3-bromo-4-(4-methylbenzyloxy)benzaldehyde | 428469-68-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-bromo-4-(4-methylbenzyloxy)benzaldehyde
• 英文别名: 3-Bromo-4-[(4-methylbenzyl)oxy]benzaldehyde；3-bromo-4-[(4-methylphenyl)methoxy]benzaldehyde
• CAS: 428469-68-5
• 化学式: C₁₅H₁₃BrO₂
• mdl: MFCD02611634
• 分子量: 305.171
• InChiKey: DSRKQRVUZYZAMO-UHFFFAOYSA-N

物化性质

• 沸点：
  419.4±35.0 °C(Predicted)
• 密度：
  1.398±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.133
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-bromo-4-(4-methylbenzyloxy)benzaldehyde 在 sodium methylate 作用下， 以 乙醇 、 二甲基亚砜 、 异丙醇 为溶剂， 生成 5-(3-bromo-4-((4-methylbenzyl)oxy)benzyl)pyrimidine-2,4-diamine
  参考文献：
  名称：

  作为c-Fms激酶抑制剂的5-取代苄基-2,4-二氨基嘧啶衍生物的合成

  摘要：

  摘要合成了一系列新型的5-取代的苄基-2,4-二氨基嘧啶衍生物，并通过标准MTT方法评估了其为c-Fms激酶的抑制剂。结果表明，化合物15,5- [3-甲氧基-4-（吡啶-3-基）苄基] -2,4-二氨基嘧啶具有1.45μmol/ L的IC 50抑制M-CSF的增殖。小鼠（NFS-60）依赖的髓样白血病细胞，与c-Fms激酶的选择性抑制剂GW2580相似。

  DOI：

  10.1016/j.cclet.2010.06.023
• 作为产物：
  描述：

  3-溴-4-羟基苯甲醛 、 4-甲基苄溴 在 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以88%的产率得到3-bromo-4-(4-methylbenzyloxy)benzaldehyde
  参考文献：
  名称：

  Synthesis and evaluation of 1-hydroxy/methoxy-4-methyl-2-phenyl-1H-imidazole-5-carboxylic acid derivatives as non-purine xanthine oxidase inhibitors

  摘要：

  Xanthine oxidase is a key enzyme that catalyses hypoxanthine and xanthine to uric acid, whose overproduction leads to the gout-causing hyperuricemia. In this study, a series of 1-hydroxy/methoxy-4-methy1-2-phenyl-1H-imidazole-5-carboxylic acid derivatives (4a-4k and 6a-6k) was synthesized and evaluated for their inhibitory potency against xanthine oxidase. The 1-hydroxyl substituted derivatives 4a-4k showed excellent inhibitory potency with IC50 values ranging from 0.003 mu M to 1.2 mu M, with compounds 4d (IC50 = 0.003 mu M), 4e (IC50 = 0.003 FM), and 4f (IC50 = 0.006 mu M) manifesting the most potent xanthine oxidase inhibitory potency that were comparable with that of Febuxostat (IC50 = 0.01 410). Lineweaver-Burk plot analysis revealed that representative compound 4f acted as a mixed-type inhibitor for xanthine oxidase. The basis of significant inhibition of xanthine oxidase by 4f was rationalized by its molecular docking into the active site of xanthine dehydrogenase. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.08.056

文献信息

• Selective inhibition of <i>Rhizopus</i> eumelanin biosynthesis by novel natural product scaffold-based designs caused significant inhibition of fungal pathogenesis
  作者：Sameh S. M. Soliman、Rania Hamdy、Samia A. Elseginy、Teclegiorgis Gebremariam、Alshaimaa M. Hamoda、Mohamed Madkour、Thenmozhi Venkatachalam、Mai N. Ershaid、Mohammad G. Mohammad、Georgios Chamilos、Ashraf S. Ibrahim

  DOI：10.1042/bcj20200310

  日期：2020.7.17

  naturally in most living organisms. Fungal melanin is a major putative virulence factor of Mucorales fungi that allows intracellular persistence by inducing phagosome maturation arrest. Recently, it has been shown that the black pigments of Rhizopus delemar is of eumelanin type, that requires the involvement of tyrosinase (a copper-dependent enzyme) in its biosynthesis. Herein, we have developed a series

