2,4,5-三甲氧基苄胺 | 154584-98-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2,4,5-三甲氧基苄胺
• 英文名称: 2,4,5-trimethoxybenzylamine
• 英文别名: (2,4,5-Trimethoxyphenyl)methanamine
• CAS: 154584-98-2
• 化学式: C₁₀H₁₅NO₃
• mdl: MFCD03411011
• 分子量: 197.234
• InChiKey: CXFDSHYASCMRFH-UHFFFAOYSA-N

物化性质

• 沸点：
  306.3±37.0 °C(Predicted)
• 密度：
  1.087±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  53.7
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  2,4,5-三甲氧基苄胺 、 6-氯-9-(四氢-2-吡喃基)嘌呤 在 三乙胺 作用下， 以 丙醇 、 正丁醇 为溶剂， 反应 3.0h， 以95%的产率得到6-(2,4,5-trimethoxybenzylamino)-9-(tetrahydropyran-2-yl)-9H-purine
  参考文献：
  名称：

  Synthesis, characterization and biological activity of ring-substituted 6-benzylamino-9-tetrahydropyran-2-yl and 9-tetrahydrofuran-2-ylpurine derivatives

  摘要：

  In an attempt to improve specific biological functions of cytokinins routinely used in plant micropropagation, 33 6-benzylamino-9-tetrahydropyran-2-ylpurine (THPP) and 9-tetrahydrofuran-2-ylpurine (THFP) derivatives, with variously positioned hydroxy and methoxy functional groups on the benzyl ring, were prepared. The new derivatives were prepared by condensation of 6-chloropurine with 3,4-dihydro-2H-pyran or 2,3-dihydrofuran and then by the condensation of these intermediates with the corresponding benzylamines. The prepared compounds were characterized by elemental analyses, TLC, HPLC, melting point determinations, CI+ MS and H-1 NMR spectroscopy. The cytokinin activity of all the prepared derivatives was assessed in three classical cytokinin bioassays (tobacco callus, wheat leaf senescence and Amaranthus bioassay). The derivatives 6-(3-hydroxybenzylamino)-9-tetrahydropyran-2-ylpurine (3) and 6-(3-hydroxybenzylamino)-9-tetrahydrofuran-2-ylpurine (23) were selected, because of the high affinity of their parent compound meta-topolin (mT, 6-(3-hydroxybenzylamino) purine) to cytokinin receptors, as model compounds for studying their perception by the receptors CRE1/AHK4 and AHK3 in a bacterial assay. Both receptors perceived these two derivatives less well than they perceived the parent compound. Subsequently, the susceptibility of several new derivatives to enzyme degradation by cytokinin oxidase/dehydrogenase was studied. Substitution of tetrahydropyran-2-yl (THP) at the N-9 position decreased the turnover rates of all new derivatives to some extent. To provide a practical perspective, the cytotoxicity of the prepared compounds against human diploid. broblasts (BJ) and the human cancer cell lines K-562 and MCF-7 was also assayed in vitro. The prepared compounds showed none or marginal cytotoxicity compared to the corresponding N-9-ribosides. Finally, the pH stability of the two model compounds was assessed in acidic and neutral water solutions (pH 3-7) by high-performance liquid chromatography (HPLC). (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.01.041
• 作为产物：
  描述：

  chloro-acetic acid-(2,4,5-trimethoxy-benzylamide) 在 盐酸 作用下， 生成 2,4,5-三甲氧基苄胺
  参考文献：
  名称：

  Monti, Gazzetta Chimica Italiana, 1930, vol. 60, p. 777,778

  摘要：

  DOI：

文献信息

• Method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK)
  申请人：CHEN Han-Min

  公开号：US20140303112A1

  公开（公告）日：2014-10-09

  The present invention relates to a method for treating disease or condition susceptible to amelioration by AMPK activators and compounds of formula which are useful to activate AMP-activated protein kinase (AMPK) and the use of the compounds in the prevention or treatment of disease, including pre-diabetes, type 2 diabetes, syndrome X, metabolic syndrome and obesity.

