Ethyl 2-amino-4-(4-hydroxyphenyl)thiophene-3-carboxylate | 849659-37-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩类
• 英文名称: Ethyl 2-amino-4-(4-hydroxyphenyl)thiophene-3-carboxylate
• CAS: 849659-37-6
• 化学式: C₁₃H₁₃NO₃S
• 分子量: 263.317
• InChiKey: VILWSIIEOZJZGX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Ethyl 2-amino-4-(4-hydroxyphenyl)thiophene-3-carboxylate 在 N-氯代丁二酰亚胺 、 五氯化磷 、 sodium hydride 、 溶剂黄146 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-chloro-4-hydroxy-3-(4-hydroxyphenyl)-6-oxo-6,7-dihydrothieno[2,3-b]pyridine-5-carbonitrile
  参考文献：
  名称：

  Discovery and SAR development of thienopyridones: A class of small molecule AMPK activators

  摘要：

  AMP-activated protein kinase (AMPK) is well established as a sensor and regulator of intracellular and whole-body energy metabolism. A high-throughput screen was performed in order to identify chemotypes that are bound by AMPK. A novel thienopyridone compound (1) was identified and subsequently optimized. The structure-activity relationships that emerged from this effort are described. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.04.011
• 作为产物：
  描述：

  氰乙酸乙酯 、 对羟基苯乙酮 在 吗啉 、 sulfur 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 以37%的产率得到Ethyl 2-amino-4-(4-hydroxyphenyl)thiophene-3-carboxylate
  参考文献：
  名称：

  芳基烷基酮在 2-氨基噻吩的一锅 Gewald 合成中

  摘要：

  通过芳基烷基酮与氰基乙酸乙酯和元素硫在乙酸吗啉和过量吗啉存在下的一锅 Gewald 反应，在 4-位带有各种芳基的 2-氨基噻吩-3-羧酸盐很容易以良好到中等的产率获得.

  DOI：

  10.1055/s-2006-951484

文献信息

• Novel 4-Oxothienopyrimidinyl Propanoic Acid Derivatives as AMPActivated Protein Kinase (AMPK) Activators
  作者：Pradip Sasmal、Mahaboobi Jaleel、P. Rao、M. Munikumar、Megha Bhattacharya、Nutakki Kumar、Poondla. Neelima、Khaji Rawoof、P. Rao、Chandrasekhar Abbineni、M. Roshaiah、S. Sridhar、Thammera Kumar、Menon Vinu、Vijay Potluri、Parimal Misra、Rashmi Talwar、Saibal Das

  DOI：10.2174/1570180811666140122003044

  日期：2014.5.31

  Adenosine 5’-monophosphate (AMP) activated protein kinase (AMPK) is a highly conserved sensor of cellular energy. AMPK has been recognized as a key regulator of mammalian metabolic function and has emerged as an attractive target for the treatment of metabolic disorders, including obesity and type 2 diabetes. The synthesis and biological evaluation of novel 3-(4-oxothieno[2,3-d]pyrimidin-3(4H)-yl)propanoic acid derivatives as AMPK activators are described. The in vivo proof of principle for plasma glucose lowering effect is exemplified with a lead compound from this series.

  腺苷5'-单磷酸(AMP)激活的蛋白激酶(AMPK)是一种高度保守的细胞能量感应器。AMPK已被确认为调节哺乳动物代谢功能的关键因子,并已成为治疗包括肥胖和2型糖尿病在内的代谢紊乱的理想靶点。本文描述了新型3-(4-氧代噻吩并[2,3-d]嘧啶-3(4H)-基)丙酸衍生物作为AMPK激活剂的合成和生物学评价。体内实验证明了本系列中的先导化合物具有降低血浆葡萄糖水平的原理验证作用。
• [EN] THIOPHENE-BASED COMPOUNDS EXHIBITING ATP-UTILIZING ENZYME INHIBITORY ACTIVITY, AND COMPOSITIONS, AND USES THEREOF<br/>[FR] COMPOSES A BASE DE THIOPHENE PRESENTANT UNE ACTIVITE D'INHIBITION D'ENZYMES UTILISANT L'ATP, COMPOSITIONS CONTENANT CES COMPOSES ET UTILISATIONS
  申请人：AMPHORA DISCOVERY CORP

  公开号：WO2005033102A2

  公开（公告）日：2005-04-14

  Thiophene-based compounds of formula (I) exhibiting ATP-utilizing enzyme inhibitory activity, methods of using compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions comprising compounds exhibiting ATP-utilizing enzyme inhibitory activity, are disclosed. These compounds are useful in the treatment of Alzheimer’s disease, stroke, diabetes, obesity, inflammation and cancer.
• Discovery and SAR development of thienopyridones: A class of small molecule AMPK activators
  作者：Gang Zhao、Rajesh R. Iyengar、Andrew S. Judd、Barbara Cool、William Chiou、Lemma Kifle、Ernst Frevert、Hing Sham、Philip R. Kym

  DOI：10.1016/j.bmcl.2007.04.011

  日期：2007.6

  AMP-activated protein kinase (AMPK) is well established as a sensor and regulator of intracellular and whole-body energy metabolism. A high-throughput screen was performed in order to identify chemotypes that are bound by AMPK. A novel thienopyridone compound (1) was identified and subsequently optimized. The structure-activity relationships that emerged from this effort are described. (c) 2007 Elsevier Ltd. All rights reserved.
• Aryl Alkyl Ketones in a One-Pot Gewald Synthesis of 2-Aminothiophenes
  作者：Victor Tormyshev、Anthony Flinn、Dmitry Trukhin、Olga Rogozhnikova、Tatiana Mikhalina、Tatiana Troitskaya

  DOI：10.1055/s-2006-951484

  日期：2006.9

  2-Aminothiophene-3-carboxylates bearing various aryl groups at the 4-position are readily obtained in good to moderate yields by the one-pot Gewald reaction of aryl alkyl ketones with ethyl cyanoacetate and elemental sulfur in the presence of morpholinium acetate and excess morpholine.

  通过芳基烷基酮与氰基乙酸乙酯和元素硫在乙酸吗啉和过量吗啉存在下的一锅 Gewald 反应，在 4-位带有各种芳基的 2-氨基噻吩-3-羧酸盐很容易以良好到中等的产率获得.