2-ethoxybenzenediazonium chloride | 3371-07-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-ethoxybenzenediazonium chloride
• 英文别名: {2-C2H5OC6H4N2}Cl；o-Ethoxybenzenediazonium chloride；2-ethoxybenzenediazonium;chloride
• CAS: 3371-07-1
• 化学式: C₈H₉N₂O*Cl
• 分子量: 184.625
• InChiKey: XAQUIOSBVRWKRI-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  -0.43
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-ethoxybenzenediazonium chloride 在 sodium azide 作用下， 生成 1-azido-2-ethoxybenzene
  参考文献：
  名称：

  Chen, Zi-Bao; Dong, Hong-Ru; Jin, Chi-Qiong, Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 2021, vol. 60B, # 12, p. 1629 - 1635

  摘要：

  DOI：
• 作为产物：
  描述：

  氨基苯乙醚 在 盐酸 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 1.0h， 生成 2-ethoxybenzenediazonium chloride
  参考文献：
  名称：

  (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides as tubulin polymerization inhibitors: Structure-based bioisosterism design, synthesis, biological evaluation, molecular docking and in silico ADME prediction

  摘要：

  A series of (E)-N-Aryl-2-oxo-2-(3,4,5-trimethoxyphenyl)acetohydrazonoyl cyanides have been synthesized and evaluated for their anticancer activity in human hepatocellular liver carcinoma HepG2 and breast adenocarcinoma MCF-7 cell lines. Among all the tested compounds, compound 3a, 3e and 3n displayed more activity than lead compound with IC50 value of 0.26-0.61 mu M. Meanwhile, these compounds (3a, 3e and 3n) showed potent antiproliferative activity against a panel of cancer cells and the HCT-8/T multidrug resistant cell line with IC50 values in the range of 0.077-7.44 mu M. Flow cytometric analyses revealed that compound 3n induced cell cycle arrest in G2/M phases in a dose dependent manner. The compound 3n also displayed potent tubulin polymerization inhibition with an IC50 value of 0.9 mu M, with ten folds more active than colchicine (IC50 = 9 mu M). Molecular docking studies revealed that compound 3n efficiently interacted with the colchicine binding site of tubulin through hydrophobic, cation-pi and hydrogen bond interaction. Furthermore, in silico pharmacokinetic prediction shown that these compounds have a good ADME-related physicochemical parameters. These results demonstrate that 3n exhibits potent cytotoxicity in cancer cells by targeting the colchicine binding site of tubulin and potentially acts as a therapeutic lead compound for the development of anticancer drugs.

  DOI：

  10.1016/j.bmcl.2018.09.004

文献信息

• Nitrogen bridgehead compounds. Part 18. New antiallergic 4H-pyrido[1,2-a]pyrimidin-4-ones. Part I
  作者：Istvan Hermecz、Tibor Breining、Zoltan Meszaros、Agnes Horvath、Lelle Vasvari-Debreczy、Franz Dessy、Christine DeVos、Ludovic Rodriquez

  DOI：10.1021/jm00352a008

  日期：1982.10

  A new type of antiallergic agent, 9-hydrazono-6,7,8,9-tetrahydro-4H-pyrido[1,2-a]pyrimidin-4-ones, was synthesized and evaluated for inhibitory effects in the rat reagenic passive cutaneous anaphylaxis (PCA) screen. Several racemic 6-methyl derivatives were found to be more potent than disodium chromoglycate intravenously and some were also active orally. Structure-activity relationships are discussed

  合成了一种新型的抗过敏药9-肼基-6,7,8,9-四氢-4H-吡啶并[1,2-a]嘧啶-4-酮，并评估了其对大鼠自发性被动皮肤的抑制作用。过敏反应（PCA）屏幕。已发现几种消旋的6-甲基衍生物在静脉内比色甘氨酸二钠更有效，有些还具有口服活性。讨论了构效关系。在具有6S和6R绝对构型的对映异构体之间的6-甲基系列中观察到高立体特异性，前者更具活性。化合物17，（+）-6（S）-甲基-9-（苯肼基）-4-氧代-4H-吡啶并[1,2-a]嘧啶-3-羧酸[Chinoin-1045; [UCB L140]，ED50值为1.0 mumol / kg po，目前正在临床研究中。
• The structure of the diazonium coupling products of sulfones
  作者：A.S.A.S. Shawali、M.I. Ali、M.M. Naoum、A.L. Elansari

