3,5-dinitro-benzoic acid-(4-isopropyl-benzyl ester) | 93332-05-9

• 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: 3,5-dinitro-benzoic acid-(4-isopropyl-benzyl ester)
• 英文别名: 3,5-Dinitro-benzoesaeure-(4-isopropyl-benzylester)；3,5-Dinitro-benzoesaeure-<4-isopropyl-benzylester>；4-Isopropylbenzyl 3,5-dinitrobenzoate；(4-propan-2-ylphenyl)methyl 3,5-dinitrobenzoate
• CAS: 93332-05-9
• 化学式: C₁₇H₁₆N₂O₆
• 分子量: 344.324
• InChiKey: ZYZMORLKVZPEMC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  118
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  4-异丙基苯甲酸甲酯 在 甲醇 、 copper oxide-chromium oxide barium oxide 、 氢气 作用下， 155.0~160.0 ℃ 、39.22 MPa 条件下， 生成 3,5-dinitro-benzoic acid-(4-isopropyl-benzyl ester)
  参考文献：
  名称：

  芳族酯加氢水解成醇。

  摘要：

  DOI：

  10.1021/ja01181a067

文献信息

• 3,5-Dinitrobenzoate and 3,5-Dinitrobenzamide Derivatives: Mechanistic, Antifungal, and In Silico Studies
  作者：Allana B. S. Duarte、Yunierkis Perez-Castillo、Patrícia Néris Andrade、Ricardo D. de Castro、Damião P. de Sousa

  DOI：10.1155/2022/2336175

  日期：2022.9.19

  Fungal infections, including those caused by Candida spp., are recognized in immunocompromised individuals for their high rates of morbidity and mortality. Microorganism resistance to conventional drugs compromises treatment effectiveness and yet also reveals the need to develop new drugs. In many compounds, nitro groups contribute to antimicrobial activity; thus, the inhibitory activity of a collection of twenty esters and amides (derived from 3,5-dinitrobenzoic acid) against Candida spp. was elucidated using microdilution methods to determine the Minimum Inhibitory Concentration (MIC) and Minimum Fungicide Concentration (MFC), as well as probable mechanisms of action. The structures of the synthesized compounds were characterized by FTIR spectroscopy, 1H-NMR, 13C NMR, and HRMS. Of the tested derivatives, ten presented fungicidal activity against at least one of the tested strains. Ethyl 3,5-dinitrobenzoate (2) exhibited the most potent antifungal activity against Candida albicans (MIC = 125 µg/mL; 0.52 mM), Candida krusei (MIC = 100 µg/mL; 4.16 mM), and Candida tropicalis (MIC = 500 µg/ml; 2.08 mM). The structure of the second most potent derivative (propyl 3,5-dinitrobenzoate (3) reveals that esters with short alkyl side chains exhibit better biological activity profiles. Compounds 2 and 3 presented a mechanism of action involving the fungal cell membrane. Though compound 2 modeling against C. albicans revealed a multitarget antifungal mechanism of action, involving various cellular processes, interference in the synthesis of ergosterol was observed. Our results demonstrate that certain ester derivatives containing aromatic ring nitro groups may be useful in the search for new antifungal drugs.

  真菌感染，包括由念珠菌属引起的感染，在免疫力低下的人群中发病率和死亡率都很高。微生物对传统药物的耐药性损害了治疗效果，同时也揭示了开发新药物的必要性。在许多化合物中，硝基都具有抗菌活性；因此，我们使用微量稀释法阐明了二十种酯类和酰胺类化合物（源自 3,5- 二硝基苯甲酸）对念珠菌属的抑制活性，以确定最低抑制浓度 (MIC) 和最低杀菌浓度 (MFC)，以及可能的作用机制。傅立叶变换红外光谱、1H-NMR、13C NMR 和 HRMS 对合成化合物的结构进行了表征。在测试的衍生物中，有十种对至少一种受试菌株具有杀菌活性。3,5-二硝基苯甲酸乙酯（2）对白色念珠菌（MIC = 125 µg/mL; 0.52 mM）、克鲁塞念珠菌（MIC = 100 µg/mL; 4.16 mM）和热带念珠菌（MIC = 500 µg/ml; 2.08 mM）具有最强的抗真菌活性。第二种最有效的衍生物（3,5-二硝基苯甲酸丙酯（3））的结构表明，具有短烷基侧链的酯类具有更好的生物活性。化合物 2 和 3 的作用机制涉及真菌细胞膜。虽然化合物 2 针对白僵菌的建模揭示了涉及各种细胞过程的多靶点抗真菌作用机制，但也观察到了对麦角甾醇合成的干扰。我们的研究结果表明，某些含有芳香环硝基的酯类衍生物可能有助于寻找新的抗真菌药物。
• Seidel; Schinz; Mueller, Helvetica Chimica Acta, 1944, vol. 27, p. 669
  作者：Seidel、Schinz、Mueller

  DOI：——

  日期：——
• Hydrogenolysis of Aromatic Esters to Alcohols
  作者：Ralph Mozingo、Karl Folkers

  DOI：10.1021/ja01181a067

  日期：1948.1

表征谱图