1-[(3-甲氧基苯基)甲基]咪唑 | 56643-94-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 中文名称: 1-[(3-甲氧基苯基)甲基]咪唑
• 英文名称: N-(3-methoxybenzyl)-imidazole
• 英文别名: 1-(3-methoxybenzyl)-1H-imidazole；N-(3-methoxybenzyl)imidazole；1-(3-methoxybenzyl)imidazole；1-(3-methoxy-benzyl)-1H-imidazole；1-(3-methoxy-benzyl)-1H-imidazole；1-[(3-methoxyphenyl)methyl]imidazole
• CAS: 56643-94-8
• 化学式: C₁₁H₁₂N₂O
• mdl: MFCD16302735
• 分子量: 188.229
• InChiKey: OLIXBQIGIJMNBA-UHFFFAOYSA-N

物化性质

• 沸点：
  122 °C(Press: 0.5 Torr)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.181
• 拓扑面积：
  27
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-[(3-甲氧基苯基)甲基]咪唑 在 sodium acetate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Palladium Complexes with Tridentate N-Heterocyclic Carbene Ligands: Selective “Normal” and “Abnormal” Bindings and Their Anticancer Activities

  摘要：

  A series of new imidazolium salts was synthesized by simple quaternization reactions of 1-benzyl-1H-imidazole or 1-benzyl-2-methyl-1H-imidazole and their derivatives with 2-chloro-N-(pyridin-2-ylmethyl)acetamide. These resulting imidazolium salts were successfully employed as ligand precursors for the syntheses of novel palladium(II) complexes bearing tridentate ligands of N-heterocyclic carbene, amidate, and pyridine donor moieties. Simple tuning of the reaction conditions allowed selective coordination of the N-heterocyclic carbene moiety in either "normal" or "abnormal" binding modes. An isomeric pair of palladium complexes with `normal" and "abnormal" N-heterocyclic carbenes was successfully characterized by single-crystal X-ray diffraction studies. Theoretical calculations indicated that the palladium complex with "normal" NHC coordination was more thermally stable than its isomeric complex with "abnormal" NHC binding. The potential of these two sets of palladium complexes as anticancer drugs was evaluated, and the results showed that some of these novel complexes exhibited promising inhibition activity against human ovarian cancer cell lines. The inhibition activity of these novel complexes was highly structurally dependent. While the nNHC complex bearing an N-3-methoxybenzyl group appeared to be the most active compound, its isomeric aNHC complex did not exhibit any inhibition activity toward TOV21G cells. In contrast, in the case of an isomeric pair of palladium complexes bearing N-4-fluorobenzyl groups, the aNHC complex showed activity superior to that of the nNHC complex.

  DOI：

  10.1021/acs.organomet.5b00586
• 作为产物：
  描述：

  咪唑 、 3-甲氧基氯苄 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 生成 1-[(3-甲氧基苯基)甲基]咪唑
  参考文献：
  名称：

  钯配合物与乙烯桥联的双（N-杂环卡宾）的CC偶联反应

  摘要：

  合成了一系列具有各种N-取代基的新的乙烯桥联的双（咪唑鎓）卤化物。这些咪唑鎓卤化物与Pd（OAc）2的络合产生了新的Pd（II）乙烯桥联的双（卡宾）络合物。确定了一些新的咪唑鎓盐和Pd（II）配合物的晶体学分析。这些七元的palladacycles在铃木和Heck偶联反应中的应用产生了与六元类似物类似的催化活性。

  DOI：

  10.1016/j.tet.2004.04.070

文献信息

• Palladium-Catalyzed Intramolecular Arylation of N-Benzyl-2-iodoimidazoles: A Facile and Rapid Access to 5H-Imidazo[2,1-a]isoindoles
  作者：Joëlle Dubois、Renata de Figueiredo、Sylviane Thoret、Caroline Huet

  DOI：10.1055/s-2007-965896

  日期：2007.2

  The first example of a Pd-catalyzed intramolecular aryl­ation involving the C-2 position of an imidazole ring is presented. Application of this reaction led to the formation of 5H-imidazo[2,1-a]isoindole in one step from N-benzyl-2-iodoimidazole. Microwave irradiation enhanced the rate of reaction allowing the synthesis of various imidazo[2,1-a]isoindole analogues.

