4-(4'-nitrobenzoyloxy)benzaldehyde | 131266-91-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 缩酚酸和缩酚酸环醚类
• 英文名称: 4-(4'-nitrobenzoyloxy)benzaldehyde
• 英文别名: 4-formylphenyl 4-nitrobenzoate；(4-formylphenyl) 4-nitrobenzoate
• CAS: 131266-91-6
• 化学式: C₁₄H₉NO₅
• 分子量: 271.229
• InChiKey: UUXVSACZCQXWIP-UHFFFAOYSA-N

物化性质

• 熔点：
  205.5-207 °C
• 沸点：
  477.8±30.0 °C(Predicted)
• 密度：
  1.381±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  89.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4'-nitrobenzoyloxy)benzaldehyde 在 溶剂黄146 作用下， 反应 2.0h， 生成 4-{[(1-acetyl-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)imino]methyl}phenyl 4-nitrobenzoate
  参考文献：
  名称：

  Synthesis and Antioxidant and Antibacterial Activities of Novel 4-({[3-Alkyl(aryl)-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl]imino}­methyl)phenyl 4-Nitrobenzoate Derivatives

  摘要：

  DOI：

  10.1134/s1070428022120132
• 作为产物：
  描述：

  对硝基苯甲酸 在 氯化亚砜 、 三乙胺 作用下， 生成 4-(4'-nitrobenzoyloxy)benzaldehyde
  参考文献：
  名称：

  Design, Synthesis and Evaluation of Rhodanine Derivatives as Aldose Reductase Inhibitors

  摘要：

  Aldose reductase (ALR) enzyme plays a significant role in conversion of excess amount of glucose into sorbitol in diabetic condition, inhibitors of which decrease the secondary complication of diabetes mellitus. To understand the structural interaction of inhibitors with ALR enzyme and develop more effective ALR inhibitors, a series of substituted 5‐phenylbenzoate containing N‐substituted rhodanine derivatives were synthesized and evaluated for their in vitro ALR inhibitory activity. Docking studies of these compounds were carried out, which revealed that the 5‐phenylbenzoate moiety deeply influenced the key π‐π stacking while 4‐oxo‐2‐thioxothiazolidines contributed in hydrogen bond interactions. The phenyl ring of benzylidene system occupied in specific pocket constituted from Phe115, Phe122, Leu300 and Cys303 while the rhodanine ring forms a tight net of hydrogen bond with Val47 at anionic binding site of the enzyme. The structural insights obtained from the docking study gave better understanding of rhodanine and macromolecular interaction and will help us in further designing and improving of ALR inhibitory activity of rhodanine analogs.

  DOI：

  10.1111/cbdd.12369

文献信息

• Effects of Branching of the Ester Alkyl Chain on the Mesomorphic Properties of Alkyl 4-[4-(4-Substituted benzoyloxy)benzylideneamino]benzoates
  作者：Hiroyuki Matsuzaki、Yoshio Matsunaga

  DOI：10.1246/bcsj.63.2300

  日期：1990.8

  The mesomorphic properties of five homologous series of alkyl 4-[4-(4-X-substituted benzoyloxy)benzylideneamino]benzoates, where X=CN,NO2, CH3, Cl, and CH3COO, have been studied. The ester alkyl groups employed were the following eleven types: ethyl and propyl and their mono-, di-, and trimethyl-substituted ones. Although the introduction of the first branching methyl group to the ester alkyl chain depresses the nematic stability, the second and/or third groups may either further depress or enhance the stability, depending upon the nature of the substituent X. While all of the members of the cyano and nitro derivatives are purely nematogenic, many members of the other three series display a smectic A phase, as well as a nematic phase. In addition to the above-mentioned esters, the butyl, pentyl, and their monomethyl-substituted esters were examined in order to demonstrate that the effects on the thermal stability of the smectic A phase of the branching of the ester alkyl chain and those of the substituent X are also interdependent.

  五个同系物系列的烷基4-[4-(4-X取代苯甲氧基)苯亚胺]苯甲酸酯的介质相性质进行了研究，其中X=CN，NO2，CH3，Cl和 COO。所采用的酯烷基有以下十一种类型：乙基、丙基及其单、双、三甲基取代物。尽管向酯烷基链引入第一个分枝甲基会降低向列相的稳定性，但第二个和/或第三个取代基可能会进一步降低或增强稳定性，这取决于取代基X的性质。虽然所有的氰基和硝基衍生物都是纯粹的向列液晶，但其他三类中的许多成员显示出层状A相，以及向列相。除了上述酯类之外，还检查了丁基、戊基及其单甲基取代的酯，以证明酯烷基链的分枝及取代基X对层状A相热稳定性的影响也是相互依存的。
• Design, Synthesis, Biological Evaluation and In Silico Study of Benzyloxybenzaldehyde Derivatives as Selective ALDH1A3 Inhibitors
  作者：Ali I. M. Ibrahim、Balqis Ikhmais、Elisabet Batlle、Waed K. AbuHarb、Vibhu Jha、Khaled T. Jaradat、Rafael Jiménez、Raquel Pequerul、Xavier Parés、Jaume Farrés、Klaus Pors

