(1H-imidazol-1-yl)(2-nitrophenyl)methanone

• 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: (1H-imidazol-1-yl)(2-nitrophenyl)methanone
• 英文别名: Imidazol-1-yl-(2-nitrophenyl)methanone；imidazol-1-yl-(2-nitrophenyl)methanone
• 化学式: C₁₀H₇N₃O₃
• 分子量: 217.184
• InChiKey: OMJYOLUZWWTQKE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1H-imidazol-1-yl)(2-nitrophenyl)methanone 在 ammonium acetate 、 三乙胺 作用下， 反应 3.0h， 生成 2-硝基苯甲酰胺
  参考文献：
  名称：

  Efficient Synthesis of Primary Amides from Carboxylic Acids Using N,N′-Carbonyldiimidazole and Ammonium Acetate in Ionic Liquid

  摘要：

  A novel and efficient method for the conversion of carboxylic acids to primary amides using N,N '-carbonyldiimidazole in combination with ammonium acetate/triethyl amine system in [BMIM]BF4 is developed.

  DOI：

  10.1080/00397911.2010.518331
• 作为产物：
  描述：

  邻硝基苯甲酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 (1H-imidazol-1-yl)(2-nitrophenyl)methanone
  参考文献：
  名称：

  抗癌天然产物（±）-Peharmaline A及其类似物的全合成

  摘要：

  抗癌天然产物（±）-Peharmaline A的第一个全合成过程分三个步骤完成。亮点是立体选择性Pictet-Spengler反应，然后以一锅法构建vasicinone部分。发达的途径可用于获得peharmaline类似物，这为生物学评估期间进行系统的结构-活性关系研究提供了机会。

  DOI：

  10.1002/ejoc.201800949

文献信息

• Total Synthesis of an Anticancer Natural Product (±)-Peharmaline A and Its Analogues
  作者：Akshay S. Kulkarni、Rahul D. Shingare、Rambabu Dandela、D. Srinivasa Reddy

  DOI：10.1002/ejoc.201800949

  日期：2018.12.13

  The first total synthesis of the anticancer natural product (±)‐peharmaline A was accomplished in three steps. A stereoselective Pictet–Spengler reaction followed by the construction of the vasicinone moiety in a one‐pot fashion are the highlights. The developed route is useful to access peharmaline analogues, which opens opportunities for systematic structure–activity relationship studies during biological

  抗癌天然产物（±）-Peharmaline A的第一个全合成过程分三个步骤完成。亮点是立体选择性Pictet-Spengler反应，然后以一锅法构建vasicinone部分。发达的途径可用于获得peharmaline类似物，这为生物学评估期间进行系统的结构-活性关系研究提供了机会。
• Identification of new modulator of DNA repairing pathways based on natural product (±)-peharmaline A
  作者：Akshay S. Kulkarni、Anshurekha Dash、Rahul D. Shingare、Jagdish Chand、Diksha Manhas、Aman Singh、Utpal Nandi、Anindya Goswami、D. Srinivasa Reddy

  DOI：10.1016/j.bmc.2023.117365

  日期：2023.8

  (±)-peharmaline A, a hybrid natural product isolated from seeds of Peganum harmala L. possesses significant cytotoxic activities. Herein, we have described the design, and synthesis of a novel library of close and simplified analogues around the anticancer natural product (±)-peharmaline A and investigated their cytotoxic activities, which led to the identification of three structurally simplified lead compounds

