5-{[4-(2-phenylethoxy)phenyl]methylidene}-2,4-thiazolidinedione

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 5-{[4-(2-phenylethoxy)phenyl]methylidene}-2,4-thiazolidinedione
• 英文别名: 5-[4-(2-phenylethoxy)phenylmethylene]-2,4-thiazolidinedione；(5Z)-5-[[4-(2-phenylethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
• 化学式: C₁₈H₁₅NO₃S
• 分子量: 325.388
• InChiKey: LRCWUYIAYBFELQ-VBKFSLOCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  80.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-{[4-(2-phenylethoxy)phenyl]methylidene}-2,4-thiazolidinedione 、 氯乙腈 在 NaH 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以75%的产率得到2,4-Dioxo-5-[4-(2-phenylethoxy)phenylmethylene]-3-thiazolidineacetonitrile
  参考文献：
  名称：

  Monoamine oxidase-B (MAO-B) inhibitory 5-substituted

  摘要：

  本发明涉及单胺氧化酶B（MAO-B）抑制剂5-取代的2,4-噻唑烷二酮，例如式I，以及其制药组合物、制备方法和在哺乳动物中治疗认知障碍、神经功能障碍和/或情绪障碍，例如但不限于退行性神经系统疾病的使用方法。##STR1##

  公开号：

  US05326770A1
• 作为产物：
  描述：

  乙基溴苯 在 哌啶 、 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 5-{[4-(2-phenylethoxy)phenyl]methylidene}-2,4-thiazolidinedione
  参考文献：
  名称：

  Synthesis, biological activity and structure–activity relationships of new benzoic acid-based protein tyrosine phosphatase inhibitors endowed with insulinomimetic effects in mouse C2C12 skeletal muscle cells

  摘要：

  Insulin resistance is a complex altered metabolic condition characterized by impaired insulin signaling and implicated in the pathogenesis of serious human diseases, such as diabetes, obesity, neurodegenerative pathologies. In pursuing our aim to identify new agents able to improve cellular insulin sensitivity, we have synthesized new 4-[(5-arylidene-4-oxo-2-phenylimino/oxothiazolidin-3-yl)methyl] benzoic acids (5, 8) and evaluated their inhibitory activity towards human protein tyrosine phosphatases PTP1B, LMW-PTP and TCPTP, enzymes which are involved in the development of insulin resistance. Compounds 5 and 8 showed from moderate to significant selectivity toward PTP1B over both the highly homologous TCPTP and the two isoforms of human LMW-PTP. In addition, most of the tested compounds selectively inhibited LMW-PTP IF1 over the isoform IF2. Docking studies into the active sites of PTP1B and LMW-PTP aided the rationalization of the observed PTP inhibitory profile. Moreover, most tested compounds were capable to induce the insulin metabolic pathway in mouse C2C12 skeletal muscle cells by remarkably stimulating both IR beta phosphorylation and 2-deoxyglucose cellular uptake. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.11.001

文献信息

• NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF
  申请人：Cho Hoon

  公开号：US20110269954A1

  公开（公告）日：2011-11-03

  The present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and the uses thereof. More specifically, the present invention relates to novel thiazolidinedione derivatives expressed by the following formula (I) and a pharmaceutical composition comprising the same. The novel thiazolidinedione derivatives of formula (I) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins as well as useful for the prevention of hair loss and the stimulation of hair growth, and osteogenic stimulation and wound healing.

  本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物及其用途。更具体地说，本发明涉及由以下式（I）表示的新型噻唑烷二酮衍生物以及包含其的药物组合物。根据本发明的式（I）的新型噻唑烷二酮衍生物可以通过抑制分解前列腺素的15-羟基前列腺素脱氢酶（15-PGDH）的活性，有效用于预防或治疗心血管疾病、胃肠道疾病和肾脏疾病，同时也用于预防脱发和促进头发生长，以及促进骨生成和伤口愈合。
• In Search for Multi-Target Ligands as Potential Agents for Diabetes Mellitus and Its Complications—A Structure-Activity Relationship Study on Inhibitors of Aldose Reductase and Protein Tyrosine Phosphatase 1B
  作者：Rosaria Ottanà、Paolo Paoli、Mario Cappiello、Trung Ngoc Nguyen、Ilenia Adornato、Antonella Del Corso、Massimo Genovese、Ilaria Nesi、Roberta Moschini、Alexandra Naß、Gerhard Wolber、Rosanna Maccari