  本发明涉及一种治疗疾病或病情的方法，该疾病或病情容易通过AMPK激活剂和公式化合物得到改善，这些化合物有助于激活AMP激活蛋白激酶（AMPK），并将这些化合物用于预防或治疗疾病，包括糖尿病前期、2型糖尿病、X综合症、代谢综合征和肥胖症。
• Site-Specific Deoxyfluorination of Small Peptides with [¹⁸ F]Fluoride
  作者：Jens Rickmeier、Tobias Ritter

  DOI：10.1002/anie.201807983

  日期：2018.10.22

  Radiolabeled receptor‐binding peptides are an important class of positron emission tomography tracers owing to achievable high binding affinities and their rapid blood clearance. Herein, a method to introduce a 4‐[18F]fluoro‐phenylalanine residue into peptide sequences is reported, by chemoselective radio‐deoxyfluorination of a tyrosine residue using a traceless activating group. The replacement of

  放射性标记的受体结合肽是一类重要的正电子发射断层扫描示踪剂，这是由于可实现的高结合亲和力和快速的血液清除作用。本文报道了一种通过使用无痕活化基团对酪氨酸残基进行化学选择性放射脱氧氟化来将4- [ 18 F]氟-苯丙氨酸残基引入肽序列的方法。仅用[ 18 F]氟化物取代一个氢原子可将肽的结构扰动降至最低，这在示踪剂候选物的标记中是理想的。
• Substituted 6-(Benzylamino) Purine Riboside Derivatives, Use Thereof and Compositions Containing These Derivatives
  申请人：Szucova Lucie

  公开号：US20120071433A1

  公开（公告）日：2012-03-22

  The invention relates to 2-substituted-6-(substituted benzylamino)purine riboside derivatives of the general formula I. These compounds possess antiapoptotic, anti-inflammatory and differentiating activities. The invention relates also to the compositions, which contain these derivatives as active ingredients.

  该发明涉及一般式I的2-取代-6-(取代苯基氨基)嘌呤核苷衍生物。这些化合物具有抗凋亡、抗炎和分化活性。该发明还涉及包含这些衍生物作为活性成分的组合物。
• 2-Amino-3-hydroxy-4-tert-leucyl-amino-5 phenyl-pentanoic acid amide derivatives
  申请人：——

  公开号：US20030166572A1

  公开（公告）日：2003-09-04

  The invention relates to compounds of formula (I), wherein the substituents and symbols are defined as indicated in the description, to processes for the preparation thereof, to medicaments comprising those compounds, and to the use thereof in the preparation of pharmaceutical compositions for the therapeutic treatment of warm-blooded animals, including humans.

  该发明涉及式（I）的化合物，其中取代基和符号如描述中所示定义，以及其制备方法，包含这些化合物的药物，以及在制备用于治疗温血动物（包括人类）的药物组合物中的应用。
• Sequential Oxidative Fragmentation and Skeletal Rearrangement of Peroxides for the Synthesis of Quinazolinone Derivatives
  作者：Akash S. Ubale、Moseen A. Shaikh、Boopathy Gnanaprakasam

  DOI：10.1021/acs.joc.1c00889

  日期：2021.7.16

  For the first time, the sequential reaction of peroxyoxindole that involves base-promoted oxidative fragmentation to isocyanate formation and primary amine or amino alcohol accelerated skeletal rearrangement to synthesize exo-olefinic-substituted quinazolinone or oxazoloquinazolinone is reported. The advantages of this new reaction include a broad substrate scope and transition-metal-free and room-temperature

  首次报道了过氧吲哚的顺序反应，包括碱促进氧化断裂形成异氰酸酯和伯胺或氨基醇加速骨架重排以合成外烯烃取代的喹唑啉酮或恶唑并喹唑啉酮。这种新反应的优点包括广泛的底物范围和无过渡金属和室温条件。异氰酸酯作为加速氧化骨架重排的关键中间体的形成已通过捕获实验和光谱证据得到证实。