  首次报道了一种钯催化下的咪唑环C-2位点参与的分子内芳基化反应。应用此反应，可以一步从N-苄基-2-碘咪唑合成5H-咪唑并[2,1-a]异吲哚。微波辐照加速了反应速率，使得多种咪唑并[2,1-a]异吲哚类似物的合成成为可能。
• Antithyroid Drugs and their Analogues Protect Against Peroxynitrite-Mediated Protein Tyrosine Nitration-A Mechanistic Study
  作者：Krishna P. Bhabak、Govindasamy Mugesh

  DOI：10.1002/chem.200902145

  日期：2010.1.25

  the presence of a thione or selone moiety is important for an efficient inhibition. Similarly, the replacement of NH moiety in MMI by N‐methyl or N‐m‐methoxybenzyl substituents dramatically reduces the antioxidant activity of the parent compound. Theoretical studies indicate that the substitution of NH moiety by NMe significantly increases the energy required for the oxidation of sulfur center by

  本文描述了一些常用的抗甲状腺药物及其类似物对过氧亚硝酸盐介导的蛋白质硝化作用的影响。通过蛋白质印迹分析研究了牛血清白蛋白（BSA）和细胞色素c中酪氨酸残基的硝化作用。这些研究表明，抗甲状腺药甲巯咪唑（MMI）6- n包含硫酮部分的-2-丙基-2-硫氧嘧啶（PTU）和6-甲基-2-硫氧嘧啶（MTU）显着降低BSA和细胞色素c的酪氨酸硝化作用。虽然MMI表现出良好的过氧亚硝酸盐（PN）清除活性，但硫尿嘧啶化合物PTU和MTU的效力略低于MMI。S-和Se-甲基化的化合物在酪氨酸的硝化中显示出弱的抑制作用，表明硫酮或selone部分的存在对于有效抑制很重要。类似地，替换N个在MMI H部分由Ñ甲基或ñ -米甲氧基苄基的取代基显着地降低了母体化合物的抗氧化活性。理论研究表明，N的替代NMe的H部分显着增加了PN氧化硫中心所需的能量。然而，在MMI的硒类似物中的这种取代增加了母体化合物的活性。
• Arylmethylazoles and their salts, processes for their preparation,
  申请人：Hoechst Aktiengesellschaft

  公开号：US04876354A1

  公开（公告）日：1989-10-24

  Arylmethylazoles of the formula I ##STR1## in which Aryl is (substituted) phenyl or naphthyl; Z is CH or N; R.sup.1 and Q are H or alkyl; R.sup.2 is H, alk(en)yl or alkynyl; R.sup.3 and R.sup.4 are H, alkyl or other hydrocarbons; or R.sup.3 and R.sup.4 together are a --(CH.sub.2).sub.2-11 chain or a bridged --(CH.sub.2).sub.4-5 chain, and their acid addition salts, stereoisomers and optically active enantiomers possess outstanding antimycotic and antidepressant activity. They are obtained, inter alia, from arylmethylazoles II ##STR2## which are reacted with a strong base and then with a carbonyl compound III O.dbd.CR.sup.3 R.sup.4 ; thereafter, the product is reacted with the protic acid or with an alkyl halide IV R.sup.2 Hal. If desired, the products are converted to the acid addition salts, or the stereoisomers or optically active enantiomers are resolved.

  Arylmethylazoles的化学式为I，其中Aryl是（取代）苯或萘；Z是CH或N；R.sup.1和Q是H或烷基；R.sup.2是H，烯丙基或炔基；R.sup.3和R.sup.4是H，烷基或其他碳氢化合物；或者R.sup.3和R.sup.4一起是一个--(CH.sub.2).sub.2-11链或一个桥联的--(CH.sub.2).sub.4-5链，它们的酸盐、立体异构体和光学活性对映异构体具有出色的抗真菌和抗抑郁活性。它们可以从Arylmethylazoles II中获得，该化合物与强碱反应，然后与一个醛化合物III O.dbd.CR.sup.3 R.sup.4反应；之后，将产物与质子酸或烷基卤化物IV R.sup.2 Hal反应。如果需要，将产物转化为酸盐，或者将立体异构体或光学活性对映异构体分离。
• N-Benzyl-imidazoles as selective inhibitors of the thromboxane
  申请人：Pfizer Inc.

  公开号：US04448781A1

  公开（公告）日：1984-05-15

  The N-(substituted benzyl) imidazoles are selective enzyme inhibitors and thus are useful in the treatment of heart disease, circulatory and vascular problems.

  N-（取代苄基）咪唑是选择性酶抑制剂，因此在治疗心脏病、循环系统问题和血管问题方面很有用。
• 1-(1-aryl-2-hydroxyethyl)-imidazoles and salts thereof, medicaments
  申请人：Hoechst Aktiengesellschaft

  公开号：US04999352A1

  公开（公告）日：1991-03-12

  1-(1-Aryl-2-hydroxyethyl)-imidazoles and salts thereof, processes for the preparation thereof, medicaments containing these compounds, and the use thereof. The invention relates to 1-(1-aryl-2-hydroxyethyl)-imidazoles of the formula I ##STR1## in which R.sup.1, R.sup.2, R.sup.3, Q, W, X and Y have the meanings specified, and also to medicaments based on these compounds, in particular those having an antimycotic and an antidepressive action.

  本发明涉及公式I中的1-(1-芳基-2-羟乙基)-咪唑及其盐，以及其制备方法、含有这些化合物的药物和其用途。其中，R.sup.1、R.sup.2、R.sup.3、Q、W、X和Y具有指定的含义。本发明还涉及基于这些化合物的药物，特别是具有抗真菌和抗抑郁作用的药物。