  DOI：10.3390/molecules26020330

  日期：——

  possibility to target both aldose reductase (AR) and protein tyrosine phosphatase 1B (PTP1B), two enzymes strictly implicated in the development of DM and its complications, we synthesised 3-(5-arylidene-4-oxothiazolidin-3-yl)propanoic acids and analogous 2-butenoic acid derivatives, with the aim of balancing the effectiveness of dual AR/PTP1B inhibitors which we had identified as designed multiple ligands

  糖尿病 (DM) 是一种复杂的疾病，目前影响超过 4.6 亿人，是全球主要的死亡原因之一。它的发展意味着许多代谢功能障碍和高血糖引起的慢性并发症的发生。可以合理设计多种配体用于治疗多因素疾病，例如 DM，其精确目标是同时控制与疾病相关的多种致病机制，并提供比选择性药物组合更有效、更安全的治疗方法。我们之前的研究结果强调了靶向醛糖还原酶 (AR) 和蛋白酪氨酸磷酸酶 1B (PTP1B) 的可能性，这两种酶与 DM 及其并发症的发展密切相关，我们合成了 3-(5-arylidene-4-oxothiazolidin-3-yl) 丙酸和类似的 2-丁烯酸衍生物，目的是平衡双 AR/PTP1B 抑制剂的有效性，我们已将其鉴定为设计的多配体 (DMLs) ）。在测试的化合物中，4f 在低微摩尔浓度下表现出均衡的 AR/PTP1B 抑制作用，以及在鼠 C2C12 细胞培养物中有趣的胰岛素敏化活性。此处强调的
• US5326770A
  申请人：——

  公开号：US5326770A

  公开（公告）日：1994-07-05
• US8637558B2
  申请人：——

  公开号：US8637558B2

  公开（公告）日：2014-01-28
• [EN] NOVEL THIAZOLIDINEDIONE DERIVATIVE AND USE THEREOF<br/>[FR] NOUVEAU DÉRIVÉ DE THIAZOLIDINEDIONE ET SES APPLICATIONS
  申请人：IND ACADEMIC COOP

  公开号：WO2010077101A4

  公开（公告）日：2011-01-13

  [EN] The present invention relates to a novel Thiazolidinedione derivative expressed by the following chemical formula (1) and uses thereof. More specifically, the present invention relates to a novel Thiazolidinedione derivative expressed by the following chemical formula (1) and a pharmaceutical composition comprising the same. The novel Thiazolidinedione derivative of the following chemical formula (1) according to the present invention can be effectively used for the prevention or treatment of cardiovascular disease, gastrointestinal disease and renal disease by inhibiting the activity of 15-hydroxyprostaglandin dehydrogenase (15-PGDH) that decomposes prostaglandins, for preventing hair loss while stimulating hair growth, for osteogenic stimulation and for the treatment of burns.
  [FR] La présente invention concerne un nouveau dérivé de thiazolidinedione de formule chimique (1) suivante et ses applications. Plus spécifiquement, la présente invention concerne un nouveau dérivé de thiazolidinedione de formule chimique (1) suivante et une composition pharmaceutique l'incluant. Le nouveau dérivé de thiazolidinedione de formule chimique (1) suivante selon la présente invention peut être employé efficacement dans le traitement prophylactique ou thérapeutique d'une maladie cardio-vasculaire, d'une maladie gastro-intestinale et d'une maladie rénale en inhibant l'activité de la 15-hydroxyprostaglandine déshydrogénase (15-PGDH) qui décompose les prostaglandines, dans la prévention de la chute de cheveux en stimulant la croissance capillaire, dans la stimulation ostéogène et dans le traitement des brûlures.