  肿瘤块复杂的异质环境通常会导致耐药性并促进化疗不敏感，从而在癌症患者中引发更多的恶性表型。事实证明，主要的 DNA 损伤性癌症药物在提高化疗耐药性方面并不成功。(±)-peharmaline A 是从骆驼蓬种子中分离出来的杂种天然产物，具有显着的细胞毒活性。在此，我们描述了围绕抗癌天然产物 (±)-peharmaline A 的新型紧密和简化类似物库的设计和合成，并研究了它们的细胞毒性活性，从而鉴定了三种结构简化的先导化合物，它们表现出更好的效力比母体天然产物。其中，peharmaline A 的去甲氧基类似物的抗癌潜力被进一步研究，促使去甲氧基类似物作为有效的 DNA 损伤诱导剂，减弱负责 DNA 损伤修复的蛋白质的表达。因此，这种去甲氧基类似物需要进行详细的研究，以确认其抗癌活性的基于分子机制的研究。 __________________________________________
• Organo-functionalized trimethoxysilanes featuring thioester linkage: Synthetic and UV–Vis spectral investigations
  作者：Gurjaspreet Singh、Sunita Rani、Amandeep Saroa、Aanchal Arora

  DOI：10.1016/j.jorganchem.2016.02.013

  日期：2016.4

  The current work reveals a series of new organo-functionalized trimethoxysilanes (OfTMS) linked via a 3C tether to the thioester group along with the inclusion of versatile aromatic and heteroaromatic sequences. The synthetic procedure implicates the one-pot thioesterification reaction of the precursor carboxylic acids (1a-r) with 3-mercaptopropyltrimethoxysilane (MPTMS), stimulated by 1,1'-carbonyldiimidazole (CDI). The OfTMS have been attentively characterized by elemental analysis, infrared and [H-1, C-13] NMR spectroscopic techniques. The UV-Vis absorption behaviour demonstrates that the alkoxysilanes possess high sensitivity to the changes caused in the environment on account of different substitutions. Furthermore, the solvent effect on the absorption spectra has been scrutinized and quantified using the Kamlet-Taft approach. Importantly, the fabricated stable alkoxysilanes can be aspired for advance applications in the field of material science. (C) 2016 Elsevier B.V. All rights reserved.
• Synthesis of Dithiolethiones and Identification of Potential Neuroprotective Agents via Activation of Nrf2-Driven Antioxidant Enzymes
  作者：Zi-Long Song、Feifei Bai、Baoxin Zhang、Jianguo Fang

  DOI：10.1021/acs.jafc.9b06360

  日期：2020.2.19

  Oxidative stress is implicated in the pathogenesis of a wide variety of neurodegenerative disorders, and accordingly, dietary supplement of exogenous antioxidants or/and upregulation of the endogenous antioxidant defense system are promising for therapeutic intervention or chemoprevention of neurodegenerative diseases. Nrf2, a master regulator of the cellular antioxidant machinery, cardinally participates in the transcription of cytoprotective genes against oxidative/electrophilic stresses. Herein, we report the synthesis of 59 structurally diverse dithiolethiones and evaluation of their neuroprotection against 6-hydroxydopamine- or H2O2 -induced oxidative damages in PC12 cells, a neuron-like rat pheochromocytoma cell line. Initial screening identified compounds 10 and 11 having low cytotoxicity but conferring remarkable protection on PC12 cells from oxidative-mediated damages. Further studies demonstrated that both compounds upregulated a battery of antioxidant genes as well as corresponding genes' products. Significantly, silence of Nrf2 expression abolishes cytoprotection of 10 and 11, indicating targeting Nrf2 activation is pivotal for their cellular functions. Taken together, the two lead compounds discovered here with potent neuroprotective functions against oxidative stress via Nrf2 activation merit further development as therapeutic or chemopreventive candidates for neurodegenerative disorders.
• Efficient Synthesis of Primary Amides from Carboxylic Acids Using <i>N,N</i>′-Carbonyldiimidazole and Ammonium Acetate in Ionic Liquid
  作者：Kwan Soo Lee、Kee D. Kim

  DOI：10.1080/00397911.2010.518331

  日期：2011.12.1

  A novel and efficient method for the conversion of carboxylic acids to primary amides using N,N '-carbonyldiimidazole in combination with ammonium acetate/triethyl amine system in [BMIM]BF4 is developed.