3-甲氧基-4-(3-苯氧基丙氧基)苯甲醛 | 656810-27-4

• 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: 3-甲氧基-4-(3-苯氧基丙氧基)苯甲醛
• 英文名称: 3-methoxy-4-(3-phenoxypropoxy)benzaldehyde
• CAS: 656810-27-4
• 化学式: C₁₇H₁₈O₄
• 分子量: 286.328
• InChiKey: ISBVIQMNYKEZQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(4-吗啉基)丙腈 、 3-甲氧基-4-(3-苯氧基丙氧基)苯甲醛 在 sodium methylate 作用下， 以 二甲基亚砜 为溶剂， 生成
  参考文献：
  名称：

  Target Guided Synthesis of 5-Benzyl-2,4-diamonopyrimidines: Their Antimalarial Activities and Binding Affinities to Wild Type and Mutant Dihydrofolate Reductases from Plasmodium falciparum

  摘要：

  The resistance to pyrimethamine (PYR) of Plasmodium falciparum arising from mutation at position 108 of dihydrofolate reductase (pfDHFR) from serine to asparagine (S108N) is due to steric interaction between the bulky side chain of N108 and Cl atom of the 5-p-Cl aryl group of PYR, which consequently resulted in the reduction in binding affinity between the enzyme and inhibitor. Molecular modeling suggested that the flexible antifolate, such as trimethoprim (TMP) derivatives, could avoid this steric constraint and should be considered as new, potentially effective compounds. The hydrophobic interaction between the side chain of inhibitor and the active site of the enzyme around position 108 was enhanced by the introduction of a longer and more hydrophobic side chain on TMP's 5-benzyl moiety. The prepared compounds, especially those bearing aromatic substituents, exhibited better binding affinities to both wild type and mutant enzymes than the parent compound. Binding affinities of these compounds correlated well with their antimalarial. activities against both wild type and resistant parasites. Molecular modeling of the binding of such compounds with pfDHFR also supported the experimental data and clearly showed that aromatic substituents play an important role in enhancing binding affinity. In addition, some compounds with 6-alkyl substituents showed relatively less decrease in binding constants with the mutant enzymes and relatively good antimalarial. activities against the parasites bearing the mutant enzymes.

  DOI：

  10.1021/jm0303352
• 作为产物：
  描述：

  香草醛 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 3-甲氧基-4-(3-苯氧基丙氧基)苯甲醛
  参考文献：
  名称：

  第一代树枝状抗氧化剂含有 Meldrum 的酸部分作为表面基团

  摘要：

  各种抗氧化剂可以减少自由基引起的氧化应激。一种新的、有前途的抗氧化剂是单取代的 Meldrum 酸。此处展示了第一个具有 1,3-二恶烷-4,6-二酮单元作为表面基团的树枝状结构。这些化合物是通过苯酚的烷基化、Knoevenagel 缩合和顺序还原合成的。所有化合物对 1,1-二苯基-2-苦基肼 (DPPH) 的抗自由基活性 (AA) 为 80-90%，IC 50在 10-35 μM 之间变化。这些数据与维生素 C 相当，t-丁基对苯二酚 (TBHQ) 或维生素 E。抗加尔万氧基 (GO) 的 AA 随表面基团的数量增加而增加。对于具有至少两个 1,3-二恶烷-4,6-二酮部分的化合物，AA 与丁基化羟基甲苯 (BHT) 相当。所有衍生物中都突出了具有柔性甘油核心的结构。尽管甘油衍生物对 DPPH 的 AA 与具有芳香核的那些相当，但对 GO 更有效（AA = 95%，IC 50 = 60

  DOI：

  10.1039/d1nj03830c

文献信息

• Design, synthesis, bioactivity and mechanism of dithioacetal derivatives containing dioxyether moiety
  作者：Yanju Wang、Jian Zhang、Fangcheng He、Xiuhai Gan、Baoan Song、Deyu Hu

  DOI：10.1016/j.bmcl.2019.06.030

  日期：2019.8

  The present work designed and synthesized a series of dithioacetal derivatives containing dioxyether, as well as evaluated their antiviral activities against tobacco mosaic virus (TMV). Bioassays demonstrated that the target compounds showed excellent anti-TMV activities in vivo and in vitro. Compound 24c has excellent anti-TMV activities, and its curative, protective and inactivating activities for

  本工作设计并合成了一系列含有二氧醚的二硫缩醛衍生物，并评估了其对烟草花叶病毒（TMV）的抗病毒活性。生物测定法证明目标化合物在体内和体外均显示出优异的抗TMV活性。化合物24c具有优异的抗TMV活性，对TMV的治愈，保护和灭活活性分别为50.9％，58.9％和81.8％，明显优于利巴韦林（分别为50.2％，41.3％和69.5％）。 ）。此外，EC 50对化合物24c的抗TMV具有灭活活性为67.9 mg / L，优于利巴韦林（149.5 mg / L）。透射电子显微镜显示，化合物24c对TMV颗粒的形态造成了很大的破坏，导致断裂和弯曲。分子对接模型显示该化合物与氨基酸GLN57，ASN73，TYR139和SER138的活性位点形成了五个常规氢键。此外，荧光滴定和微量热泳的测试结果表明，化合物24c与TMV外壳蛋白（TMV CP）具有很强的结合力，缔合常数（K a）为1.04×10 5  L
• Syntheses and evaluation of novel isoliquiritigenin derivatives as potential dual inhibitors for amyloid-beta aggregation and 5-lipoxygenase
  作者：Yi-Ping Chen、Zi-Ying Zhang、Yan-Ping Li、Ding Li、Shi-Liang Huang、Lian-Quan Gu、Jun Xu、Zhi-Shu Huang

