4-methoxy-N-(4-hydroxy-3-methoxybenzylidene)aniline | 24033-07-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 4-methoxy-N-(4-hydroxy-3-methoxybenzylidene)aniline
• 英文别名: 2-methoxy-4-(((4-methoxyphenyl)imino)methyl)phenol；2-methoxy-4-[(4-methoxy-phenylimino)-methyl]-phenol；4-Vanillylidenamino-anisol；Vanillyliden-p-anisidin；4-(4-Oxy-3-methoxy-benzalamino)-phenol-methylaether；Vanillal-p-anisidin；2-Methoxy-alpha-(4-methoxyphenylimino)-para-cresol；2-methoxy-4-[(4-methoxyphenyl)iminomethyl]phenol
• CAS: 24033-07-6
• 化学式: C₁₅H₁₅NO₃
• 分子量: 257.289
• InChiKey: KDIGZGCAYQKYEH-UHFFFAOYSA-N

物化性质

• 熔点：
  138 °C(Solv: methanol (67-56-1))
• 沸点：
  439.5±45.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  51
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-methoxy-N-(4-hydroxy-3-methoxybenzylidene)aniline 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 生成 2-methoxy-4-(((4-methoxyphenyl)amino)methyl)phenol
  参考文献：
  名称：

  Synthesis and biological evaluation of novel N, N′-disubstituted urea and thiourea derivatives as potential anti-melanoma agents

  摘要：

  Two series of urea and thiourea derivatives (1a-11a, 1b-11b) have been synthesized; all the 22 compounds were reported for the first time. Their anti-proliferative activities against the melanoma cell line B16-F10 were evaluated. Among the compounds tested, compound 6b exhibited the most potent activity in melanoma cells growth inhibition (IC50 = 0.33 mu M). The bioassay tests showed that anti-proliferative activities of these novel compounds were possibly caused by inhibition of ERK1/2 phosphorylation level. Therefore, compound 6b can be a potential anti-melanoma agent and an inhibitor of ERK1/2 phosphorylation deserving further research.

  DOI：

  10.3109/14756366.2011.608665
• 作为产物：
  描述：

  (E)-2-methoxy-4-((tetrafluoro-λ⁵-boranyl)diazenyl)phenol 在 sodium acetate 、 palladium diacetate 、 iron(II) chloride 作用下， 以 乙腈 为溶剂， 反应 12.0h， 生成 4-methoxy-N-(4-hydroxy-3-methoxybenzylidene)aniline
  参考文献：
  名称：

  4-羟基丁苯与芳基叠氮化物的铁催化硝基转移反应：通过C═C键裂解合成亚胺。

  摘要：

  打破C bondC债券以获取C═N债券的领域仍然不发达。报道了一种在非氧化条件下通过4-羟基苯乙烯与芳基叠氮化物的铁催化的腈转移反应产生亚胺的烯烃的C═C键裂解的新方案。各种顺序一锅法反应的成功表明，该方法的良好兼容性使其对于合成应用非常有吸引力。在实验观察的基础上，还提出了合理的反应机理。

  DOI：

  10.1021/acs.orglett.9b03160

文献信息

• Synthesis, structure-activity relationships and preliminary mechanism study of N-benzylideneaniline derivatives as potential TLR2 inhibitors
  作者：Shaoyi Cai、Gengzheng Zhu、Xiaohong Cen、Jingjie Bi、Jingru Zhang、Xiaoshan Tang、Kun Chen、Kui Cheng

  DOI：10.1016/j.bmc.2018.03.001

  日期：2018.5

  we designed and synthesized 50 N-benzylideneaniline compounds with the help of CADD. And subsequent in vitro studies leading to the optimized compound SMU-A0B13 with most potent inhibitory activity to TLR2 (IC50=18.21 ± 0.87 μM). Preliminary mechanism studies indicated that this TLR2 inhibitor can work through the NF-κB signaling pathway with high specificity and low toxicity, and can also efficiently

  Toll样受体2（TLR2）可以识别病原体相关的分子模式以防御入侵的生物，并且已成为有吸引力的治疗靶标。直到今天，还没有在临床试验中开发出TLR2小分子拮抗剂。本文中，我们借助CADD设计并合成了50种 N-苄叉基苯胺化合物。随后进行的体外研究产生了对TLR2具有最强抑制活性的优化化合物SMU-A0B13（IC 50= 18.21±0.87μM）。初步的机制研究表明，该TLR2抑制剂可通过NF-κB信号通路发挥高特异性和低毒性的作用，并且还可以有效下调HEK-blue hTLR2，人PBMC和SHE中的炎性细胞因子，例如SEAP，TNF-α和NO。原始的264.7细胞系。此外，对接情况还表明SMU-A0B13可以很好地与TLR2-TIR（PDB：1FYW）活性域结合，这可能解释了其生物活性。
• Synthesis, Characterization and Antimicrobial Evaluation of some Schiff Bases and their Thiazolidinone Products
  作者：DESTA GEBRETEKLE、ABI TADESSE、R. K. UPADHYAY、AMAN DEKEBO

