3-methoxy-4-(3-trifluoromethylbenzyloxy)benzaldehyde | 380427-19-0

• 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: 3-methoxy-4-(3-trifluoromethylbenzyloxy)benzaldehyde
• 英文别名: 3-Methoxy-4-{[3-(trifluoromethyl)benzyl]oxy}benzaldehyde；3-methoxy-4-[[3-(trifluoromethyl)phenyl]methoxy]benzaldehyde
• CAS: 380427-19-0
• 化学式: C₁₆H₁₃F₃O₃
• mdl: MFCD02255725
• 分子量: 310.273
• InChiKey: CRFMIKVKMCYUNP-UHFFFAOYSA-N

物化性质

• 熔点：
  64-65°C

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  6

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2913000090

反应信息

• 作为反应物：
  描述：

  3-methoxy-4-(3-trifluoromethylbenzyloxy)benzaldehyde 在 sodium tetrahydroborate 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Pyrido [1,2-a] 嘧啶酮中离子化合物含有香兰素部分：设计、合成、抗菌活性和机理

  摘要：

  米黄单胞菌光伏。oryzicola ( Xoo ) 是一种导致水稻白叶枯病的植物病原体，其防治仍具有挑战性。为了发现创新和极强的抗菌剂，引入香草醛部分以开发一系列新型介离子衍生物。化合物15对Xoo表现出优异的体外抗菌活性，50%有效浓度值（EC 50）为27.5 μg/mL，优于阳性对照剂噻二唑铜（97.1 μg/mL），与化合物“ A11 ” (17.4 μg/mL)。温室盆栽实验还揭示了化合物15100 μg/mL 对水稻白叶枯病的体内治疗效果为 38.5%，保护效果为 36.8%，高于噻二唑铜（分别为 31.2% 和 32.6%）和化合物“ A11 ”（分别为 29.6% 和 33.2%） ）。化合物15通过调节光合途径增强了相关防御酶的活性，增加了叶绿素含量，促进了水稻对细菌侵染的抵抗力。该研究为后续介离子衍生物的结构修饰和机理研究提供了依据。

  DOI：

  10.1021/acs.jafc.2c01838
• 作为产物：
  描述：

  香草醛 、 1-氯甲基-3-三氟甲基苯 在 potassium carbonate 、 potassium iodide 作用下， 以 乙腈 为溶剂， 生成 3-methoxy-4-(3-trifluoromethylbenzyloxy)benzaldehyde
  参考文献：
  名称：

  通过基于新型天然产物支架的设计选择性抑制真黑根霉生物合成，从而显着抑制真菌发病机制。

  摘要：

  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

  DOI：

  10.1042/bcj20200310

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
• Discovery and SAR of hydrazide antagonists of the pituitary adenylate cyclase-activating polypeptide (PACAP) receptor type 1 (PAC1-R)
  作者：Xenia Beebe、Daria Darczak、Rachel A. Davis-Taber、Marie E. Uchic、Victoria E. Scott、Michael F. Jarvis、Andrew O. Stewart

  DOI：10.1016/j.bmcl.2008.01.052

  日期：2008.3

  Potent small molecule antagonists for the PAC(1)-R have been discovered. Previously known antagonists for the PAC(1)-R were slightly truncated peptide ligands. The hydrazides reported here are the first small molecule antagonists ever reported for this class B GPCR. (C) 2008 Elsevier Ltd. All rights reserved.
• 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.
• 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.