N-(2-fluoro-5-nitro-phenyl)-benzamide | 144205-37-8

• 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-(2-fluoro-5-nitro-phenyl)-benzamide
• 英文别名: N-(2-fluoro-5-nitrophenyl)benzamide
• CAS: 144205-37-8
• 化学式: C₁₃H₉FN₂O₃
• mdl: MFCD01119708
• 分子量: 260.224
• InChiKey: BHZRTFDAJFZYBG-UHFFFAOYSA-N

物化性质

• 沸点：
  305.1±32.0 °C(Predicted)
• 密度：
  1.411±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 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：
  4

反应信息

• 作为反应物：
  描述：

  N-(2-fluoro-5-nitro-phenyl)-benzamide 在 盐酸 、 tin(II) chloride dihdyrate 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 1.0h， 生成 N-3-(benzoylamino-4-fluorophenylaminoarbonothioyl)-3,4,5-trimethoxybenzamide
  参考文献：
  名称：

  Acylthiourea, Acylurea, and Acylguanidine Derivatives with Potent Hedgehog Inhibiting Activity

  摘要：

  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.

  DOI：

  10.1021/jm2013369
• 作为产物：
  描述：

  苯甲酸 在 吡啶 、 氯化亚砜 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 N-(2-fluoro-5-nitro-phenyl)-benzamide
  参考文献：
  名称：

  Discovery of 5,6-Bis(4-methoxy-3-methylphenyl)pyridin-2-amine as a WSB1 Degrader to Inhibit Cancer Cell Metastasis

  摘要：

  DOI：

  10.1021/acs.jmedchem.1c00586
• 作为试剂：
  描述：

  、 2-氟-5-硝基苯胺 、 吡啶 、 苯甲酰氯 、 N-(2-fluoro-5-nitro-phenyl)-benzamide 在 钯 氩 、 水 、 N-(2-fluoro-5-nitro-phenyl)-benzamide 作用下， 以 二氯甲烷 、 甲醇 、 tetrahydrofuran methanol 为溶剂， 反应 3.25h， 以After 45 minutes a white precipitate formed的产率得到N-(5-amino-2-fluoro-phenyl)-benzamide
  参考文献：
  名称：

  Indazole compounds and pharmaceutical compositions for inhibiting protein kinases, and methods for their use

  摘要：

  本文描述了调节和/或抑制某些蛋白激酶活性的吲唑化合物。这些化合物及含有它们的药物组合物能够介导酪氨酸激酶信号转导，从而调节和/或抑制不必要的细胞增殖。本发明还涉及含有这些化合物的药物组合物的治疗或预防用途，以及通过给予这些化合物的有效量来治疗癌症和与不必要的血管生成和/或细胞增殖相关的其他疾病状态，如糖尿病性视网膜病变，新生血管型青光眼，类风湿性关节炎和牛皮癣的方法。

  公开号：

  US06884890B2

文献信息

• Substituted anilino-quinazoline (or quinoline) compounds and use thereof
  申请人：Astrazeneca AB

  公开号：US06593333B1

  公开（公告）日：2003-07-15

  The invention concerns amide derivatives of Formula (I), wherein: G is N or CH; R1 is a group such as hydroxy, halo, trifluoromethyl, C1-6alkyl and C1-6alkoxy; each of R2 and R3 is hydrogen, halo, C1-6alkyl, C2-6alkenyl or C2-6alkynyl; R4 is a group such as hydrogen, hydroxy, C1-6alkyl, C1-6alkoxy and C3-7cycloalkyl, or R4 is of the Formula (IC): —K—J, wherein J is aryl, heteroaryl or heterocyclyl and K is a bond or a group such as oxy and imino, R5 is a group such as hydrogen, halo and trifluoromethyl: m is 1-3 and q is 0-4; or pharmaceutically acceptable salts or in vivo cleavable esters thereof; processes for their preparation, pharmaceutical compositions containing them and their use in the treatment of diseases or medical conditions mediated by cytokines.

  该发明涉及式（I）的酰胺衍生物，其中：G为N或CH；R1为羟基、卤素、三氟甲基、C1-6烷基和C1-6烷氧基等基团；R2和R3中的每一个为氢、卤素、C1-6烷基、C2-6烯基或C2-6炔基；R4为氢、羟基、C1-6烷基、C1-6烷氧基和C3-7环烷基等基团，或R4为式（IC）中的基团：—K—J，其中J为芳基、杂芳基或杂环烷基，K为键或氧基、亚胺基等基团；R5为氢、卤素和三氟甲基等基团；m为1-3，q为0-4；或其药学上可接受的盐或体内可水解酯；其制备方法，含有它们的药物组合物以及它们在治疗由细胞因子介导的疾病或医疗状况中的用途。
• Decarboxylative/Oxidative Amidation of Aryl α-Ketocarboxylic Acids with Nitroarenes and Nitroso Compounds in Aqueous Medium
  作者：Dinesh S. Barak、Dipak J. Dahatonde、Shashikant U. Dighe、Ruchir Kant、Sanjay Batra

  DOI：10.1021/acs.orglett.0c03666

  日期：2020.12.4

  of aryl α-ketocarboxylic acids with 5-aryl-3-nitroisoxazole-4-carboxylates and substituted dinitrobenzenes under oxidative aqueous conditions to afford N-aryl amides is described. The reaction is suggested to proceed via a radical pathway in which a benzoyl nitroxyl radical, the key intermediate formed from reaction between nitroarene and benzoyl radical from glyoxalic acid, couples with hydroxyl radical

