4-phenacyloxy-3-methoxybenzaldehyde | 723332-14-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-phenacyloxy-3-methoxybenzaldehyde
• 英文别名: 3-methoxy-4-(2-oxo-2-phenylethoxy)benzaldehyde；3-methoxy-4-phenacyloxy-benzaldehyde；3-methoxy-4-phenacyloxybenzaldehyde
• CAS: 723332-14-7
• 化学式: C₁₆H₁₄O₄
• mdl: MFCD03961133
• 分子量: 270.285
• InChiKey: YCEPMNIGSKPMIO-UHFFFAOYSA-N

物化性质

• 熔点：
  121-122 °C
• 沸点：
  461.5±35.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.125
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

安全信息

• 危险等级：
  IRRITANT
• 海关编码：
  2914509090

反应信息

• 作为反应物：
  描述：

  海因 、 4-phenacyloxy-3-methoxybenzaldehyde 在 碳酸氢钠 、 C.I.酸性橙108 作用下， 以 乙醇 、 水 为溶剂， 以57%的产率得到(Z)-5-(3-methoxy-4-(2-oxo-2-phenylethoxy)benzylidene)imidazolidine-2,4-dione
  参考文献：
  名称：

  Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis

  摘要：

  Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. In the process of discovery of new antiproliferative and anti-metastatic agents against prostate cancer, marine-derived phenylmethylene hydantoin (PMH) derivatives were identified with activity level range between 50 and 200 mu M. 3D-QSAR CoMFA model was used in virtual screening of commercially available derivatives of PMH. PMH derivatives with manifold increase in anti-migratory and anti-invasive activities were discovered using wound-healing and Cultrex invasion assays. Benzene ring replacement with other heterocyclic rings did not significantly improve the methylene hydantoins activities. Multivariate analysis performed on the whole series of methylene hydantoins, which further supported the findings of CoMFA model. Predictive QSAR model with conventional r(2) and cross-validated coefficient (q(2)) values up to 0.982 and 0.803 were established. The molecular volume (MV) and the log P were identified as critical parameters for methylene hydatoins migration inhibitory activity. PMH is a novel anti-metastatic lead class with potential therapeutic activity against prostate cancer. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.08.066
• 作为产物：
  描述：

  香草醛 、 2-溴苯乙酮 在 potassium carbonate 作用下， 生成 4-phenacyloxy-3-methoxybenzaldehyde
  参考文献：
  名称：

  新型卤素和脒基取代的苯并噻唑和苯并咪唑的合成、抗增殖评估和 QSAR 分析。

  摘要：

  6-卤素取代的苯并噻唑的合成是通过 4-羟基苯甲醛和 2-氨基苯硫酚缩合，然后用适当的卤化物进行 O-烷基化，而 6-脒基取代的苯并噻唑是通过 5-脒基-2-氨基苯硫酚和相应的缩合合成的苯甲醛。虽然来自未取代和卤素取代的苯并噻唑系列的大多数化合物对测试的肿瘤细胞系显示出边缘抗增殖活性，但脒基苯并唑表现出更强的抑制活性。一般来说，咪唑基苯并噻唑显示出明显的非选择性活性，但 36c 除外，它对 HuT78 细胞具有强烈的抑制作用 (IC50 = 1.6 µM)，而对正常 BJ 细胞没有不利的细胞毒性 (IC50 >100 µM)。与苯并噻唑相比，含有 1,2,3-三唑环的苯并咪唑结构类似物 45a-45c 和 46c 对 HuT78 细胞表现出显着和选择性的抗增殖活性，IC50 < 10 µM。此外，在苯氧基单元上含有甲氧基的化合物 45c 和 46c 对正常 BJ 细胞没有毒性。在所有测试的

  DOI：

  10.3390/ijms232415843

文献信息

• Design, synthesis, antitrypanosomal activity, DNA/RNA binding and in vitro ADME profiling of novel imidazoline-substituted 2-arylbenzimidazoles
  作者：Andrea Bistrović Popov、Luka Krstulović、Sanja Koštrun、Dubravko Jelić、Ana Bokulić、Marijana Radić Stojković、Iva Zonjić、Martin C. Taylor、John M. Kelly、Miroslav Bajić、Silvana Raić-Malić

  DOI：10.1016/j.ejmech.2020.112802

  日期：2020.12

  Novel imidazoline benzimidazole derivatives containing diversely substituted phenoxy moieties were synthesized with the aim of evaluating their antitrypanosomal activity, DNA/RNA binding affinity and in vitro ADME properties. The presence of the diethylaminoethyl subunit in 18a–18c led to enhanced antitrypanosomal potency, particularly for 18a and 18c, which contain unsubstituted and methoxy-substituted

