bisjulolidylselenoxanthone | 1608131-05-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: bisjulolidylselenoxanthone
• CAS: 1608131-05-0
• 化学式: C₂₅H₂₆N₂OSe
• 分子量: 449.454
• InChiKey: AXUFEKJGKNVXFQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.81
• 重原子数：
  29.0
• 可旋转键数：
  0.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  23.55
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  bisjulolidylselenoxanthone 在 正丁基锂 、 二异丙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 17.53h， 生成
  参考文献：
  名称：

  Selenorhodamine photosensitizers with the Texas-red core for photodynamic therapy of cancer cells

  摘要：

  We examined two selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenoxanthylium analogue of the Texas-red core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp)-expressing Colo-26 cells. These compounds were examined for their photophysical properties (absorption, fluorescence, and ability to generate singlet oxygen), for their uptake into Colo-26 cells in the absence or presence of verapamil, for their dark and phototoxicity toward Colo-26 cells, and for their co-localization with mitochondrial-specific agents in Colo-26 cells. Both compounds were extremely effective photosensitizers with values of EC50 <= 4 x 10(-8) M toward Colo-26 cells with 1.0 J cm(-2) laser light delivered at 630 +/- 2 nm. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2015.06.006
• 作为产物：
  描述：

  在 三乙胺 、 三氯氧磷 作用下， 以 乙腈 为溶剂， 以70%的产率得到bisjulolidylselenoxanthone
  参考文献：
  名称：

  Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines

  摘要：

  Analogues of Texas red incorporating the heavy chalcogens S, Se, and Te atoms in the xanthylium core were prepared from the addition of aryl Grignard reagents to appropriate chalcogenoxanthone precursors. The xanthones were prepared via directed metalation of amide precursors, addition of dichalcogenide electrophiles, and electrophilic cyclization of the resulting chalcogenides with phosphorus oxychloride and triethylamine. The Texas red analogues incorporate two fused julolidine rings containing the rhodamine nitrogen atoms. Analogues containing two "half-julolidine" groups (a trimethyltetrahydroquinoline) and one julolidine and one "half-julolidine" were also prepared. The photophysics of the Texas red analogues were examined. The S-analogues were highly fluorescent, the Se-analogues generated single oxygen (O-1(2)) efficiently upon irradiation, and the Te-analogues were easily oxidized to rhodamines with the telluroxide oxidation state. The tellurorhodamine telluroxides absorb at wavelengths >= 690 nm and emit with fluorescence maxima >720 nm. A mesityl-substituted tellurorhodamine derivative localized in the mitochondria of Colo-26 cells (a murine colon carcinoma cell line) and was oxidized in vitro to the fluorescent telluroxide.

  DOI：

  10.1021/om500346j

文献信息

• Importance of Singlet Oxygen in Photocatalytic Reactions of 2-Aryl-1,2,3,4-tetrahydroisoquinolines Using Chalcogenorosamine Photocatalysts
  作者：Jennifer L. Clark、Jackie E. Hill、Irving D. Rettig、Joshua J. Beres、Roman Ziniuk、Tymish Y. Ohulchanskyy、Theresa M. McCormick、Michael R. Detty

  DOI：10.1021/acs.organomet.9b00126

  日期：2019.6.24

  photocatalytic aza-Henry reaction between these substrates and nitromethane was more efficient with selenorosamine and tellurorosamine photocatalysts than with thiorosamine and rosamine photocatalysts, corresponding to the propensity of the photocatalysts to generate singlet oxygen (1O2). Appropriately, yields for the photocatalytic aza-Henry reaction were greatly reduced when the reactions were conducted under

  使用硫族原糖胺光催化剂和LED辐照可实现2-芳基-1,2,3,4-四氢异喹啉的有氧氧化。这些底物与硝基甲烷之间的光催化aza-Henry反应与硒代罗斯明和碲代罗拉明光催化剂相比，比硫代硫胺和罗萨明光催化剂更有效，这与光催化剂产生单线态氧（1 O 2）的倾向相对应。适当地，当反应在氮气氛下进行时，光催化氮杂-亨利反应的产率大大降低。将2-芳基1,2,3,4-四氢异喹啉氧化为相应的2-芳基-3,4-二氢异喹啉酮13a – 13c在2％的乙腈水溶液中加入硒代rosamine和tellurorosamine光催化剂。已表明二-2-芳基-1,2,3,4-四氢异喹啉-1-基过氧化物14a和14b是该反应的中间体。硫代罗拉明光催化剂在辐照时确实会生成1 O 2，但未产生2-芳基-3,4-二氢异喹诺酮类化合物。这些结果表明，1 O 2和硫属元素胺的硫属元素原子（相应的过氧化过氧化物，过氧化过氧化物或过氧化