m-azidobenzophenone

• 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: m-azidobenzophenone
• 英文别名: 3-azidobenzophenone；(3-Azidophenyl)-phenylmethanone
• 化学式: C₁₃H₉N₃O
• 分子量: 223.234
• InChiKey: NCLNHRBANMOMAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  31.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  m-azidobenzophenone 、 甲醇 以24%的产率得到
  参考文献：
  名称：

  OHBA YOSHIHIRO; KUBO SHINJI; NAKAI MASAAKI; NAGAI ATSUNORI; YOSHIMOTO MAS+, BULL. CHEM. SOC. JAP., 59,(1986) N 7, 2317-2320

  摘要：

  DOI：
• 作为产物：
  描述：

  3-氨基苯基苯甲酮 在 sodium azide 、 硫酸 、 sodium nitrite 作用下， 生成 m-azidobenzophenone
  参考文献：
  名称：

  利用取代芳基叠氮化物的热解合成 3H-氮杂

  摘要：

  几种对位取代的芳基叠氮化物（pR-C6H4N3；R=COCH3、CO2CH3、COPh）在甲醇中的热解得到中等产率的 5-取代的 2-甲氧基-3H-氮杂。间位取代的芳基叠氮化物（mR-C6H4N3；R=COCH3、CO2CH3、COPh、NO2）的热解得到 4-取代的 2-甲氧基-3H-氮杂和 6-取代的 2-甲氧基-3H-氮杂。相比之下，哌啶中对叠氮基苯乙酮的热解得到 5-乙酰基-2-哌啶基-3H-氮杂和一种不寻常的产物，6-乙酰基-2-哌啶基-3H-氮杂和对氨基苯乙酮。

  DOI：

  10.1246/bcsj.59.2317

文献信息

• Synthesis of the 3<i>H</i>-Azepines Utilizing the Thermolysis of Substituted Aryl Azides
  作者：Yoshihiro Ohba、Shinji Kubo、Masaaki Nakai、Atsunori Nagai、Masayo Yoshimoto

  DOI：10.1246/bcsj.59.2317

  日期：1986.7

  Thermolysis of several p-substituted aryl azides (p-R-C6H4N3; R=COCH3, CO2CH3, COPh) in methanol gave 5-substituted 2-methoxy-3H-azepines in moderate yields. Thermolysis of m-substituted aryl azides (m-R-C6H4N3; R=COCH3, CO2CH3, COPh, NO2) gave 4-substituted 2-methoxy-3H-azepines and 6-substituted 2-methoxy-3H-azepines in good yields. In contrast, thermolysis of p-azidoacetophenone in piperidine gave

  几种对位取代的芳基叠氮化物（pR-C6H4N3；R=COCH3、CO2CH3、COPh）在甲醇中的热解得到中等产率的 5-取代的 2-甲氧基-3H-氮杂。间位取代的芳基叠氮化物（mR-C6H4N3；R=COCH3、CO2CH3、COPh、NO2）的热解得到 4-取代的 2-甲氧基-3H-氮杂和 6-取代的 2-甲氧基-3H-氮杂。相比之下，哌啶中对叠氮基苯乙酮的热解得到 5-乙酰基-2-哌啶基-3H-氮杂和一种不寻常的产物，6-乙酰基-2-哌啶基-3H-氮杂和对氨基苯乙酮。
• Small Molecule Inhibition of MicroRNA miR-21 Rescues Chemosensitivity of Renal-Cell Carcinoma to Topotecan
  作者：Yuta Naro、Nicholas Ankenbruck、Meryl Thomas、Yaniv Tivon、Colleen M. Connelly、Laura Gardner、Alexander Deiters

  DOI：10.1021/acs.jmedchem.7b01891

  日期：2018.7.26

  Chemical probes of microRNA (miRNA) function are potential tools for understanding miRNA biology that also provide new approaches for discovering therapeutics for miRNA-associated diseases. MicroRNA-21 (miR-21) is an oncogenic miRNA that is overexpressed in most cancers and has been strongly associated with driving chemoresistance in cancers such as renal cell carcinoma (RCC). Using a cell-based luciferase reporter assay to screen small molecules, we identified a novel inhibitor of miR-21 function. Following structure-activity relationship studies, an optimized lead compound demonstrated cytotoxicity in several cancer cell lines. In a chemoresistant-RCC cell line, inhibition of miR-21 via small molecule treatment rescued the expression of tumor-suppressor proteins and sensitized cells to topotecan-induced apoptosis. This resulted in a > 10-fold improvement in topotecan activity in cell viability and clonogenic assays. Overall, this work reports a novel small molecule inhibitor for perturbing miR-21 function and demonstrates an approach to enhancing the potency of chemotherapeutics specifically for cancers derived from oncomir addiction.
• OHBA YOSHIHIRO; KUBO SHINJI; NAKAI MASAAKI; NAGAI ATSUNORI; YOSHIMOTO MAS+, BULL. CHEM. SOC. JAP., 59,(1986) N 7, 2317-2320
  作者：OHBA YOSHIHIRO、 KUBO SHINJI、 NAKAI MASAAKI、 NAGAI ATSUNORI、 YOSHIMOTO MAS+

  DOI：——

  日期：——
• US4145364A
  申请人：——

  公开号：US4145364A

  公开（公告）日：1979-03-20
• A general procedure for carbon isotope labeling of linear urea derivatives with carbon dioxide
  作者：Victor Babin、Antoine Sallustrau、Olivier Loreau、Fabien Caillé、Amélie Goudet、Héloïse Cahuzac、Antonio Del Vecchio、Frédéric Taran、Davide Audisio

  DOI：10.1039/d1cc02665h

  日期：——

  Carbon isotope labeling is a traceless technology, which allows tracking the fate of organic compounds either in the environment or in living organisms. This article reports on a general approach to label urea derivatives with all carbon isotopes, including 14C and 11C, based on a Staudinger aza-Wittig sequence. It provides access to all aliphatic/aromatic urea combinations.

  碳同位素标记是一种无痕技术，可以跟踪环境或生物体中有机化合物的命运。本文报告了基于 Staudinger aza-Wittig 序列用所有碳同位素（包括14 C 和11 C）标记尿素衍生物的一般方法。它提供了对所有脂肪族/芳香族尿素组合的访问。