trans-1,2-bis[3-(1-guaiazulenecarboxaldehyde)]ethylene | 431042-82-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: trans-1,2-bis[3-(1-guaiazulenecarboxaldehyde)]ethylene
• 英文别名: 3-[(E)-2-(3-formyl-8-methyl-5-propan-2-ylazulen-1-yl)ethenyl]-4-methyl-7-propan-2-ylazulene-1-carbaldehyde
• CAS: 431042-82-9
• 化学式: C₃₂H₃₂O₂
• 分子量: 448.605
• InChiKey: PMAWPXSPPRJBFE-VAWYXSNFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  34.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  trans-1,2-bis[3-(1-guaiazulenecarboxaldehyde)]ethylene 在 吡啶 、 magnesium sulfate 、 tris-(4-bromophenyl)aminium hexachloroantimonate 作用下， 以 various solvent(s) 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Stilbazulenyl Nitrone (STAZN):  A Nitronyl-Substituted Hydrocarbon with the Potency of Classical Phenolic Chain-Breaking Antioxidants

  摘要：

  Stilbazulenyl nitrone (STAZN), 8, a nitronyl-substituted hydrocarbon, is a novel second-generation azulenyl nitrone with significantly enhanced potency as a chain-breaking antioxidant vs conventional a-phenyl nitrones previously investigated as antioxidant therapeutics. A convenient H-1 NMR-based assay for assessing the potency of chain-breaking antloxidants has shown that STAZN is ca. 300 times more potent in inhibiting the free radical-mediated aerobic peroxidation of cumene than is PBN and the experimental stroke drug NXY-059. Such levels of antioxidant efficacy are unprecedented among archetypal a-phenyl nitrone spin traps. Furthermore, STAZN outperforms such classical phenolic antioxidants as BHT and probucol and rivals the antioxidant potency of Vitamin E in a polar medium comprised of 80,. cumene and 20% methanol, The Voloclarskii electron-transfer mechanism involving the intermediacy of the STAZN radical cation has been implicated in attempts to ascertain the basis for the increased potency of STAZN over the three a-phenyl nitrones PBN, S-PBN, and NXY-059.

  DOI：

  10.1021/ja011507s
• 作为产物：
  描述：

  愈创奥 在 barium dihydroxide 、 四(三苯基膦)钯 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 、 丙酮 、 甲苯 为溶剂， 反应 4.25h， 生成 trans-1,2-bis[3-(1-guaiazulenecarboxaldehyde)]ethylene
  参考文献：
  名称：

  Stilbazulenyl Nitrone (STAZN):  A Nitronyl-Substituted Hydrocarbon with the Potency of Classical Phenolic Chain-Breaking Antioxidants

  摘要：

  Stilbazulenyl nitrone (STAZN), 8, a nitronyl-substituted hydrocarbon, is a novel second-generation azulenyl nitrone with significantly enhanced potency as a chain-breaking antioxidant vs conventional a-phenyl nitrones previously investigated as antioxidant therapeutics. A convenient H-1 NMR-based assay for assessing the potency of chain-breaking antloxidants has shown that STAZN is ca. 300 times more potent in inhibiting the free radical-mediated aerobic peroxidation of cumene than is PBN and the experimental stroke drug NXY-059. Such levels of antioxidant efficacy are unprecedented among archetypal a-phenyl nitrone spin traps. Furthermore, STAZN outperforms such classical phenolic antioxidants as BHT and probucol and rivals the antioxidant potency of Vitamin E in a polar medium comprised of 80,. cumene and 20% methanol, The Voloclarskii electron-transfer mechanism involving the intermediacy of the STAZN radical cation has been implicated in attempts to ascertain the basis for the increased potency of STAZN over the three a-phenyl nitrones PBN, S-PBN, and NXY-059.

