4,5-Dimethoxy-2-methylaminoacetophenon | 124959-09-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,5-Dimethoxy-2-methylaminoacetophenon
• 英文别名: 1-[4,5-dimethoxy-2-(methylamino)phenyl]ethanone；4',5'-Dimethoxy-2'-(methylamino)acetophenone
• CAS: 124959-09-7
• 化学式: C₁₁H₁₅NO₃
• 分子量: 209.245
• InChiKey: UPDCATWDFILYDV-UHFFFAOYSA-N

物化性质

• 沸点：
  357.1±42.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  47.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4,5-Dimethoxy-2-methylaminoacetophenon 在 potassium tert-butylate 、 三乙胺 、 叔丁醇 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 生成 1-Methyl-2-phenyl-6,7-dimethoxychinolon-(4)
  参考文献：
  名称：

  Evolution from a Natural Flavones Nucleus to Obtain 2-(4-Propoxyphenyl)quinoline Derivatives As Potent Inhibitors of the S. aureus NorA Efflux Pump

  摘要：

  Overexpression of efflux pumps is an important mechanism by which bacteria evade the effects of substrate antimicrobial agents. Inhibition of such pumps is a promising strategy to circumvent this resistance mechanism. NorA is a Staphylococcus aureus efflux pump that confers reduced susceptibility to many structurally unrelated agents, including fluoroquinolones, resulting in a multidrug resistant phenotype. In this work, a series of 2-phenyl-4(1H)-quinolone and 2-phenyl-4-hydroxyquinoline derivatives, obtained by modifying the flavone nucleus of known efflux pump inhibitors (EPIs), were synthesized in an effort to identify more potent S. aureus NorA EPIs. The 2-phenyl-4-hydroxyquinoline derivatives 28f and 29f display potent EPI activity against SA-1199B, a strain that overexpresses norA, in an ethidium bromide efflux inhibition assay. The same compounds, in combination with ciprofloxacin, were able to completely restore its antibacterial activity against both S. aureus SA-K2378 and SA-1199B, narA-overexpressing strains.

  DOI：

  10.1021/jm200370y
• 作为产物：
  描述：

  2-氟-4,5-二甲氧基苯基氰 以 四氢呋喃 、 水 、 乙腈 为溶剂， 反应 18.0h， 生成 4,5-Dimethoxy-2-methylaminoacetophenon
  参考文献：
  名称：

  镍/光共催化烯烃的不对称酰基氨基甲酰化

  摘要：

  通过手性镍-PHOX 配合物和四丁基十钨酸铵的协同催化，开发了一种前所未有的不对称酰基氨基甲酰化，该方法连接在芳基氨基甲酰氯上的侧链烯烃与脂肪族和芳香族醛。该反应代表了氢原子转移光化学和不对称过渡金属催化在烯烃双官能化中的第一个例子。使用该协议，在温和的条件下以高度对映选择性的方式提供了具有挑战性的四元立体中心的各种 oxindoles。

  DOI：

  10.1021/jacs.9b12554

文献信息

• One-Pot, Three-Component Assembly of Indoloquinolines: Total Synthesis of Isocryptolepine
  作者：Alexander V. Aksenov、Dmitrii A. Aksenov、Naila A. Orazova、Nicolai A. Aksenov、Georgii D. Griaznov、Annelise De Carvalho、Robert Kiss、Véronique Mathieu、Alexander Kornienko、Michael Rubin

  DOI：10.1021/acs.joc.6b03084

  日期：2017.3.17

  Indolo[3,2-c]quinolones have been efficiently synthesized via an acid-mediated, one-pot, three-component condensation of arylhydrazines, o-aminoacetophenones, and triazines or nitriles. The synthetic application of this method is showcased by the concise synthesis of isocryptolepine alkaloid and a series of its synthetic analogues with demonstrated cancer cell antiproliferative activities.

