4,4′-[ethane-1,2-diylbis(oxy)]bis(3-methoxy-benzaldehyde) | 5784-66-7

• 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: 4,4′-[ethane-1,2-diylbis(oxy)]bis(3-methoxy-benzaldehyde)
• 英文别名: 4,4'-[ethane-1,2-diylbis(oxy)]bis(3-methoxybenzaldehyde)；4,4'-diformyl-2,2'-dimethoxy-1,2-diphenoxyethane；3,3'-dimethoxy-4,4'-ethanediyldioxy-di-benzaldehyde；3,3'-Dimethoxy-4,4'-aethandiyldioxy-di-benzaldehyd；1,2-di(2-methoxy-4-formyl)phenoxyethane；4,4'-(ethylenedioxy)di-m-anisaldehyde；4-[2-(4-Formyl-2-methoxyphenoxy)ethoxy]-3-methoxybenzaldehyde
• CAS: 5784-66-7
• 化学式: C₁₈H₁₈O₆
• mdl: MFCD00021061
• 分子量: 330.337
• InChiKey: FXCAWIBAYDHMSX-UHFFFAOYSA-N

物化性质

• 熔点：
  180-181 °C
• 沸点：
  530.9±50.0 °C(Predicted)
• 密度：
  1.224±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,4′-[ethane-1,2-diylbis(oxy)]bis(3-methoxy-benzaldehyde) 在 [RuCl(6-(4-methoxyphenyl)-2-aminomethylpyridine)(1,1′-bis(diphenylphosphino)ferrocene)] 、 sodium isopropylate 、 异丙醇 作用下， 反应 0.07h， 以99%的产率得到1,2-bis(4-hydroxymethyl-2-methoxyphenoxy)ethane
  参考文献：
  名称：

  CNN夹钳式钌络合物，用于生物质衍生的羰基化合物的有效转移加氢。

  摘要：

  配体HCNNOMe（6-（4-甲氧基苯基）-2-氨基甲基吡啶）可以通过羟胺和加氢（H2，1 atm）与Pd的反应，由市售的6-（4-甲氧基苯基）吡啶-2-甲醛轻松制得。 /C。由[RuCl2（PPh3）3]合成了钳形配合物顺式-[RuCl（CNNOMe）（PPh3）2]（1）和[RuCl（CNNOMe）（PP）]（PP = dppb，2;和dppf，3）。 ，HCNNOMe和PP（分别用于2和3）在2-丙醇中，NEt3回流，以85-93％的收率分离。1（CO，1 atm）的羰基化得到[RuCl（CNNOMe）（CO）（PPh3）]（4）（79％产率），可与Na [BArf4]和PCy3干净地反应，得到阳离子反式-[Ru（CNNOMe） ）（CO）（PCy3）（PPh3）] [BArf4]（5）（92％收率）。这些坚固的钳形配合物在木质纤维素生物质羰基化合物的转移加氢（TH）中显示出极高的催

  DOI：

  10.1039/c9dt04292j
• 作为产物：
  描述：

  香草醛 在 potassium carbonate 、 丙酮 作用下， 生成 4,4′-[ethane-1,2-diylbis(oxy)]bis(3-methoxy-benzaldehyde)
  参考文献：
  名称：

  �ber basische �ther des Vanillins und seiner Derivate

  摘要：

  DOI：

  10.1007/bf00906086

文献信息

• Targeting Receptor Tyrosine Kinase VEGFR-2 in Hepatocellular Cancer: Rational Design, Synthesis and Biological Evaluation of 1,2-Disubstituted Benzimidazoles
  作者：Heba T. Abdel-Mohsen、Mona A. Abdullaziz、Ahmed M. El Kerdawy、Fatma A. F. Ragab、Keith J. Flanagan、Abeer E. E. Mahmoud、Mamdouh M. Ali、Hoda I. El Diwani、Mathias O. Senge

