4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(3R)-piperidinyloxy]benzaldehyde | 199109-03-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(3R)-piperidinyloxy]benzaldehyde
• 英文别名: 4-[(3R)-1-[(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)methyl]piperidin-3-yl]oxybenzaldehyde
• CAS: 199109-03-0
• 化学式: C₃₃H₃₉NO₄
• 分子量: 513.677
• InChiKey: BMOPSVPKLZYNJM-IIGOATNISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.8
• 重原子数：
  38
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  48
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2,4-噻唑烷二酮 、 4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(3R)-piperidinyloxy]benzaldehyde 在 哌啶 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 2.0h， 以57%的产率得到(5Z)-5-[[4-[(3R)-1-[(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)methyl]piperidin-3-yl]oxyphenyl]methylidene]-1,3-thiazolidine-2,4-dione
  参考文献：
  名称：

  Novel Antidiabetic and Hypolipidemic Agents. 5. Hydroxyl versus Benzyloxy Containing Chroman Derivatives

  摘要：

  Several thiazolidinediones having chroman moieties were synthesized and evaluated for their euglycemic and hypolipidemic activities. Some of the analogues having an aminoalkyl group as a linker between the chroman ring and 4-[5-(2,4-dioxo-1,3-thiazolidinyl)methyl]phenoxy moiety seem to be better than troglitazone. In vitro transactivation assays of PPAR gamma have been carried out with these glitazones to understand their molecular mechanism. For the first time we have found that some of the unsaturated thiazolidinediones are superior to their saturated counterpart in the in vivo assay. A more potent thiazolidinedione analogue than troglitazone is reported. Pharmacokinetic studies have shown that protection of the OH group in the chroman moiety leads to a decrease in metabolism, thereby resulting in a superior pharmacological profile.

  DOI：

  10.1021/jm9805541
• 作为产物：
  描述：

  (2R/S)-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]carbinol 在 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 11.0h， 生成 4-[N-[(2R/S)-6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethyl]-(3R)-piperidinyloxy]benzaldehyde
  参考文献：
  名称：

  Novel Antidiabetic and Hypolipidemic Agents. 5. Hydroxyl versus Benzyloxy Containing Chroman Derivatives

  摘要：

  Several thiazolidinediones having chroman moieties were synthesized and evaluated for their euglycemic and hypolipidemic activities. Some of the analogues having an aminoalkyl group as a linker between the chroman ring and 4-[5-(2,4-dioxo-1,3-thiazolidinyl)methyl]phenoxy moiety seem to be better than troglitazone. In vitro transactivation assays of PPAR gamma have been carried out with these glitazones to understand their molecular mechanism. For the first time we have found that some of the unsaturated thiazolidinediones are superior to their saturated counterpart in the in vivo assay. A more potent thiazolidinedione analogue than troglitazone is reported. Pharmacokinetic studies have shown that protection of the OH group in the chroman moiety leads to a decrease in metabolism, thereby resulting in a superior pharmacological profile.

  DOI：

  10.1021/jm9805541

文献信息

• Novel Antidiabetic and Hypolipidemic Agents. 5. Hydroxyl versus Benzyloxy Containing Chroman Derivatives
  作者：K. Anji Reddy、B. B. Lohray、V. Bhushan、A. Sekar Reddy、N. V. S. Rao Mamidi、P. Papi Reddy、V. Saibaba、N. Jaipal Reddy、A. Suryaprakash、Parimal Misra、Reeba K. Vikramadithyan、R. Rajagopalan

  DOI：10.1021/jm9805541

  日期：1999.8.1

  Several thiazolidinediones having chroman moieties were synthesized and evaluated for their euglycemic and hypolipidemic activities. Some of the analogues having an aminoalkyl group as a linker between the chroman ring and 4-[5-(2,4-dioxo-1,3-thiazolidinyl)methyl]phenoxy moiety seem to be better than troglitazone. In vitro transactivation assays of PPAR gamma have been carried out with these glitazones to understand their molecular mechanism. For the first time we have found that some of the unsaturated thiazolidinediones are superior to their saturated counterpart in the in vivo assay. A more potent thiazolidinedione analogue than troglitazone is reported. Pharmacokinetic studies have shown that protection of the OH group in the chroman moiety leads to a decrease in metabolism, thereby resulting in a superior pharmacological profile.