(Z)-5-[2,4-bis(benzyloxy)benzylidene]thiazolidine-2,4-dione | 1257999-22-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (Z)-5-[2,4-bis(benzyloxy)benzylidene]thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[2,4-bis(phenylmethoxy)phenyl]methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1257999-22-6
• 化学式: C₂₄H₁₉NO₄S
• 分子量: 417.485
• InChiKey: FYTYCNJXFACJEO-XKZIYDEJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  89.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 2,4-二苄氧基苯甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 以87%的产率得到(Z)-5-[2,4-bis(benzyloxy)benzylidene]thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators

  摘要：

  Benzylidene-2,4-thiazolidinedione derivatives with substitutions at both the ortho and para-positions of the phenyl group were synthesized as PTP1B inhibitors with IC50 values in a low micromolar range. Compound 18l, the lowest, bore an IC50 of 1.3 mu M. In a peroxisome proliferator-activated receptor-gamma (PPAR-gamma) promoter reporter gene assay, 18l was found to activate the transcription of the reporter gene with potencies comparable to those of troglitazone, rosiglitazone, and pioglitazone. In vivo efficacy of 18l as an anti-obesity and hypoglycemic agent was evaluated in a mouse model system. Compound 18l significantly suppressed weight gain and significantly improved blood parameters such as TG, total cholesterol and NEFA without overt toxic effects. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.08.130

文献信息

• [EN] THIAZOLIDINE DERIVATIVES FOR THE TREATMENT AND PREVENTION OF METABOLIC BONE DISORDERS<br/>[FR] DERIVES DE THIAZOLIDINE UTILES POUR LE TRAITEMENT ET LA PREVENTION DE TROUBLES METABOLIQUES DES OS
  申请人：ROCHE DIAGNOSTICS GMBH

  公开号：WO2000018746A1

  公开（公告）日：2000-04-06

  The object of the present invention are compounds of general formula (I), in which: m signifies a number between 0-8; q signifies a number between 0-8; A signifies a single or double bond; R1 signifies hydrogen or, when X and Z are oxygen, also -(CH2)-COR4 with a =0-6; R2, R3 signify hydrogen or lower alkyl, whereby R2 and R3 can be the same or different and, when m signifies 2-8, R2 and R3 in the group CR2=CR3 can have various significances within the following sequence; R4 signifies hydroxyl, lower alkoxy or the NR1R2 residue, whereby R1 and R2 can be the same or different; X signifies oxygen or imino; Z signifies oxygen, sulfur or imino; W signifies an optionally mono- or polysubstituted saturated or unsaturated mono-, bi- or tricycle which can contain one or more hetero atoms, as well as their physiologically compatible salts, esters, optically active forms, racemates, tautomers, as well as derivatives which can be metabolized in vivo to compounds of general formula (I), as well as the use of these compounds for the production of medicaments for the prophylaxis or therapy of metabolic bone disorders.