2-(4-nitrobenzyl)benzo[d]oxazole | 101554-07-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并恶唑类
• 英文名称: 2-(4-nitrobenzyl)benzo[d]oxazole
• 英文别名: 2-[(4-nitrophenyl)methyl]-1,3-benzoxazole
• CAS: 101554-07-8
• 化学式: C₁₄H₁₀N₂O₃
• 分子量: 254.245
• InChiKey: PAYFKLJVGWALEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  71.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  二苯基二硒醚 、 2-(4-nitrobenzyl)benzo[d]oxazole 在 potassium phosphate 、 copper(l) iodide 作用下， 以 二甲基亚砜 为溶剂， 反应 2.0h， 以57%的产率得到2-((4-nitrophenyl)(phenylselanyl)methyl)benzoxazole
  参考文献：
  名称：

  脂肪族羧酸等价物的直接 α-硫属元素化

  摘要：

  通过将脂肪族羧酸转化为相应的苯唑类，开发了一种将脂肪族羧酸进行 α-硫属元素化的新方法。由 Cu I 、DMSO 和碱组成的催化剂体系通过独特的机制运行，以获取一系列具有实际意义的硫醚和硒醚，否则这些化合物难以实现。应用潜力已通过利用所得硫属化合物作为合成生物学相关分子和合成中间体的前体来举例说明。

  DOI：

  10.1021/acs.orglett.9b02424
• 作为产物：
  描述：

  对硝基苯乙酸 、 2-氨基苯酚 在 polyphosphoric acid 作用下， 反应 3.0h， 生成 2-(4-nitrobenzyl)benzo[d]oxazole
  参考文献：
  名称：

  一些苯并恶唑衍生物的合成、抗菌活性和分子模型研究

  摘要：

  背景：随着传染性疾病的增加和抗药性迅速发展，开发新型抗微生物剂的需求显然。 目的：本研究旨在合成苯并噁唑衍生物，进行抗微生物敏感性测试和计算机解析其作用机制。同时，比较本研究结果与我们小组以前的研究结果，为设计具有更好抗微生物活性的新分子铺平道路。另一个目标是药效团分析和体外ADMET分析。 方法：本研究进行了合成、抗微生物敏感性测试、分子对接、药效团分析和ADMET预测。 结果：抗微生物活性研究表明，合成的化合物在高浓度下对标准菌株和临床分离物具有活性。然后，将抗微生物测试结果与我们小组以前测试的类似苯并噁唑化合物进行比较。本研究发现，在噁唑和苯环之间没有亚甲基桥的苯并噁唑衍生物比有亚甲基桥的更活跃。这也得到了本研究进行的分子建模的确认。计算结果表明，抗菌活性可以通过DNA酶抑制实现。药效团分析表明，氢键受体（HBA）、氢键供体（HBD）和疏水性特征将有助于抑制作用。此外，体外ADMET性质调查表明，这些化合物具有理想的药代动力学。 结论：尽管通过抑制DNA酶的抗菌活性是选择性的，但是合成的化合物的活性比标准高得多。因此，在未来的抗微生物研究中，最好专注于没有亚甲基桥的苯并噁唑衍生物。由于这些化合物具有适当的体外ADMET性质，应该对它们进行筛选，以了解其他药理活性。建议通过体外或体内研究来支持分子建模结果。

  DOI：

  10.2174/1570180819666220408133643

文献信息

• Pd^II-Catalyzed methoxylation of C(sp³)–H bonds adjacent to benzoxazoles and benzothiazoles
  作者：Jogendra Kumar、Aniket Gupta、Sukalyan Bhadra

  DOI：10.1039/c9ob00337a

  日期：——

  The Pd(OAc)2/PhI(OAc)2 catalyst system promotes the highly regioselective dehydrogenative methoxylation of a C(sp3)–H bond adjacent to benzoxazole and benzothiazole rings. The title transformation constitutes the first example of a Pd-catalyzed C(sp3)–H activating methoxylation at the proximal-selective α-position with regard to a directing auxiliary and provides expedient access to an important class

