2-(5-溴-2-硝基苯基)乙酸 | 124840-61-5

• 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-(5-溴-2-硝基苯基)乙酸
• 中文别名: 5-溴-2-硝基苯乙酸
• 英文名称: 2-(5-bromo-2-nitrophenyl)aceticacid
• 英文别名: 2-nitro-5-bromophenylacetic acid；3-Brom-6-nitro-phenylessigsaeure；5-bromo-2-nitrophenylacetic acid；2-(5-Bromo-2-nitrophenyl)acetic acid
• CAS: 124840-61-5
• 化学式: C₈H₆BrNO₄
• 分子量: 260.044
• InChiKey: ZKKCLKYKTRUIKW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  83.1
• 氢给体数：
  1
• 氢受体数：
  4

安全信息

• 海关编码：
  2916399090
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  2-(5-溴-2-硝基苯基)乙酸 在 硫酸 作用下， 以 乙醇 为溶剂， 以99.2%的产率得到5-溴-2-硝基苯乙酸乙酯
  参考文献：
  名称：

  Dual inhibitors of RAF-MEK-ERK and PI3K-PDK1-AKT pathways: Design, synthesis and preliminary anticancer activity studies of 3-substituted-5-(phenylamino) indolone derivatives

  摘要：

  The dysfunction and mutual compensatory activation of RAF-MEK-ERK and PI3K-PDK1-AKT pathways have been demonstrated as the hallmarks in several primary and recurrent cancers. The strategy of concurrent blocking of these two pathways shows clinical merits on effective cancer therapy, such as combinatory treatments and dual-pathway inhibitors. Herein, we report a novel prototype of dual-pathway inhibitors by means of merging the core structural scaffolds of a MEK1 inhibitor and a PDK1 inhibitor. A library of 43 compounds that categorized into three series (Series I-III) was synthesized and tested for antitumor activity in lung cancer cells. The results from structure-activity relationship (SAR) analysis showed the following order of antitumor activity that 3-hydroxy-5-(phenylamino) indolone (Series III) > 3-alkenyl-5-(phenylamino) indolone (Series I) > 3-alkyl-5-(phenylamino) indolone (Series II). A lead compound 9za in Series III showed most potent antitumor activity with IC50, value of 1.8 +/- 0.8 mu M in A549 cells. Moreover, antitumor mechanism study demonstrated that 9za exerted significant apoptotic effect, and cellular signal pathway analysis revealed the potent blockage of phosphorylation levels of ERK and AKT in RAF-MEK-ERK and PI3K-PDK1-AKT pathways, respectively. The results reported here provide robust experimental basis for the discovery and optimization of dual pathway agents for anti-lung cancer therapy.

  DOI：

  10.1016/j.bmc.2019.01.028
• 作为产物：
  描述：

  3-溴氰苄 在 盐酸 、 硫酸 、 硝酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 2-(5-溴-2-硝基苯基)乙酸
  参考文献：
  名称：

  Zur Synthese von Tiliacora-Alkaloiden, 2. Mitt.: Darstellung des unsymmetrischen Biphenyl-Schwanzteils

  摘要：

  Die Biphenyl-Derivate S-1 和 S-3 werden aus den Phenylessigsäureestern 3, 4 和 5 durch gemischte Ullmann-Reaktion erhalten。Aufgrund der selektiv abspaltbaren Carboxy-Schutzgruppen eignen sich S-1 和 S-3 zur konstitutionsselektiven Verknüpfung mit dem früher beschriebenen unsymmetrischen Dibenzo-1,4-dioxin-Derivat K1)。

  DOI：

  10.1002/ardp.19893220806

文献信息

• 双取代吲哚-2(1H)-酮类衍生物及其制备方法 和应用
  申请人：中南大学

  公开号：CN106316923B

  公开（公告）日：2019-06-18

  本发明公开了一种双取代吲哚‑2(1H)‑酮类衍生物及其制备方法和应用，所述双取代吲哚‑2(1H)‑酮类衍生物的化学结构式如下所示：上述衍生物可以用于在抗肿瘤药物的制备。
• Novel synthesis of benzofuran- and indol-2-yl-methanamine derivatives
  作者：Joachim Schlosser、Eugen Johannes、Melanie Zindler、Jan Lemmerhirt、Benjamin Sommer、Martin Schütt、Christian Peifer

