N-(2-甲氧基苯基)-2-硝基苯甲酰胺 | 17296-34-3

• 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: N-(2-甲氧基苯基)-2-硝基苯甲酰胺
• 英文名称: N-(2-methoxyphenyl)-2-nitrobenzamide
• 英文别名: 2'-methoxy-2-nitrobenzanilide；2-Nitro-benzoesaeure-<2-methoxy-anilid>；2-Nitro-benzoesaeure-(2-methoxy-anilid)
• CAS: 17296-34-3
• 化学式: C₁₄H₁₂N₂O₄
• mdl: MFCD00578805
• 分子量: 272.26
• InChiKey: WIHYBOCTPLSXPP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  84.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-甲氧基苯基)-2-硝基苯甲酰胺 在 tin(II) chloride dihdyrate 作用下， 以 乙酸乙酯 为溶剂， 以59%的产率得到2-氨基-N-(2-甲氧基苯基)-苯甲酰胺
  参考文献：
  名称：

  SAR and Lead Optimization of an HIV-1 Vif-APOBEC3G Axis Inhibitor

  摘要：

  We describe structure activity relationship and optimization studies of RN-18, an HIV-1 Vif-APOBEC3G axis inhibitor. Targeted modifications of RN-18 ring C, ring B, ring A, bridge A B, and bridge B C were performed to identify the crucial structural features, which generated new inhibitors with similar (4g and 4i) and improved (5, 8b, and 11) activities. Two potent water-soluble RN-18 analogues, 17 and 19, are also disclosed, and we describe the results of pharmacological studies with compound 19. The findings described here will be useful in the development of more potent Vif inhibitors and in the design of probes to identify the target protein of RN-18 and its analogues.

  DOI：

  10.1021/ml300037k
• 作为产物：
  描述：

  邻硝基苯甲酸 、 邻甲氧基苯胺 在 氯化亚砜 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 苯 、 二氯甲烷 为溶剂， 以78%的产率得到N-(2-甲氧基苯基)-2-硝基苯甲酰胺
  参考文献：
  名称：

  SAR and Lead Optimization of an HIV-1 Vif-APOBEC3G Axis Inhibitor

  摘要：

  We describe structure activity relationship and optimization studies of RN-18, an HIV-1 Vif-APOBEC3G axis inhibitor. Targeted modifications of RN-18 ring C, ring B, ring A, bridge A B, and bridge B C were performed to identify the crucial structural features, which generated new inhibitors with similar (4g and 4i) and improved (5, 8b, and 11) activities. Two potent water-soluble RN-18 analogues, 17 and 19, are also disclosed, and we describe the results of pharmacological studies with compound 19. The findings described here will be useful in the development of more potent Vif inhibitors and in the design of probes to identify the target protein of RN-18 and its analogues.

  DOI：

  10.1021/ml300037k

文献信息

• A Convenient Synthesis of 2-Arylindazol-3-Ones
  作者：Clive W. Bird、Joanne C. W. Chng、Nasim H. Rama、Aamer Saeed

  DOI：10.1080/00397919108016781

  日期：1991.2

  The reductive cyclisation of o-nitrobenzanilides with zinc and sodium hydroxide in aqueous methanol provides a convenient source of 2-arylindazol-3-ones.
• Evans, Neil A., Australian Journal of Chemistry, 1981, vol. 34, # 3, p. 691 - 695
  作者：Evans, Neil A.

  DOI：——

  日期：——
• Competing oxygen migrations inortho nitro aromatic thioamides on electron impact
  作者：D. V. Ramana、S. K. Viswanadham

  DOI：10.1002/oms.1210180407

  日期：1983.4

  AbstractInteresting competitive oxygen migrations from the nitro group to the nitrogen and to the sulfur have been noticed during the mass spectral decomposition of ortho nitro aromatic thioamides on electron impact. The migration of the oxygen to the nitrogen of the thioamide function results in the formation of stable o‐nitrosothiobenzoyl cation. The other novel ortho effect noticed in the ortho isomers is the transfer of an oxygen from the nitro group to the sulfur followed by the ejection of SO from the molecular ions. A mechanism involving the initial oxygen migration to the sulfur through a favourable 6‐membered transition state followed by cyclization with the concomitant expulsion of SO is proposed for this process. Other interesting decomposition processes occurring as a consequence of this ortho effect have also been noticed. The proposed mechanisms for these processes are supported by mass analysed ion kinetic energy spectra and high voltage scans.
• EVANS N. A., AUSTRAL. J. CHEM., 1981, 34, NO 3, 691-695
  作者：EVANS N. A.

  DOI：——

  日期：——
• SAR and Lead Optimization of an HIV-1 Vif-APOBEC3G Axis Inhibitor
  作者：Idrees Mohammed、Maloy K. Parai、Xinpeng Jiang、Natalia Sharova、Gatikrushna Singh、Mario Stevenson、Tariq M. Rana

  DOI：10.1021/ml300037k

  日期：2012.6.14

  We describe structure activity relationship and optimization studies of RN-18, an HIV-1 Vif-APOBEC3G axis inhibitor. Targeted modifications of RN-18 ring C, ring B, ring A, bridge A B, and bridge B C were performed to identify the crucial structural features, which generated new inhibitors with similar (4g and 4i) and improved (5, 8b, and 11) activities. Two potent water-soluble RN-18 analogues, 17 and 19, are also disclosed, and we describe the results of pharmacological studies with compound 19. The findings described here will be useful in the development of more potent Vif inhibitors and in the design of probes to identify the target protein of RN-18 and its analogues.