(Z)-5-[4-benzyloxy-2-(4-fluorobenzyloxy)benzylidene]thiazolidine-2,4-dione | 1257999-27-1

• 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-[4-benzyloxy-2-(4-fluorobenzyloxy)benzylidene]thiazolidine-2,4-dione
• 英文别名: (5Z)-5-[[2-[(4-fluorophenyl)methoxy]-4-phenylmethoxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione
• CAS: 1257999-27-1
• 化学式: C₂₄H₁₈FNO₄S
• 分子量: 435.476
• InChiKey: YPPZQANRGKMBPW-UUYOSTAYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  31
• 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：
  6

反应信息

• 作为产物：
  描述：

  2,4-噻唑烷二酮 、 4-benzyloxy-2-(4-fluorobenzyloxy)benzaldehyde 在 哌啶 作用下， 以 乙醇 为溶剂， 以90%的产率得到(Z)-5-[4-benzyloxy-2-(4-fluorobenzyloxy)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

• Novel thiazolidinedione derivatives with anti-obesity effects: Dual action as PTP1B inhibitors and PPAR-γ activators
  作者：Bharat Raj Bhattarai、Bhooshan Kafle、Ji-Sun Hwang、Seung Wook Ham、Keun-Hyeung Lee、Hwangseo Park、Inn-Oc Han、Hyeongjin Cho

  DOI：10.1016/j.bmcl.2010.08.130

  日期：2010.11

  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.