  DOI：10.1016/j.ejmech.2013.05.015

  日期：2013.8

  A series of new isoliquiritigenin (ISL) derivatives were synthesized and evaluated as dual inhibitors for amyloid-beta (Aβ) aggregation and 5-lipoxygenase (5-LO). It was found that all these synthetic compounds inhibited Aβ (1–42) aggregation effectively with their IC50 values ranged from 2.2 ± 1.5 μM to 23.8 ± 2.0 μM. These derivatives also showed inhibitory activity to 5-LO with their IC50 values

  合成了一系列新的异源寡糖原蛋白（ISL）衍生物，并将其评估为β-淀粉样蛋白（Aβ）聚集和5-脂氧合酶（5-LO）的双重抑制剂。发现所有这些合成化合物均能有效抑制Aβ（1-42）聚集，其IC 50值为2.2±1.5μM至23.8±2.0μM。这些衍生物还显示出对5-LO的抑制活性，其IC 50值范围为6.1±0.1μM至35.9±0.3μM。研究了它们的结构-活性关系（SAR）和抑制机理。这项研究为进一步开发ISL衍生物作为阿尔茨海默氏病（AD）的多功能药物提供了潜在的重要信息。
• 1st generation dendrimeric antioxidants containing Meldrum's acid moieties as surface groups
  作者：Inese Mieriņa、Elīna Peipiņa、Klaudija Aišpure、Māra Jure

  DOI：10.1039/d1nj03830c

  日期：——

  These data are comparable with vitamin C, t-butylhydroquinone (TBHQ) or vitamin E. The AA against galvinoxyl (GO) increased with the number of surface groups. The AA was comparable with butylated hydroxytoluene (BHT) for compounds with at least two moieties of 1,3-dioxane-4,6-dione. The structure with a flexible glycerol core is highlighted among all the derivatives. Although the AA against DPPH for the

  各种抗氧化剂可以减少自由基引起的氧化应激。一种新的、有前途的抗氧化剂是单取代的 Meldrum 酸。此处展示了第一个具有 1,3-二恶烷-4,6-二酮单元作为表面基团的树枝状结构。这些化合物是通过苯酚的烷基化、Knoevenagel 缩合和顺序还原合成的。所有化合物对 1,1-二苯基-2-苦基肼 (DPPH) 的抗自由基活性 (AA) 为 80-90%，IC 50在 10-35 μM 之间变化。这些数据与维生素 C 相当，t-丁基对苯二酚 (TBHQ) 或维生素 E。抗加尔万氧基 (GO) 的 AA 随表面基团的数量增加而增加。对于具有至少两个 1,3-二恶烷-4,6-二酮部分的化合物，AA 与丁基化羟基甲苯 (BHT) 相当。所有衍生物中都突出了具有柔性甘油核心的结构。尽管甘油衍生物对 DPPH 的 AA 与具有芳香核的那些相当，但对 GO 更有效（AA = 95%，IC 50 = 60
• Target Guided Synthesis of 5-Benzyl-2,4-diamonopyrimidines: Their Antimalarial Activities and Binding Affinities to Wild Type and Mutant Dihydrofolate Reductases from <i>Plasmodium falciparum</i>
  作者：Chawanee Sirichaiwat、Chakapong Intaraudom、Sumalee Kamchonwongpaisan、Jarunee Vanichtanankul、Yodhathai Thebtaranonth、Yongyuth Yuthavong

  DOI：10.1021/jm0303352

  日期：2004.1.1

  The resistance to pyrimethamine (PYR) of Plasmodium falciparum arising from mutation at position 108 of dihydrofolate reductase (pfDHFR) from serine to asparagine (S108N) is due to steric interaction between the bulky side chain of N108 and Cl atom of the 5-p-Cl aryl group of PYR, which consequently resulted in the reduction in binding affinity between the enzyme and inhibitor. Molecular modeling suggested that the flexible antifolate, such as trimethoprim (TMP) derivatives, could avoid this steric constraint and should be considered as new, potentially effective compounds. The hydrophobic interaction between the side chain of inhibitor and the active site of the enzyme around position 108 was enhanced by the introduction of a longer and more hydrophobic side chain on TMP's 5-benzyl moiety. The prepared compounds, especially those bearing aromatic substituents, exhibited better binding affinities to both wild type and mutant enzymes than the parent compound. Binding affinities of these compounds correlated well with their antimalarial. activities against both wild type and resistant parasites. Molecular modeling of the binding of such compounds with pfDHFR also supported the experimental data and clearly showed that aromatic substituents play an important role in enhancing binding affinity. In addition, some compounds with 6-alkyl substituents showed relatively less decrease in binding constants with the mutant enzymes and relatively good antimalarial. activities against the parasites bearing the mutant enzymes.