N-(4-formylbenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide | 1255892-34-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(4-formylbenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide
• 英文别名: TMAm；N-[(4-formylphenyl)methyl]-5,5,8,8-tetramethyl-6,7-dihydronaphthalene-2-carboxamide
• CAS: 1255892-34-2
• 化学式: C₂₃H₂₇NO₂
• 分子量: 349.473
• InChiKey: ZYRCBVGGPGHTNL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  46.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-(4-(hydroxymethyl)benzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide 在 manganese(IV) oxide 作用下， 以 二氯甲烷 为溶剂， 生成 N-(4-formylbenzyl)-5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamide
  参考文献：
  名称：

  Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for Retinitis Pigmentosa

  摘要：

  The Retinitis pigmentosa (RP)-causing mutant of rhodopsin, P23H rhodopsin, is folding-defective and unable to traffic beyond the endoplasmic reticulum (ER). This ER retention, and in some cases aggregation, are proposed to result in ER-stress and eventually cell death. The endogenous rhodopsin ligand 11-cis-retinal and its isomer 9-cis-retinal have been shown to act as pharmacological chaperones, promoting proper folding and trafficking of the P23H rhodopsin. In spite of this promising effect, the development of retinals and related polyenealdehydes as pharmacological agents has been hampered by their undesirable properties, which include chemical instability, photolability, and potential retinoidal actions. Here, we report the design and synthesis of a class of more stable nonpolyene-type rhodopsin ligands, structurally distinct from, and with lower toxicity than, retinals. A structure-activity relationship study was conducted using cell-surface expression assay to quantify folding/trafficking efficiency of P23H rhodopsin. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.08.014