  DOI：10.3390/molecules25040770

  日期：——

  In this study, a novel series of 1,2-disubstituted benzo[d]imidazoles was rationally designed as VEGFR-2 inhibitors targeting hepatocellular carcinoma. Our design strategy is two-fold; it aimed first at studying the effect of replacing the 5-methylfuryl moiety of the well-known antiangiogenic 2-furylbenzimidazoles with an isopropyl moiety on the VEGFR-2 inhibitory activity and the cytotoxic activity. Our second objective was to further optimize the structures of the benzimidazole derivatives through elongation of the side chains at their one-position for the design of more potent type II-like VEGFR-2 inhibitors. The designed 1,2-disubstituted benzimidazoles demonstrated potent cytotoxic activity against the HepG2 cell line, reaching IC50 = 1.98 μM in comparison to sorafenib (IC50 = 10.99 μM). In addition, the synthesized compounds revealed promising VEGFR-2 inhibitory activity in the HepG2 cell line, e.g., compounds 17a and 6 showed 82% and 80% inhibition, respectively, in comparison to sorafenib (% inhibition = 92%). Studying the effect of 17a on the HepG2 cell cycle demonstrated that 17a arrested the cell cycle at the G2/M phase and induced a dose-dependent apoptotic effect. Molecular docking studies of the synthesized 1,2-disubstituted benzimidazoles in the VEGFR-2 active site displayed their ability to accomplish the essential hydrogen bonding and hydrophobic interactions for optimum inhibitory activity.

  在这项研究中，一系列新型的1,2-二取代苯并[d]咪唑被合理设计为靶向肝细胞癌的VEGFR-2抑制剂。我们的设计策略是双重的；首先旨在研究将众所周知的抗血管生成的2-呋喃基苯并咪唑的5-甲基呋喃基团替换为异丙基基团对VEGFR-2抑制活性和细胞毒活性的影响。我们的第二个目标是通过延长它们的一位点的侧链来进一步优化苯并咪唑衍生物的结构，设计更强效的类II型VEGFR-2抑制剂。设计的1,2-二取代苯并咪唑表现出强大的细胞毒活性，对HepG2细胞系的IC50 = 1.98 μM，而索拉非尼的IC50 = 10.99 μM。此外，合成的化合物在HepG2细胞系中显示出有希望的VEGFR-2抑制活性，例如，化合物17a和6分别显示出82%和80%的抑制作用，而索拉非尼的抑制率为92%。研究17a对HepG2细胞周期的影响表明，17a在G2/M期阻滞细胞周期并诱导剂量依赖的凋亡效应。对合成的1,2-二取代苯并咪唑在VEGFR-2活性位点的分子对接研究显示它们能够完成必要的氢键和疏水相互作用，以实现最佳的抑制活性。
• Design, synthesis, <i>in silico</i> docking studies and biological evaluation of novel quinoxaline-hydrazide hydrazone-1,2,3-triazole hybrids as α-glucosidase inhibitors and antioxidants
  作者：Triloknadh Settypalli、Venkata Rao Chunduri、Aruna Kumari Maddineni、Nagaraju Begari、Rajasekhar Allagadda、Peddanna Kotha、Appa Rao Chippada

  DOI：10.1039/c9nj02580d

  日期：——

  A new series of quinoxaline-hydrazidehydrazone-1,2,3-triazole hybrids, 14a–j, 15a–j and 16a–e, was designed, synthesized and screened for in vitro α-glucosidase and antioxidant activities. For the synthesis of the target compounds, quinoxaline hydrazides were condensed with benzaldehyde triazoles in the presence of AcOH (cat) in ethanol. The key step in the preparation of compounds 8a–j was the Cu(I)-catalyzed

  设计，合成并筛选了一系列新的喹喔啉-酰肼-1,2,3-三唑杂种14a–j，15a–j和16a–e，用于体外α-葡萄糖苷酶和抗氧化活性。为了合成目标化合物，在乙醇中存在AcOH（催化剂）的情况下，将喹喔啉酰肼与苯甲醛三唑缩合。在化合物的制备中的关键步骤8A-J是铜（我）催化的[3 + 2]环加成反应加成（CuAAC）与适当的炔烃（6，7）和叠氮化物，和图13A-J由与最终步骤相同的点击反应，由简单的醛制备而成。通过邻苯二胺和丙酮酸经三步反应，包括环化，烷基化和酰化反应，合成喹喔啉酰肼（3，3a）。在这些杂种中，14a（IC 50 = 21.92μgmL -1），14b（IC 50 = 22.32μgmL -1），14c（IC 50 = 23.58μgmL -1）和15a（IC 50 = 24.50μgmL -1））与标准阿卡波糖（IC 50 = 22.32μgmL -1）相比，显示出良好的α
• Guanylhydrazones and their use to treat inflammatory conditions
  申请人：The Picower Institute for Medical Research

