1,3-bis(carbazol-9-yl)-2-propanol glycidyl ether | 82684-71-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 1,3-bis(carbazol-9-yl)-2-propanol glycidyl ether
• 英文别名: 1,3-bis(carbazol-9-yl)propan-2-oxymethyloxirane；1,3-di(carbazol-9-yl)-2-propanol glycidyl ether；1,3-di(9-carbazolyl)-2-propanol glycidyl ether；9-[3-carbazol-9-yl-2-(oxiran-2-ylmethoxy)propyl]carbazole
• CAS: 82684-71-7
• 化学式: C₃₀H₂₆N₂O₂
• 分子量: 446.549
• InChiKey: PGTWJVMWHCPMFD-UHFFFAOYSA-N

物化性质

• 沸点：
  691.5±55.0 °C(Predicted)
• 密度：
  1.27±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  31.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1,3-bis(carbazol-9-yl)-2-propanol glycidyl ether 在 三聚氯氰 、 硫氰酸铵 作用下， 以 四氢呋喃 为溶剂， 反应 20.0h， 以50%的产率得到1,3-bis(carbazol-9-yl)propan-2-oxymethylthiirane
  参考文献：
  名称：

  Glass-forming 1,3-bis(carbazol-9-yl)propan-2-ol based monomers and polymers

  摘要：

  Three glass-forming 1,3-bis(carbazol-9-yl)propan-2-ol based monomers, i.e. oxirane, thiirane and oxetane were synthesized. Photopolymerization of their solid amorphous layers initiated with diphenyliodonium tetrafluoroborate and the dark polymerization in solutions initiated with boron trifluoride etherate were performed. The number-average molecular weights of the obtained polymers are in the range of 1000-19,400. The highest initial polymerization rate, the highest limit conversion and the highest molecular weight were observed for the polymerization of thiirane. Optical, photophysical, electrochemical and thermal properties of the synthesized compounds were studied. UV and fluorescence spectra of the compounds have the similar profiles, due to the presence of the same chromophore. No excimer emission was observed neither for dilute solutions of monomers nor polymers. The electrochemical coupling was observed for all the synthesized 1,3-bis(carbazol-9-yl)propan-2-ol based monomers and polymers by cyclic voltammetry. The thermal degradation of the derivatives of 1,3-bis(carbazol-9-yl)propan-2-ol derivatives starts in the range of the temperatures from 317 to 402. The glass transition temperatures of the monomers range from 43 to 58 while glass transition temperatures of the polymers are in the range of 103-125. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2011.08.010
• 作为产物：
  描述：

  9-(环氧-2-甲基)-9H-咔唑 在 sodium sulfate 、 potassium hydroxide 作用下， 以 丁酮 为溶剂， 生成 1,3-bis(carbazol-9-yl)-2-propanol glycidyl ether
  参考文献：
  名称：

  Glass-forming 1,3-bis(carbazol-9-yl)propan-2-ol based monomers and polymers

  摘要：

  Three glass-forming 1,3-bis(carbazol-9-yl)propan-2-ol based monomers, i.e. oxirane, thiirane and oxetane were synthesized. Photopolymerization of their solid amorphous layers initiated with diphenyliodonium tetrafluoroborate and the dark polymerization in solutions initiated with boron trifluoride etherate were performed. The number-average molecular weights of the obtained polymers are in the range of 1000-19,400. The highest initial polymerization rate, the highest limit conversion and the highest molecular weight were observed for the polymerization of thiirane. Optical, photophysical, electrochemical and thermal properties of the synthesized compounds were studied. UV and fluorescence spectra of the compounds have the similar profiles, due to the presence of the same chromophore. No excimer emission was observed neither for dilute solutions of monomers nor polymers. The electrochemical coupling was observed for all the synthesized 1,3-bis(carbazol-9-yl)propan-2-ol based monomers and polymers by cyclic voltammetry. The thermal degradation of the derivatives of 1,3-bis(carbazol-9-yl)propan-2-ol derivatives starts in the range of the temperatures from 317 to 402. The glass transition temperatures of the monomers range from 43 to 58 while glass transition temperatures of the polymers are in the range of 103-125. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.reactfunctpolym.2011.08.010

