5-(2-甲氧基苯基)- 2-噻吩羧醛 | 479243-27-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 5-(2-甲氧基苯基)- 2-噻吩羧醛
• 中文别名: 5-(2-甲氧基苯基)噻吩-2-甲醛；5-(2-甲氧基苯基)-2-噻吩羧醛
• 英文名称: 5-(2-methoxyphenyl)thiophene-2-carbaldehyde
• CAS: 479243-27-1
• 化学式: C₁₂H₁₀O₂S
• 分子量: 218.276
• InChiKey: DYZXRQXNOYTTLY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

安全信息

• 海关编码：
  2934999090

反应信息

• 作为反应物：
  描述：

  2-硫代乙内酰脲 、 5-(2-甲氧基苯基)- 2-噻吩羧醛 在 溶剂黄146 、 β-丙氨酸 作用下， 反应 15.0h， 以54%的产率得到5-((5-(2-methoxyphenyl)thiophen-2-yl)methylene)-2-thioxoimidazolidin-4-one
  参考文献：
  名称：

  Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin

  摘要：

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).

  DOI：

  10.1021/jm401604x
• 作为产物：
  描述：

  5-溴噻吩-2-甲醛 、 2-甲氧基苯基硼酸 在 potassium phosphate 、 dichloro{bis[1-(dicyclohexylphosphanyl)piperidine]}palladium(II) 作用下， 以 甲苯 为溶剂， 反应 0.5h， 以85%的产率得到5-(2-甲氧基苯基)- 2-噻吩羧醛
  参考文献：
  名称：

  钯的二氯双（氨基膦）配合物：高度便捷，可靠且活性极强的铃木-宫浦催化剂，具有出色的官能团耐受性

  摘要：

  二氯双（氨基膦）配合物是稳定的长相形式的钯纳米颗粒，并已证明是出色的Suzuki-Miyaura催化剂。配体的简单修饰（和/或向反应混合物中加水）可以控制它们的形成。二氯双[1-（二环己基膦酰基）哌啶]钯（3）是研究体系中最活跃的催化剂，是高度便捷，可靠且极具活性的Suzuki催化剂，具有出色的官能团耐受性，可实现多种活化，非活化和失活和/或位阻功能化的定量偶联以及芳烃和苄基溴的杂环化合物，在工业用甲苯中，在0.2°C的催化剂中，在80°C时，芳基硼酸仅略有过量（1.1-1.2当量）芳基硼酸，对大气开放。通常仅在几分钟内即可实现> 95％的转化率。本文提出的反应方案是普遍适用的。副产品很少被发现。与基于膦的膦类似物相比，基于氨基膦的体系的催化活性被显着提高，这是由于钯纳米颗粒形成明显加快的结果。催化剂的分解产物是二环己基次膦酸酯，环己基膦酸酯和磷酸盐，它们很容易从偶联产物中分离出来，与非水溶性膦基体系相比，具有很大的优势。

  DOI：

  10.1002/chem.200903309

文献信息

• Alkylidene pyrazolidinedione derivatives
  申请人：——

  公开号：US20040220188A1

  公开（公告）日：2004-11-04

  The present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) for the treatment and/or prevention of diabetes type I and/or II, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity and polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel alkylidene pyrazolidinedione derivatives. (I) R1 and R2 represent independently from each other an unsubstituted or substituted aryl or heteroaryl. 1

  本发明涉及使用式(I)的烷基亚甲基吡唑啉二酮衍生物治疗和/或预防糖尿病I型和/或II型、糖耐量受损、胰岛素抵抗、高血糖、肥胖症和多囊卵巢综合症（PCOS）。特别是，本发明涉及使用式(I)的烷基亚甲基吡唑啉二酮衍生物调节，特别是抑制PTPs的活性，尤其是PTP1B、TC-PTP、SHP和GLEPP-1的活性。本发明还涉及新的烷基亚甲基吡唑啉二酮衍生物。(I)中，R1和R2各自独立地表示未取代或取代的芳基或杂环芳基。
• Copper-Catalyzed Direct CH Arylation of Thieno[3,4-<i>c</i>]pyrrole-4,6-dione (TPD): Toward Efficient and Low-Cost Synthesis of π-Functional Small Molecules
  作者：Yi-Ting Song、Po-Han Lin、Ching-Yuan Liu