  Pd（OAc）2 / PhI（OAc）2催化剂体系促进与苯并恶唑和苯并噻唑环相邻的C（sp 3）–H键的高区域选择性脱氢甲氧基化。标题转换构成了Pd催化的C（sp 3）-H在定向辅助剂的近端选择性α位置上激活甲氧基化的第一个例子，并提供了方便的途径来访问重要的一类由唑修饰的甲基醚（高达90％的分离产率）。通过消除苯并恶唑助剂获得α-甲氧基乙酸，并获得O-甲基化Breslow中间体的前体，证明了该方法的合成实用性。
• Catalytic Direct Cyanomethylenation of C(sp³)–H Bonds via a One-Step Double C–C Bond Formation
  作者：Anupam Kumar Singh、Jogendra Kumar、Sukalyan Bhadra

  DOI：10.1021/acs.joc.1c02297

  日期：2022.1.21

  An elegant and catalytic procedure for the one-step cyanomethylenation of C(sp3)–H bonds adjacent to benzazoles and ketones is described herein using DMF as a C-1 unit and TMSCN as the cyanide source. The copper-mediated reaction between DMF and TMSCN gives a cyanomethylene radical intermediate that reacts with 2-alkylbenzazoles or alkylketones to furnish desired cyanomethylenated compounds under palladium

  本文使用 DMF 作为 C-1 单元和 TMSCN 作为氰化物源，描述了与苯并唑和酮相邻的 C(sp 3 )-H 键的一步氰亚甲基化的优雅和催化过程。DMF 和 TMSCN 之间的铜介导反应产生氰亚甲基自由基中间体，该中间体在钯催化下与 2-烷基苯唑或烷基酮反应以提供所需的氰亚甲基化合物。随后氰基甲基化产物的相互转化使该协议具有综合吸引力。
• Quantum mechanical and spectroscopic (FT-IR, FT-Raman, 1H NMR and UV) investigations of 2-(p-nitrobenzyl) benzoxazole
  作者：J.B. Bhagyasree、Hema Tresa Varghese、C. Yohannan Panicker、Jadu Samuel、Christian Van Alsenoy、Serap Yilmaz、Ilkay Yildiz、Esin Aki

  DOI：10.1016/j.molstruc.2013.04.044

  日期：2013.8

  The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 2-(p-nitrobenzyl)benzoxazole have been investigated experimentally and theoretically using Gaussian09 software package. Potential energy distribution of the normal modes of vibrations are done using GAR2PED program. The optimized geometrical parameters are in agreement with that of similar derivatives. The energy and oscillator strength calculated by Time Dependent Density Functional Theory results almost compliments with experimental findings. Gauge-including atomic orbital H-1 NMR chemical shifts calculations were carried out by using B3LYP functional with 6-31G* basis sets. The HOMO and LUMO analysis is used to determine the charge transfer with in the molecule. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using NBO analysis. MEP was performed by the DFT method and the infrared and Raman intensities have also been reported. Mulliken's net charges have been calculated and compared with the atomic natural charges. The calculated first hyperpolarizability of the title compound is 82.31 time that of the standard NLO material urea and hence is an attractive object for future studies of nonlinear optical properties. (c) 2013 Elsevier B.V. All rights reserved.
• Direct α-Chalcogenation of Aliphatic Carboxylic Acid Equivalents
  作者：Aniket Gupta、Ajijur Rahaman、Sukalyan Bhadra

  DOI：10.1021/acs.orglett.9b02424

  日期：2019.8.2

  A novel approach to α-chalcogenation of aliphatic carboxylic acids has been developed by means of transforming them as the corresponding benzazoles. The catalyst system, consisting of CuI, DMSO, and a base, operates through a unique mechanism to access a range of practically significant thio- and selenoethers that are otherwise challenging to achieve. The applicative potentials have been exemplified