  黑色素是在大多数生物体中自然合成的深色色素。真菌黑色素是毛霉菌属真菌的主要假定毒力因子，通过诱导吞噬体成熟阻滞允许细胞内持续存在。最近，已经表明，Rhizopus delemar 的黑色色素属于真黑素类型，这需要酪氨酸酶（一种依赖铜的酶）参与其生物合成。在此，我们开发了一系列化合物 (UOSC-1-14) 来选择性靶向根霉黑色素，并在治疗上探索了这种机制。这些化合物是基于从植物来源鉴定的天然产物孜然醛的支架设计的，并已显示出对黑色素生成的非选择性抑制。虽然所有合成的化合物都显示出对根霉黑色素产生的显着抑制和对哺乳动物细胞的有限毒性，但基于它们对真菌黑色素的选择性抑制，只有四种化合物（UOSC-1、2、13 和 14）被选为有前景的候选物。化合物UOSC-2的活性与阳性对照曲酸相当。选定的候选物通过靶向真菌酪氨酸酶显示出对根霉黑色素的显着抑制，但对人黑色素没有显着抑制作用，IC50 比参考标准曲酸低
• Design and synthesis of new drugs inhibitors of Candida albicans hyphae and biofilm formation by upregulating the expression of TUP1 transcription repressor gene
  作者：Rania Hamdy、Sameh S.M. Soliman、Abrar I. Alsaadi、Bahgat Fayed、Alshaimaa M. Hamoda、Samia A. Elseginy、Mohamed I. Husseiny、Ashraf S. Ibrahim

  DOI：10.1016/j.ejps.2020.105327

  日期：2020.5

  Candida albicans is a common human fungal pathogen that causes disease ranging from superficial to lethal infections. C. albicans grows as budding yeast which can transform into hyphae in response to various environmental or biological stimuli. Although both forms have been associated with virulence, the hyphae form is responsible for the formation of multi-drug resistance biofilm. Here, new compounds were designed to selectively inhibit C. albicans hyphae formation without affecting human cells to afford sufficient safety. The newly designed 5-[3-substitued-4-(4-substituedbenzyloxy)-benzylidene]-2-thioxo-thiazolidin-4-one derivatives, named SR, showed very specific and effective inhibition activity against C. albicans hyphae formation. SR compounds caused hyphae inhibition activity at concentrations 10-40 fold lower than the concentration required to inhibit Candida yeast and bacterial growths. The anti-hyphae inhibition activities of SR compounds were via activation of the hyphae transcription repressor gene, TUP1. Correlation studies between the expression of TUP1 gene and the activity of SR compounds confirmed that the anti-C. albicans activities of SR compounds were via inhibition of hyphae formation. The newly designed SR compounds showed 10-40% haemolytic activity on human erythrocytes when compared to 100% haemolysis by 0.1% triton employed as positive control. Furthermore, theoretical prediction of absorption, distribution, metabolism, excretion, and toxicity (ADMET) of SR compounds confirmed their safety, efficient metabolism and possible oral bioavailability. With the minimal toxicity and significant activity of the newly-designed SR compounds, a future optimization of pharmaceutical formulation may develop a promising inhibitor of hyphal formation not only for C. albicans but also for other TUP1- dependent dimorphic fungal infections.
• Small Molecule Inhibitors of Fungal Hyphae and Biofilm Formation
  申请人：University of Sharjah

  公开号：US20210179571A1

  公开（公告）日：2021-06-17

  Novel compounds having inhibitory activity on the formation of fungal hyphae and biofilms, and therapeutic formulations and methods based on the novel inhibitors.
• [EN] SMALL MOLECULE INHIBITORS OF FUNGAL HYPHAE AND BIOFILM FORMATION<br/>[FR] INHIBITEURS À PETITES MOLÉCULES DE LA FORMATION D'HYPHES FONGIQUES ET DE BIOFILMS
  申请人：UNIV OF SHARJAH

  公开号：WO2021117014A2

  公开（公告）日：2021-06-17

  Novel compounds having inhibitory activity on the formation of fungal hyphae and biofilms, and therapeutic formulations and methods based on the novel inhibitors.