  公开号：US05750573A1

  公开（公告）日：1998-05-12

  This invention concerns new methods and compositions that are useful in preventing and ameliorating cachexia, the clinical syndrome of poor nutritional status and bodily wasting associated with cancer and other chronic diseases. More particularly, the invention relates to aromatic guanylhydrazone (more properly termed amidinohydrazone) compositions and their use to inhibit the uptake of arginine by macrophages and/or its conversion to urea. These compositions and methods are also useful in preventing the generation of nitric oxide (NO) by cells, and so to prevent NO-mediated inflammation and other responses in persons in need of same. In another embodiment, the compounds can be used to inhibit arginine uptake in arginine-dependent tumors and infections.

  这项发明涉及新的方法和组合物，可用于预防和改善消瘦症，即与癌症和其他慢性疾病相关的营养状况不佳和身体消耗的临床综合征。更具体地，该发明涉及芳香基胍基脲（更确切地称为胍基脲）组合物及其用于抑制巨噬细胞对精氨酸的摄取和/或其转化为尿素。这些组合物和方法还可用于预防细胞产生一氧化氮（NO），从而预防需要相同的人体内的NO介导的炎症和其他反应。在另一实施例中，这些化合物可用于抑制精氨酸依赖性肿瘤和感染中的精氨酸摄取。
• Biferrocenyl Schiff bases as efficient corrosion inhibitors for an aluminium alloy in HCl solution: a combined experimental and theoretical study
  作者：Uzma Nazir、Zareen Akhter、Naveed Kausar Janjua、Muhammad Adeel Asghar、Sehrish Kanwal、Tehmeena Maryum Butt、Asma Sani、Faroha Liaqat、Rizwan Hussain、Faiz Ullah Shah

  DOI：10.1039/c9ra10692h

  日期：——

  anticorrosion efficiency as compared with Fcua due to the electron donating methoxy and ethoxy group substitutions, respectively. Polarization curves also indicated that the studied biferrocenyl Schiff bases were mixed type anticorrosive materials. The inhibition of the aluminium alloy surface by biferrocenyl Schiff bases was evidenced through scanning electron microscopy (SEM) studies. Semi-empirical quantum mechanical

  采用 Tafel 极化、电化学阻抗谱 (EIS)、失重测量、FT-IR 光谱和扫描电子显微镜 (SEM) 技术研究了一些二茂铁基席夫碱对 AA2219-T6 铝合金在酸性介质中的缓蚀能力。通过量子化学计算探索了分子构型对缓蚀行为的影响。二茂铁席夫碱 4,4'-((((ethane-1,2-diylbis(oxy))bis(4,1-phenylene))bis(methaneylylidene))bis(azaneylylidene))bisferrocene ( Fcua ), 4,4 '-((((乙烷-1,2-二基双(氧基))双(2-甲氧基-1,4-亚苯基))双(甲亚基))双(氮杂亚基))双二茂铁( Fcub) 和 4,4'-((((ethane-1,2-diylbis(oxy))bis(2-ethoxy-1,4-phenylene))bis(methaneylylidene))bis(
• [EN] CINNAMIC ACID DIMERS, THEIR PREPARATION AND THE USE THEREOF FOR TREATING NEURODEGENERATIVE DISEASE<br/>[FR] DIMERES D'ACIDE CINAMIQUE, PREPARATION ASSOCIEE ET UTILISATION CORRESPONDANTE DANS LE TRAITEMENT DES MALADIES NEURODEGENERATIVES
  申请人：KOREA INST SCI & TECH

  公开号：WO2003099269A1

  公开（公告）日：2003-12-04

  The present invention relates to cinnamic acid dimers, their preparation and the use thereof for treating neurodegenerative disease, which have excellent effect on enhancing the learning and memory-retention ability in vivo and have fewer side-effects by showing no hormone properties, even when administered for a long period of time, and thus which can be used for neurodegenerative disease including dementia.

  本发明涉及肉桂酸二聚体、其制备和用于治疗神经退行性疾病的用途，其在体内具有极好的增强学习和记忆保持能力的效果，并且在长时间内使用时没有激素特性，因此副作用较少，可用于治疗包括痴呆在内的神经退行性疾病。