4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde | 138564-69-9

• 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-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde
• 英文别名: 6-benzyloxy-2-[(4-formylphenyl)oxymethyl]-2,5,7,8-tetramethylchroman；4-[(2,5,7,8-tetramethyl-6-phenylmethoxy-3,4-dihydrochromen-2-yl)methoxy]benzaldehyde
• CAS: 138564-69-9
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: JZPYJHSJHRVRCB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]benzaldehyde 在 哌啶 、 盐酸 、 溶剂黄146 、 苯甲酸 作用下， 以 甲苯 为溶剂， 反应 52.0h， 生成 (5Z)-5-[1-[4-(6-hydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)phenyl]methylylidene]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：

  对氟苯甲醛 、 (2R/S)-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-yl]carbinol 在 potassium tert-butylate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以60%的产率得到4-[6-benzyloxy-2,5,7,8-tetramethylchroman-2-ylmethoxy]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

• Benzylidenethiazolidine derivatives and their use for the inhibition
  申请人：Sankyo Company, Limited

  公开号：US05387596A1

  公开（公告）日：1995-02-07

  Benzylidenethiazolidine compounds of formula (I): ##STR1## [in which R.sup.1, R.sup.2 and R.sup.5 are each hydrogen or alkyl; R.sup.3 and R.sup.4 are each hydrogen, alkyl, formyl, alkylcarbonyl, arylcarbonyl, carboxy, alkoxycarbonyl, aryloxycarbonyl, hydroxy, alkylcarbonyloxy, formyloxy, arylcarbonyloxy, optionally substituted alkoxy or halogen; W is methylene, carbonyl or a group of formula >C.dbd.N--OV, wherein V is hydrogen, alkylcarbonyl, arylcarbonyl or optionally substituted alkyl; and n is an integer of from 1 to 3] and salts thereof have the ability to inhibit the formation of lipid peroxide in the mammalian body, and can therefore be used for the treatment of arteriosclerosis and other diseases and disorders arising from an imbalance in the lipid peroxide level. They can also be used for the preparation of the corresponding benzylthiazolidine compounds, which have a generally greater hypoglycemic activity. Processes for the preparation of these compounds of formula (I) are also provided.

  Benzylidenethiazolidine化合物的化学式（I）：##STR1##[其中R.sup.1，R.sup.2和R.sup.5分别为氢或烷基；R.sup.3和R.sup.4分别为氢、烷基、甲酰基、烷基羰基、芳基羰基、羧基、烷氧羰基、芳氧羰基、羟基、烷基羰氧基、甲酰氧基、芳基羰氧基、可选择取代的烷氧基或卤素；W为亚甲基、羰基或化学式>C.dbd.N--OV的基团，其中V为氢、烷基羰基、芳基羰基或可选择取代的烷基；n为1至3的整数]及其盐具有抑制哺乳动物体内脂质过氧化物形成的能力，因此可用于治疗动脉粥样硬化和其他因脂质过氧化物水平不平衡而引起的疾病和紊乱。它们还可用于制备相应的苯基硫代乙酰胺化合物，其通常具有更强的降糖活性。还提供了制备这些化合物（I）的方法。
• Preparation of benzylthiazolidine derivatives
  申请人：Sankyo Company Limited

  公开号：EP0839812A1

  公开（公告）日：1998-05-06

  A process for preparing a compound of formula (Ia): [in which R1, R2 and R5 are each hydrogen or alkyl; R3 and R4 are each hydrogen, alkyl, formyl, alkylcarbonyl, arylcarbonyl, carboxy, alkoxycarbonyl, aryloxycarbonyl, hydroxy, alkylcarbonyloxy, formyloxy, arylcarbonyloxy, optionally substituted alkoxy or halogen; W is methylene, carbonyl or a group of formula >C=N-OV, in which V is hydrogen, alkylcarbonyl, arylcarbonyl or optionally substituted alkyl; and n is an integer of from 1 to 3] or a salt thereof by reduction of a compound of formula (I): or a salt thereof, in which R1 to R5, W and n are as defined above.

  一种制备式 (Ia) 化合物的工艺： [其中 R1、R2 和 R5 分别为氢或烷基；R3 和 R4 分别为氢、烷基、甲酰基、烷基羰基、芳基羰基、羧基、烷氧基羰基、芳氧基羰基、羟基、烷基羰氧基、甲酰基氧基、芳基羰氧基、任选取代的烷氧基或卤素；W 是亚甲基、羰基或式 >C=N-OV 的基团，其中 V 是氢、烷基羰基、芳基羰基或任选取代的烷基；以及 n 是 1 至 3 的整数]或通过还原式（I）化合物而得到的盐： 或其盐，其中 R1 至 R5、W 和 n 如上文所定义。
• Benzylidenethiazolidine derivatives, their preparation and their use for the inhibition of lipid peroxides
  申请人：Sankyo Company Limited

  公开号：EP0454501B1

  公开（公告）日：2001-09-05
• US5387596A
  申请人：——

  公开号：US5387596A

  公开（公告）日：1995-02-07
• 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.