2-(1-甲基乙氧基)-4-硝基苯胺 | 105168-93-2

• 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-(1-甲基乙氧基)-4-硝基苯胺
• 英文名称: 2-isopropoxy-4-nitroaniline
• 英文别名: 2-isopropyloxy-4-nitroaniline；2-(1-Methylethoxy)-4-nitroaniline；4-nitro-2-propan-2-yloxyaniline
• CAS: 105168-93-2
• 化学式: C₉H₁₂N₂O₃
• mdl: MFCD09031777
• 分子量: 196.206
• InChiKey: HFPHNUNMHDHACX-UHFFFAOYSA-N

物化性质

• 沸点：
  368.7±22.0 °C(Predicted)
• 密度：
  1.219±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  81.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(1-甲基乙氧基)-4-硝基苯胺 在 sodium tetrahydroborate 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 6.0h， 生成 N-methyl-2-isopropoxy-4-nitroaniline
  参考文献：
  名称：

  Structure−Activity Relationships for the Antileishmanial and Antitrypanosomal Activities of 1‘-Substituted 9-Anilinoacridines

  摘要：

  Members of the class of 9-anilinoacridine topoisomerase II inhibitors bearing lipophilic electron-donating 1'-anilino substituents are active against both the promastigote and amastigote forms of the parasite Leishmania major. A series of analogues of the known 1'-NHhexyl lead compound were prepared and evaluated against L. major in macrophage culture to further develop structure-activity relationships (SAR). Toxicity toward mammalian cells was measured in a human leukemia cell line, and the ratio of the two IC50 values (IC50(J)/IC50(L)) was used as a measure of the in vitro therapeutic index (IVTI). A 3,6-diNMe(2) substitution pattern on the acridine greatly increased toxicity to L. major without altering mammalian toxicity, increasing IVTIs over that of the lead compound. The 2-OMe, 6-Cl acridine substitution pattern used in the antimalarial drug mepacrine also resulted in potent antileishmanial activity and high IVTIs. Earlier suggestions of the utility of 2'-OR groups in lowering mammalian cytotoxicity were not borne out in this wider study. A series of very lipophilic 1'-NRR (symmetric dialkylamino)-substituted analogues showed relatively high antileishmanial potency, but no clear trend was apparent across the series, and none were superior to the 1'-NH(CH2)(5)Me subclass. Subsets of the most active 1'-N(R)(CH2)(5)Me- and 1'-N(alkyl)(2)-substituted compounds against L. major were also evaluated against Leishmania donovani, Trypanosoma cruzi, and Trypanosoma brucei, but no consistent SAR could be discerned in these physiologically diverse test systems. The present study has confirmed earlier conclusions that lipophilic electron-donating groups at the 1'-position of 9-anilinoacridines provide high activity against L. major, but the SAR patterns observed do not carry over to the other parasites studied.

  DOI：

  10.1021/jm970232h
• 作为产物：
  描述：

  2-碘代丙烷 、 2-氨基-5-硝基苯酚 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以69.3%的产率得到2-(1-甲基乙氧基)-4-硝基苯胺
  参考文献：
  名称：

  新型磺酰苯胺类似物可抑制乳腺癌细胞中芳香化酶的表达和活性，而不受COX-2抑制作用的影响。

  摘要：

  芳香酶是治疗雌激素受体阳性乳腺癌的特别有吸引力的靶标。前列腺素可提高乳腺癌细胞中的芳香酶水平，而COX抑制剂则可降低芳香酶水平。描述了衍生自COX-2选择性抑制剂NS-398的一系列新型磺酰苯胺类似物的合成和生物学评估。这些化合物以剂量和时间依赖性方式抑制SK-BR-3乳腺癌细胞中的芳香化酶活性。还在乳腺癌细胞中研究了这些化合物对COX-2抑制的作用。结构活性分析未发现芳香化酶抑制和COX-2抑制之间的相关性。微粒体芳香化酶抑制研究排除了直接酶抑制的可能性。实时PCR分析表明，磺酰苯胺类似物可减少SK-BR-3细胞中的芳香化酶基因转录。这些研究表明，新型磺酰苯胺化合物可独立于COX-2抑制而抑制SK-BR-3乳腺癌细胞中的芳香酶活性和转录。

  DOI：

  10.1021/jm051126f

文献信息

• IMIDAZO [1,2-A]PYRIDINE DERIVATIVES AS FGFR KINASE INHIBITORS FOR USE IN THERAPY
  申请人：Saxty Gordon

  公开号：US20120041000A1

  公开（公告）日：2012-02-16

  The invention relates to new bicyclic heterocyclyl derivatives of formula (I), to pharmaceutical compositions comprising said compounds and to the use of said compounds in the treatment of diseases, e.g. cancer.

