3-硝基-N-(4-溴苯基)苯甲酰胺 | 99514-88-2

• 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: 3-硝基-N-(4-溴苯基)苯甲酰胺
• 英文名称: N-(4-bromophenyl)-3-nitrobenzamide
• CAS: 99514-88-2
• 化学式: C₁₃H₉BrN₂O₃
• mdl: MFCD00437399
• 分子量: 321.13
• InChiKey: BCNOELQOESJJCH-UHFFFAOYSA-N

物化性质

• 熔点：
  182 °C
• 沸点：
  367.0±27.0 °C(Predicted)
• 密度：
  1.635±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  19
• 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：
  74.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-硝基-N-(4-溴苯基)苯甲酰胺 在 硝酸 作用下， 生成 3-nitro-benzoic acid-(4-bromo-2,6-dinitro-anilide)
  参考文献：
  名称：

  van Horssen, Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 245,251

  摘要：

  DOI：
• 作为产物：
  描述：

  间硝基苯甲酸 在 草酰氯 、 三乙胺 作用下， 以 苯 为溶剂， 反应 4.0h， 生成 3-硝基-N-(4-溴苯基)苯甲酰胺
  参考文献：
  名称：

  脒基和非脒基苯甲酰胺的合成和体外和体内抗凝和抗血小板活性

  摘要：

  合成了三种脒基和十种非脒基苯甲酰胺，作为基于 3-氨基苯甲酸支架的抗凝剂和抗血小板化合物。通过筛选体外活化部分凝血活酶时间 (aPTT) 和凝血酶原时间 (PT) 的延长，初步评估了 13 种合成化合物 1-13、2b 和 3b 作为前药的抗凝活性。从获得的 aPTT 结果，两种脒基苯甲酰胺，N-(3'-脒基苯基)-3-(噻吩-2''-基羰基氨基)苯甲酰胺 (1, 33.2 ± 0.7 s) 和 N-(4'-脒基苯基)-3-选择 (噻吩-2''-基羰基氨基) 苯甲酰胺 (2, 43.5 ± 0.6 s) 来研究进一步的抗凝和抗血小板活性。1 (33.2 ± 0.7 s) 和 2 (43.5 ± 0.6 s) 的 aPTT 结果与体外 30 μM 的肝素 (62.5 ± 0.8 s) 进行了比较。我们研究了 1 和 2 对小鼠血液抗凝活性（离体）和尾部出血时间（体内）的影响。切尾/流血时间测定表明，1

  DOI：

  10.3390/molecules21050676

文献信息

• Photocaging of Pyridinylimidazole-Based Covalent JNK3 Inhibitors Affords Spatiotemporal Control of the Binding Affinity in Live Cells
  作者：Beate Sandra Hoffelner、Stanislav Andreev、Nicole Plank、Pierre Koch

  DOI：10.3390/ph16020264

  日期：——

  The concept of photocaging represents a promising approach to acquire spatiotemporal control over molecular bioactivity. To apply this strategy to pyridinylimidazole-based covalent JNK3 inhibitors, we used acrylamido-N-(4-((4-(4-(4-fluorophenyl)-1-methyl-2-(methylthio)-1H-imidazol-5-yl)pyridin-2-yl)amino)phenyl)benzamide (1) as a lead compound to design novel covalent inhibitors of JNK3 by modifying the amide bond moiety in the linker. The newly synthesized inhibitors demonstrated IC50 values in the low double-digit nanomolar range in a radiometric kinase assay. They were further characterized in a NanoBRETTM intracellular JNK3 assay, where covalent engagement of the target enzyme was confirmed by compound washout experiments and a loss in binding affinity for a newly generated JNK3(C154A)-NLuc mutant. The most potent compound of the series, N-(3-acrylamidophenyl)-4-((4-(4-(4-fluorophenyl)-1-methyl-2-(methylthio)-1H-imidazol-5-yl)pyridin-2-yl)amino)benzamide (13), was equipped with a photolabile protecting group leading to a nearly 10-fold decrease in intracellular JNK3 binding affinity, which was fully recovered by UV irradiation at a wavelength of 365 nm within 8 min. Our results highlight that photocaged covalent inhibitors can serve as a pharmacological tool to control JNK3 activity in live cells with light.