  DOI：

  10.1021/ja011507s

文献信息

• [EN] AZULENYL NITRONE SPIN TRAPPING AGENTS, METHODS OF MAKING AND USING SAME<br/>[FR] AGENTS DE PIEGEAGE DE SPIN A BASE D'AZULENYL NITRONE, PROCEDES DE PREPARATION ET D'UTILISATION DE CEUX-CI
  申请人：TEES THE FLORIDA INTERNAT UNIV

  公开号：WO2006036768A3

  公开（公告）日：2006-09-28
• Kinetic Studies on Stilbazulenyl-bis<i>-</i>nitrone (STAZN), a Nonphenolic Chain-Breaking Antioxidant in Solution, Micelles, and Lipid Membranes
  作者：Subhash C. Mojumdar、David A. Becker、Gino A. DiLabio、James J. Ley、L. Ross C. Barclay、K. U. Ingold

  DOI：10.1021/jo030390i

  日期：2004.4.1

  The rate constants, k(inh), for reaction of stilbazulenyl-bis-nitrone (STAZN, 1) with peroxyl radicals and the number of radicals trapped, n, are compared with those of phenolic antioxidants 2,2,5,7,8-pentamethyl-6-hydroxychroman (PMHC, 4a), 2,5,7,8-tetramethyl-6-hydroxychroman-2-carboxylic acid (Trolox, 4b), and 2,6-di-tert-butyl-4-methoxyphenol (DBHA, 5). The behavior of STAZN depended markedly on the media and type of initiator used, water-soluble or lipid-soluble. In styrene/chlorobenzene and initiation by azo-bis(isobutyronitrile) (AIBN), k(inh) (STAZN) = 0.64 k(inh) (5) = 0.02k(inh) (4a). On addition of methanol, the kinh of STAZN increased 6-fold to be four times that of 5 while that of 4a decreased 6-fold. In aqueous SDS-micelles containing methyl linoleate and initiation with water-soluble azo-bis(amidinopropane)2HCl, ABAP, the relative kinh values were 1 greater than or equal to 4b > 5. In dilinoleoylphosphatidyl choline (DLPC) bilayers and initiation with lipid-soluble azo-bis-2.4(dimethylvaleronitrile) (DMVN), the k(inh) order was 5 > 4b > 1. During initiation with ABAP in micelles and bilayers, the calculated values of kinh for STAZN changed during the induction period. The experimental results are interpreted in terms of the conformation of STAZN, which is transoid in homogeneous solution but cisoid in aqueous dispersions of lipids. In such dispersions, the STAZN lies at the lipid-water interface where it traps water-soluble peroxyl radicals by a single electron-transfer mechanism. The cisoid conformation at lipid-water interfaces is supported by theoretical calculations.
• Azulenyl Nitrone Spin Trapping Agents, Methods of Making and Using Same
  申请人：Becker David A.

  公开号：US20080167474A1

  公开（公告）日：2008-07-10

  The present invention provides azulenyl nitrones, such as those having the following general formula: (I) compositions comprising the same and methods of their use for the treatment or prevention of oxidative, ischemic, ischemia/reperfusion-related and chemokine-mediated conditions.
• US7910729B2
  申请人：——

  公开号：US7910729B2

  公开（公告）日：2011-03-22
• Stilbazulenyl Nitrone (STAZN):  A Nitronyl-Substituted Hydrocarbon with the Potency of Classical Phenolic Chain-Breaking Antioxidants
  作者：David A. Becker、James J. Ley、Luis Echegoyen、Robert Alvarado

  DOI：10.1021/ja011507s

  日期：2002.5.1

  Stilbazulenyl nitrone (STAZN), 8, a nitronyl-substituted hydrocarbon, is a novel second-generation azulenyl nitrone with significantly enhanced potency as a chain-breaking antioxidant vs conventional a-phenyl nitrones previously investigated as antioxidant therapeutics. A convenient H-1 NMR-based assay for assessing the potency of chain-breaking antloxidants has shown that STAZN is ca. 300 times more potent in inhibiting the free radical-mediated aerobic peroxidation of cumene than is PBN and the experimental stroke drug NXY-059. Such levels of antioxidant efficacy are unprecedented among archetypal a-phenyl nitrone spin traps. Furthermore, STAZN outperforms such classical phenolic antioxidants as BHT and probucol and rivals the antioxidant potency of Vitamin E in a polar medium comprised of 80,. cumene and 20% methanol, The Voloclarskii electron-transfer mechanism involving the intermediacy of the STAZN radical cation has been implicated in attempts to ascertain the basis for the increased potency of STAZN over the three a-phenyl nitrones PBN, S-PBN, and NXY-059.