3-bromo-1-(4',4''-dimethoxytrityloxy)propane | 167700-34-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-bromo-1-(4',4''-dimethoxytrityloxy)propane
• 英文别名: 1-[3-Bromopropoxy-(4-methoxyphenyl)-phenylmethyl]-4-methoxybenzene
• CAS: 167700-34-7
• 化学式: C₂₄H₂₅BrO₃
• 分子量: 441.365
• InChiKey: CFCYXCVHNYJXLB-UHFFFAOYSA-N

物化性质

• 沸点：
  506.3±50.0 °C(Predicted)
• 密度：
  1.261±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-bromo-1-(4',4''-dimethoxytrityloxy)propane 在 sodium hydroxide 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 16.05h， 生成 3-(4,4'-dimethoxytrityloxy)prop-1-yl 2-benzoyloxy-3-(1,3-dioxan-2-yl)-5-iodobenzoate
  参考文献：
  名称：

  Synthesis of Linear and Tripoidal Oligo(phenylene ethynylene)-Based Building Blocks for Application in Modular DNA-Programmed Assembly

  摘要：

  Rigid linear and tripoidal organic modules based on the oligo(phenylene ethynylene) backbone having salicylaldehyde-derived termini are synthesized. A highly functionalized 5-iodosalicyl aldehyde was prepared and coupled to each ethynyl group of 1,4-diethynylbenzene or 1,3,5-triethynylbenzene in Sonogashira couplings. The two or three termini of the compounds are functionalized for incorporation in linear and branched oligonucleotide strands. For the linear module (LM), the two termini are equipped with amide spacers, and one of these was functionalized with a DMTr (dimethoxytrityl)-protected hydroxy group and the other with a phosphoramidite. One of the tripoidal modules is prepared with DMTr groups in two of its three termini. A tripoidal module is also synthesized with three different groups on its hydroxy termini: a phosphoramidite, a DMTr group, and an Fmoc group. Extended studies have shown that these rigid linear and tripoidal organic modules can be incorporated into short oligonucleotides. Several of these modules can be applied for DNA-directed assembly and covalent coupling into structures of predetermined connectivity. Such structures have potential application for molecular electronics and nanotechnology.

  DOI：

  10.1021/jo035764m
• 作为产物：
  描述：

  4,4'-双甲氧基三苯甲基氯 、 3-溴-1-丙醇 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 以90%的产率得到3-bromo-1-(4',4''-dimethoxytrityloxy)propane
  参考文献：
  名称：

  核酸模板上的红光触发光还原。

  摘要：

  在互补核酸（NA）存在下，用红光（660 nm）照射后，缀合Sn（IV）（焦脱镁叶绿素a）二氯化物-（肽核酸）催化还原偶氮苯衍生物。这是第一个红光诱导的NA模板光还原。它对NA模板中的单个错配高度敏感，可以检测低至5 nM的NA。

  DOI：

  10.1039/d0cc03086d

文献信息

• A new 9-alkyladenine-cyclic methylglyoxal diadduct activates wt- and F508del-cystic fibrosis transmembrane conductance regulator (CFTR) in vitro and in vivo
  作者：Benjamin Boucherle、Johanna Bertrand、Bruno Maurin、Brice-Loïc Renard、Antoine Fortuné、Brice Tremblier、Frédéric Becq、Caroline Norez、Jean-Luc Décout

  DOI：10.1016/j.ejmech.2014.06.028

  日期：2014.8

  Cystic fibrosis transmembrane conductance regulator (CFTR) is the main chloride channel present in the apical membrane of epithelial cells and the F508 deletion (F508del-CFTR) in the CF gene is the most common cystic fibrosis-causing mutation. In the search for a pharmacotherapy of cystic fibrosis caused by the F508del-CFTR, a bi-therapy could be developed associating a corrector of F508del-CFTR trafficking and an activator of the channel activity of CFTR. Here, we report on the synthesis of 9-alkyladenine derivatives analogues of our previously discovered activator of wt-CFTR and F508del-CFTR, GPact-11a, and the identification of a new activator of these channels, GPact-26a, through various flux assays on human airway epithelial CF and non-CF cell lines and in vivo measurement of rat salivary secretion. This study reveals that the possible modifications of the side chain introduced at the N9 position of the main pharmacophore are highly limited since only an allyl group can replace the propyl side chain present in GPact-11a to lead to a strong activation of wt-CFTR in CHO cells. Docking simulations of the synthesised compounds and of four described modulators performed using a 3D model of the wt-type CFTR protein suggest five possible binding sites located at the interface of the nucleotide binding domains NBD1/NBD2. However, the docking study did not allow the differentiation between active and non-active compounds.
• Shchepinov, M. S.; Esipov, D. S.; Korobko, V. G., Russian Journal of Bioorganic Chemistry, 1994, vol. 20, # 8-9, p. 520 - 528
  作者：Shchepinov, M. S.、Esipov, D. S.、Korobko, V. G.、Dobrynin, V. N.

  DOI：——

  日期：——
• Triazolylpyrenes: Synthesis, FluorescenceProperties, and Incorporation into DNA
  作者：Sarah Werder、Vladimir L. Malinovskii、Robert Häner

  DOI：10.1021/ol8006474

  日期：2008.5.1

  Synthesis of 1,6- and 1,8-triazolylpyrenes and their incorporation into oligonucleotides is described. In hybrids, triazolylpyrenes adopt interstrand stacking interactions. Exciton coupling is observed for the duplex containing a pair of the 1,6-isomer indicating a well-defined helical arrangement of the triazolylpyrene building blocks. Triazole substitution results in pronounced red-shifts of monomer as well as excimer fluorescence. Furthermore, quantum yields of the formed excimers are remarkably high.
• [EN] MACROMOLECULAR ARCHITECTURES<br/>[FR] ARCHITECTURES MACROMOLECULAIRES
  申请人：UNIV AARHUS

  公开号：WO2004050231A2

  公开（公告）日：2004-06-17

  A macromolecular architecture suitable for use in molecular electronics. And in the manufacture of conductors and semi-conductors has been synthesised using linear and branched oligomers of organic molecules. The incorporation of a bi-or tri-functional organic compound in an oligonucleotide chain and the application of these for formation of covalently linked organic and metal-organic oligomers has led to a novel molecular architecture. Furthermore, the iterative serial synthesis of linear and branched organic oligomers by automated methods such as DNA-synthesis or peptide synthesis, using bi- or tri-functional organic monomers is described herein. The novel compounds may be used to position and arrange nanoscale substrates such as biomolecules, biological structures, colloids, supramolecular structures forming covalently linked assemblies for use as conducting wires and components in electronic devices.
• Red light-triggered photoreduction on a nucleic acid template
  作者：Subrata Dutta、Jennifer Rühle、Margot Schikora、Nina Deussner-Helfmann、Mike Heilemann、Timofei Zatsepin、Patrick Duchstein、Dirk Zahn、Günther Knör、Andriy Mokhir

  DOI：10.1039/d0cc03086d

  日期：——

  a)dichloride–(peptide nucleic acid) catalyzes reduction of azobenzene derivatives in the presence of complementary nucleic acid (NA) upon irridiation with red light (660 nm). This is the first red light-induced NA-templated photoreduction. It is highly sensitive to single mismatches in the NA-template and can detect down to 5 nM NAs.

  在互补核酸（NA）存在下，用红光（660 nm）照射后，缀合Sn（IV）（焦脱镁叶绿素a）二氯化物-（肽核酸）催化还原偶氮苯衍生物。这是第一个红光诱导的NA模板光还原。它对NA模板中的单个错配高度敏感，可以检测低至5 nM的NA。