N-(3-nitrophenyl)thiophene-2-carboxamide | 39880-87-0

• 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: N-(3-nitrophenyl)thiophene-2-carboxamide
• 英文别名: 3'-nitro-2-thiophenecarboxanilide
• CAS: 39880-87-0
• 化学式: C₁₁H₈N₂O₃S
• mdl: MFCD00438995
• 分子量: 248.262
• InChiKey: VFDHCXRHENGDQA-UHFFFAOYSA-N

物化性质

• 熔点：
  143-144 °C
• 沸点：
  315.0±22.0 °C(Predicted)
• 密度：
  1.463±0.06 g/cm3(Predicted)
• 保留指数：
  2435

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(3-nitrophenyl)thiophene-2-carboxamide 在 铁粉 、 溶剂黄146 、 calcium chloride 作用下， 以 乙醇 、 水 为溶剂， 生成 N-(3-(2-methyl-4-oxoquinazolin-3(4H)-yl)phenyl)thiophene-2-carboxamide
  参考文献：
  名称：

  喹唑啉酮类似物作为抗MRSA的潜在抗菌剂的设计，合成，计算机模拟研究和生物学筛选。

  摘要：

  类型或耐药性的出现在细菌感染的治疗中已发展成复杂的局面。将抗菌素耐药性现象视为寻找更好的抗菌剂的药物化学家的最大挑战之一，这些抗菌剂具有潜在的窄谱活性，耐药性发展低，对宿主毒性低的特点。肽聚糖的交联是青霉素结合蛋白（PBP）催化以维持细菌细胞中细胞壁完整性的关键步骤。但是，由于获得了额外的PBP2a，这些青霉素结合蛋白（PBP）对耐甲氧西林的金黄色葡萄球菌（MRSA）产生了耐药性。文献中报道了各种喹唑啉酮类似物作为针对MRSA的潜在抗菌剂。在当前的研究中，已经设计了新的喹唑啉酮类似物，并通过分子对接，计算机内和MM-GBSA研究指导。通过药物化学途径合成了新设计的分子，并使用IR，NMR和HR-MS技术对其进行了表征。分别使用链霉素，卡那霉素和利奈唑胺作为标准药物，对野生型革兰氏阴性菌（大肠杆菌），革兰氏阳性菌（金黄色葡萄球菌）和耐药MRSA细菌菌株进行了合成化合物的生物学评估。体外评估结

  DOI：

  10.1016/j.bmc.2019.05.012
• 作为产物：
  描述：

  2-噻吩甲酸 在 氯化亚砜 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 N-(3-nitrophenyl)thiophene-2-carboxamide
  参考文献：
  名称：

  噻吩和呋喃的芳香族化合物的核磁共振波谱分析法测定噻吩和呋喃的芳香指数

  摘要：

  一系列的米-和p -取代的苯甲酸，2-噻吩甲酸，和2-糠酸酰替苯胺的制备和它们的1 H和13 C NMR光谱特性进行了研究。通常，在酰基芳香环的质子和碳信号的化学位移与Hammettσ之间观察到良好的相关性。在二甲亚砜-d 6中，苯甲酰苯胺的羰基碳的化学位移值与2-硫代酰胺和2-呋喃酰胺的化学位移图具有极好的相关性，其斜率值分别为0.79和0.52 。该斜率可以被认为是一组芳香性指数。

  DOI：

  10.1002/jhet.5570390616

文献信息

• 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.
• Design, synthesis, in-silico studies and biological screening of quinazolinone analogues as potential antibacterial agents against MRSA
  作者：Shahnawaz I. Qureshi、Hemchandra K. Chaudhari

  DOI：10.1016/j.bmc.2019.05.012

  日期：2019.6

  Various Quinazolinone analogues are reported in literature as potential anti-bacterial agents against MRSA. In present study new quinazolinone analogues has been designed, guided by molecular docking, In-silico and MM-GBSA study. Newly designed molecules have been synthesized by medicinal chemistry route and their characterization was done by using IR, NMR, & HR-MS techniques. Biological evaluation of synthesized

  类型或耐药性的出现在细菌感染的治疗中已发展成复杂的局面。将抗菌素耐药性现象视为寻找更好的抗菌剂的药物化学家的最大挑战之一，这些抗菌剂具有潜在的窄谱活性，耐药性发展低，对宿主毒性低的特点。肽聚糖的交联是青霉素结合蛋白（PBP）催化以维持细菌细胞中细胞壁完整性的关键步骤。但是，由于获得了额外的PBP2a，这些青霉素结合蛋白（PBP）对耐甲氧西林的金黄色葡萄球菌（MRSA）产生了耐药性。文献中报道了各种喹唑啉酮类似物作为针对MRSA的潜在抗菌剂。在当前的研究中，已经设计了新的喹唑啉酮类似物，并通过分子对接，计算机内和MM-GBSA研究指导。通过药物化学途径合成了新设计的分子，并使用IR，NMR和HR-MS技术对其进行了表征。分别使用链霉素，卡那霉素和利奈唑胺作为标准药物，对野生型革兰氏阴性菌（大肠杆菌），革兰氏阳性菌（金黄色葡萄球菌）和耐药MRSA细菌菌株进行了合成化合物的生物学评估。体外评估结
• Determination of aromaticity indices of thiophene and furan by nuclear magnetic resonance spectroscopic analysis of their anilides
  作者：Chang Kiu Lee、Ji Sook Yu、Young Ran Ji

  DOI：10.1002/jhet.5570390616

  日期：2002.11

  A series of m- and p-substituted anilides of benzoic acid, 2-thienoic acid, and 2-furoic acid were prepared and their 1H and 13C nmr spectroscopic characteristics were examined. In general, good correlations were observed between the chemical shifts of proton and carbon signals of the acyl aromatic rings and the Hammett σ. Plots of the chemical shift values of the carbonyl carbons of the benzanilides

  一系列的米-和p -取代的苯甲酸，2-噻吩甲酸，和2-糠酸酰替苯胺的制备和它们的1 H和13 C NMR光谱特性进行了研究。通常，在酰基芳香环的质子和碳信号的化学位移与Hammettσ之间观察到良好的相关性。在二甲亚砜-d 6中，苯甲酰苯胺的羰基碳的化学位移值与2-硫代酰胺和2-呋喃酰胺的化学位移图具有极好的相关性，其斜率值分别为0.79和0.52 。该斜率可以被认为是一组芳香性指数。