Δ-4H-2,6-bis(4-anilino)selenopyran-4-one | 477941-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Δ-4H-2,6-bis(4-anilino)selenopyran-4-one
• 英文别名: 2,6-Bis(4-aminophenyl)selenopyran-4-one
• CAS: 477941-20-1
• 化学式: C₁₇H₁₄N₂OSe
• 分子量: 341.271
• InChiKey: LDPAHMQTIKXFIF-UHFFFAOYSA-N

物化性质

• 沸点：
  580.1±50.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.1
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Δ-4H-2,6-bis(4-anilino)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28%的产率得到2,6-bis(4-anilino)-4-(4-N,N-dimethylanilino)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：

  1,5-Bis-(4-amino-phenyl)-penta-1,4-diyn-3-one 在 sodium selenide 、 sodium tetrahydroborate 、 sodium ethanolate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 Δ-4H-2,6-bis(4-anilino)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

• Comparison of the dark and light-induced toxicity of thio and seleno analogues of the thiopyrylium dye AA1
  作者：Michael R Detty、Scott L Gibson、Russell Hilf

  DOI：10.1016/j.bmc.2004.03.025

  日期：2004.5

  2.6-Bis(4-anilino)-4-(4-N,N-dimethylanilino)thiopyrylium chloride (AA1) and -selenopyrylium chloride (AA1-Se) and 2,6-bis(4-anilino)-4-(4-N-morpholinophenyl)thiopyrylium chloride (1) and -selenopyrylium chloride (2) were prepared via the addition of 4-N,N-dimethylanilino magnesium bromide and 4-N-morpholinophenyl magnesium bromide to chalcogenopyranones 3 followed by treatment with HCl gas then water. Cellular uptake of these dyes varied from 12 +/- 3 fmol/cell for AA1 to 150 40 fmol/cell for AA1-Se. upon exposure to 5 x 10(-5) M Solutions of the dyes for 3 h. Exposure of cell cultures to 1.8 J/cm(2) of 360-750-nm light 191 following incubation with 1 x 10(-6) M of either AA1, 1, or 2 for 24 It resulted in no significant additional phototoxicity while AA1-Se showed a significant (P < 0.05) reduction in cell viability from 81% to 46%. Thiopyrylium dyes AA1 and 1 showed significant dark toxicity relative to selenopyrylium dyes AA1-Se and 2, respectively. AA1 was the only one of the four dyes to show inhibition of whole-cell mitochondrial cytochrome c oxidase activity in the dark. Irradiation of whole cells or mitochondrial suspensions treated with AA1, AA1-Se. or 2 gave inhibition of mitochondrial cytochrome c oxidase activity. Studies of JC-1-efflux indicated that all four cationic dyes accelerated the loss of JC-1 from the mitochondria, which Suggests that all four dyes target the mitochondria. (C) 2004 Elsevier Ltd. All rights reserved.
• 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.