4-氨基-3-硝基苯硼酸 | 89466-07-9

• 物质功能分类: 化学试剂 - 有机试剂 - 硼酸
• 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: 4-氨基-3-硝基苯硼酸
• 英文名称: (4-amino-3-nitrophenyl)boronic acid
• 英文别名: 4-Amino-3-nitrophenylboronic acid
• CAS: 89466-07-9
• 化学式: C₆H₇BN₂O₄
• mdl: MFCD07437851
• 分子量: 181.944
• InChiKey: IRTXQNNJQZNKRP-UHFFFAOYSA-N

物化性质

• 熔点：
  215-225 °C (dec.)
• 沸点：
  439.5±55.0 °C(Predicted)
• 密度：
  1.48±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.46
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  5

安全信息

• WGK Germany：
  3
• 危险性防范说明：
  P261,P301+P312,P302+P352,P304+P340,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

反应信息

• 作为反应物：
  描述：

  4-氨基-3-硝基苯硼酸 在 bis-triphenylphosphine-palladium(II) chloride 、 potassium carbonate 、 三苯基膦 、 sodium thiomethoxide 作用下， 以 丙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 4-(4-amino-3-nitrophenyl)pyrimidin-5-ol
  参考文献：
  名称：

  Discovery of BAY-985, a Highly Selective TBK1/IKKε Inhibitor

  摘要：

  The serine/threonine kinase TBK1 (TANK-binding kinase 1) and its homologue IKK epsilon are noncanonical members of the inhibitor of the nuclear factor kappa B (I kappa B) kinase family. These kinases play important roles in multiple cellular pathways and, in particular, in inflammation. Herein, we describe our investigations on a family of benzimidazoles and the identification of the potent and highly selective TBK1/IKK epsilon inhibitor BAY-985. BAY-985 inhibits the cellular phosphorylation of interferon regulatory factor 3 and displays antiproliferative efficacy in the melanoma cell line SK-MEL-2 but showed only weak antitumor activity in the SK-MEL-2 human melanoma xenograft model.

  DOI：

  10.1021/acs.jmedchem.9b01460
• 作为产物：
  描述：

  4-甲基-3-硝基苯硼酸 在 sodium hydroxide 、 potassium permanganate 、 sodium azide 、 五氯化磷 、 硫酸 作用下， 生成 4-氨基-3-硝基苯硼酸
  参考文献：
  名称：

  Torssell et al., Arkiv foer Kemi, 1957, vol. 10, p. 497,503

  摘要：

  DOI：

文献信息

• SUBSTITUTED BENZIMDAZOLE DERIVATIVES USEFUL AS TRPM8 RECEPTOR MODULATORS
  申请人：PLAYER Mark R.

  公开号：US20120202856A1

  公开（公告）日：2012-08-09

  The present invention is directed to benzimidazole derivatives, pharmaceutical compositions containing them and their use in the treatment of disorders and conditions modulated by TRP M8, including for example, inflammatory pain, inflammatory hyperalgesia, inflammatory hypersensitivity condition, neuropathic pain, neuropathic cold allodynia, inflammatory somatic hyperalgesia, inflammatory visceral hyperalgesia, cardiovascular disease aggravated by cold and pulmonary disease aggravated by cold.

  本发明涉及苯并咪唑衍生物，包含它们的药物组合物以及它们在治疗由TRP M8调节的疾病和症状中的应用，例如炎症性疼痛、炎症性过敏症、炎症性过敏性疾病、神经病性疼痛、神经性寒冷触痛、炎症性体部过敏症、炎症性内脏过敏症、受冷加重的心血管疾病和受冷加重的肺部疾病。
• PYRAZOLOPYRIMIDINE ANALOGS AND THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS
  申请人：Zask Arie

  公开号：US20080234262A1

  公开（公告）日：2008-09-25

  The present invention relates to Pyrazolopyrimidine Analogs, methods of making Pyrazolopyrimidine Analogs, compositions comprising a Pyrazolopyrimidine Analog, and methods for treating mTOR-related disorders comprising administering to a subject in need thereof an effective amount of a Pyrazolopyrimidine Analog. The invention also relates to treating PI3K-related disorders comprising administering to a subject in need thereof an effective amount of a Pyrazolopyrimidine Analog.

