4-(2-bromoethyl)-N,N-dimethylaniline | 56153-01-6

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: 4-(2-bromoethyl)-N,N-dimethylaniline
• CAS: 56153-01-6
• 化学式: C₁₀H₁₄BrN
• 分子量: 228.132
• InChiKey: PADFZBCISPJFMT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  12
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  4-(2-bromoethyl)-N,N-dimethylaniline 在 偶氮二异丁腈 、 三正丁基氢锡 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 21.0h， 生成 (+)-octahydro-3,6α-dimethyl-3,12-epoxy-9β-(3'-(p-N,N-dimethylaminophenyl)propyl)-12H-pyrano[4,3j]-1,2-benzodioxepin-10(3H)-one
  参考文献：
  名称：

  Structure−Activity Relationships of the Antimalarial Agent Artemisinin. 8. Design, Synthesis, and CoMFA Studies toward the Development of Artemisinin-Based Drugs against Leishmaniasis and Malaria

  摘要：

  Artemisinin (1) and its analogues have been well studied for their antimalarial activity. Here we present the antimalarial activity of some novel C-9-modified artemisinin analogues synthesized using artemisitene as the key intermediate. Further, antileishmanial activity of more than 70 artemisinin derivatives against Leishmania donovani promastigotes is described for the first time. A comprehensive structure-activity relationship study using CoMFA is discussed. These analogues exhibited leishmanicidal activity in micromolar concentrations, and the overall activity profile appears to be similar to that against malaria. Substitution at the C-9beta position was shown to improve the activity in both cases. The 10-deoxo derivatives showed better activity compared to the corresponding lactones. In general, compounds with C-9alpha substitution exhibited lower antimalarial as well as antileishmanial activities compared to the corresponding C-9beta analogues. The importance of the peroxide group for the observed activity of these analogues against leishmania was evident from the fact that 1-deoxyartemisinin analogues did not exhibit antileishmanial activity. The study suggests the possibility of developing artemisinin analogues as potential drug candidates against both malaria and leishmaniasis.

  DOI：

  10.1021/jm030181q
• 作为产物：
  描述：

  4-(二甲基氨基)苯乙醇 在 四溴化碳 、 三苯基膦 作用下， 以 二氯甲烷 为溶剂， 以48.2 %的产率得到4-(2-bromoethyl)-N,N-dimethylaniline
  参考文献：
  名称：

  通过 乙烯基碳阳离子中间体 （Vinyl Carbocation Intermediates） 获得中等尺寸的环

  摘要：

  由于环应变，中型环（8-11 元环）的合成通常比较小的环（5-7 元环）更具挑战性。在此，我们报道了一种形成 8 元和 9 元环的催化方法，该方法通过乙烯基碳阳离子中间体的分子内 Friedel-Crafts 反应进行。这些反应性物质是通过 Lewis 酸性锂阳离子弱配位阴离子盐对乙烯基甲苯磺酸盐进行电离而催化生成的。

  DOI：

  10.1021/acs.orglett.3c04014

文献信息

• [EN] OXADIAZOLONES AS TRANSIENT RECEPTOR POTENTIAL CHANNEL INHIBITORS<br/>[FR] OXADIAZOLONES EN TANT QU'INHIBITEURS DE CANAL POTENTIEL RÉCEPTEUR TRANSITOIRE
  申请人：HOFFMANN LA ROCHE

  公开号：WO2018096159A1

  公开（公告）日：2018-05-31

  The invention relates to compounds of formula (I) and pharmaceutically acceptable salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula (I) as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

  该发明涉及式(I)的化合物及其药用可接受的盐。此外，本发明涉及制备方法和使用式(I)的化合物的方法，以及含有这种化合物的药物组合物。这些化合物可能在治疗由TRPA1介导的疾病和症状，如疼痛方面有用。
• [EN] ARTEMISININ-BASED PEROXIDE COMPOUNDS AS BROAD SPECTRUM ANTI-INFECTIVE AGENTS<br/>[FR] COMPOSES DE PEROXYDE A BASE D'ARTEMISININE TENANT LIEU D'AGENTS ANTI-INFECTIEUX A LARGE SPECTRE
  申请人：UNIV MISSISSIPI

  公开号：WO2003095444A1

  公开（公告）日：2003-11-20

  Described herein is the synthesis, bioassay results and utility of new C-9 and C-10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文描述了合成、生物测定结果以及新的C-9和C-10取代青蒿素衍生物的用途，这些衍生物具有易于功能化的基团，通过碳链或杂原子连接到青蒿素骨架上。同时还展示了这类化合物在广谱抗寄生虫活性方面的表现。其中一些类似物具有明显的细胞毒性，专门用于治疗癌症性疾病。
• Hydroxy-morphinane. 11. Mitteilung. N-Arylalkyl-morphiane
  作者：A. Grüssner、J. Hellerbach、O. Schnider

  DOI：10.1002/hlca.19570400514

  日期：——

  The preparation of a series of new 3-hydroxy-N-phenylalkyl- and -N-phenacyl-morphinans by different methods is described.

  描述了通过不同方法制备一系列新的3-羟基-N-苯基烷基-和-N-苯甲酰基吗啡喃。
• THERAPEUTIC COMPOUNDS AND THEIR USE IN CANCER
  申请人：Bajji C. Ashok

  公开号：US20070299258A1

  公开（公告）日：2007-12-27

  The invention relates to compounds of Formulae I-III and their therapeutic uses.

  这项发明涉及到I-III式化合物及其治疗用途。
• Artemisinin-based peroxide compounds as broad spectrum anti-infective agents
  申请人：Avery Mitchell

  公开号：US20050240034A1

  公开（公告）日：2005-10-27

  Described herein is the synthesis, bioassay results and utility of new C- 9 and C- 10 substituted artemisinin derivatives with easily functionalizable groups attached to the artemisinin skeleton through carbon chain or heteroatoms. Described also is the demonstration of this class of compounds for their broad-spectrum anti-parasitic activity. Certain of these analogs possess noticeable cytotoxicity deliberately focused on treatment of cancerous diseases.

  本文介绍了一种新型C-9和C-10取代青蒿素衍生物的合成、生物测定结果和实用性，这些衍生物通过碳链或杂原子与青蒿素骨架连接，具有易于官能团化的基团。同时，本文还展示了这类化合物的广谱抗寄生虫活性。其中某些类似物具有明显的细胞毒性，可用于治疗癌症疾病。