2-methoxy-benzoic acid-(3-nitro-anilide) | 96748-34-4

• 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: 2-methoxy-benzoic acid-(3-nitro-anilide)
• 英文别名: 2-Methoxy-benzoesaeure-(3-nitro-anilid)；2-Methoxy-N-(3-nitrophenyl)benzamide；2-Methoxy-benzoesaeure-<3-nitro-anilid>
• CAS: 96748-34-4
• 化学式: C₁₄H₁₂N₂O₄
• mdl: MFCD00429204
• 分子量: 272.26
• InChiKey: JZUXINQGRPQHNI-UHFFFAOYSA-N

物化性质

• 熔点：
  146-147 °C
• 沸点：
  361.7±27.0 °C(Predicted)
• 密度：
  1.333±0.06 g/cm3(Predicted)
• 保留指数：
  2591

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 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：

  2-methoxy-benzoic acid-(3-nitro-anilide) 在 sodium tetrahydroborate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 8.0h， 生成 N-[3-[(2-ethoxybenzoyl)amino]phenyl]-2-methoxybenzamide
  参考文献：
  名称：

  Potent and selective inhibitors of the TASK-1 potassium channel through chemical optimization of a bis-amide scaffold

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2014.06.032
• 作为产物：
  描述：

  甲氧基苯甲酰氯 、 间硝基苯胺 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到2-methoxy-benzoic acid-(3-nitro-anilide)
  参考文献：
  名称：

  Optimization and Antifungal Activity of Amide Analogues

  摘要：

  以水杨酸为先导化合物，设计并合成了一系列水杨酸类似物（化合物 1-16）。在实验室中对其抗植物病原真菌的活性进行了评估。结果表明，这些化合物对 Sclerotinia sclerotiorum 和 Bipolaris maydis (Nisikado et Miyake) Shoem 具有一定的抗真菌活性。其中，2-(3-氟苯基氨基甲酰基)苯基乙酸酯（1）和 2-(3-氯苯基氨基甲酰基)苯基乙酸酯（2）在 100 mg L-1 浓度下的生长抑制率分别达到 91.1 %、92.8 % 和 90.1 %、90.1 %。

  DOI：

  10.14233/ajchem.2013.13895

文献信息

• N-Acylthiourea and N-Acylurea Inhibitors of the Hedgehog Protein Signalling Pathway
  申请人：Ruat Martial

  公开号：US20110275663A1

  公开（公告）日：2011-11-10

  The present invention relates to the use of acylthiourea or acylurea derivatives for the treatment of pathologies involving a tissue dysfunction associated with a deregulation of the Hedgehog protein signalling pathway, and also to novel acylthiourea or acylurea derivatives as such, to their use as a medicinal product, and to pharmaceutical compositions containing them.

  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。
• 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.
• Synthesis and SAR of novel, non-MPEP chemotype mGluR5 NAMs identified by functional HTS
  作者：Ya Zhou、Alice L. Rodriguez、Richard Williams、C. David Weaver、P. Jeffrey Conn、Craig W. Lindsley

  DOI：10.1016/j.bmcl.2009.10.059

  日期：2009.12

  This Letter describes the discovery and SAR of three novel series of mGluR5 non-competitive antagonists/negative allosteric modulators (NAMs) not based on manipulation of an MPEP/MTEP chemotype identified by a functional HTS approach. This work demonstrates fundamentally new mGluR5 NAM chemotypes with submicromolar potencies, and further examples of a mode of pharmacology 'switch' to provide PAMs with a non-MPEP scaffold. (C) 2009 Elsevier Ltd. All rights reserved.
• Phatak; Jadhav, Journal of the Indian Chemical Society, 1958, vol. 35, p. 717
  作者：Phatak、Jadhav

  DOI：——

  日期：——
• N-ACYLTHIOUREES ET N-ACYLUREES INHIBITEURS DE LA VOIE DE SIGNALISATION DES PROTEINES HEDGEHOG
  申请人：Centre National de la Recherche Scientifique

  公开号：EP2291352B1

  公开（公告）日：2017-09-13