing 4-(thiazol-5-yl)but-3-yn-2-amino motif: Polar region modifications

  摘要：

  The structure-activity relationship study focused on the polar region of the HTS hit A-80040 (1) producing several series of potent and selective ACC2 inhibitors. The SAR suggests a compact lipophilic pocket that does not tolerate polar and ionic groups. Replacement of the hydroxyurea group with isoxazoles improves ACC2 selectivity while maintaining potency. Variations at the propargylic site of 11a reduce ACC2 potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.047
• 作为产物：
  描述：

  4-异丙氧基苯酚 在 正丁基锂 、 potassium carbonate 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 4.0h， 生成 5-iodo-2-(4-isopropoxyphenoxy)thiazole
  参考文献：
  名称：

  The synthesis and structure–activity relationship studies of selective acetyl-CoA carboxylase inhibitors containing 4-(thiazol-5-yl)but-3-yn-2-amino motif: Polar region modifications

  摘要：

  The structure-activity relationship study focused on the polar region of the HTS hit A-80040 (1) producing several series of potent and selective ACC2 inhibitors. The SAR suggests a compact lipophilic pocket that does not tolerate polar and ionic groups. Replacement of the hydroxyurea group with isoxazoles improves ACC2 selectivity while maintaining potency. Variations at the propargylic site of 11a reduce ACC2 potency. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2006.12.047

文献信息

• NOVEL ACETYL-COA CARBOXYLASE (ACC) INHIBITORS AND THEIR USE IN DIABETES, OBESITY AND METABOLIC SYNDROME
  申请人：Gu Yu Gui

  公开号：US20080161368A1

  公开（公告）日：2008-07-03

  The present invention relates to compounds of formula (I): Pharmaceutical compositions and methods that are useful in the treatment or prevention of metabolic diseases or conditions are also provided.

  本发明涉及以下式（I）的化合物： 还提供了在治疗或预防代谢性疾病或状况中有用的药物组合物和方法。
• <i>N</i>-{3-[2-(4-Alkoxyphenoxy)thiazol-5-yl]-1-methylprop-2-ynyl}carboxy Derivatives as Acetyl-CoA Carboxylase InhibitorsImprovement of Cardiovascular and Neurological Liabilities via Structural Modifications
  作者：Yu Gui Gu、Moshe Weitzberg、Richard F. Clark、Xiangdong Xu、Qun Li、Nathan L. Lubbers、Yi Yang、David W. A. Beno、Deborah L. Widomski、Tianyuan Zhang、T. Matthew Hansen、Robert F. Keyes、Jeffrey F. Waring、Sherry L. Carroll、Xiaojun Wang、Rongqi Wang、Christine H. Healan-Greenberg、Eric A. Blomme、Bruce A. Beutel、Hing L. Sham、Heidi S. Camp

  DOI：10.1021/jm070035a

  日期：2007.3.1

  A preliminary safety evaluation of ACC2 inhibitor 1-(S) revealed serious neurological and cardiovascular liabilities of this chemotype. A systematic structure-toxicity relationship study identified the alkyne linker as the key motif responsible for these adverse effects. Toxicogenomic studies in rats showed that 1-(R) and 1-(S) induced gene expression patterns similar to that seen with several known

  ACC2抑制剂1-（S）的初步安全性评估显示，该化学型严重的神经系统和心血管疾病。一项系统的结构-毒性关系研究确定了炔烃连接体为造成这些不利影响的关键基序。在大鼠中进行的毒理基因组研究表明，1-（R）和1-（S）诱导的基因表达模式与几种已知的心脏毒性剂（如阿霉素）相似。用替代的连接基团取代炔烃导致了一系列新的ACC抑制剂，其心血管和神经系统特性得到了显着改善。
• Acetyl-CoA carboxylase (ACC) inhibitors and their use in diabetes, obesity and metabolic syndrome
  申请人：Abbott Laboratories

  公开号：US07928243B2

  公开（公告）日：2011-04-19

  The present invention relates to compounds of formula (I): Pharmaceutical compositions and methods that are useful in the treatment or prevention of metabolic diseases or conditions are also provided.

  本发明涉及化合物(I)的公式：提供了在治疗或预防代谢性疾病或病症方面有用的药物组合物和方法。
• US7928243B2
  申请人：——

  公开号：US7928243B2

  公开（公告）日：2011-04-19
• [EN] NOVEL ACETYL-COA CARBOXYLASE (ACC) INHIBITORS AND THEIR USE IN DIABETES, OBESITY AND METABOLIC SYNDROME<br/>[FR] NOUVEAUX INHIBITEURS D'ACÉTYL-COA-CARBOXYLASE (ACC) ET UTILISATION DANS LE TRAITEMENT DU DIABÈTE, DE L'OBÉSITÉ ET DU SYNDROME MÉTABOLIQUE
  申请人：ABBOTT LAB

  公开号：WO2008079610A2

  公开（公告）日：2008-07-03

  [EN] The present invention relates to compounds of formula (I); Pharmaceutical compositions and methods that are useful in the treatment or prevention of metabolic diseases or conditions are also provided.
  [FR] L'invention concerne les composés représentés par la formule (I), des compositions pharmaceutiques et des procédés servant au traitement et à la prévention de maladies et de troubles métaboliques.