5-{4-[2-(methylamino)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione | 158562-98-2

• 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-(methylamino)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione
• 英文别名: 5-[4-(2-methylamino-ethoxy)-benzyl]-thiazolidine-2,4-dione；5-[4-(2-Methylaminoethoxy)-benzyl]-thiazolidine-2,4-dione；5-[[4-[2-(methylamino)ethoxy]phenyl]methyl]-1,3-thiazolidine-2,4-dione
• CAS: 158562-98-2
• 化学式: C₁₃H₁₆N₂O₃S
• 分子量: 280.348
• InChiKey: BPSKNLFJDYBECE-UHFFFAOYSA-N

物化性质

• 沸点：
  488.7±25.0 °C(Predicted)
• 密度：
  1.266±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  92.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  5-{4-[2-(methylamino)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione 在 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 5-<<4-<2-(2-benzoxazolylmethylamino)ethoxy>phenyl>methyl>-3-methyl-2,4-thiazolidinedione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017
• 作为产物：
  描述：

  对羟基苯甲醛 在 palladium on activated charcoal 盐酸 、 氢气 、 哌啶鎓苯甲酸盐 、 sodium hydride 作用下， 以 1,4-二氧六环 、 乙醇 、 甲苯 为溶剂， 25.0~80.0 ℃ 、101.33 kPa 条件下， 反应 96.0h， 生成 5-{4-[2-(methylamino)ethoxy]benzyl}-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  [[.omega.-(Heterocyclylamino)alkoxy]benzyl]-2,4-thiazolidinediones as potent antihyperglycemic agents

  摘要：

  A series of [(ureidoethoxy)benzyl]-2,4-thiazolidinediones and [[(heterocyclylamino)alkoxy]-benzyl]-2,4-thiazolidinediones was synthesized from the corresponding aldehydes. Compounds from the urea series, exemplified by 16, showed antihyperglycemic potency comparable with known agents of the type such as pioglitazone and troglitazone (CS-045). The benzoxazole 49, a cyclic analogue of 16, was a very potent enhancer of insulin sensitivity, and by modification of the aromatic heterocycle, an aminopyridine, 37, was identified as a lead compound from SAR studies. Evaluation of antihyperglycemic activity together with effects on blood hemoglobin content, to determine the therapeutic index, was performed in 8-day repeat administration studies in genetically obese C57 Bl/6 ob/ob mice. From these studies, BRL 49653 (37) has been selected, on the basis of antihyperglycemic potency combined with enhanced selectivity against reductions in blood hemoglobin content, for further evaluation.

  DOI：

  10.1021/jm00049a017

文献信息

• 1,2-dithiolane derivatives
  申请人：University of Mississippi

  公开号：US06353011B1

  公开（公告）日：2002-03-05

  This invention provides new thiazolindinedione derivatives and new arylacetic acid derivatives. These compounds are useful for the treatment of cardiovascular diseases, certain endocrine diseases, certain inflammatory diseases, certain neoplastic (malignant) and non-malignant proliferative diseases, certain neuro-psychiatric disorders, certain viral diseases, and diseases associated with these viral infections as discussed herein.

  这项发明提供了新的噻唑烷二酮衍生物和新的芳基乙酸衍生物。这些化合物对治疗心血管疾病、某些内分泌疾病、某些炎症性疾病、某些恶性和非恶性增殖性疾病、某些神经精神障碍、某些病毒性疾病以及与这些病毒感染相关的疾病是有用的。
• [EN] DESIGN AND SYNTHESIS OF OPTIMIZED LIGANDS FOR PPAR<br/>[FR] CONCEPTION ET SYNTHESE DE LIGANDS OPTIMISE POUR PPAR
  申请人：BETHESDA PHARMACEUTICALS INC

  公开号：WO2005009437A1

  公开（公告）日：2005-02-03

  This invention provides new chemical entities useful for treating a variety of clinical disorders including those that areinfluenced by the activity of peroxisome proliferator activated receptors (PPAR). The structures of the compounds and methods to design, make and use the compounds are provided. Compounds and methods for administering therapeutic compositions comprising the compounds in cases of the disease psoriasis are provided. An exemplary compound having the formula compound is 5­adamantan-2-yl-pentanoic acid 2-[4-(2,4-dioxo-thiazolidin-5-yl-methyl)-phenoxy]-ethyl}-methyl-amide is provided.

  这项发明提供了新的化学实体，可用于治疗各种临床疾病，包括那些受过氧化物酶体增殖物激活受体（PPAR）活性影响的疾病。提供了这些化合物的结构以及设计、制造和使用这些化合物的方法。提供了在牛皮癣病例中使用这些化合物的治疗组合物的化合物和方法。提供了一个具有以下结构的示例化合物：5-金刚烷基-2-基戊酸2-[4-(2,4-二氧-噻唑啉-5-基-甲基)-苯氧基]-乙基}-甲基酰胺。
• Thiazolidinedione derivatives as antidiabetic agents
  申请人：Vita-Invest S.A.

  公开号：US07001910B1

  公开（公告）日：2006-02-21

  The present invention refers to compounds of the general formula (I), to their possible pharmaceutically acceptable salts and tautomeric forms. The present invention also refers to a process for their production and to their use as antidiabetic and *hypoglycemic agents, alone or in combination with other antidiabetic agents, such as sulfonilureas or biguanides, as well as for the treatment of complications associated to the resistance to the insulin, such as hypertension, hyperuricemia or other cardiovascular, metabolic, endocrine conditions, or other conditions related with diabetes.

  本发明涉及一般式(I)的化合物，其可能的药学上可接受的盐和互变异构体形式。本发明还涉及一种制备它们的方法，以及它们作为抗糖尿病和降糖剂的用途，单独或与其他抗糖尿病药物（如磺脲类或双胍类药物）结合使用，并用于治疗与胰岛素抵抗有关的并发症，如高血压、高尿酸血症或其他与糖尿病有关的心血管、代谢、内分泌疾病或其他疾病。
• Solid-phase synthesis of hybrid thiazolidinedione-fatty acid PPARγ ligands
  作者：Nicholas C.O. Tomkinson、Andrea M. Sefler、Kelli D. Plunket、Steven G. Blanchard、Derek J. Parks、Timothy M. Willson

  DOI：10.1016/s0960-894x(97)10017-8

  日期：1997.10

  A library of thiazolidinedione-fatty acid hybrid molecules was designed to probe the relationship between natural and synthetic PPAR ligands. Solid-phase synthesis of the library led to the identification of several high affinity PPAR gamma ligands. (C) 1997 Elsevier Science Ltd.
• THIAZOLIDINEDIONE DERIVATIVES AS ANTIDIABETIC AGENTS
  申请人：VITA-INVEST, S.A.

  公开号：EP1231211B1

  公开（公告）日：2003-05-28