  DOI：10.1016/s0040-4020(01)93827-x

  日期：1972.1

  IR and UV spectroscopy were used to assign structures to diazonium coupling products V-VII of ethyl p-toluenesulfonylacetate, benzenesulfonylacetophenone and benzenesulfonylacetanilide. The data have established that such coupling products exist largely as chelated hydrazones. An alternative synthesis of coupling products V and VII from the corresponding arylhydrazidic chlorides and sodium arenesulfinate

  使用IR和UV光谱法将结构分配给对甲苯磺酰基乙酸乙酯，苯磺酰基乙酰苯和苯磺酰基乙酰苯胺的重氮偶合产物V-VII 。数据已经证实这种偶联产物主要以螯合存在。描述了由相应的芳基肼基氯化物和芳烃亚磺酸钠的偶联产物V和VII的替代合成。
• An azo coupling of berberine derivatives: an experimental and quantum-chemical study
  作者：Andrey A. Popov、Angelina N. Dryapak、Oleg N. Burov、Mikhail E. Kletskii、Alexander D. Zagrebaev、Anna V. Tkachuk、Sergey V. Kurbatov、Anna V. Aleshukina、Elena V. Goloshova、Kristina G. Markova、Iraida S. Berezinskaya、Tatiana I. Tverdokhlebova

  DOI：10.1007/s10593-023-03239-2

  日期：2023.8

  B3LYP/6-31G(d,p) basis set. In weakly alkaline media, berberrubine can be substituted at position 12 by azo coupling reactions with aryldiazonium salts. This process proceeds in steps: first, berberrubine transforms into the zwitterionic form of 9-oxoberberine, which then enters as a nucleophile into an azo coupling reaction with aryldiazonium salts to form a single product with the trans configuration of

  通过实验和基于 B3LYP/6-31G(d,p) 基组中的密度泛函理论的量子化学计算证明了合成 12-(芳基重氮)小檗红素的可能性。在弱碱性介质中，小檗红素可通过与芳基重氮盐的偶氮偶联反应在 12 位被取代。该过程分步骤进行：首先，小檗红素转化为两性离子形式的 9-氧化小檗碱，然后作为亲核试剂进入与芳基重氮盐的偶氮偶联反应，形成单一产物，其片段相对于 N= 为反式构型。 N双键。由此产生的 12-(芳基重氮基)小檗红素可用作抗生素药物，如多重耐药性鲁氏不动杆菌培养物中所示。
• Structure-Based Lead Optimization and Biological Evaluation of BAX Direct Activators as Novel Potential Anticancer Agents
  作者：Mariano Stornaiuolo、Giuseppe La Regina、Sara Passacantilli、Gianluca Grassia、Antonio Coluccia、Valeria La Pietra、Mariateresa Giustiniano、Hilde Cassese、Salvatore Di Maro、Diego Brancaccio、Sabrina Taliani、Armando Ialenti、Romano Silvestri、Claudia Martini、Ettore Novellino、Luciana Marinelli

  DOI：10.1021/jm501123r

  日期：2015.3.12

  The first direct activator of BAX, a pro-apoptotic member of the BCL-2 family, has been recently identified. Herein, a structure-based lead optimization turned out into a small series of analogues, where 8 is the most potent compound published so far. 8 was used as pharmacological tool to ascertain, for the first time, the anticancer potential of BAX direct activators and the obtained results would suggest that BAX direct activators are potential future anticancer drugs rather than venoms.
• Synthesis and biological activity of a novel class of pyridazine analogues as non-competitive reversible inhibitors of protein tyrosine phosphatase 1B (PTP1B)
  作者：C Liljebris

  DOI：10.1016/s0968-0896(02)00176-1

  日期：2002.10

  A series of novel pyridazine analogues were prepared and the structure activity relationship of their behavior as inhibitors of PTP1B was evaluated. Most of the analogues had potencies in the low micromolar range. The in vitro kinetics of this compound series demonstrated that they were reversible non-competitive binders. This indicates that there may exist another site in the enzyme through which enzyme activity can be inhibited, which is not a recognized interaction domain. Some of the analogues exhibited high selectivity for other PTPases, for example, compound 12mp showed 20-fold selectivity for PTP1B (IC50 = 5.6 muM) versus both TCPTP and LAR (>100 muM, respectively). In contrast to many tyrosine phosphatase mimetic inhibitors, this compound class lacks negative charge and thus showed high permeability across cell membranes. Selective analogues in the series were analyzed in an in vitro cellular assay, which showed increased insulin-stimulated insulin receptor phosphorylation. (C) 2002 Elsevier Science Ltd. All rights reserved.