  本发明涉及吡唑并嘧啶类似物，制备吡唑并嘧啶类似物的方法，包含吡唑并嘧啶类似物的组合物，以及治疗与mTOR相关疾病的方法，包括向需要治疗的受试者施用有效量的吡唑并嘧啶类似物。本发明还涉及治疗PI3K相关疾病的方法，包括向需要治疗的受试者施用有效量的吡唑并嘧啶类似物。
• [EN] 6-SUBSTITUTED INDOLE COMPOUNDS<br/>[FR] COMPOSÉS INDOLES SUBSTITUÉS EN POSITION 6
  申请人：GILEAD SCIENCES INC

  公开号：WO2022140325A1

  公开（公告）日：2022-06-30

  The present disclosure relates generally to certain compounds, pharmaceutical compositions comprising said compounds, and methods of making and using said compounds and pharmaceutical compositions. The compounds and compositions provided herein may be used for the treatment or prevention of an autoimmune disease and/or inflammatory condition, including systemic lupus erythematosus and cutaneous lupus erythematosus.

  本公开涉及某些化合物、包含所述化合物的制药组合物以及制备和使用所述化合物和制药组合物的方法。本文提供的化合物和组合物可用于治疗或预防自身免疫性疾病和/或炎症病状，包括全身性红斑狼疮和皮肤型红斑狼疮。
• Discovery of 2-(Cyclohexylmethylamino)pyrimidines as a New Class of Reversible Valosine Containing Protein Inhibitors
  作者：Giovanni Cervi、Paola Magnaghi、Daniela Asa、Nilla Avanzi、Alessandra Badari、Daniela Borghi、Michele Caruso、Alessandra Cirla、Liviana Cozzi、Eduard Felder、Arturo Galvani、Fabio Gasparri、Antonio Lomolino、Steven Magnuson、Beatrice Malgesini、Ilaria Motto、Maurizio Pasi、Simona Rizzi、Barbara Salom、Graziella Sorrentino、Sonia Troiani、Barbara Valsasina、Thomas O’Brien、Antonella Isacchi、Daniele Donati、Roberto D’Alessio

  DOI：10.1021/jm501313x

  日期：2014.12.26

  Valosine-containing protein (VCP), also known as p97 or cdc48 in yeast, is a highly abundant protein belonging to the AAA ATPase family involved in a number of essential cellular functions, including ubiquitin-proteasome mediated protein degradation, Golgi reassembly, transcription activation, and cell cycle control. Altered expression of VCP has been detected in many cancer types sometimes associated with poor prognosis. Furthermore, VCP mutations are causative of some neurodegenerative disorders. In this paper we report the discovery, synthesis, and structure-activity relationships of substituted 2-aminopyrimidines, representing a new class of reversible VCP inhibitors. This class of compounds, identified in a HTS campaign against recombinant VCP, has been progressively expanded and manipulated to increase biochemical potency and gain cellular activity.
• Design and Optimization of Benzimidazole-Containing Transient Receptor Potential Melastatin 8 (TRPM8) Antagonists
  作者：Daniel J. Parks、William H. Parsons、Raymond W. Colburn、Sanath K. Meegalla、Shelley K. Ballentine、Carl R. Illig、Ning Qin、Yi Liu、Tasha L. Hutchinson、Mary Lou Lubin、Dennis J. Stone、Judith F. Baker、Craig R. Schneider、Jianya Ma、Bruce P. Damiano、Christopher M. Flores、Mark R. Player

  DOI：10.1021/jm101075v

  日期：2011.1.13

  Transient receptor potential melastatin 8 (TRPM8) is a nonselective cation channel that is thermo-responsive to cool to cold temperatures (8-28 degrees C) and also may be activated by chemical agonists such as menthol and Antagonism of TRPM8 activation is currently under investigation for the treatment of painful conditions related to cold, such as cold allodynia and cold hyperalgesia The design, synthesis, and optimization of a class of selective TRPM8 antagonists based on a benzimidazole scaffold is described, leading to the identification of compounds that exhibited potent antagonism of TRPM8 in cell-based functional assays for human, rat, and canine TRPM8 channels Numerous compounds in the series demonstrated excellent in vivo activity in the TRPM8-selective "wet-dog shakes" (WDS) pharmacodynamic model and in the rat chronic constriction injury (CCI)-induced model of neuropathic pain Taken together the present results suggest that the in vivo antagonism of TRPM8 constitutes a viable new strategy for treating a variety of disorders associated with cold hypersensitivity, including certain types of neuropathic pain