Δ-4H-2-(4-anilino)-6-(4-N-morpholinophenyl)selenopyran-4-one | 477941-65-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 恶嗪烷类
• 英文名称: Δ-4H-2-(4-anilino)-6-(4-N-morpholinophenyl)selenopyran-4-one
• 英文别名: 2-(4-Aminophenyl)-6-(4-morpholin-4-ylphenyl)selenopyran-4-one
• CAS: 477941-65-4
• 化学式: C₂₁H₂₀N₂O₂Se
• 分子量: 411.362
• InChiKey: ZHKYGOILHVKXBR-UHFFFAOYSA-N

物化性质

• 沸点：
  634.4±55.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.86
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  Δ-4H-2-(4-anilino)-6-(4-N-morpholinophenyl)selenopyran-4-one 、 4-(N,N-二甲基)苯胺溴化镁 在 hexafluorophosphoric acid 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以72%的产率得到2-(4-anilino)-4-(4-N,N-dimethylanilino)-6-(4-N-morpholinophenyl)selenopyrylium hexafluorophosphate
  参考文献：
  名称：

  In Vitro Photodynamic Properties of Chalcogenopyrylium Analogues of the Thiopyrylium Antitumor Agent AA1

  摘要：

  Several series of chalcogenopyrylium dyes were prepared with one or two 4-anilino substituents at the 2- and 6-positions and with phenyl, 4-N,N-dimethylanilino, or 4-(N-morphilino)phenyl substituents at 2- and/or 4-positions. The dye series are all related in structure to AA1, a thiopyrylium dye that targets mitochondria. The chalcogenopyrylium. nuclei included sulfur, selenium, and tellurium at the 1-position. Key intermediates in the dye synthesis were the corresponding Delta-4H-chalcogenopyran-4-ones. All of the dyes of this study were evaluated for dark and phototoxicity toward Colo-26 cells in vitro. There was no correlation of dark toxicity with either the reduction potential of the chalcogenopyrylium dye or the n-octanol/water partition coefficient, log P. Several of the dyes of this study (thiopyrylium dyes 1-S and 13-S, selenopyrylium dyes 1-Se, 2-Se, 3-Se, 4-Se, 13-Se, 14-Se, and 27-Se, and telluropyrylium dye 13-Te) showed added phototoxicity upon irradiation. Dyes with the highest therapeutic ratio as measured by dark toxicity/phototoxicity (15 J cm(-2) of 360-800-nm light) had values of log P of 1.0-1.2. Studies of cytochrome c oxidase activity in whole R3230AC cells suggested that dyes I-S and 3-Se, with values of log P of 2.2 and 1.7, respectively, were localized in the mitochondria. Cytocrome c oxidase activity in whole cells was inhibited by 1-S and 3-Se in the dark. Chalcogenopyrylium dyes 2-Se, 4-Se, 13-Te, and 14-Se inhibited whole-cell cytochrome c oxidase activity only following irradiation, which suggests that these dyes relocalized to mitochondria following irradiation.

  DOI：

  10.1021/jm020260m
• 作为产物：
  描述：

  4-(4-碘苯基)吗啉 在 manganese(IV) oxide 、 bis-triphenylphosphine-palladium(II) chloride 、 sodium selenide 、 sodium tetrahydroborate 、 正丁基锂 、 sodium ethanolate 、 copper(II) iodide 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 Δ-4H-2-(4-anilino)-6-(4-N-morpholinophenyl)selenopyran-4-one
  参考文献：
  名称：

  In Vitro Photodynamic Properties of Chalcogenopyrylium Analogues of the Thiopyrylium Antitumor Agent AA1

  摘要：

  Several series of chalcogenopyrylium dyes were prepared with one or two 4-anilino substituents at the 2- and 6-positions and with phenyl, 4-N,N-dimethylanilino, or 4-(N-morphilino)phenyl substituents at 2- and/or 4-positions. The dye series are all related in structure to AA1, a thiopyrylium dye that targets mitochondria. The chalcogenopyrylium. nuclei included sulfur, selenium, and tellurium at the 1-position. Key intermediates in the dye synthesis were the corresponding Delta-4H-chalcogenopyran-4-ones. All of the dyes of this study were evaluated for dark and phototoxicity toward Colo-26 cells in vitro. There was no correlation of dark toxicity with either the reduction potential of the chalcogenopyrylium dye or the n-octanol/water partition coefficient, log P. Several of the dyes of this study (thiopyrylium dyes 1-S and 13-S, selenopyrylium dyes 1-Se, 2-Se, 3-Se, 4-Se, 13-Se, 14-Se, and 27-Se, and telluropyrylium dye 13-Te) showed added phototoxicity upon irradiation. Dyes with the highest therapeutic ratio as measured by dark toxicity/phototoxicity (15 J cm(-2) of 360-800-nm light) had values of log P of 1.0-1.2. Studies of cytochrome c oxidase activity in whole R3230AC cells suggested that dyes I-S and 3-Se, with values of log P of 2.2 and 1.7, respectively, were localized in the mitochondria. Cytocrome c oxidase activity in whole cells was inhibited by 1-S and 3-Se in the dark. Chalcogenopyrylium dyes 2-Se, 4-Se, 13-Te, and 14-Se inhibited whole-cell cytochrome c oxidase activity only following irradiation, which suggests that these dyes relocalized to mitochondria following irradiation.

  DOI：

  10.1021/jm020260m

文献信息

• In Vitro Photodynamic Properties of Chalcogenopyrylium Analogues of the Thiopyrylium Antitumor Agent AA1
  作者：Nancy K. Brennan、Jonathan P. Hall、Sherry R. Davies、Sandra O. Gollnick、Allan R. Oseroff、Scott L. Gibson、Russell Hilf、Michael R. Detty

  DOI：10.1021/jm020260m

  日期：2002.11.1

  Several series of chalcogenopyrylium dyes were prepared with one or two 4-anilino substituents at the 2- and 6-positions and with phenyl, 4-N,N-dimethylanilino, or 4-(N-morphilino)phenyl substituents at 2- and/or 4-positions. The dye series are all related in structure to AA1, a thiopyrylium dye that targets mitochondria. The chalcogenopyrylium. nuclei included sulfur, selenium, and tellurium at the 1-position. Key intermediates in the dye synthesis were the corresponding Delta-4H-chalcogenopyran-4-ones. All of the dyes of this study were evaluated for dark and phototoxicity toward Colo-26 cells in vitro. There was no correlation of dark toxicity with either the reduction potential of the chalcogenopyrylium dye or the n-octanol/water partition coefficient, log P. Several of the dyes of this study (thiopyrylium dyes 1-S and 13-S, selenopyrylium dyes 1-Se, 2-Se, 3-Se, 4-Se, 13-Se, 14-Se, and 27-Se, and telluropyrylium dye 13-Te) showed added phototoxicity upon irradiation. Dyes with the highest therapeutic ratio as measured by dark toxicity/phototoxicity (15 J cm(-2) of 360-800-nm light) had values of log P of 1.0-1.2. Studies of cytochrome c oxidase activity in whole R3230AC cells suggested that dyes I-S and 3-Se, with values of log P of 2.2 and 1.7, respectively, were localized in the mitochondria. Cytocrome c oxidase activity in whole cells was inhibited by 1-S and 3-Se in the dark. Chalcogenopyrylium dyes 2-Se, 4-Se, 13-Te, and 14-Se inhibited whole-cell cytochrome c oxidase activity only following irradiation, which suggests that these dyes relocalized to mitochondria following irradiation.