  DOI：10.1016/j.tetlet.2014.11.015

  日期：2015.1

  We report on a novel synthesis towards benzofuran-2-yl-methanamine and indol-2-yl-methanamine derivatives by using ortho-methoxy and ortho-nitro substituted phenylacetic acids as starting material, respectively. For each compound series, a key intermediate bearing the oxazole-4-carboxylic acid methylester moiety was produced. Refluxing the ortho-methoxy series in HBr/HAc produced the desired benzofuran-2-yl-methanamines. Accordingly, for the synthesis of indoles the nitro-group was first reduced and reaming these intermediates in HCl gave the corresponding indol-2-yl-methanamines. The method worked well with electron donating substituents. Limitations regarding electron withdrawing substituents are discussed. This straightforward synthetic procedure can be a useful approach to generate a variety of substituted benzofuran-2-yl-methanamine and indol-2-yl-methanamine compounds by starting from readily available phenylacetic acid derivatives. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis and biological evaluation of 3-ethylidene-1,3-dihydro-indol-2-ones as novel checkpoint 1 inhibitors
  作者：Nan-Horng Lin、Ping Xia、Peter Kovar、Chang Park、Zehan Chen、Haiying Zhang、Saul H. Rosenberg、Hing L. Sham

  DOI：10.1016/j.bmcl.2005.09.064

  日期：2006.1

  Chk1 inhibitors have emerged as a novel class of neoplastic agents for abrogating the G2 DNA damage checkpoint arrest. Analogs of the Chk1 inhibitor, 3-ethylidene-1,3-dihydro-indol-2-one, were synthesized and tested in vitro for their inhibitory activities. The most promising compound identified from this series is analog 28, which possesses potent enzymatic and cellular activities.
• Discovery and Characterization of RGH-122, a Potent, Selective, and Orally Bioavailable V1a Receptor Antagonist
  作者：Ferenc Baska、Éva Bozó、Zsolt Szeleczky、Gábor Szántó、Krisztina Vukics、Zoltán Szakács、Katalin Domány-Kovács、Dalma Kurkó、Elemér Vass、Márta Thán、Mónika Vastag、Krisztina Temesvári、Sándor Lévai、Attila Sándor Halász、Krisztina Szondiné Kordás、Viktor Román、István Greiner、Imre Bata

  DOI：10.1021/acs.jmedchem.3c01868

  日期：2024.1.11
• [EN] 6-OXODECAHYDROPYRROLO[1,2-A][1,5]DIAZOCINE AND 6-OXODECAHYDRO-4H-PYRROLO[2,1-D][1,5]THIAZOCINE DERIVATIVES AS STAT3 AND STAT6 MODULATORS FOR THE TREATMENT OF CANCER AND INFLAMMATORY CONDITIONS<br/>[FR] DÉRIVÉS DE 6-OXODÉCAHYDROPYRROLO [1,2-A] [1,5] DIAZOCINE ET DE 6-OXODÉCAHYDRO-4 H-PYRROLO [2,1-D] [1,5] THIAZOCINE EN TANT QUE MODULATEURS STAT3 ET STAT6 POUR LE TRAITEMENT DU CANCER ET D'ÉTATS INFLAMMATOIRES
  申请人：[en]RECLUDIX PHARMA, INC.

  公开号：WO2023164680A1

  公开（公告）日：2023-08-31

  Provided are compounds of Formula (I): and pharmaceutically acceptable salts and compositions thereof, which are useful for treating a variety of conditions associated with STAT3 and/or STAT6, such as e.g. cancer and inflammatory conditions. Preferred compounds are 6-oxodecahydropyrrolo[1,2-a][1,5]diazocine and 6-oxodecahydro-4H-pyrrolo[2,1-d][1,5]thiazocine derivatives.