文献信息

• Development of a versatile DNMT and HDAC inhibitor C02S modulating multiple cancer hallmarks for breast cancer therapy
  作者：Zigao Yuan、Shaopeng Chen、Chunmei Gao、Qiuzi Dai、Cunlong Zhang、Qinsheng Sun、Jin-Shun Lin、Chun Guo、Yuzong Chen、Yuyang Jiang

  DOI：10.1016/j.bioorg.2019.03.027

  日期：2019.6

  enzymatic inhibitory potency needs to be improved. Herein we reported the development of a novel dual DNMT and HDAC inhibitor C02S which showed potent enzymatic inhibitory activities against DNMT1, DNMT3A, DNMT3B and HDAC1 with IC50 values of 2.05, 0.93, 1.32, and 4.16 µM, respectively. Further evaluations indicated that C02S could inhibit DNMT and HDAC at cellular levels, thereby inversing mutated methylation

  DNMT和HDAC彼此密切相关，并涉及各种人类疾病，尤其是癌症。这两种酶已被广泛认为是药物发现的抗肿瘤靶标。此外，研究表明由DNMT和HDAC抑制剂组成的联合疗法具有治疗优势。我们已经报告了DNMT和HDAC双重抑制剂15a，其中DNMT的酶促抑制效能需要提高。本文中，我们报道了新型DNMT和HDAC双重抑制剂CO2S的开发，该抑制剂显示出对DNMT1，DNMT3A，DNMT3B和HDAC1的有效酶抑制活性，IC 50值分别为2.05、0.93、1.32和4.16 µM。进一步评估表明，CO2S可以在细胞水平上抑制DNMT和HDAC，从而逆转突变的甲基化和乙酰化并增加肿瘤抑制蛋白的表达。此外，CO 2 S调节多种生物学过程，包括诱导凋亡和G0 / G1细胞周期停滞，抑制血管生成，阻断迁移和侵袭，并最终抑制体外肿瘤细胞增殖和体内肿瘤生长。
• Multifunctional red phosphorescent bis-cyclometallated iridium complexes based on 2-phenyl-1,2,3-benzotriazole ligand and carbazolyl moieties
  作者：Tadas Malinauskas、Maryte Daskeviciene、Karolis Kazlauskas、Hai-Ching Su、Juozas Vidas Grazulevicius、Saulius Jursenas、Chung-Chih Wu、Vytautas Getautis

  DOI：10.1016/j.tet.2011.01.026

  日期：2011.3

  Multifunctional phosphorescent bis-cyclometallated iridium(III) complexes based on the 2-phenyl-1,2,3-benzotriazole moiety and bearing branched hole-transporting carbazole fragments were synthesized. The isolated compounds were found to be amorphous and expressed very good solubility. Introduction of flexible aliphatic chains of various lengths into the iridium complexes enabled manipulation of their glass transition temperature. The iridium complexes exhibited red phosphorescence emission at 650 nm with the lifetime of 5.7 mu s and phosphorescence quantum yields of 0.22 and 0.17 in solution and solid state, respectively, at room temperature. The shielding effect of the carbazolyl moieties on the concentration quenching of phosphorescence of the iridium centers was found to result in the increased excited state lifetime and quantum yield due to the suppressed exciton migration. Non-optimized OLED devices, based on the phosphorescent bis-cyclometallated iridium(III) complex without host material were fabricated and their electroluminescence properties were evaluated. (C) 2011 Elsevier Ltd. All rights reserved.
• New Carbazolyl Containing Molecular Glasses for Optoelectronics
  作者：G. Sinkeviciute、A. Stanisauskaite、V. Gaidelis、V. Jankauskas、E. Montrimas

  DOI：10.1080/15421400701229875

  日期：2007.6.11
• Reaction of epoxypropylcarbazole derivatives with 2-phenylindole
  作者：V. Getautis、M. Daskevicene、A. Stanisauskaite

  DOI：10.1007/bf02256910

  日期：2000.7
• Synthesis of carbazole containing Organic Photosemiconductors using dimercapto compounds
  作者：S. Kutkevicius、A. Stanisauskaite、V. Getautis、A. Railaite、S. Uss

  DOI：10.1002/prac.19953370165

  日期：——