5-(4-hydroxy-benzyl)-3-triphenylmethylthiazolidine-2,4-dione | 150556-72-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 5-(4-hydroxy-benzyl)-3-triphenylmethylthiazolidine-2,4-dione
• 英文别名: 5-(4-hydroxybenzyl)-3-triphenylmethylthiazolidine-2,4-dione；5-(4-hydroxybenzyl)-3-tritylthiazolidine-2,4-dione；5-(4-hydroxybenzyl)-3-tritylthiazolidin-2,4-dione；5-[(4-hydroxyphenyl)methyl]-3-trityl-1,3-thiazolidine-2,4-dione
• CAS: 150556-72-2
• 化学式: C₂₉H₂₃NO₃S
• 分子量: 465.573
• InChiKey: GNWRWOJMBZGNPL-UHFFFAOYSA-N

物化性质

• 沸点：
  655.9±65.0 °C(Predicted)
• 密度：
  1.313±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  82.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-(4-hydroxy-benzyl)-3-triphenylmethylthiazolidine-2,4-dione 在 三丁基膦 、 溶剂黄146 、 1,1'-azodicarbonyl-dipiperidine 作用下， 以 甲苯 为溶剂， 反应 7.0h， 生成 5-{4-(3,7-Dimethyl-3H-imidazo[4,5-b]pyridin-2-ylmethoxy)benzyl}thiazolidine-2,4-dione
  参考文献：
  名称：

  一系列噻唑烷-2,4-二酮的分子设计，合成和降血糖活性。

  摘要：

  从其相应的吡啶设计并合成了一系列咪唑并吡啶噻唑烷-2,4-二酮。这些化合物代表新型降血糖化合物罗格列酮（5）的构象受限类似物。评估该系列在体外对胰岛素诱导的3T3-L1脂肪细胞分化的影响以及在体内遗传性糖尿病KK小鼠中的降血糖活性。讨论了构效关系。基于体内效力，5- [4-（5-甲氧基-3-甲基-3H-咪唑并[4，5-b]吡啶-2-基甲氧基）苄基]噻唑烷-2,4-二酮（19a ）被选为在临床环境中进一步研究的候选人。

  DOI：

  10.1021/jm990522t
• 作为产物：
  描述：

  5-(4-acetoxybenzyl)-3-triphenylmethyl-thiazolidine-2,4-dione 在 盐酸 作用下， 以 甲醇 、 甲苯 为溶剂， 生成 5-(4-hydroxy-benzyl)-3-triphenylmethylthiazolidine-2,4-dione
  参考文献：
  名称：

  Thiazolidine compounds containing a quinone group, their preparation and

  摘要：

  式(I)的化合物：##STR1##（其中：R.sup.1是烷基；R.sup.2和R.sup.3分别是烷基或烷氧基，或者R.sup.2和R.sup.3共同形成一个可选择取代的苯环，当R.sup.2和R.sup.3共同形成该苯环时，R.sup.1是氢、卤素或烷基；R.sup.4和R.sup.5均表示氢，或共同表示一个碳-碳键；W是单键或烷基；Z是氢原子或阳离子），具有有价值的治疗和预防活性，包括抗糖尿病活性。

  公开号：

  US05338855A1

文献信息

• Materials and methods for the treatment of diabetes, hyperlipidemia, hypercholesterolemia, and atherosclerosis
  申请人：——

  公开号：US20030236227A1

  公开（公告）日：2003-12-25

  The subject invention provides pharmaceutical compounds useful in the treatment of Type II diabetes. These compounds are advantageous because they are readily metabolized by the metabolic drug detoxification systems. Particularly, thiazolidinedione analogs that have been designed to include esters within the structure of the compounds are provided. This invention is also drawn to methods of treating disorders, such as diabetes, comprising the administration of therapeutically effective compositions comprising compounds that have been designed to be metabolized by serum or intracellular hydrolases and esterases. Pharmaceutical compositions of the ester-containing thiazolidinedione analogs are also taught.

  该发明提供了在治疗2型糖尿病中有用的药物化合物。这些化合物具有优势，因为它们可以被代谢药物解毒系统迅速代谢。特别地，设计了包含酯基的噻唑烷二酮类似物的化合物。该发明还涉及治疗疾病的方法，如糖尿病，包括给予经设计为能够被血清或细胞内酯酶代谢的化合物的治疗有效组合物。还教授了含酯基的噻唑烷二酮类似物的药物组合物。
• Benzimidazole derivatives, their preparation and their therapeutic use
  申请人：Sankyo Company, Limited

  公开号：US05886014A1

  公开（公告）日：1999-03-23

  Compounds of formula (I): ##STR1## \x9bwherein: X represents an optionally substituted benzimidazole group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethlyl group; R represents hydrogen, alkyl, alkoxy, halogen, hydroxy, nitro, amino or aralkyl; and m is an integer from 1 to 5!; have valuable activity for the treatment and/or prophylaxis of a variety of disorders, including one or more of: hyperlipemia, hyperglycemia, obesity, impaired glucose tolerance (IGT), insulin resistance and diabetic complications.