  吲哚并[3，2- c ]喹诺酮已通过芳基肼，邻氨基苯乙酮和三嗪或腈的酸介导的一锅三组分缩合反应得到了有效合成。该方法的合成应用通过异隐油菜碱生物碱及其一系列具有证明的癌细胞抗增殖活性的合成类似物的简明合成得以展示。
• A nitroalkane-based approach to one-pot three-component synthesis of isocryptolepine and its analogs with potent anti-cancer activities
  作者：Nicolai A. Aksenov、Alexander V. Aksenov、Alexander Kornienko、Annelise De Carvalho、Véronique Mathieu、Dmitrii A. Aksenov、Sergei N. Ovcharov、Georgii D. Griaznov、Michael Rubin

  DOI：10.1039/c8ra08155g

  日期：——

  acid-mediated one-pot three-component synthesis of indoloquinoline scaffold is developed. This improved version of the process involves electrophilically activated nitroalkanes for the installation of strategic C–C and C–N bonds and ring C assembly. This modification allows the elimination of unnecessary solvent change operations and all steps are carried out in a true, uninterrupted one-pot manner. A

  开发了二代多聚磷酸介导的一锅三组分合成吲哚喹啉支架。该工艺的改进版本涉及用于安装战略 C-C 和 C-N 键和环 C 组装的亲电活化硝基烷烃。这种修改可以消除不必要的溶剂更换操作，并且所有步骤都以真正的、不间断的一锅法进行。进一步的改进涉及原位安装邻氨基的可能性。该方法的合成应用通过简明合成异隐萜生物碱及其具有有效抗癌活性的合成类似物来展示。
• Quinolone sulphonates having antihypertensive activity
  申请人：The Boots Company, PLC

  公开号：US04997840A1

  公开（公告）日：1991-03-05

  Quinolone sulphonates of formula I ##STR1## in which R.sub.1 is lower alkyl; R.sub.2 is lower alkyl; and R.sub.3, R.sub.4 and R.sub.5, which may be the same or different, are hydrogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, halo, halogenated lower alkyl, halogenated lower alkoxy, cyano, phenyl or phenyl substituted by 1 or 2 groups independently selected from lower alkyl, lower alkoxy and halo, have antihypertensive activity. Processes for preparing compounds of formula I and pharmaceutical compositions containing them are described. Compounds of formula I are also indicated for use in the treatment of heart failure and ischaemic heart disease.

  化学式I的喹诺酮磺酸盐：##STR1## 其中，R.sub.1为低碳基；R.sub.2为低碳基；R.sub.3、R.sub.4和R.sub.5可以相同也可以不同，分别为氢、低碳基、低氧基、低硫基、低硫氧基、低硫酰基、卤素、卤素化的低碳基、卤素化的低氧基、氰基、苯基或由1或2个从低碳基、低氧基和卤素中独立选择的基取代的苯基。这些化合物具有降压作用。本文还描述了制备化学式I化合物和含有它们的药物组合物的方法。化学式I的化合物也适用于治疗心力衰竭和缺血性心脏病。
• Therapeutic agents
  申请人：The Boots Company PLC

  公开号：EP0330340A1

  公开（公告）日：1989-08-30

  Quinolone sulphonates of formula I in which R₁ is lower alkyl; R₂ is lower alkyl; and R₃, R₄ and R₅, which may be the same or different, are hydrogen, lower alkyl, lower alkoxy, lower alkylthio, lower alkylsulphinyl, lower alkylsulphonyl, halo, halogenated lower alkyl, halogenated lower alkoxy, cyano, phenyl or phenyl substituted by 1 or 2 groups independently selected from lower alkyl, lower alkoxy and halo, have antihypertensive activity. Processes for preparing compounds of formula I and pharmaceutical compositions containing them are described. Compounds of formula I are also indicated for use in the treatment of heart failure and ischaemic heart disease.

  式 I 的喹诺酮磺酸盐 其中 R₁ 是低级烷基；R₂ 是低级烷基；以及 R₃、R₄ 和 R₅（可以相同或不同）为氢、低级烷基、低级烷氧基、低级烷硫基、低级烷基亚磺酰基、低级烷基磺酰基、卤素、卤代低级烷基、卤代低级烷氧基、氰基、苯基或被 1 或 2 个独立选自低级烷基、低级烷氧基和卤素的基团取代的苯基，具有抗高血压活性。 描述了制备式 I 化合物和含有它们的药物组合物的工艺。 式 I 化合物还可用于治疗心力衰竭和缺血性心脏病。
• N-Alkylated 2-Trifluoromethyl-4-quinolones by Addition of Base and an Alkylating Agent to 2-Trifluoroacetylaminoacetophenones
  作者：Donald W. Combs、Marianne S. Reed、Dieter H. Klaubert

  DOI：10.1080/00397919208021309

  日期：1992.1

  2-Trifluoroacetylaminoacetophenones 1 are cyclized to N-alkyl-2-trifluoromethyl-4-quinolones 2 in one pot with concomitant N-alkylation in 40 to 74% yield using potassium hydroxide in acetone containing an alkylating agent.