9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-selenochromeno[3,2-g]quinolin-6(2H)-one | 1608130-96-6

• 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: 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-selenochromeno[3,2-g]quinolin-6(2H)-one
• 英文别名: 9-(Dimethylamino)-1,4,4-trimethyl-2,3-dihydroselenochromeno[3,2-g]quinolin-6-one；9-(dimethylamino)-1,4,4-trimethyl-2,3-dihydroselenochromeno[3,2-g]quinolin-6-one
• CAS: 1608130-96-6
• 化学式: C₂₁H₂₄N₂OSe
• 分子量: 399.394
• InChiKey: RBVLZZHQZJPNNY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-selenochromeno[3,2-g]quinolin-6(2H)-one 在 hexafluorophosphoric acid 作用下， 以 二氯甲烷 为溶剂， 生成 9-(5-(piperidylcarbamothioyl)thiophen-2-yl)selenorhodamine chloride
  参考文献：
  名称：

  [EN] METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS
  [FR] PROCÉDÉS ET COMPOSÉS DE PHOTOTHÉRAPIE FAISANT APPEL À DES PHOTOSENSIBILISANTS DE TYPE CHALCOGÉNORHODAMINE

  摘要：

  一种从血细胞组合物中选择性消耗致病性T淋巴细胞的方法是通过(a)在体外将细胞组合物与有效量的活性化合物结合，然后(b)在体外用光辐照细胞，时间和强度足以选择性地杀死该细胞组合物中的致病性T淋巴细胞。还描述了作为这种活性化合物有用的硫属罗丹明光敏剂。

  公开号：

  WO2015187940A1
• 作为产物：
  描述：

  piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone 在 四甲基乙二胺 、 仲丁基锂 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 生成 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-selenochromeno[3,2-g]quinolin-6(2H)-one
  参考文献：
  名称：

  [EN] METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS
  [FR] PROCÉDÉS ET COMPOSÉS DE PHOTOTHÉRAPIE FAISANT APPEL À DES PHOTOSENSIBILISANTS DE TYPE CHALCOGÉNORHODAMINE

  摘要：

  一种从血细胞组合物中选择性消耗致病性T淋巴细胞的方法是通过(a)在体外将细胞组合物与有效量的活性化合物结合，然后(b)在体外用光辐照细胞，时间和强度足以选择性地杀死该细胞组合物中的致病性T淋巴细胞。还描述了作为这种活性化合物有用的硫属罗丹明光敏剂。

  公开号：

  WO2015187940A1

文献信息

• Synthesis and Properties of Heavy Chalcogen Analogues of the Texas Reds and Related Rhodamines
  作者：Mark W. Kryman、Gregory A. Schamerhorn、Jacqueline E. Hill、Brandon D. Calitree、Kellie S. Davies、Michelle K. Linder、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1021/om500346j

  日期：2014.5.27

  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.
• Selenorhodamine Photosensitizers for Photodynamic Therapy of P-Glycoprotein-Expressing Cancer Cells
  作者：Jacqueline E. Hill、Michelle K. Linder、Kellie S. Davies、Geri A. Sawada、Janet Morgan、Tymish Y. Ohulchanskyy、Michael R. Detty

  DOI：10.1021/jm501259v

  日期：2014.10.23

  We examined a series of selenorhodamines with amide and thioamide functionality at the 5-position of a 9-(2-thienyl) substituent on the selenorhodamine core for their potential as photosensitizers for photodynamic therapy (PDT) in P-glycoprotein (P-gp) expressing 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, for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their colocalization with mitochondrial specific agents in Colo-26 cells. Thioamide derivatives 16b and 18b were more effective photosensitizers than amide derivatives 15b and 17b. Selenorhodamine thioamides 16b and 18b were useful in a combination therapy to treat Colo-26 cells in vitro: a synergistic therapeutic effect was observed when Colo-26 cells were exposed to PDT and treatment with the cancer drug doxorubicin.