α-phenyl-4-bromo-2-nitrophenethyl alcohol | 149913-78-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: α-phenyl-4-bromo-2-nitrophenethyl alcohol
• 英文别名: 2-(4-bromo-2-nitrophenyl)-1-phenylethanol
• CAS: 149913-78-0
• 化学式: C₁₄H₁₂BrNO₃
• 分子量: 322.158
• InChiKey: PCPUENCZGFXSGZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  66
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  α-phenyl-4-bromo-2-nitrophenethyl alcohol 在 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以40%的产率得到2-(4-bromo-2-nitrophenyl)-1-phenylethanone
  参考文献：
  名称：

  New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer

  摘要：

  We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.

  DOI：

  10.1021/acs.jmedchem.5b00310
• 作为产物：
  描述：

  4-溴-2-硝基甲苯 、 苯甲醛 在 sodium ethanolate 作用下， 以 二甲基亚砜 为溶剂， 反应 24.0h， 以82%的产率得到α-phenyl-4-bromo-2-nitrophenethyl alcohol
  参考文献：
  名称：

  钯或钌催化的2-苯基吲哚的合成

  摘要：

  在钯络合物作为催化剂存在下，碳酸烯丙基α-苯基-2-氨基苯乙基碳酸酯进行平稳的脱羧-脱氢反应，以在乙腈中于80°提供2-苯基吲哚衍生物。在反应中，氢化钌络合物显示出更有效的催化活性。还通过钌催化的环化反应由相应的α-苯基-2-氨基苯乙基醇和碳酸烯丙酯制备2-苯基吲哚。

  DOI：

  10.1002/jhet.5570290509

文献信息

• Palladium- or ruthenium-catalyzed synthesis of 2-phenylindoles
  作者：Taeko Izumi、Toshiko Yokota

  DOI：10.1002/jhet.5570290509

  日期：1992.8

  presence of palladium complex as catalyst. In the reaction, the ruthenium hydride complex showed more effective catalytic activities. 2-Phenylindoles were also prepared from the corresponding α-phenyl-2-aminophenethylalcohols and allyl methyl carbonate by ruthenium-catalyzed cyclization.

  在钯络合物作为催化剂存在下，碳酸烯丙基α-苯基-2-氨基苯乙基碳酸酯进行平稳的脱羧-脱氢反应，以在乙腈中于80°提供2-苯基吲哚衍生物。在反应中，氢化钌络合物显示出更有效的催化活性。还通过钌催化的环化反应由相应的α-苯基-2-氨基苯乙基醇和碳酸烯丙酯制备2-苯基吲哚。
• New Indole Tubulin Assembly Inhibitors Cause Stable Arrest of Mitotic Progression, Enhanced Stimulation of Natural Killer Cell Cytotoxic Activity, and Repression of Hedgehog-Dependent Cancer
  作者：Giuseppe La Regina、Ruoli Bai、Antonio Coluccia、Valeria Famiglini、Sveva Pelliccia、Sara Passacantilli、Carmela Mazzoccoli、Vitalba Ruggieri、Annalisa Verrico、Andrea Miele、Ludovica Monti、Marianna Nalli、Romina Alfonsi、Lucia Di Marcotullio、Alberto Gulino、Biancamaria Ricci、Alessandra Soriani、Angela Santoni、Michele Caraglia、Stefania Porto、Eleonora Da Pozzo、Claudia Martini、Andrea Brancale、Luciana Marinelli、Ettore Novellino、Stefania Vultaggio、Mario Varasi、Ciro Mercurio、Chiara Bigogno、Giulio Dondio、Ernest Hamel、Patrizia Lavia、Romano Silvestri

  DOI：10.1021/acs.jmedchem.5b00310

  日期：2015.8.13

  We designed 39 new 2-phenylindole derivatives as potential anticancer agents bearing the 3,4,5-trimethoxyphenyl moiety with a sulfur, ketone, or methylene bridging group at position 3 of the indole and with halogen or methoxy substituent(s) at positions 4-7. Compounds 33 and 44 strongly inhibited the growth of the P-glycoprotein-overexpressing multi-drug-resistant cell lines NCI/ADR-RES and Messa/Dx5. At 10 nM, 33 and 44 stimulated the cytotoxic activity of NK cells. At 20-50 nM, 33 and 44 arrested >80% of HeLa cells in the G2/M phase of the cell cycle, with stable arrest of mitotic progression. Cell cycle arrest was followed by cell death. Indoles 33, 44, and 81 showed strong inhibition of the SAG-induced Hedgehog signaling activation in NIH3T3 Shh-Light II cells with IC50 values of 19, 72, and 38 nM, respectively. Compounds of this class potently inhibited tubulin polymerization and cancer cell growth, including stimulation of natural killer cell cytotoxic activity and repression of Hedgehog-dependent cancer.