4-methoxy-N-(3-nitrophenyl)benzamide | 96748-36-6

• 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: 4-methoxy-N-(3-nitrophenyl)benzamide
• 英文别名: 4-methoxy-benzoic acid-(3-nitro-anilide)；4-Methoxy-benzoesaeure-(3-nitro-anilid)；4-Methoxy-benzoesaeure-<3-nitro-anilid>
• CAS: 96748-36-6
• 化学式: C₁₄H₁₂N₂O₄
• 分子量: 272.26
• InChiKey: LIBZVTMLPNDDQD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 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：

  4-methoxy-N-(3-nitrophenyl)benzamide 在 palladium on activated charcoal 甲酸铵 、 copper(l) chloride 、 sodium hydroxide 作用下， 以 甲醇 、 丙酮 、 乙腈 为溶剂， 80.0~120.0 ℃ 、350.01 kPa 条件下， 反应 1.52h， 生成 3,4,5-trimethoxy-N-[(3-(4-methoxybenzoyl)aminophenylamino)carbonyl]benzamide
  参考文献：
  名称：

  N-Acylthiourea and N-Acylurea Inhibitors of the Hedgehog Protein Signalling Pathway

  摘要：

  本发明涉及使用酰基硫脲或酰基脲衍生物治疗涉及组织功能障碍的病理情况，该功能障碍与Hedgehog蛋白信号通路的失调有关，并且涉及作为药物产品的新型酰基硫脲或酰基脲衍生物，它们的用途以及含有它们的药物组成物。

  公开号：

  US20110275663A1
• 作为产物：
  描述：

  间硝基苯胺 生成 4-methoxy-N-(3-nitrophenyl)benzamide
  参考文献：
  名称：

  694.idi盐的合成

  摘要：

  DOI：

  10.1039/jr9490003319

文献信息

• <i>N</i>-Heterocyclic carbene (NHC) catalyzed amidation of aldehydes with amines <i>via</i> the tandem <i>N</i>-hydroxysuccinimide ester formation
  作者：Ashmita Singh、A. K. Narula

  DOI：10.1039/d1nj00591j

  日期：——

  A facile method for the amidation of aldehydes by a cascade approach was developed. This methodology, reported for the first time, uses a N-heterocyclic carbene (NHC) as the catalyst, and N-hydroxysuccinimide (NHS) mediated synthesis of amides utilising TBHP as the oxidant. Various substituted aldehydes reacted smoothly with NHS giving the corresponding active esters in moderate to good yields, which

  提出了一种通过级联方法将醛酰胺化的简便方法。首次报道的这种方法是使用N-杂环卡宾（NHC）作为催化剂，以及使用TBHP作为氧化剂的N-羟基琥珀酰亚胺（NHS）介导的酰胺合成。各种取代的醛与NHS平稳反应，以中等至良好的收率得到相应的活性酯，并在一锅中轻松转化为酰胺。此外，合成了莫氯贝胺药物以代表所开发方法的实用性。
• Potent and selective inhibitors of the TASK-1 potassium channel through chemical optimization of a bis-amide scaffold
  作者：Daniel P. Flaherty、Denise S. Simpson、Melissa Miller、Brooks E. Maki、Beiyan Zou、Jie Shi、Meng Wu、Owen B. McManus、Jeffrey Aubé、Min Li、Jennifer E. Golden

  DOI：10.1016/j.bmcl.2014.06.032

  日期：2014.8

  TASK-1 is a two-pore domain potassium channel that is important to modulating cell excitability, most notably in the context of neuronal pathways. In order to leverage TASK-1 for therapeutic benefit, its physiological role needs better characterization; however, designing selective inhibitors that avoid the closely related TASK-3 channel has been challenging. In this study, a series of bis-amide derived compounds were found to demonstrate improved TASK-1 selectivity over TASK-3 compared to reported inhibitors. Optimization of a marginally selective hit led to analog 35 which displays a TASK-1 IC50=16 nM with 62-fold selectivity over TASK-3 in an orthogonal electrophysiology assay.
• Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity
  作者：Antonio Solinas、Hélène Faure、Hermine Roudaut、Elisabeth Traiffort、Angèle Schoenfelder、André Mann、Fabrizio Manetti、Maurizio Taddei、Martial Ruat

  DOI：10.1021/jm2013369

  日期：2012.2.23

  The Smoothened (Smo) receptor is the major transducer of the Hedgehog (Hh) signaling pathway. On the basis of the structure of the acylthiourea Smo antagonist (MRT-10), a number of different series of analogous compounds were prepared by ligand-based structural optimization. The acylthioureas, originally identified as actives, were converted into the corresponding acylureas or acylguanidines. In each series, similar structural trends delivered potent compounds with IC50 values in the nanomolar range with respect to the inhibition of the Hh signaling pathway in various cell-based assays and of BODIPY-cyclopamine binding to human Smo. The similarity of their biological activities, in spite of discrete structural differences, may reveal the existence of hydrogen-bonding interactions between the ligands and the receptor pocket. Biological potency of compounds 61, 72, and 86 (MRT-83) were comparable to those of the clinical candidate GDC-0449. These findings suggest that these original molecules will help delineate Smo and Hh functions and can be developed as potential anticancer agents.
• Shpan'ko, I. V.; Likhomanenko, E. E., Journal of Organic Chemistry USSR (English Translation), 1986, vol. 22, # 9, p. 1702 - 1710
  作者：Shpan'ko, I. V.、Likhomanenko, E. E.

  DOI：——

  日期：——
• Likhomanenko, E. E.; Shpan'ko, I. V.; Litvinenko, L. M., Journal of Organic Chemistry USSR (English Translation), 1985, vol. 21, # 12, p. 2341 - 2347
  作者：Likhomanenko, E. E.、Shpan'ko, I. V.、Litvinenko, L. M.、Goncharov, A. N.

  DOI：——

  日期：——