4-<2-(2-thienyl)ethoxy>benzaldehyde | 85259-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-<2-(2-thienyl)ethoxy>benzaldehyde
• 英文别名: 4-(2-thiopheneethoxy)benzaldehyde；4-(2-Thiophen-2-ylethoxy)benzaldehyde
• CAS: 85259-28-5
• 化学式: C₁₃H₁₂O₂S
• 分子量: 232.303
• InChiKey: FYBGWJROPGIEHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  16
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  54.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-<2-(2-thienyl)ethoxy>benzaldehyde 在 氯化亚砜 、 sodium hydrogensulfite 作用下， 以 氯仿 、 水 、 乙酸乙酯 为溶剂， 反应 24.5h， 生成
  参考文献：
  名称：

  Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.

  摘要：

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。

  DOI：

  10.1248/cpb.30.3601
• 作为产物：
  描述：

  2-噻吩乙醇 在 potassium carbonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 23.0h， 生成 4-<2-(2-thienyl)ethoxy>benzaldehyde
  参考文献：
  名称：

  Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist

  摘要：

  The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure-activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-gamma (PPAR gamma) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-gamma (PPAR gamma) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor.[GRAPHICS].

  DOI：

  10.1007/s00706-018-2207-x

文献信息

• Synthesis and SAR of thiazolidinedione derivatives as 15-PGDH inhibitors
  作者：Ying Wu、Hsin-Hsiung Tai、Hoon Cho

  DOI：10.1016/j.bmc.2010.01.016

  日期：2010.2

  Prostaglandins have a short life in vivo because they are metabolized rapidly by oxidation to 15-ketoprostaglandins catalyzed by a cytosolic enzyme known as NAD(+)-dependent 15-hydroxyprostaglandin dehydrogenase (15-PGDH). Previously, CT-8, a thiazolidinedione analogue, was found to be a potent inhibitor of 15-PGDH. Structure-activity analysis indicated that the N-methylation of thiazolidine-2,4-dione, CT-8, abolished the inhibitory activity, whereas the introduction of an ethyl hydroxyl group at amine in CT-8 still had a good inhibitory effect. Based on the structures of the thiazolidinediones analogues and inhibitory activity, a range of benzylidene thiazolidinedione derivatives were synthesized with different substituents on the phenyl ring and their inhibitory activity was evaluated. Replacement of the cyclohexylethyl group of CT-8 with the hetero five-member ring increased the inhibitory potency. However, replacement of the cyclohexylethyl group with a hetero six-member ring decreased the inhibitory potency significantly. It was found that compound 2 (5-(4-(2-(thiophen-2yl) ethoxy) benzylidene) thiazolidine-2,4-dione) was the most potent inhibitor that was effective in the nanomolar range. (C) 2010 Elsevier Ltd. All rights reserved.
• Studies on antidiabetic agents. III. 5-Arylthiazolidine-2,4-diones as potent aldose reductase inhibitors.
  作者：TAKASHI SOHDA、KATSUTOSHI MIZUNO、EIKO IMAMIYA、HIROYUKI TAWADA、KANJI MEGURO、YUTAKA KAWAMATSU、YUJIRO YAMAMOTO

  DOI：10.1248/cpb.30.3601

  日期：——

  Thiazolidine-2, 4-dione derivatives having one or two substituent (s) such as phenyl, heteryl and alkyl group (s) at the 5-position were synthesized and evaluated as aldose reductase inhibitors. Inhibition by the active compounds of the swelling of the lens in a rat-lens-culture assay was also measured. Among these compounds, a series of 5-(3, 4-dialkoxyphenyl) thiazolidine-2, 4-diones showed pronounced activities in both assays. Structure-activity relationships are discussed and a new approach to the synthesis of 5-arylthiazolidine-2, 4-diones is described.

  具有一个或两个取代基（如苯基、杂基和烷基）的噻唑烷-2,4-二酮衍生物在5位合成并评估为醛糖还原酶抑制剂。在鼠晶状体培养检测中，活性化合物的抑制作用也被测量。在这些化合物中，一系列5-(3,4-二烷氧基苯基)噻唑烷-2,4-二酮在两种检测中显示出显著的活性。结构-活性关系进行了讨论，并描述了一种合成5-芳基噻唑烷-2,4-二酮的新方法。
• Design, synthesis, molecular docking, and in vitro antidiabetic activity of novel PPARγ agonist
  作者：Radha Nandan Chaturvedi、Krishnaiah Pendem、Vipul P. Patel、Mukta Sharma、Sunita Malhotra

  DOI：10.1007/s00706-018-2207-x

  日期：2018.11

  The present work describes the design, synthesis, molecular docking, biological evaluation, and assessment of structure-activity relationship of new derivatives based upon the molecular skeleton of the drug pioglitazone, a compound which is currently used for the management of type 2 diabetes mellitus. Pioglitazone has several side effects such as weight gain, edema, congestive heart failure, and bladder cancer. Therefore, there is a strong demand for identification of new lead candidates in the treatment of type 2 diabetes mellitus. A series of 24 compounds were prepared and evaluated for their peroxisome proliferator-activated receptor-gamma (PPAR gamma) binding affinity assay and the IC50 values were determined. Among these compounds, six compounds exhibited promising IC50 values as compared to standard drugs pioglitazone and rosiglitazone. Furthermore, in order to confirm the target of these molecules, molecular docking study was carried out with peroxisome proliferator-activated receptor-gamma (PPAR gamma) protein. Molecular modeling studies suggested that these compounds appropriately interact in the active sites of receptor.[GRAPHICS].