  描述了在氧化水性条件下芳基α-酮羧酸与5-芳基-3-硝基异恶唑-4-羧酸酯和取代的二硝基苯的脱羧/氧化酰胺化，得到N-芳基酰胺。建议该反应通过自由基途径进行，其中苯甲酰基硝基氧基自由基是由乙二醛酸与硝基芳烃和苯甲酰基自由基之间的反应形成的关键中间体，与水的羟基自由基偶联生成酰胺。机械学的见解允许通过芳基α-酮羧酸和亚硝基化合物之间的反应将策略的范围扩展到酰胺的合成。
• Design, Synthesis, and Biological Evaluation of Novel Type I¹/₂ p38α MAP Kinase Inhibitors with Excellent Selectivity, High Potency, and Prolonged Target Residence Time by Interfering with the R-Spine
  作者：Niklas M. Walter、Heike K. Wentsch、Mike Bührmann、Silke M. Bauer、Eva Döring、Svenja Mayer-Wrangowski、Adrian Sievers-Engler、Nicole Willemsen-Seegers、Guido Zaman、Rogier Buijsman、Michael Lämmerhofer、Daniel Rauh、Stefan A. Laufer

  DOI：10.1021/acs.jmedchem.7b00745

  日期：2017.10.12

  We recently reported 1a (skepinone-L) as a type I p38α MAP kinase inhibitor with high potency and excellent selectivity in vitro and in vivo. However, as a type I inhibitor, it is entirely ATP-competitive and shows just a moderate residence time. Thus, the scope was to develop a new class of advanced compounds maintaining the structural binding features of skepinone-L scaffold like inducing a glycine

  我们最近报告了1a（skepinone-L）作为I型p38αMAP激酶抑制剂，在体外和体内均具有很高的效价和出色的选择性。但是，作为I型抑制剂，它完全具有ATP竞争能力，并且仅显示适度的停留时间。因此，研究范围是开发一种新型的高级化合物，该化合物可维持skepinone-L支架的结构结合特征，例如在铰链区诱导甘氨酸翻转，并同时占据疏水区I和II。用适当的残基扩展该支架会干扰激酶的R-Spine。通过合成69种化合物，我们可以将一个实例的目标停留时间显着延长至3663 s，同时具有出色的选择性得分0.006和出色的效能1.0 nM。通过共结晶验证了这种新的结合模式，1 / 2的结合。此外，微粒体研究显示了最有效的，本文报道的代表的便利的代谢稳定性。
• Indazole compounds useful as protein kinase inhibitors
  申请人：——

  公开号：US20040009968A1

  公开（公告）日：2004-01-15

  The present invention provides compounds of formula I: 1 or a pharmaceutically acceptable derivative thereof, wherein R 1 , R 2 , V 1 , V 2 , and V 3 are as described in the specification. These compounds are inhibitors of protein kinase, particularly inhibitors of AKT, PKA, PDK1, p70S6K, or ROCK kinase, mammalian protein kinases involved in proliferative and neurodegenerative disorders. The invention also provides pharmaceutical compositions comprising the compounds of the invention and methods of utilizing those compositions in the treatment of various disorders.

  本发明提供了公式I:1的化合物或其药用可接受的衍生物，其中R1、R2、V1、V2和V3如规范中描述。这些化合物是蛋白激酶的抑制剂，特别是AKT、PKA、PDK1、p70S6K或ROCK激酶的抑制剂，这些哺乳动物蛋白激酶参与增殖性和神经退行性疾病。该发明还提供了包括该发明的化合物的药物组合物以及利用这些组合物在治疗各种疾病中的方法。
• [EN] INDAZOLE COMPOUNDS AND PHARMACEUTICAL COMPOSITIONS FOR INHIBITING PROTEIN KINASES, AND METHODS FOR THEIR USE<br/>[FR] COMPOSES D'INDAZOLE ET COMPOSITIONS PHARMACEUTIQUES INHIBANT LES PROTEINES KINASES, ET PROCEDES D'UTILISATION DE CEUX-CI
  申请人：AGOURON PHARMA

  公开号：WO2001002369A2

  公开（公告）日：2001-01-11

  Indazole compounds that modulate and/or inhibit the activity of certain protein kinases are described. These compounds and pharmaceutical compositions containing them are capable of mediating tyrosine kinase signal transduction and thereby modulate and/or inhibit unwanted cell proliferation. The invention is also directed to the therapeutic or prophylactic use of pharmaceutical compositions containing such compounds, and to methods of treating cancer and other disease states associated with unwanted angiogenesis and/or cellular proliferation, such as diabetic retinopathy, neovascular glaucoma, rheumatoid arthritis, and psoriasis, by administering effective amounts of such compounds.

  本文描述了调节和/或抑制某些蛋白激酶活性的吲唑化合物。这些化合物和含有它们的药物组合物能够介导酪氨酸激酶信号转导，从而调节和/或抑制不需要的细胞增殖。本发明还涉及含有这些化合物的药物组合物的治疗或预防用途，并通过给予有效量的这些化合物的方法治疗癌症和其他与不需要的血管生成和/或细胞增殖有关的疾病状态，例如糖尿病视网膜病变、新生血管性青光眼、类风湿性关节炎和牛皮癣。