(2,4,5-trifluorobenzyl)triphenylphosphonium bromide | 1269260-21-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2,4,5-trifluorobenzyl)triphenylphosphonium bromide
• 英文别名: Triphenyl-[(2,4,5-trifluorophenyl)methyl]phosphanium;bromide
• CAS: 1269260-21-0
• 化学式: Br*C₂₅H₁₉F₃P
• 分子量: 487.299
• InChiKey: FHAQFYJXRLJRPM-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  0
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2E,4E,6E-2,6-Dimethyl-7-ethoxycarbonyl-2,4,6-heptatrienal 、 (2,4,5-trifluorobenzyl)triphenylphosphonium bromide 在 1,2-环氧丁烷 、 水 、 sodium hydroxide 作用下， 以 甲醇 、 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 (2E,4E,6E,8E)-3,7-dimethyl-9-(2,4,5-trifluorophenyl)nona-2,4,6,8-tetraenoic acid
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008
• 作为产物：
  描述：

  2,4,5-三氟苯甲醛 在 sodium tetrahydroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 6.83h， 生成 (2,4,5-trifluorobenzyl)triphenylphosphonium bromide
  参考文献：
  名称：

  Syntheses, antiproliferative activity and theoretical characterization of acitretin-type retinoids with changes in the lipophilic part

  摘要：

  Acitretin analogs, incorporating changes in the lipophilic part, were efficiently synthesized from commercially available aromatic aldehydes or methyl ketones using the Wittig or Horner-Wadsworth-Emmons reaction. Their antiproliferative activity was evaluated against human breast MCF-7 epithelial cells. Analogs 3, 4, 8 and 11 exhibited strong, dose-dependent, antiproliferative activity on the tested cell line. Analog 3, incorporating three methoxy groups in the aromatic ring, exhibited the strongest inhibitory effect at 10 mu M. High-level all electron conventional ab initio and density functional theory quantum chemical calculations were performed to obtain the molecular structure, electron charge distribution and polarization properties of all compounds of interest in this work. The most active analogs were planar and were characterized by larger dipole moments than the other synthesized molecules. Another factor of importance to the analysis of the activity of these molecules is the dipole polarizability. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.008

文献信息

• [EN] DISUBTITUTED AZETIDINES, PYRROLIDINES, PIPERIDINES AND AZEPANES AS INHIBITORS OF MONOAMINE OXIDASE B FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES<br/>[FR] AZÉTIDINES, PYRROLIDINES, PIPÉRIDINES ET AZÉPANES DI-SUBSTITUÉS EN TANT QU'INHIBITEURS DE MONOAMINE OXYDASE B POUR LE TRAITEMENT DE MALADIES NEURODÉGÉNÉRATIVES
  申请人：UNIV OF LJUBLJANA

  公开号：WO2018055096A1

  公开（公告）日：2018-03-29

  This invention relates to new inhibitors of MAO-Bwith the general formula I, where substituents are described in patent description. Compounds can be in the form of pure enantiomers or as racemic mixtures, or in the form of pharmaceutically acceptable salts. The present invention relates to the use of these inhibitors for the alleviation of symptoms and treatment of acute and chronic neurological disorders, cognitive and neurodegenerative diseases.

  这项发明涉及具有一般式I的新MAO-B抑制剂，其中取代基在专利描述中有描述。化合物可以是纯对映体的形式，也可以是消旋混合物的形式，或者是药用盐的形式。本发明涉及利用这些抑制剂缓解症状和治疗急性和慢性神经疾病、认知和神经退行性疾病。
• Stereoselective Activity of 1-Propargyl-4-styrylpiperidine-like Analogues That Can Discriminate between Monoamine Oxidase Isoforms A and B
  作者：Damijan Knez、Natalia Colettis、Luca G. Iacovino、Matej Sova、Anja Pišlar、Janez Konc、Samo Lešnik、Josefina Higgs、Fabiola Kamecki、Irene Mangialavori、Ana Dolšak、Simon Žakelj、Jurij Trontelj、Janko Kos、Claudia Binda、Mariel Marder、Stanislav Gobec

  DOI：10.1021/acs.jmedchem.9b01886

  日期：2020.2.13

  . While the cis isomers are potent human MAO-A inhibitors, the trans analogues selectively target only the MAO-B isoform. The inhibition was studied by kinetic analysis, UV-vis spectrum measurements, and X-ray crystallography. The selective inhibition of the MAO-A and MAO-B isoforms was confirmed ex vivo in mouse brain homogenates, and additional in vivo studies in mice show the therapeutic potential

  最近，这种酶活性与心血管疾病，神经疾病和肿瘤疾病之间的相关性加剧了人们对单胺氧化酶（MAOs）兴趣的兴起。这促进了对选择性MAO-A和MAO-B抑制剂的更多研究。在这里，我们阐明了如何通过顺式和反式1-炔丙基-4-苯乙烯基哌啶的几何异构体实现对MAO-A和MAO-B的选择性抑制。尽管顺式异构体是有效的人MAO-A抑制剂，但反式类似物仅选择性靶向MAO-B同工型。通过动力学分析，UV-可见光谱测量和X射线晶体学研究了抑制作用。在小鼠脑匀浆中离体证实了对MAO-A和MAO-B同工型的选择性抑制，小鼠中的其他体内研究表明1-炔丙基-4-苯乙烯基哌啶对中枢神经系统疾病的治疗潜力。这项研究代表了顺式/反式异构体立体选择性活性的独特案例，可以区分结构上相关的酶同工型。
• Synthesis of Terminally Fluorinated [7]Helicenes and Their Application to Photochemical Domino Reactions
  作者：Chikako Matsuda、Yuto Suzuki、Hiroshi Katagiri、Takashi Murase

  DOI：10.1002/asia.202001295

  日期：2021.3

  intramolecular Diels−Alder reactions of helicenes deform their π‐conjugated screw‐shaped skeletons. In particular, terminally tetrafluorinated [7]helicene (F4‐[7]helicene) undergoes a photoinduced Diels−Alder reaction followed by a photoinduced double fluorine atom transfer. Herein, we thoroughly investigated this photochemical domino process by decreasing the level of fluorine substitution. F3‐[7]Helicenes

  螺旋分子的分子内Diels-Alder反应使它们的π共轭螺旋形骨架变形。特别是，末端四氟化[7]（烯（F 4- [7] ic烯）经历光诱导的Diels-Alder反应，随后发生光诱导的双氟原子转移。在本文中，我们通过降低氟取代水平来彻底研究了该光化学多米诺过程。F 3 [7]在亲双烯体末端带有两个氟原子的螺内酯经历了光诱导的Diels-Alder反应，但是整个多米诺骨牌过程变慢了。F 2‐ [7] ic烯（仅在亲二烯体末端被氟化）也具有光不稳定性。结果，两个氟原子足以使光化学多米诺反应发生。X射线晶体学分析表明，F 2- [7]螺旋比F 4- [7]螺旋压缩少，表明末端多氟化增强了分子内芳烃-氟芳烃的堆积相互作用，从而促进了转变。
• DISUBTITUTED AZETIDINES, PYRROLIDINES, PIPERIDINES AND AZEPANES AS INHIBITORS OF MONOAMINE OXIDASE B FOR THE TREATMENT OF NEURODEGENERATIVE DISEASES
  申请人：University of Ljubljana

  公开号：EP3426634A1

  公开（公告）日：2019-01-16