  DOI：10.3390/molecules26195770

  日期：——

  investigated for ALDH1A1, ALDH1A3 and ALDH3A1 selectivity and cytotoxicity using ALDH-positive A549 and ALDH-negative H1299 cells. Two compounds (ABMM-15 and ABMM-16), with a benzyloxybenzaldehyde scaffold, were found to be the most potent and selective inhibitors for ALDH1A3, with IC50 values of 0.23 and 1.29 µM, respectively. The results also show no significant cytotoxicity for ABMM-15 and ABMM-16 on either

  醛脱氢酶 1A3 (ALDH1A3) 最近受到癌症领域研究人员的关注。几项研究报告了 ALDH1A3 在不同癌症类型中的过度表达，已发现这与治疗恢复不佳有关。因此，寻找针对 ALDH1A3 的选择性抑制剂可能会为癌症治疗带来新的治疗选择。在本研究中，基于生理底物相似性设计了 ALDH1A3 选择性候选物，使用 ALDH 阳性 A549 和 ALDH 阴性 H1299 细胞合成和研究了 ALDH1A1、ALDH1A3 和 ALDH3A1 的选择性和细胞毒性。发现具有苄氧基苯甲醛支架的两种化合物（ABMM-15 和 ABMM-16）是最有效和选择性的 ALDH1A3 抑制剂，IC 50值分别为 0.23 和 1.29 µM。结果还显示 ABMM-15 和 ABMM-16 对任一细胞系都没有显着的细胞毒性。然而，与 A549 细胞相比，一些其他候选物（ABMM-6、ABMM-24、ABMM-32）对
• Schiff Base Derivatives of 4-Aminoantipyrine as Promising Molecules: Synthesis, Structural Characterization, and Biological Activities
  作者：Reşit Çakmak、Eyüp Başaran、Mehmet Boğa、Ömer Erdoğan、Ercan Çınar、Özge Çevik

  DOI：10.1134/s1068162022020182

  日期：2022.4

  fibroblast cell lines. According to the results obtained, compound (VI) (IC50: 16.82 ± 0.17 μM) showed higher ABTS cation radical scavenging activity than BHA (IC50: 17.59 ± 0.10 μM). In CUPRAC assay, it was determined that the activity ordering of the bioactive molecules has been determined as VII > X > VII > α-TOC > IX > I > II > V > VI. In AChE assay, compound (I) indicated a high potent inhibition activity

  摘要 在这项研究中，合成了一些源自 4-氨基安替比林 (4-AAP) ( VI – X ) 的席夫碱，通过元素分析 (C、H、N) 和三种光谱技术 (FT-IR、1 H 和13 C NMR），然后通过采用四种不同的方法研究它们的抗氧化活性。随后，测试了合成的分子对乙酰胆碱酯酶（AChE）、丁酰胆碱酯酶（BChE）、酪氨酸酶的抑制作用。更重要的是，还评估了所有标题分子对 HeLa 人宫颈癌和 L929 小鼠成纤维细胞系的细胞毒作用。根据所得结果，化合物 ( VI ) (IC 50: 16.82 ± 0.17 μM) 显示出比 BHA 更高的 ABTS 阳离子自由基清除活性 (IC 50 : 17.59 ± 0.10 μM)。在 CUPRAC 测定中，确定生物活性分子的活性排序已确定为VII > X > VII > α-TOC > IX > I > II > V > VI。在 AChE 测定中，化合物
• Molecular Hybrid Design, Synthesis, In Vitro Cytotoxicity, In Silico ADME and Molecular Docking Studies of New Benzoate Ester-Linked Arylsulfonyl Hydrazones
  作者：Erdem Ergan、Reşit Çakmak、Eyüp Başaran、Suraj N. Mali、Senem Akkoc、Sivakumar Annadurai

  DOI：10.3390/molecules29153478

  日期：——

  μM for the A549 cell line and 27.70–170.30 μM for the MCF-7 cell line. Among these compounds, compound 15 (IC50 = 29.59 μM against A549 cell line and IC50 = 27.70 μM against MCF-7 cell line) showed the highest cytotoxic activity against these two cancer cell lines compared to the reference drug cisplatin (IC50 = 22.42 μM against A549 cell line and IC50 = 18.01 μM against MCF-7 cell line). From docking

  在本文中，我们介绍了两种已知的磺酰肼（1和2）及其新的磺酰腙衍生物（9-20）的合成和表征，以及它们对人肺的细胞毒性特性的体外和计算机研究（A549 ）和人类乳腺癌（MCF-7）癌细胞系。通过多步反应首次合成了高收率的目标化合物（9-20），并通过元素分析和各种光谱技术（包括 FT-IR、1H-和 13C-NMR）确认了其结构。本研究中这些化合物（1、2 和 9-20）的抗增殖特性是使用 3-(4,5-二甲基噻唑-2-基)-2,5-二苯基溴化四唑(MTT)法。除化合物 1 和 2 外，其他化合物 (9-20) 在浓度低于 200 µM 时表现出细胞毒活性。新合成的化合物 (9-20) 在微摩尔水平上表现出抗增殖活性，A549 细胞系的 IC50 值范围为 29.59-176.70 μM，MCF-7 细胞系的 IC50 值范围为 27.70-170.30 μM。在这些化合物中，与参考药物顺铂（针对
• Bromination of Benzoic Esters of Some Phenolic Compounds
  作者：L. Chas Raiford、John E. Milbery

  DOI：10.1021/ja01327a060

  日期：1934.12