  DOI：10.13005/ojc/280431

  日期：2012.12.22

  Six isomeric nitro- and methoxy anilines were condensed with vanillin to obtain Schiff's bases. A new series of 2-(4-hydroxy-3-methoxy phenyl)-1-thiazolidinone derivatives were synthesized by the cyclocondensation of Schiff's bases with mercapto acetic acid. The chemical structures of synthesized compounds were confirmed by elemental analysis, molecular weight determination, IR, 1 H & 13 C and DEPT-135

  将六种异构的硝基和甲氧基苯胺与香兰素缩合，以获得席夫氏碱。通过席夫碱与巯基乙酸的环缩合反应，合成了一系列新的2-（4-羟基-3-甲氧基苯基）-1-噻唑烷酮衍生物。合成的化合物的化学结构通过元素分析，分子量测定，IR，1 H和13 C和DEPT-135 NMR光谱测定得到证实。通过分别使用氨苄青霉素和巴维斯汀参考药物，体外研究了金​​黄色葡萄球菌和大肠埃希氏菌和黑曲霉和巴氏根瘤菌的抗菌和抗真菌活性。
• Structure–fluorescence activation relationships of a large Stokes shift fluorogenic RNA aptamer
  作者：Christian Steinmetzger、Irene Bessi、Ann-Kathrin Lenz、Claudia Höbartner

  DOI：10.1093/nar/gkz1084

  日期：——

  The Chili RNA aptamer is a 52 nt long fluorogen-activating RNA aptamer (FLAP) that confers fluorescence to structurally diverse derivatives of fluorescent protein chromophores. A key feature of Chili is the formation of highly stable complexes with different ligands, which exhibit bright, highly Stokes-shifted fluorescence emission. In this work, we have analyzed the interactions between the Chili RNA and a family of conditionally fluorescent ligands using a variety of spectroscopic, calorimetric and biochemical techniques to reveal key structure–fluorescence activation relationships (SFARs). The ligands under investigation form two categories with emission maxima of ∼540 or ∼590 nm, respectively, and bind with affinities in the nanomolar to low-micromolar range. Isothermal titration calorimetry was used to elucidate the enthalpic and entropic contributions to binding affinity for a cationic ligand that is unique to the Chili aptamer. In addition to fluorescence activation, ligand binding was also observed by NMR spectroscopy, revealing characteristic signals for the formation of a G-quadruplex only upon ligand binding. These data shed light on the molecular features required and responsible for the large Stokes shift and the strong fluorescence enhancement of red and green emitting RNA–chromophore complexes.

  Chili RNA适配体是一种长达52个核苷酸的荧光激活RNA适配体（FLAP），它可以将荧光蛋白色团的结构多样性衍生物赋予荧光。Chili的一个关键特征是与不同配体形成高度稳定的复合物，这些复合物表现出明亮、高Stokes位移的荧光发射。在这项工作中，我们使用各种光谱、热力学和生化技术分析了Chili RNA与一系列有条件荧光配体之间的相互作用，以揭示关键的结构-荧光激活关系（SFARs）。所研究的配体分为两类，分别具有∼540或∼590 nm的发射极大值，并以纳摩尔至低微摩尔的亲和力结合。等温滴定量热法被用来阐明唯一适用于Chili适配体的阳离子配体的焓和熵对结合亲和力的贡献。除了荧光激活外，还通过NMR光谱观察到配体结合，揭示了仅在配体结合时形成G四链体的特征信号。这些数据揭示了红色和绿色发射RNA-色团复合物的大Stokes位移和强荧光增强所需和负责的分子特征。

• Method of inhibiting NADPH oxidase
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US05939460A1

  公开（公告）日：1999-08-17

  The instant methods employs pharmaceutical compositions comprising aromatic azines; and imines, of the Formula 1 to selectively inhibit inflammation by preventing the oxidating burst from phagocytic leukocytes caused by NADPH Oxidase.

  该即时方法采用含有芳香基氮杂环和Formula 1中的亚胺的药物组合物，通过防止NADPH氧化酶引起的吞噬性白细胞的氧化爆发，选择性地抑制炎症。
• Gopalakrishnan, Mannathusamy; Sureshkumar, Purushothaman; Kanagarajan, Vijayakumar, Journal of Chemical Research, 2005, # 5, p. 299 - 303
  作者：Gopalakrishnan, Mannathusamy、Sureshkumar, Purushothaman、Kanagarajan, Vijayakumar、Thanusu, Jeyaraman、Govindaraju, Ramalingam

  DOI：——

  日期：——