  式(I)的化合物：##STR1##其中：X代表可选择取代的苯并咪唑基团；Y代表氧或硫原子；Z代表2,4-二氧代噻唑啉-5-基甲基、2,4-二氧代噻唑啉-5-基甲基、2,4-二氧代噻唑啉-5-基甲基、3,5-二氧代噻唑啉-2-基甲基或N-羟基脲基甲基基团；R代表氢、烷基、烷氧基、卤素、羟基、硝基、氨基或芳基烷基；m为1到5的整数；对于治疗和/或预防多种疾病，包括高脂血症、高血糖症、肥胖、糖耐量受损（IGT）、胰岛素抵抗和糖尿病并发症具有有价值的活性。
• Aromatic amino-alcohol derivatives having anti-diabetic and anti-obesity
  申请人：Sankyo Company, Limited

  公开号：US05576340A1

  公开（公告）日：1996-11-19

  Compounds of formula (I): ##STR1## (wherein: R.sup.0 is hydrogen, methyl or hydroxymethyl; R.sup.1 is substituted alkyl; R.sup.2 and R.sup.3 are each hydrogen, halogen, hydroxy, alkoxy, carboxy, alkoxycarbonyl, alkyl, nitro, haloalkyl, or substituted alkyl; X is oxygen or sulfur; and Ar optionally substituted phenyl or naphthyl); and pharmaceutically acceptable salts thereof have a variety of valuable pharmaceutical activities, including anti-diabetic and anti-obesity activities; in addition, they are capable of treating or preventing hyperlipemia and hyperglycemia and, by inhibiting the action of aldose reductase, they can also be effective in the treatment and prevention of complications of diabetes.

  化合物的化学式（I）：##STR1##（其中：R.sup.0为氢、甲基或羟甲基；R.sup.1为取代烷基；R.sup.2和R.sup.3分别为氢、卤素、羟基、烷氧基、羧基、烷氧羰基、烷基、硝基、卤代烷基或取代烷基；X为氧或硫；Ar为可选的取代苯基或萘基）；以及其药学上可接受的盐具有多种有价值的药理活性，包括抗糖尿病和抗肥胖活性；此外，它们能够治疗或预防高脂血症和高血糖，并通过抑制醛糖还原酶的作用，它们还可以有效地治疗和预防糖尿病并发症。
• Substituted fused heterocyclic compound
  申请人：Sankyo Company, Limited

  公开号：US06432993B1

  公开（公告）日：2002-08-13

  Substituted fused heterocyclic compounds of the formula (I) and pharmacologically acceptable salts thereof: wherein R1 is a group of the formula (II) or (III): R4 is a substituted phenyl or a pyridyl which may have a substituent. R5 is hydrogen or the like. R6 is hydrogen, a C1-6 alkyl group or the like. D is oxygen or sulfur. E is a CH group or nitrogen. R2 is hydrogen or the like. R3 is a 2,4-dioxothiazolidin-5-ylmethyl group or the like. A is a C1-6 alkylene group. B is oxygen or sulfur. These compounds and salts are useful as the active ingredient of pharmaceutical compositions which can be used to treat patients because these compounds and salts have excellent insulin-resistance improving action, lipid-peroxide-production inhibitory action, 5-lipoxygenase inhibitory action and the like.

  式（I）的取代融合杂环化合物及其药学上可接受的盐： 其中R1是式（II）或（III）的基团： R4是取代苯基或可能有取代基的吡啶基。R5是氢或类似物。R6是氢、C1-6烷基或类似物。D是氧或硫。E是CH基团或氮。R2是氢或类似物。R3是2,4-二氧代噻唑啉-5-基甲基基团或类似物。A是C1-6烷基基团。B是氧或硫。这些化合物和盐可用作药物组合物的活性成分，可用于治疗患者，因为这些化合物和盐具有出色的改善胰岛素抵抗作用、抑制脂质过氧化产物生成作用、5-脂氧合酶抑制作用等。
• Heterocyclic compounds having anti-diabetic activity and their use
  申请人：Sankyo Company, Limited

  公开号：US05624935A1

  公开（公告）日：1997-04-29

  Compounds of formula (I): ##STR1## [wherein: X represents an unsubstituted or substituted indolyl, indolinyl, azaindolyl, azaindolinyl, imidazopyridyl or imidazopyrimidinyl group; Y represents an oxygen or sulfur atom; Z represents a 2,4-dioxothiazolidin-5-ylidenylmethyl, 2,4-dioxothiazolidin-5-ylmethyl, 2,4-dioxooxazolidin-5-ylmethyl, 3,5-dioxooxadiazolidin-2-ylmethyl or N-hydroxyureidomethyl group; R represents a hydrogen atom, an alkyl group, an alkoxy group, a halogen atom, a hydroxy group, a nitro group, an aralkyl group or a unsubstituted or substituted amino group; and m is an integer of from 1 to 5] have hypoglycemic and anti-diabetic activities.

  式(I)的化合物：##STR1## [其中：X代表未取代或取代的吲哚基、吲哚啉基、氮杂吲哚基、氮杂吲哚啉基、咪唑吡啶基或咪唑吡嘧啶基；Y代表氧原子或硫原子；Z代表2,4-二氧代噻唑啉-5-基甲基、2,4-二氧代噻唑啉-5-基甲基、2,4-二氧代噁唑啉-5-基甲基、3,5-二氧代噁二唑啉-2-基甲基或N-羟基脲基甲基；R代表氢原子、烷基、烷氧基、卤原子、羟基、硝基、芳基烷基或未取代或取代的氨基；m为1至5的整数]具有降血糖和抗糖尿病活性。