  DOI：10.1002/adsc.201400524

  日期：2014.12.15

  AbstractA series of thieno[3,4‐c]pyrrole‐4,6‐dione (TPD)‐based functional small molecules were efficiently synthesized through direct CH arylations using inexpensive copper salts. In this study, we examined all required reaction parameters including various copper complexes, ligands, bases, and (co)solvents. Under the optimum reaction conditions, the CH arylation proceeded smoothly and a variety of functional groups such as ester, nitrile, fluoride, chloride, triazene, and amine were tolerated. This method provides a step‐economical and relatively low‐cost synthetic alternative to presently used coupling reactions for the preparation of TPD‐containing π‐functional materials.magnified image
• ALKYLIDENE PIRAZOLIDINEDIONE DERIVATIVES AND THEIR USE FOR TREATING DIABETES AND OBESITY
  申请人：Applied Research Systems ARS Holding N.V.

  公开号：EP1399156A2

  公开（公告）日：2004-03-24
• [EN] ALKYLIDENE PYRAZOLIDINEDIONE DERIVATIVES<br/>[FR] DERIVES D'ALKYLIDENE PYRAZOLIDINEDIONE
  申请人：APPLIED RESEARCH SYSTEMS

  公开号：WO2002102359A2

  公开（公告）日：2002-12-27

  The present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) for the treatment and/or prevention of diabetes type I and/or II, impaired glucose tolerance, insulin resistance, hyperglycemia, obesity and polycystic ovary syndrome (PCOS). In particular, the present invention is related to the use of alkylidene pyrazolidinedione derivatives of formula (I) to modulate, notably to inhibit the activity of PTPs, in particular PTP1B, TC-PTP, SHP and GLEPP-1. The present invention is furthermore related to novel alkylidene pyrazolidinedione derivatives. (I) R1 and R2 represent independently from each other an unsubstituted or substituted aryl or heteroaryl.
• Exploration of a Series of 5-Arylidene-2-thioxoimidazolidin-4-ones as Inhibitors of the Cytolytic Protein Perforin
  作者：Julie A. Spicer、Gersande Lena、Dani M. Lyons、Kristiina M. Huttunen、Christian K. Miller、Patrick D. O’Connor、Matthew Bull、Nuala Helsby、Stephen M. F. Jamieson、William A. Denny、Annette Ciccone、Kylie A. Browne、Jamie A. Lopez、Jesse Rudd-Schmidt、Ilia Voskoboinik、Joseph A. Trapani

  DOI：10.1021/jm401604x

  日期：2013.12.12

  A series of novel 5-arylidene-2-thioxoimidazolidin-4-ones were investigated as inhibitors of the lymphocyte-expressed pore-forming protein perform. Structure activity relationships were explored through variation of an isoindolinone or 3,4-dihydroisoquinolinone subunit on a fixed 2-thioxoimidazolidin-4-one/thiophene core. The ability of the resulting compounds to inhibit the lytic activity of both isolated perform protein and perforin delivered in situ by natural killer cells was determined. A number of compounds showed excellent activity at concentrations that were nontoxic to the killer cells, and several were a significant improvement on previous classes of inhibitors, being substantially more potent and soluble. Representative examples showed rapid and reversible binding to immobilized mouse perforin at low concentrations (<= 2.5 mu M) by surface plasmon resonance and prevented formation of perforin pores in target cells despite effective target cell engagement, as determined by calcium influx studies. Mouse PK studies of two analogues showed T-1/2 values of 1.1-1.2 h (dose of 5 mg/kg iv) and MTDs of 60-80 mg/kg (ip).