  通过将脂肪族羧酸转化为相应的苯唑类，开发了一种将脂肪族羧酸进行 α-硫属元素化的新方法。由 Cu I 、DMSO 和碱组成的催化剂体系通过独特的机制运行，以获取一系列具有实际意义的硫醚和硒醚，否则这些化合物难以实现。应用潜力已通过利用所得硫属化合物作为合成生物学相关分子和合成中间体的前体来举例说明。
• Synthesis, Antimicrobial Activity, and Molecular Modeling Studies of Some Benzoxazole Derivatives
  作者：Muhammed Tilahun Muhammed、Gulcan Kuyucuklu、Fatma Kaynak-Onurdag、Esin Aki-Yalcin

  DOI：10.2174/1570180819666220408133643

  日期：2022.8

  The need to develop novel antimicrobial agents is apparent as infectious diseases are increasing and resistance is rapidly developing against the drugs used in the treatment.

  This study aimed at the synthesis, antimicrobial susceptibility testing, and computational elucidation of the mechanism of action of benzoxazole derivatives. It also aimed to compare the results obtained in this study with the previous studies by our group. This would pave the way for designing novel molecules with better antimicrobial activity. The other goal was pharmacophore analysis and in silico ADMET analysis of them.

  In this study, synthesis, antimicrobial susceptibility testing, molecular docking, pharmacophore analysis, and ADMET prediction were carried out.

  The antimicrobial activity studies demonstrated that the synthesized compounds were active against standard strains and clinical isolates at high concentrations. Then, the antimicrobial testing results were compared to similar benzoxazoles tested by our group previously. Benzoxazole derivatives without a methylene bridge between oxazole and phenyl ring were found to be more active than those with the methylene bridge. This was also confirmed by molecular modeling undertaken in this study. The computational results indicated that the antibacterial activity could be achieved by DNA gyrase inhibition. Pharmacophore analysis showed that hydrogen bond acceptor (HBA), hydrogen bond donor (HBD), and hydrophobicity features would contribute to the inhibition. In addition, in silico ADMET property investigation of the compounds exhibited that they had the desired pharmacokinetics.

  Although antibacterial activity by inhibiting DNA gyrase is selective, the synthesized compounds were active at much higher concentrations than the standards. Therefore, in prospective antimicrobial studies, it is better to focus on benzoxazole derivatives without the methylene bridge. Since the compounds had suitable in silico ADMET properties, screening them against the other pharmacologic activities should be carried out. It is recommended to support the molecular modeling results with in vitro or in vivo studies.

  背景：随着传染性疾病的增加和抗药性迅速发展，开发新型抗微生物剂的需求显然。 目的：本研究旨在合成苯并噁唑衍生物，进行抗微生物敏感性测试和计算机解析其作用机制。同时，比较本研究结果与我们小组以前的研究结果，为设计具有更好抗微生物活性的新分子铺平道路。另一个目标是药效团分析和体外ADMET分析。 方法：本研究进行了合成、抗微生物敏感性测试、分子对接、药效团分析和ADMET预测。 结果：抗微生物活性研究表明，合成的化合物在高浓度下对标准菌株和临床分离物具有活性。然后，将抗微生物测试结果与我们小组以前测试的类似苯并噁唑化合物进行比较。本研究发现，在噁唑和苯环之间没有亚甲基桥的苯并噁唑衍生物比有亚甲基桥的更活跃。这也得到了本研究进行的分子建模的确认。计算结果表明，抗菌活性可以通过DNA酶抑制实现。药效团分析表明，氢键受体（HBA）、氢键供体（HBD）和疏水性特征将有助于抑制作用。此外，体外ADMET性质调查表明，这些化合物具有理想的药代动力学。 结论：尽管通过抑制DNA酶的抗菌活性是选择性的，但是合成的化合物的活性比标准高得多。因此，在未来的抗微生物研究中，最好专注于没有亚甲基桥的苯并噁唑衍生物。由于这些化合物具有适当的体外ADMET性质，应该对它们进行筛选，以了解其他药理活性。建议通过体外或体内研究来支持分子建模结果。