2,4-噻唑烷二酮,5-[[4-(苯基甲氧基)苯基]甲基]- | 187142-96-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 2,4-噻唑烷二酮,5-[[4-(苯基甲氧基)苯基]甲基]-
• 英文名称: 5-(4-benzyloxyphenylmethyl)-2,4-thiazolidinedione
• 英文别名: 5-(4-(benzyloxy)benzyl)thiazolidine-2,4-dione；5-[(4-phenylmethoxyphenyl)methyl]-1,3-thiazolidine-2,4-dione
• CAS: 187142-96-7
• 化学式: C₁₇H₁₅NO₃S
• 分子量: 313.377
• InChiKey: UGTRMSWYUSDXMG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 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：

  2,4-噻唑烷二酮,5-[[4-(苯基甲氧基)苯基]甲基]- 在 盐酸 、 potassium carbonate 、 溶剂黄146 作用下， 以 丙酮 为溶剂， 反应 25.5h， 生成 [5-(4-hydroxybenzyl)-2,4-dioxothiazolidin-3-yl]acetic acid
  参考文献：
  名称：

  In vitro aldose reductase inhibitory activity of 5-benzyl-2,4-thiazolidinediones

  摘要：

  Several 5-benzyl-2,4-thiazolidinediones (5-7) were synthesised and tested as in vitro aldose reductase (ALR2) inhibitors. Most of them particularly N-unsubstituted 5-benzyl-2,4-thiazolidinediones 5 and (5-benzyl-2,4-dioxothiazolidin-3-yl)acetic acids 7, displayed moderate to high inhibitory activity levels. In detail, the insertion of an acetic chain on N-3 significantly enhanced ALR2 inhibitory potency, leading to acids 7 which proved to be the most effective among the tested compounds. In addition, in N-unsubstituted derivatives 5 the presence of an additional aromatic ring on the 5-benzyl moiety was generally beneficial. In fact, the ALR2 inhibition results of compounds 5-7, compared to those of the previously assayed corresponding 5-arylidene-2,4-thiazolidinediones, indicated that N-unsubstituted derivatives 5b, c and d, which bore an additional aromatic group in the para position of the 5-benzyl residue were significantly more effective than their 5-arylidene counterparts; in all other cases, the saturation of the exocyclic double bond C=C in 5 brought about a moderate decrease in activity. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.08.056
• 作为产物：
  描述：

  (Z)-5-(4-benzyloxyphenylmethylene)-2,4-thiazolidinedione 在 sodium hydroxide sodium tetrahydroborate 、 N,N-二甲基甘氨酸 作用下， 以 四氢呋喃 、 水 为溶剂， 以46%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：

  Structure–activity requirements for the antiproliferative effect of troglitazone derivatives mediated by depletion of intracellular calcium

  摘要：

  Depletion of calcium from the endoplasmic reticulum has shown to affect protein synthesis and cell proliferation. The anticancer effect of troglitazone was reported to be mediated by depletion of intracellular calcium stores resulting in inhibition of translation initiation. The unsaturated form of troglitazone displays similar anticancer properties in vitro. In this letter, we report our findings on the minimum structural requirements for both compounds to retain their calcium release and antiproliferative activities. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.02.087

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。
• Pharmaceutical Preparations Comprising Insulin, Zinc Ions and Zinc-Binding Ligand
  申请人：Kaarsholm Niels Christian

  公开号：US20090123563A1

  公开（公告）日：2009-05-14

  Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.

  这段话的中文翻译如下：使用分支配体的新型制备物，用于R-状态胰岛素六聚体的HisB10 Zn2+位点。这些制备物具有长效作用，旨在为灵活的注射方案设计。
• 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。
• Regiospecific Reduction of 5-Benzylidene-2,4-Thiazolidinediones and 4-Oxo-2-thiazolidinethiones using Lithium Borohydride in Pyridine and Tetrahydrofuran
  作者：Robert G Giles、Norman J Lewis、John K Quick、Michael J Sasse、Michael W.J Urquhart、Latifa Youssef

  DOI：10.1016/s0040-4020(00)00361-6

  日期：2000.6

  The novel regiospecific and general reduction of 5-benzylidene-2,4-thiazolidinediones and 5-benzylidene-4-oxo-2-thiazolidinethiones to the corresponding 5-benzyl derivatives has been accomplished using lithium borohydride in pyridine and tetrahydrofuran. Sodium borohydride and lithium chloride can also be used under these conditions, which represents a cheaper alternative to lithium borohydride. (C) 2000 Elsevier Science Ltd. All rights reserved.
• 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.