  合成了含有不同取代的苯氧基部分的新型咪唑啉苯并咪唑衍生物，目的是评估它们的抗锥虫活性，DNA / RNA结合亲和力和体外ADME特性。在18a – 18c中二乙基氨基乙基亚基的存在增强了抗锥虫的效力，特别是对于18a和18c，它们含有未取代的和甲氧基取代的苯氧基部分。发现它们对非洲锥虫的功效比硝呋替莫要强2倍以上。荧光和CD光谱，热变性测定和计算分析表明偏爱18a – 18c富含AT的DNA及其次要沟结合方式。用较少的碱性和可离子化的含氮部分取代the基不能改善所研究化合物的膜渗透性。由于结构的多样化，这些化合物显示出一系列的物理化学特征，导致可变的体外ADME特性，为进一步优化生物学特性留有空间。
• Synthesis and Characterization of 4-Phenacyloxy Benzaldehyde Derivatives
  作者：Undri Rastuti、Dwi Siswanta、Jumina Jumina

  DOI：10.13005/ojc/320515

  日期：2016.10.25

  Some new 4-phenacyloxy benzaldehyde derivatives (PB1-PB4) have been synthesized through substitution reaction of 4-hydroxy-benzaldehyde derivatives and phenacyl bromide derivatives using triethylamine as the catalyst in the micellar media at room temperature. Physical data from IR, 1H-NMR, 13C-NMR and GC-MS were used to characterize the compounds structure. The yield of the PB1-PB4 compounds was 46-66%

  在室温下，以三乙胺为催化剂，通过4-羟基苯甲醛衍生物和苯甲酰溴衍生物的取代反应，合成了一些新的4-苯甲酰氧基苯甲醛衍生物（PB1-PB4）。来自IR，1 H-NMR，13 C-NMR和GC-MS的物理数据用于表征化合物的结构。PB1-PB4化合物的收率为46-66％，纯度为91-96％。该化合物已作为抗菌剂进行了测试。
• Novel tetrahydropyrimidinyl-substituted benzimidazoles and benzothiazoles: synthesis, antibacterial activity, DNA interactions and ADME profiling
  作者：Valentina Rep、Rebeka Štulić、Sanja Koštrun、Bojan Kuridža、Ivo Crnolatac、Marijana Radić Stojković、Hana Čipčić Paljetak、Mihaela Perić、Mario Matijašić、Silvana Raić-Malić

  DOI：10.1039/d2md00143h

  日期：——

  A series of tetrahydropyrimidinyl-substituted benzimidazoles attached to various aliphatic or aromatic residues via phenoxymethylene were synthesised to investigate their antibacterial activities against selected Gram-positive and Gram-negative bacteria. The influence of the type of substituent at the C-3 and C-4 positions of the phenoxymethylene linker on the antibacterial activity was observed, showing

  合成了一系列通过苯氧基亚甲基连接到各种脂肪族或芳香族残基上的四氢嘧啶基取代的苯并咪唑，以研究它们对选定的革兰氏阳性和革兰氏阴性细菌的抗菌活性。观察了苯氧亚甲基连接体C-3和C-4位取代基类型对抗菌活性的影响，表明芳香族部分提高了抗菌效力。在所有评估的化合物中，苯甲酰基取代的苯并咪唑衍生物15a是最活跃的化合物，特别是针对革兰氏阴性病原体大肠杆菌（ MIC = 1 μg mL -1）和粘膜炎莫拉氏菌（MIC = 2 μg mL -1 ））。化合物15a还对敏感和耐药的化脓性链球菌菌株表现出最有希望的抗菌活性（MIC = 2 μg mL -1）。显着的稳定作用和正诱导的 CD 带强烈支持最具生物活性的苯并咪唑在富含 AT 的 DNA 小沟内的结合，这与对接研究一致。预测的物理化学和 ADME 特性位于类药物空间内，但膜渗透性较低，需要进一步优化。我们的研究结果鼓励进一步开发新型结构相关的 5(
• Einhorn; von Hofe, Chemische Berichte, 1894, vol. 27, p. 2463,2464
  作者：Einhorn、von Hofe

  DOI：——

  日期：——
• Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis
  作者：Mohammad A. Khanfar、Khalid A. El Sayed

  DOI：10.1016/j.ejmech.2010.08.066

  日期：2010.11

  Prostrate cancer constitutes the second leading cause of cancer deaths in men in United States. In the process of discovery of new antiproliferative and anti-metastatic agents against prostate cancer, marine-derived phenylmethylene hydantoin (PMH) derivatives were identified with activity level range between 50 and 200 mu M. 3D-QSAR CoMFA model was used in virtual screening of commercially available derivatives of PMH. PMH derivatives with manifold increase in anti-migratory and anti-invasive activities were discovered using wound-healing and Cultrex invasion assays. Benzene ring replacement with other heterocyclic rings did not significantly improve the methylene hydantoins activities. Multivariate analysis performed on the whole series of methylene hydantoins, which further supported the findings of CoMFA model. Predictive QSAR model with conventional r(2) and cross-validated coefficient (q(2)) values up to 0.982 and 0.803 were established. The molecular volume (MV) and the log P were identified as critical parameters for methylene hydatoins migration inhibitory activity. PMH is a novel anti-metastatic lead class with potential therapeutic activity against prostate cancer. (C) 2010 Elsevier Masson SAS. All rights reserved.