Toluene-4-sulfonic acid 2,3-diphenyl-indolizin-1-yl ester | 852063-75-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: Toluene-4-sulfonic acid 2,3-diphenyl-indolizin-1-yl ester
• 英文别名: (2,3-Diphenylindolizin-1-yl) 4-methylbenzenesulfonate
• CAS: 852063-75-3
• 化学式: C₂₇H₂₁NO₃S
• 分子量: 439.535
• InChiKey: AWGVJTOBWKWKRB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  32
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  56.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Toluene-4-sulfonic acid 2,3-diphenyl-indolizin-1-yl ester 在 tetramethylammonium tetrafluoroborate 作用下， 以 乙腈 为溶剂， 以64%的产率得到2,3-diphenyl-1-oxoindolizinium tetrafluoroborate
  参考文献：
  名称：

  Electrochemical studies of biologically active indolizines

  摘要：

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.02.078
• 作为产物：
  描述：

  二苯基环丙烯酮 在 4-二甲氨基吡啶 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 Toluene-4-sulfonic acid 2,3-diphenyl-indolizin-1-yl ester
  参考文献：
  名称：

  吲哚嗪1-磺酸盐是大豆中15-脂加氧酶的有效抑制剂。

  摘要：

  通过用吡啶将环丙烯酮环化，然后用磺酰卤捕获中间物1-吲哚嗪醇，已经制备了许多吲哚嗪1-磺酸盐，并将其作为15-脂加氧酶（15-LO）的抑制剂进行了研究。这些化合物的IC（50）值介于15和42 microM之间；所有这些都比众所周知的15-LO抑制剂槲皮素（IC（50）51 microM）更具活性。各种各样的取代基具有良好的耐受性。酶抑制不受预温育或去污剂存在的影响，并且未观察到明显的颗粒形成。因此，极不可能出现来自吲哚嗪类聚集体的抑制，即混杂抑制。

  DOI：

  10.1016/j.bmc.2005.02.056

文献信息

• Indolizine 1-sulfonates as potent inhibitors of 15-lipoxygenase from soybeans
  作者：Solomon Teklu、Lise-Lotte Gundersen、Tove Larsen、Karl E. Malterud、Frode Rise

  DOI：10.1016/j.bmc.2005.02.056

  日期：2005.5

  trapping of the intermediate 1-indolizinol with a sulfonyl halide, and examined as inhibitors of 15-lipoxygenase (15-LO). The compounds display IC(50) values between 15 and 42 microM; all are more active than the well-known 15-LO inhibitor quercetin (IC(50) 51 microM). A wide variety of substituents are well tolerated. The enzyme inhibition was not affected by preincubation or the presence of a detergent

  通过用吡啶将环丙烯酮环化，然后用磺酰卤捕获中间物1-吲哚嗪醇，已经制备了许多吲哚嗪1-磺酸盐，并将其作为15-脂加氧酶（15-LO）的抑制剂进行了研究。这些化合物的IC（50）值介于15和42 microM之间；所有这些都比众所周知的15-LO抑制剂槲皮素（IC（50）51 microM）更具活性。各种各样的取代基具有良好的耐受性。酶抑制不受预温育或去污剂存在的影响，并且未观察到明显的颗粒形成。因此，极不可能出现来自吲哚嗪类聚集体的抑制，即混杂抑制。
• Electrochemical studies of biologically active indolizines
  作者：Solomon Teklu、Lise-Lotte Gundersen、Frode Rise、Mats Tilset

  DOI：10.1016/j.tet.2005.02.078

  日期：2005.5

  The electrochemical behavior of indolizine ethers, esters, tosylates, sulfonates and other indolizine and azaindolizine derivatives has been investigated by cyclic voltammetry and preparative electrolysis. The cyclic voltammetric data show that the E degrees values, taken as the midpoints between the anodic and cathodic peak potentials, are sensitive to the identities of the substituents at C-1, C-2 and C-7 positions. The E degrees values have been correlated with the Hammett substituent parameters. As expected, low E degrees values are seen for electron donating substituents and higher E degrees values are seen for electron withdrawing substituents. The cyclic voltammograms of indolizine derivatives with an oxygen atom connected to the CA position exhibit a one-electron reversible oxidation and a further, less well-defined, one-electron irreversible oxidation at higher E degrees values. The cyclic voltammograms of indolizines with hydrogen atom or thienyl substituents connected to the G I position exhibit only a one-electron irreversible oxidation. Electrochemical bulk oxidations of indolizines with an oxygen atom at the C-1 position afforded oxoindolizinium salts in decent yields, whereas indolizines with a hydrogen atom at C-1 afforded 1,1' dimers of indolizines as products in good yields. Bulk oxidation of 1-(alpha-hydroxybenzyl)-2,3-diphenylindolizine-7-carbonitfile afforded an unexpected ketone product in which the carbonyl group of the indolizine is connected at C-8 instead of at the C-I position of the starting material. The findings described herein support our hypothesis that certain indolizine derivatives may inhibit lipid peroxidation by an electron transfer mechanism. (c) 2005 Elsevier Ltd. All rights reserved.