2-(4-硝基苯胺基)苯甲酰胺 | 95216-61-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-(4-硝基苯胺基)苯甲酰胺
• 英文名称: 2-(4-nitrophenylamino)benzamide
• 英文别名: 2-(4-Nitroanilino)benzamide
• CAS: 95216-61-8
• 化学式: C₁₃H₁₁N₃O₃
• 分子量: 257.249
• InChiKey: MZQVXSSVFCCFCV-UHFFFAOYSA-N

物化性质

• 熔点：
  193-195 °C(Solv: ethanol (64-17-5); N,N-dimethylformamide (68-12-2))
• 沸点：
  493.2±30.0 °C(Predicted)
• 密度：
  1.382±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  19
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-硝基苯胺基)苯甲酰胺 在 palladium 10% on activated carbon 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 N-(4-2-carbamoylphenylaminophenyl)picolinamide
  参考文献：
  名称：

  Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors

  摘要：

  Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2-anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of alpha-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.

  DOI：

  10.1021/jm3002108
• 作为产物：
  描述：

  N-叔丁基苯酰胺 在 silver hexafluoroantimonate 、 dichloro(pentamethylcyclopentadienyl)rhodium (III) dimer 、 叔丁基二甲硅基三氟甲磺酸酯 作用下， 以 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 30.0h， 生成 2-(4-硝基苯胺基)苯甲酰胺
  参考文献：
  名称：

  铑催化的直接C ？苯甲酰胺与芳基叠氮化物的H胺化：二芳基胺的合成路线

  摘要：

  勿乱，勿扰：已开发出使用芳基叠氮化物作为胺源的铑催化的苯甲酰胺和酮肟的分子间CH胺化反应。该反应具有广泛的底物范围，具有出色的官能团耐受性，不需要外部氧化剂，释放N 2作为唯一的副产物，并以高收率生产二芳基胺。

  DOI：

  10.1002/anie.201205723

文献信息

• Studies on 4(1H)-Quinazolinones. 5. Synthesis and Antiinflammatory Activity of 4(1H)-Quinazolinone Derivatives
  作者：Ken-ichi Ozaki、Yoshihisa Yamada、Toyonari Oine、Tōru Ishizuka、Yoshio Iwasawa

  DOI：10.1021/jm50001a006

  日期：1985.5

  new 4(1H)-quinazolinones were synthesized and evaluated in the carrageenin-induced paw edema test. Most of the compounds were obtained by the cyclization of the appropriately substituted anthranilamides with acid chlorides, followed by further chemical transformation. Structure-activity data suggest that 2-isopropyl-1-phenyl-, 2-cyclopropyl-1-phenyl-, and 1-isopropyl-2-phenyl-4(1H)-quinazolinones afford

  合成了许多新的4（1H）-喹唑啉酮，并在角叉菜胶诱导的爪水肿试验中进行了评估。大多数化合物是通过将适当取代的邻氨基苯甲酰胺与酰氯环合，然后进一步化学转化而获得的。结构活性数据表明2-异丙基-1-苯基-，2-环丙基-1-苯基-和1-异丙基-2-苯基-4（1H）-喹唑啉酮具有最佳效价，卤素原子的存在为首选活动。肾上腺切除术不影响抗炎测试结果。1-异丙基-（2-氟苯基）-4-（1H）-喹唑啉酮（50）显示出兼顾功效和副作用的最佳结果。
• OZAKI, KEN-ICHI;YAMADA, YOSHIHISA;OINE, TOYONARI;ISHIZUKA, TORU;IWASAWA, +, J. MED. CHEM., 1985, 28, N 5, 568-576
  作者：OZAKI, KEN-ICHI、YAMADA, YOSHIHISA、OINE, TOYONARI、ISHIZUKA, TORU、IWASAWA, +

  DOI：——

  日期：——
• Design, Synthesis, and Biological Activity of a Novel Series of Human Sirtuin-2-Selective Inhibitors
  作者：Takayoshi Suzuki、Mohammed Naseer Ahmed Khan、Hideyuki Sawada、Erika Imai、Yukihiro Itoh、Katsura Yamatsuta、Natsuko Tokuda、Jun Takeuchi、Takuya Seko、Hidehiko Nakagawa、Naoki Miyata

  DOI：10.1021/jm3002108

  日期：2012.6.28

  Selective inhibitors of human sirtuin 2 (SIRT2), a deacetylase, are candidate therapeutic agents for neurodegenerative diseases such as Parkinson's disease and Huntington's disease as well as potential tools for elucidating the biological functions of SIRT2. On the basis of homology models of SIRT1 and SIRT2, we designed and prepared a series of 2-anilinobenzamide analogues. Enzyme assays using recombinant SIRT1 and SIRT2 revealed that 3'-phenethyloxy-2-anilinobenzamide analogues such as 33a and 33i are potent and selective SIRT2 inhibitors, showing more than 3.5-fold greater SIRT2-inhibitory activity and more than 35-fold greater SIRT2-selectivity compared with AGK2 (3), a previously reported SIRT2-selective inhibitor. Compound 33a also induced a dose-dependent selective increase of alpha-tubulin acetylation in human colon cancer HCT116 cells, indicating selective inhibition of SIRT2 in the cells. These 3'-phenethyloxy-2-anilinobenzamide derivatives represent an entry into a new class of SIRT2-selective inhibitors.
• Rhodium-Catalyzed Direct CH Amination of Benzamides with Aryl Azides: A Synthetic Route to Diarylamines
  作者：Jaeyune Ryu、Kwangmin Shin、Sae Hume Park、Ji Young Kim、Sukbok Chang

  DOI：10.1002/anie.201205723

  日期：2012.9.24

  No muss, no fuss: A rhodium‐catalyzed direct intermolecular CH amination of benzamides and ketoximes using aryl azides as the amine source has been developed. The reaction exhibits a broad substrate scope with excellent functional‐group tolerance, requires no external oxidants, releases N2 as the only by‐product, and produces diarylamines in high yields.

  勿乱，勿扰：已开发出使用芳基叠氮化物作为胺源的铑催化的苯甲酰胺和酮肟的分子间CH胺化反应。该反应具有广泛的底物范围，具有出色的官能团耐受性，不需要外部氧化剂，释放N 2作为唯一的副产物，并以高收率生产二芳基胺。