1-(2-(4-bromophenyl)-2-oxoethyl)-1,10-phenanthrolin-1-ium bromide | 468084-09-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 菲咯啉
• 英文名称: 1-(2-(4-bromophenyl)-2-oxoethyl)-1,10-phenanthrolin-1-ium bromide
• 英文别名: 1-(4-bromophenacyl)-1,10-phenanthrolinium bromide；N-(p-bromophenacyl)-1,10-phenanthrolinium bromide；1,10-Phenanthrolinium, 1-[2-(4-bromophenyl)-2-oxoethyl]-, bromide；1-(4-bromophenyl)-2-(1,10-phenanthrolin-1-ium-1-yl)ethanone;bromide
• CAS: 468084-09-5
• 化学式: Br*C₂₀H₁₄BrN₂O
• 分子量: 458.152
• InChiKey: VYHQUSYQFAERBQ-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  33.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-萘醌 、 1-(2-(4-bromophenyl)-2-oxoethyl)-1,10-phenanthrolin-1-ium bromide 在 tetrakispyridine cobalt(II) dichromate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以57%的产率得到15-(4'-bromobenzoyl)benzo[e]isoindolo[2,1-a][1,10]phenanthrolin-9,10-dione
  参考文献：
  名称：

  Enhancing the helical distortion in pyrrolo[1,2-a]phenanthrolines

  摘要：

  Nine new helical compounds were synthesized using a one-pot reaction between phenanthrolinium N-ylides and quinones as cyclic olefinic dipolarophiles. 1,4-naphthoquinone, 1,4-benzoquinone and 1,2-naphthoquinone were used as dipolarophiles, resulting in excellent to moderate yields. The structure of the compounds was deduced using NMR spectroscopy and the helical distortion was ascertained using X-ray analysis.

  DOI：

  10.3998/ark.5550190.0011.909
• 作为产物：
  描述：

  1,10-菲罗啉 、 2,4'-二溴苯乙酮 以 丙酮 为溶剂， 生成 1-(2-(4-bromophenyl)-2-oxoethyl)-1,10-phenanthrolin-1-ium bromide
  参考文献：
  名称：

  新型稠合菲咯啉的设计、合成、分子建模和抗癌活性

  摘要：

  三个系列的稠合吡咯并菲咯啉衍生物被设计为非他汀的类似物，并分两步合成，分别从 1,7-菲咯啉、4,7-菲咯啉和 1,10-菲咯啉开始。四种化合物中的两种（化合物 8a 和 11c）针对美国国家癌症研究所 (NCI) 的一组 60 种人类癌细胞系进行测试，对几种细胞系表现出显着的生长抑制活性。化合物 11c 在抗增殖功效方面表现出广谱，GI50 值在 0.296 至 250 μM 的范围内。分子对接研究表明，化合物 8a 和 11c 以两种不同的方式容纳在微管蛋白的秋水仙碱结合位点中。

  DOI：

  10.3390/molecules25030527

文献信息

• Synthesis of novel phenanthroline derivatives by 3+2 dipolar cycloadition reaction
  作者：Ramona Danac、Alexandra Rotaru、Gabi Drochioiu、Ioan Druta

  DOI：10.1002/jhet.5570400213

  日期：2003.3

  Eleven new 1,10-phenanthroline derivatives have been prepared by 3+2 dipolar cycloaddition reactions of 1,10-phenanthrolinium-ylides 7–12 in situ generated from corresponded salts, with dimethyl acetylene-dicarboxylate and ethyl propiolate.

  通过由相应的盐就地生成的1,10-菲咯啉鎓盐7-12 的3 + 2偶极环加成反应，乙炔-二羧酸二甲酯和丙酸乙酯，已经制备了11种新的1,10-菲咯啉衍生物。
• Helical chirality of 1-phenacyl-1,10-phenanthrolinium bromides
  作者：Florea Dumitraşcu、Mino R. Caira、Constantin Drăghici、Miron Teodor Căproiu、Andrei Bădoiu

  DOI：10.1023/b:jocc.0000044083.04054.9d

  日期：2004.9

  Evidence for non-coplanarity of the pyridine and pyridinium rings in a series of 1-phenacyl-1,10- phenanthrolinium bromides was gleaned from H-1-NMR data recorded in DMSO-d(6) solution. The X-ray structure of 1-(4-chlorophenacyl)-1,10-phenanthrolinium bromide, as representative of this series, was determined in order to establish whether such a molecular distortion occurs in the solid state. The title compound crystallizes in the space group C2/c as a sesquihydrate of formula C20H14BrClN2O . 1.5H(2)O with a = 35.7348( 3) Angstrom, b = 5.3468( 1) Angstrom, c = 21.7312( 2) Angstrom, = 116.4076(4)degrees and Z = 8. In the crystal, the helical chirality is manifested as a pronounced twist in the phenanthrolinium moiety, with the pyridine and pyridinium rings inclined at 6.8(2)degrees. This distortion is attributed to intramolecular hydrogen bonding of type C H ... N involving the methylene group and the uncharged nitrogen atom of the phenanthrolinium moiety. In the crystal, the cations surround an intricate array of water molecules and bromide ions held together by O-H ... Br- hydrogen bonds and comprising infinite chains ... Br- ... H-O-H ... Br-..., cross-linked by water molecules.
• Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines
  作者：Cristina Maria Al Matarneh、Roxana Maria Amarandi、Anda Mihaela Craciun、Ionel I. Mangalagiu、Gheorghita Zbancioc、Ramona Danac

  DOI：10.3390/molecules25030527

  日期：——

  of fused pyrrolophenanthroline derivatives were designed as analogues of phenstatin and synthesized in two steps starting with 1,7-phenanthroline, 4,7-phenanthroline and 1,10-phenanthroline, respectively. Two (Compounds 8a and 11c) of the four compounds tested against a panel of sixty human cancer cell lines of the National Cancer Institute (NCI) exhibited significant growth inhibition activity on

  三个系列的稠合吡咯并菲咯啉衍生物被设计为非他汀的类似物，并分两步合成，分别从 1,7-菲咯啉、4,7-菲咯啉和 1,10-菲咯啉开始。四种化合物中的两种（化合物 8a 和 11c）针对美国国家癌症研究所 (NCI) 的一组 60 种人类癌细胞系进行测试，对几种细胞系表现出显着的生长抑制活性。化合物 11c 在抗增殖功效方面表现出广谱，GI50 值在 0.296 至 250 μM 的范围内。分子对接研究表明，化合物 8a 和 11c 以两种不同的方式容纳在微管蛋白的秋水仙碱结合位点中。
• Enhancing the helical distortion in pyrrolo[1,2-a]phenanthrolines
  作者：Florea Dumitrascu、Mino R. Caira、Constantin Draghici、Miron Teodor Caproiu、Loredana Barbu、Dan George Dumitrescu

  DOI：10.3998/ark.5550190.0011.909

  日期：——

  Nine new helical compounds were synthesized using a one-pot reaction between phenanthrolinium N-ylides and quinones as cyclic olefinic dipolarophiles. 1,4-naphthoquinone, 1,4-benzoquinone and 1,2-naphthoquinone were used as dipolarophiles, resulting in excellent to moderate yields. The structure of the compounds was deduced using NMR spectroscopy and the helical distortion was ascertained using X-ray analysis.