4-(4-methoxybutoxy)benzaldehyde

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(4-methoxybutoxy)benzaldehyde
• 化学式: C₁₂H₁₆O₃
• 分子量: 208.257
• InChiKey: SRFAFKFULAZNSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  15
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-二羟基-2-巯基嘧啶 、 4-(4-methoxybutoxy)benzaldehyde 以 乙醇 为溶剂， 反应 2.0h， 以81%的产率得到5-(4-(4-methoxybutyl)benzylidene)-2-thioxodihydropyrimidine-4,6(1H,5H)-dione
  参考文献：
  名称：

  Inhibitory effects of 5-benzylidene barbiturate derivatives on mushroom tyrosinase and their antibacterial activities

  摘要：

  A series of novel 5-benzylidene barbiturate and thiobarbiturate derivatives were synthesized and evaluated as tyrosinase inhibitors and antibacterial agents. The results demonstrated that some compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Particularly, compounds 1a and 2a were found to be the most potent inhibitors with IC50 value of 13.98 mu M and 14.49 mu M, respectively. The inhibition mechanism study revealed that these compounds were irreversible inhibitors. The circular dichroism spectra indicated that these compounds induced conformational changes of mushroom tyrosinase upon binding. In addition, these compounds exhibited selectively antibacterial activity against Staphylococcus aureus. All these results suggested that further development of such compounds may be of interest. (c) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.05.023
• 作为产物：
  描述：

  4-氯丁基甲基醚 、 对羟基苯甲醛 在 potassium carbonate 作用下， 生成 4-(4-methoxybutoxy)benzaldehyde
  参考文献：
  名称：

  Imidazole derivatives

  摘要：

  本发明涉及以下式（I）的咪唑衍生物 其中R1是氢，可选择地取代的烷基等，R2是氢，可选择地取代的烷基等，R3是可选择地取代的杂芳基，R4是可选择地取代的环烷基，可选择地取代的苯基等，但当R1是氢，且R2和R4相同或不同，且每个是苯基或被卤原子、较低烷基或较低烷氧基取代的苯基时，R3是苯并噻唑基或被苯基取代的噻唑基，以下式（XII）的咪唑衍生物 其中R6是可选择地取代的苯基或可选择地取代的杂芳基，R7是被取代的苯基，以及其药学上可接受的盐。本发明的式（I）和（XII）的化合物及其药学上可接受的盐通过抑制Th2细胞产生IL-4和IL-5，在预防和治疗特应性皮炎、支气管哮喘、过敏性鼻炎等过敏性疾病方面具有有效性。

  公开号：

  US06288061B1

文献信息

• Rational Design and Synthesis of 4-O-Substituted Phenylmethylenethiosemicarbazones as Novel Tyrosinase Inhibitors
  作者：Wei Yi、Rihui Cao、Zhiyong Chen、Liang Yu、Huan Wen、Qin Yan、Lin Ma、Huacan Song

  DOI：10.1248/cpb.58.752

  日期：——

  In continuing our program aimed to search for tyrosinase inhibitors, a series of novel 4-O-substituted phenylmethylenethiosemicarbazones were rational designed, synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were also evaluated. A fair number of compounds were found to have significant tyrosinase inhibitiory activity. Particularly, the IC50 values of compounds 3a—g, 3j and 3s were of the same magnitude as tropolone, one of the best tyrosinase inhibitors known so far. Furthermore, the structure–activity relationships of these compounds were also investigated. All these data suggested that these molecules might be utilized for the development of new candidate for the treatment of dermatological disorders, and further development of such compounds may be of interest.

  在我们继续进行寻找酪氨酸酶抑制剂的项目中，合理设计并合成了一系列新型的4-O取代苯甲烯硫脲衍生物，同时评估了它们对蘑菇酪氨酸酶二酚酶活性的抑制效果。发现相当多的化合物具有显著的酪氨酸酶抑制活性。特别是化合物3a—g、3j和3s的IC50值与已知的最佳酪氨酸酶抑制剂之一的特罗泊酮相当。此外，这些化合物的结构—活性关系也进行了研究。所有这些数据表明，这些分子可能被用于开发治疗皮肤疾病的新候选药物，而且对这些化合物的进一步开发可能会引起兴趣。
• Synthesis, Optimization, and Structure–Activity Relationships of Imidazo[1,2-<i>a</i>]pyrimidines as Inhibitors of Group 2 Influenza A Viruses
  作者：Saad Alqarni、Laura Cooper、Jazmin Galvan Achi、Ryan Bott、Veeresh Kumar Sali、Andrew Brown、Bernard D. Santarsiero、Aleksej Krunic、Balaji Manicassamy、Norton P. Peet、Pin Zhang、Gregory R. J. Thatcher、Irina N. Gaisina、Lijun Rong、Terry W. Moore

  DOI：10.1021/acs.jmedchem.2c01329

  日期：2022.10.27

  develop novel anti-influenza therapies. Here, we present a novel imidazo[1,2-a]pyrimidine scaffold that targets group 2 IAV entry. We have explored three different regions of the lead compound, and we have developed a series of small molecules that have nanomolar activity against oseltamivir-sensitive and -resistant forms of group 2 IAVs. These small molecules target hemagglutinin (HA), which mediates

  甲型流感病毒（IAV）是一种传染性很强的病毒，可引起大流行和季节性流行，这是重大的公共卫生问题。目前的抗流感治疗受到限制，部分原因是耐药 IAV 菌株的不断出现；因此，开发新型抗流感疗法的需求尚未得到满足。在这里，我们提出了一种新颖的咪唑并 [1,2- a]靶向第 2 组 IAV 进入的嘧啶支架。我们探索了先导化合物的三个不同区域，并开发了一系列小分子，这些小分子对奥司他韦敏感和耐药形式的第 2 组 IAV 具有纳摩尔活性。这些小分子靶向介导病毒进入过程的血凝素 (HA)。用抗性突变体绘制 HA 结构的已知小分子结合空腔表明这些分子与该空腔结合并阻断 HA 介导的膜融合。
• Synthesis and biological evaluation of novel 4-hydroxybenzaldehyde derivatives as tyrosinase inhibitors
  作者：Wei Yi、Rihui Cao、Wenlie Peng、Huan Wen、Qin Yan、Binhua Zhou、Lin Ma、Huacan Song

  DOI：10.1016/j.ejmech.2009.11.007

  日期：2010.2

  A series of novel 4-hydroxybenzaldehyde derivatives were synthesized and their inhibitory effects on the diphenolase activity of mushroom tyrosinase were investigated. Most of target compounds had more potent inhibitory activities than the parent compound 4-hydroxybenzaldehyde (IC50 = 1.22 mM). Interestingly, compound 3c bearing a dimethoxyl phosphate was found to be the most potent inhibitor with IC50 value of 0.059 mM. The inhibition kinetics analyzed by Lineweaver-Burk plots revealed that compound 3c was a non-competitive inhibitor (K-I = 0.0368 mM). In particular, compound 3c showed no side effects at dose of 1600 mg/kg in mice. These results suggested that such compounds might be served as lead compounds for further designing new potential tyrosinase inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.
• COPOLYMER, AND LIQUID CRYSTAL ALIGNMENT LAYER COMPRISING HARDENED PRODUCT THEREOF
  申请人：DIC Corporation

  公开号：EP2727947B1

  公开（公告）日：2017-03-15
• US6288061B1
  申请人：——

  公开号：US6288061B1

  公开（公告）日：2001-09-11