5-(4-(benzyloxy)benzylidene)thiazolidine-2,4-dione | 262844-52-0

• 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-(benzyloxy)benzylidene)thiazolidine-2,4-dione
• 英文别名: 5-[(4-phenylmethoxyphenyl)methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 262844-52-0
• 化学式: C₁₇H₁₃NO₃S
• mdl: MFCD00300316
• 分子量: 311.361
• InChiKey: NITHMFXIRVGRJD-UHFFFAOYSA-N

物化性质

• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 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-(benzyloxy)benzylidene)thiazolidine-2,4-dione 在 水 、 sodium carbonate 作用下， 以 二甲基亚砜 为溶剂， 以81 %的产率得到2,4-噻唑烷二酮,5-[[4-(苯基甲氧基)苯基]甲基]-
  参考文献：
  名称：

  5-亚苄基噻唑烷-2,4-二酮的电化学还原：制备格列酮 API 的绿色方法

  摘要：

  描述了一种用于化学选择性还原亚苄基噻唑烷-2,4-二酮和类似杂环的无过渡金属方法，允许以高达 90% 的收率制备各种相应的还原衍生物。该协议具有简单且安全的实验装置，其中用水作为氢源。为了进一步证明这种转化的合成效用，制备了抗糖尿病 API 吡格列酮，收率为 81%。据我们所知，这是第一个用于合成吡格列酮的无氢化物和过渡金属的方案，突显了其在学术和工业合成中作为更绿色替代品的潜在用途。

  DOI：

  10.1039/d3cc02363j
• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 4-苄氧基苯甲醛 在 吗啉 作用下， 以 苯 为溶剂， 生成 5-(4-(benzyloxy)benzylidene)thiazolidine-2,4-dione
  参考文献：
  名称：

  新型5-（亚芳基）-3-（4-甲基苯甲酰基）噻唑烷-2,4-二酮的合成与结构

  摘要：

  5-取代的2，4-噻唑烷二酮的衍生物具有广谱的生物活性。在本文中，新的5-（亚芳基）-3-（4-甲基苯甲酰基）噻唑烷-2,4-二酮 带有亚芳基，例如4-苯基亚苄基 ，3,4-二甲氧基亚苄基 ，2-羟基亚苄基 ，4-乙氧基亚苄基 ，5-甲基-2-糠叉基 ，4-二甲基氨基亚苄基 ，1-萘叉 ，3,4-亚甲基二氧基亚苄基 ，4-苄氧基亚苄基 亚苄基 和4-甲氧基亚苄基 ，通过直接酰化5-亚芳基-2,4-噻唑烷二酮的碱金属盐与4-甲基苯甲酰氯。通过元素分析，IR，1 H NMR和MS光谱确认了它们的结构。在此外，该化合物的晶体结构使用单晶X射线衍射数据确定。J.杂环化​​学.2010。

  DOI：

  10.1002/jhet.288

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。
• Thiazolidinedione derivative and use thereof
  申请人：Cho Hoon

  公开号：US08637558B2

  公开（公告）日：2014-01-28

  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.

  本发明涉及以下式(I)所表示的新型噻唑烷二酮衍生物及其用途。更具体地说，本发明涉及以下式(I)所表示的新型噻唑烷二酮衍生物及其制备的药物组合物。根据本发明的新型噻唑烷二酮衍生物可以有效用于抑制降解前列腺素的15-羟基前列腺素脱氢酶（15-PGDH）的活性，从而预防或治疗心血管疾病、胃肠道疾病和肾脏疾病，并且有助于预防脱发和促进头发生长，以及促进骨生成和伤口愈合。
• Design, synthesis, and biological evaluation of novel thiazolidinediones as PPARγ/FFAR1 dual agonists
  作者：Khaled M. Darwish、Ismail Salama、Samia Mostafa、Mohamed S. Gomaa、Mohamed A. Helal

  DOI：10.1016/j.ejmech.2015.12.049

  日期：2016.2

  Diabetes mellitus is a chronic metabolic disorder that affects more than 180 million people worldwide. Peroxisome proliferator activated receptors (PPARs) are a group of nuclear receptors that have been targeted by the thiazolidinedione (TZD) class of compounds for the management of type II diabetes. PPAR gamma is known to regulate adipogenesis and glucose metabolism. Another emerging target for the design of antidiabetic agents is the free fatty acid receptor 1 (FFAR1), previously known as GPR40. Agonists of this receptor were found to enhance insulin secretion in diabetic patients. It has been reported that some thiazolidinediones (TZDs) activate FFAR1 with micromolar potency. In this study, based on docking studies into the crystal structure of PPAR gamma and a homology model of FFAR1, nineteen compounds were designed, synthesized, and biologically tested for agonistic activity on both receptors. Nine compounds showed promising dual activity, with two compounds, 11a and 5b, having affinities in the low micromolar range on both targets. These molecules represent the first antidiabetic agents that could act as insulin sensitizers as well as insulin secretagogues. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis and structure of new 5-(arylidene)-3-(4-methylbenzoyl)thiazolidine-2,4-diones
  作者：Katarina M. Popov-Pergal、Dejan Poleti、Milica P. Rančić、Antun Meden、Marija V. Pergal

  DOI：10.1002/jhet.288

  日期：——

  The derivatives of 5-substituted-2,4-thiazolidinedione have a broad spectrum of biological activities. In this article, new 5-(arylidene)-3-(4-methylbenzoyl)thiayolidine-2,4-diones with arylidene groups such as 4-phenylbenzylidene , 3,4-dimethoxybenzylidene , 2-hydroxybenzylidene , 4-ethoxybenzylidene , 5-methyl-2-furfurylidene , 4-dimethylaminobenzylidene , 1-naphthylidene , 3,4-methylenedioxybenzylidene

  5-取代的2，4-噻唑烷二酮的衍生物具有广谱的生物活性。在本文中，新的5-（亚芳基）-3-（4-甲基苯甲酰基）噻唑烷-2,4-二酮 带有亚芳基，例如4-苯基亚苄基 ，3,4-二甲氧基亚苄基 ，2-羟基亚苄基 ，4-乙氧基亚苄基 ，5-甲基-2-糠叉基 ，4-二甲基氨基亚苄基 ，1-萘叉 ，3,4-亚甲基二氧基亚苄基 ，4-苄氧基亚苄基 亚苄基 和4-甲氧基亚苄基 ，通过直接酰化5-亚芳基-2,4-噻唑烷二酮的碱金属盐与4-甲基苯甲酰氯。通过元素分析，IR，1 H NMR和MS光谱确认了它们的结构。在此外，该化合物的晶体结构使用单晶X射线衍射数据确定。J.杂环化​​学.2010。