piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone | 1391088-45-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone
• 英文别名: Piperidin-1-yl-(1,4,4-trimethyl-2,3-dihydroquinolin-6-yl)methanone
• CAS: 1391088-45-1
• 化学式: C₁₈H₂₆N₂O
• 分子量: 286.417
• InChiKey: SJGKLECONZCUQK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  23.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  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 、 环己烷 、 乙腈 为溶剂， 反应 4.0h， 生成 9-(dimethylamino)-1,4,4-trimethyl-3,4-dihydro-1H-thiochromeno[3,2-g]quinolin-6(2H)-one
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075
• 作为产物：
  描述：

  N-(3-methylbut-2-enyl)-N-methylaniline 在 硫酸 、 sulfur 、 三氟乙酸酐 、 三氯氧磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 piperidin-1-yl(1,4,4-trimethyl-1,2,3,4-tetrahydroquinolin-6-yl)methanone
  参考文献：
  名称：

  Thiorhodamines containing amide and thioamide functionality as inhibitors of the ATP-binding cassette drug transporter P-glycoprotein (ABCB1)

  摘要：

  Twelve thiorhodamine derivatives have been examined for their ability to stimulate the ATPase activity of purified human P-glycoprotein (P-gp)-His(10), to promote uptake of calcein AM and vinblastine into multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells, and for their rates of transport in monolayers of multidrug-resistant, P-gp-overexpressing MDCKII-MDR1 cells. The thiorhodamine derivatives have structural diversity from amide and thioamide functionality (N,N-diethyl and N-piperidyl) at the 5-position of a 2-thienyl substituent on the thiorhodamine core and from diversity at the 3-amino substituent with N, N-dimethylamino, fused azadecalin (julolidyl), and fused N-methylcyclohexylamine (half-julolidyl) substituents. The julolidyl and half-julolidyl derivatives were more effective inhibitors of P-gp than the dimethylamino analogues. Amide-containing derivatives were transported much more rapidly than thioamide-containing derivatives. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.05.075

文献信息

• [EN] METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS<br/>[FR] PROCÉDÉS ET COMPOSÉS DE PHOTOTHÉRAPIE FAISANT APPEL À DES PHOTOSENSIBILISANTS DE TYPE CHALCOGÉNORHODAMINE
  申请人：UNIV WAKE FOREST HEALTH SCIENCES

  公开号：WO2015187940A1

  公开（公告）日：2015-12-10

  A method of selectively depleting pathogenic T lymphocytes from a blood cell composition is carried out by (a) combining the cell composition ex vivo with an active compound in an effective amount, and then (b) irradiating the cells with light ex vivo for a time and at an intensity sufficient to selectively kill pathogenic T lymphocytes in said cell composition. Chalcogenorhodamine photosensitizers useful as such active compounds are also described.

  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。
• 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.
• METHODS AND COMPOUNDS FOR PHOTOTHERAPY WITH CHALCOGENORHODAMINE PHOTOSENSITIZERS
  申请人：Wake Forest University Health Sciences

  公开号：US20170096636A1

  公开（公告）日：2017-04-06

  A method of selectively depleting pathogenic T lymphocytes from a blood cell composition is carried out by (a) combining the cell composition ex vivo with an active compound in an effective amount, and then (b) irradiating the cells with light ex vivo for a time and at an intensity sufficient to selectively kill pathogenic T lymphocytes in said cell composition. Chalcogenorhodamine photosensitizers useful as such active compounds are also described.