  光成像的概念是一种对分子生物活性进行时空控制的有效方法。为了将这一策略应用于基于吡啶基咪唑的共价 JNK3 抑制剂，我们以丙烯酰胺基-N-(4-((4-(4-(4-氟苯基)-1-甲基-2-(甲硫基)-1H-咪唑-5-基)吡啶-2-基)氨基)苯基)苯甲酰胺 (1) 为先导化合物，通过修饰连接体中的酰胺键分子，设计出新型共价 JNK3 抑制剂。新合成的抑制剂在辐射激酶测定中的 IC50 值在两位数纳摩尔范围内。它们在 NanoBRETTM 细胞内 JNK3 检测中得到了进一步表征，通过化合物冲洗实验和对新生成的 JNK3(C154A)-NLuc 突变体的结合亲和力损失，证实了它们与目标酶的共价结合。该系列中最有效的化合物 N-(3-丙烯酰胺基苯基)-4-((4-(4-(4-氟苯基)-1-甲基-2-(甲硫基)-1H-咪唑-5-基)吡啶-2-基)氨基)苯甲酰胺 (13)带有光敏保护基团，导致细胞内 JNK3 结合亲和力下降了近 10 倍，在波长为 365 纳米的紫外线照射下，该亲和力在 8 分钟内完全恢复。我们的研究结果突出表明，光固化共价抑制剂可以作为一种药理学工具，用光来控制活细胞中 JNK3 的活性。
• Synthesis of Aryl Amides from Acyl-Bunte Salts and Aryl Azides
  作者：Li-Jia Chen、Chia-Jou Kuo、Chien-Fu Liang

  DOI：10.1021/acs.joc.3c00477

  日期：2023.8.4

  In this study, we developed an efficient method for the synthesis of aryl amides from sodium thiosulfate pentahydrate, organic anhydrides, and aryl azides. Sodium thiosulfate may be used as the sulfur source, which reacts with anhydrides to generate acyl-Bunte salt; this salt reacts with aryl azides via the in situ generation of thiocarboxylate. Using our method, we successfully synthesized a key bioactive

  在这项研究中，我们开发了一种由五水硫代硫酸钠、有机酸酐和芳基叠氮化物合成芳基酰胺的有效方法。硫代硫酸钠可以作为硫源，与酸酐反应生成酰基Bunte盐；该盐与芳基叠氮化物反应，原位生成硫代羧酸盐。使用我们的方法，我们成功合成了一种关键的生物活性化合物。一锅两步反应的优点包括操作简单、产物结构多样且收率良好、使用毒性较小、无味的试剂以及易于大规模操作。
• Synthesis and antiviral activity of sulfonamidobenzophenone oximes and sulfonamidobenzamides
  作者：Masaru Ogata、Hiroshi Matsumoto、Sumio Shimizu、Shiro Kida、Toru Wada、Motoo Shiro、Kosaburo Sato

  DOI：10.1021/jm00153a018

  日期：1986.3

  To find antiviral agents, various sulfonamidobenzophenone oximes (II) were synthesized from the appropriate m-sulfonamidobenzophenones by hydroxylamine reaction. The reaction products were generally obtained as syn/anti mixtures which were separable by fractional crystallization. The anti isomer had more potent antipoliovirus activity than the syn isomer. Various sulfonamidobenzamides (III) which were structurally related to II were synthesized by the reactions of amino-substituted benzamides with sulfuryl chloride or amines with (aminosulfonyl)benzoyl chloride. Antiviral activity was examined by the plaque-inhibition test. Compounds 5, 36, and 69 exhibited strong antipicornavirus activity. The structure-activity relationships are discussed.
• Activated charcoal supported copper nanoparticles: A readily available and inexpensive heterogeneous catalyst for the N-arylation of primary amides and lactams with aryl iodides
  作者：Rong Zhao、Wenwen Dong、Jiangge Teng、Zhiwei Wang、Yunzhong Wang、Jianguo Yang、Qiang Jia、Changhu Chu

  DOI：10.1016/j.tet.2020.131858

  日期：2021.1
• Direct Oxidative Amidation of Aldehydes with Anilines under Mechanical Milling Conditions
  作者：Jie Gao、Guan-Wu Wang

  DOI：10.1021/jo800075t

  日期：2008.4.1

  Oxone is found to be an effective oxidant for the oxidative amidation of aldehydes with anilines to furnish amides in a one-pot process under mechanical milling conditions.