2-hexyloxy-4-nitroaniline | 880145-97-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-hexyloxy-4-nitroaniline
• 英文别名: 2-hexoxy-4-nitroaniline
• CAS: 880145-97-1
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: ATLSNDCXCRZEEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  101-104 °C
• 沸点：
  407.3±25.0 °C(Predicted)
• 密度：
  1.134±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 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-hexyloxy-4-nitroaniline 在 iron(III) chloride 、 sodium hydride 、 potassium carbonate 、 锌 作用下， 以 1,4-二氧六环 、 水 、 N,N-二甲基甲酰胺 为溶剂， 生成 N-[3-(n-hexyloxy)-4-(methyl(methylsulfonyl)amino)phenyl]-4-bromobenzamide
  参考文献：
  名称：

  Synthesis and Anticancer Mechanism Investigation of Dual Hsp27 and Tubulin Inhibitors

  摘要：

  Heat shock protein 27 (Hsp27) is a chaperone protein, and its expression is increased in response to various stress stimuli including anticancer chemotherapy, which allows the cells to survive and causes drug resistance. We previously identified lead compounds that bound to Hsp27 and tubulin via proteomic approaches. Systematic ligand based optimization in the current study significantly increased the cell growth inhibition and apoptosis inducing activities of the compounds. Compared to the lead compounds, one of the new derivatives exhibited much better potency to inhibit tubulin polymerization but a decreased activity to inhibit Hsp27 chaperone function, suggesting that the structural modification dissected the dual targeting effects of the compound. The most potent compounds 20 and 22 exhibited strong cell proliferation inhibitory activities at subnanomolar concentration against 60 human cancer cell lines conducted by Developmental Therapeutic Program at the National Cancer Institute and represented promising candidates for anticancer drug development.

  DOI：

  10.1021/jm4004736
• 作为产物：
  描述：

  1-碘己烷 、 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 6.0h， 以72.9%的产率得到2-hexyloxy-4-nitroaniline
  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

• 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。
• [EN] DERIVATIVES OF PPD USEFUL FOR COLORING HAIR AND SKIN<br/>[FR] DÉRIVÉS DE PPD UTILES POUR COLORER LES CHEVEUX ET LA PEAU
  申请人：NAT UNIV SINGAPORE

  公开号：WO2019098948A1

  公开（公告）日：2019-05-23

  The is provided a compound of formula I or II or physiologically acceptable salts or solvates, or oxidised derivatives thereof: where R1 to R3, R13 and R14 are as defined herein. Also disclosed herein are methods of dyeing hair or (temporarily) tattooing the skin using the compounds of formula I or II (or physiologically acceptable salts or solvates, or oxidised derivatives thereof) in a suitable composition.

  提供一种化合物，其化学式为I或II或其生理上可接受的盐或溶剂合物，或其氧化衍生物：其中R1至R3、R13和R14的定义如本文所述。本文还揭示了使用化学式I或II的化合物（或其生理上可接受的盐或溶剂合物，或其氧化衍生物）在适当的组合物中染发或（临时）在皮肤上进行纹身的方法。
• Facile synthesis of oligo anilines as permanent hair dyes: how chemical modifications impart colour and avoid toxicity
  作者：Gopalakrishnan Venkatesan、Yuri Dancik、Arup Sinha、Mei Bigliardi、Ramasamy Srinivas、Thomas Dawson、Suresh Valiyaveettil、Paul Bigliardi、Giorgia Pastorin

  DOI：10.1039/c9nj03362a

  日期：——

  dermatitis, with the potential to develop serious toxic effects. Among these amines, para-phenylenediamine (PPD) is a small molecule form of aniline commonly used in beauty products despite being a known allergen to humans. Hence, in this study we designed and synthesized safer PPD analogues through the synthesis of oligomeric PPD and the introduction of bulky side chains on PPD to overcome the PPD dye's toxicity

  许多用于持久染发的染料都含有芳香胺，这些胺会发生氧化聚合反应，从而导致过敏性接触性皮炎，并可能产生严重的毒性作用。在这些胺中，对苯二胺（PPD）是苯胺的小分子形式，尽管它是人类已知的过敏原，但通常用于美容产品中。因此，在这项研究中，我们通过合成寡聚PPD和在PPD上引入庞大的侧链来设计和合成更安全的PPD类似物，以克服PPD染料的毒性。我们假设（a）通过在游离胺上添加PPD单体单元来增加PPD的分子大小，以及（b）在邻位进行战略性官能化具有强供电子大基团的PPD的位置能够保持染发性能，并增加与皮肤蛋白结合的抵抗力，因此减少了皮肤致敏的机会。合成了13种低聚物，目的是生产更安全的染发剂，同时最大程度地减少对人体的最终毒性。尤其是，带有大侧链的低聚物，PPD 6（13），PPD 7（14）和PPD 8（15）表现出弱至中度（27.1％，24.1％和34.0％）的敏化潜能。该结果证实了具有大而强
• 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。
• Sulfonanilide analogs as selective aromatase modulators (SAMs)
  申请人：The Ohio State University Research Foundation

  公开号：US07741520B2

  公开（公告）日：2010-06-22

  Compounds and methods suppressing aromatase activity expression in cancer cells. Provided are compounds are those of formula I: wherein R1 may be alkyl, cycloalkyl, haloalkyl, aryl, substituted aryl, haloaryl, alkoxy, alkylaryl, and arylalkyl; R2 is H, alkyl, aryl, alkylaryl, arylalkyl, and cycloalkyl; R3, with the base nitrogen, forms an amide or sulfonamide; R4 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。所提供的化合物为I式化合物，其中R1可以是烷基、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为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，所述小分子选择性芳香化酶抑制剂的分子量小于450 g/mol。还提供了一种抑制癌细胞中芳香化酶活性表达的方法，包括向需要此类治疗的受试者施用药学有效量的小分子芳香化酶抑制剂。在一个实施例中，癌细胞是乳腺癌细胞。