  这项发明涉及公式（I）的新的双环杂环基衍生物，涉及包含该类化合物的药物组合物，以及利用该类化合物治疗疾病，例如癌症。
• Novel Sulfonanilide Analogues Suppress Aromatase Expression and Activity in Breast Cancer Cells Independent of COX-2 Inhibition
  作者：Bin Su、Edgar S. Diaz-Cruz、Serena Landini、Robert W. Brueggemeier

  DOI：10.1021/jm051126f

  日期：2006.2.1

  of these compounds on COX-2 inhibition is investigated in breast cancer cells as well. Structure-activity analysis does not find a correlation between aromatase suppression and COX-2 inhibition. Microsomal aromatase inhibition studies rule out the possibility of direct enzyme inhibition. Real-time PCR analysis demonstrates that the sulfonanilide analogues decrease aromatase gene transcription in SK-BR-3

  芳香酶是治疗雌激素受体阳性乳腺癌的特别有吸引力的靶标。前列腺素可提高乳腺癌细胞中的芳香酶水平，而COX抑制剂则可降低芳香酶水平。描述了衍生自COX-2选择性抑制剂NS-398的一系列新型磺酰苯胺类似物的合成和生物学评估。这些化合物以剂量和时间依赖性方式抑制SK-BR-3乳腺癌细胞中的芳香化酶活性。还在乳腺癌细胞中研究了这些化合物对COX-2抑制的作用。结构活性分析未发现芳香化酶抑制和COX-2抑制之间的相关性。微粒体芳香化酶抑制研究排除了直接酶抑制的可能性。实时PCR分析表明，磺酰苯胺类似物可减少SK-BR-3细胞中的芳香化酶基因转录。这些研究表明，新型磺酰苯胺化合物可独立于COX-2抑制而抑制SK-BR-3乳腺癌细胞中的芳香酶活性和转录。
• New nimesulide derivatives with amide/sulfonamide moieties: Selective COX-2 inhibition and antitumor effects
  作者：Tuğba Güngör、Adem Ozleyen、Yakup Berkay Yılmaz、Pinar Siyah、Mehmet Ay、Serdar Durdağı、Tugba Boyunegmez Tumer

  DOI：10.1016/j.ejmech.2021.113566

  日期：2021.10

  Seventeen new amide/sulfonamide containing nimesulide derivatives were synthesized and characterized by several spectroscopic techniques and primarily investigated for their inhibitory potential on COX enzymes and other pro-inflammatory factors. Experimental analyses showed that among seventeen compounds, N8 and N10 have remarkable potency and selectivity for the COX-2 enzyme over COX-1 at very low

  合成了 17 种含有尼美舒利衍生物的新型酰胺/磺酰胺，并通过几种光谱技术对其进行了表征，并初步研究了它们对 COX 酶和其他促炎因子的抑制潜力。实验分析表明，在 17 种化合物中，与尼美舒利相比，N8和N10在非常低的剂量下对 COX-2 酶具有显着的效力和选择性。此外，N8和N10 都选择性地降低了脂多糖 (LPS) 刺激的 COX-2 mRNA 表达水平，而 COX-1 水平保持稳定。N8显着抑制巨噬细胞中PGE 2 的释放和一氧化氮的产生和N10治疗组。在 silico ADME/Tox 中，还进行了分子对接和分子动力学 (MD) 模拟。此外，还在一组癌细胞系中通过 MTT 和 SRB 测定筛选了所有化合物的抗增殖特性。化合物N17对结肠 (IC 50 : 9.24 μM) 和乳腺癌 (IC 50 : 11.35 μM) 癌细胞系表现出显着的抗增殖作用。N17暴露 48 小时降低了抗凋亡蛋白
• Novel sulfonanilide analogs as selective aromatase modulators (SAMs)
  申请人：Brueggemeier W. Robert

  公开号：US20080045598A1

  公开（公告）日：2008-02-21

  Compounds and methods suppressing aromatase activity expression in cancer cells. Provided are compounds are those of formula I: wherein R 1 may be alkyl, cycloalkyl, haloalkyl, aryl, substituted aryl, haloaryl, alkoxy, alkylaryl, and arylalkyl; R 2 is H, alkyl, aryl, alkylaryl, arylalkyl, and cycloalkyl; R 3 , with the base nitrogen, forms an amide or sulfonamide; R 4 is selected from nitro, amine, amide, and benzamide; or a pharmaceutically acceptable salts thereof Also provided are small molecule selective aromatase inhibitors having a molecular weight of less 500 g/mol. In some embodiments, the small molecule selective aromatase inhibitors described herein have a molecular weight of less than 450 g/mol. Also provided are methods for suppressing aromatase activity expression in cancer cells comprising the step of administering a pharmaceutically effective amount of a small molecule aromatase inhibitor to a subject in need of such treatment. In one embodiment, the cancer cells are breast cancer cells.

  抑制癌细胞中芳香化酶活性表达的化合物和方法。提供的化合物是公式I中的化合物：其中R1可能是烷基，环烷基，卤代烷基，芳基，取代芳基，卤代芳基，烷氧基，烷基芳基和芳基烷基；R2是H，烷基，芳基，烷基芳基，芳基烷基和环烷基；R3与碱性氮形成酰胺或磺酰胺；R4从硝基，胺基，酰胺和苯甲酰中选择；或其药学上可接受的盐。还提供了分子量小于500 g/mol的小分子选择性芳香化酶抑制剂。在某些实施例中，本文所述的小分子选择性芳香化酶抑制剂的分子量小于450 g/mol。还提供了一种方法，用于抑制癌细胞中芳香化酶活性表达，包括向需要这种治疗的受试者施用药学有效量的小分子芳香化酶抑制剂。在一种实施例中，癌细胞是乳腺癌细胞。
• Divakar, Kikkeri J.; Gaikwad Balkrishna V.; Tampal, Nilufer F., Journal of Chemical Research, Miniprint, 1986, # 5, p. 1687 - 1697
  作者：Divakar, Kikkeri J.、Gaikwad Balkrishna V.、Tampal, Nilufer F.、Rajappa, Srinivasachari

  DOI：——

  日期：——