4-硝基-1H-咪唑-2-甲酸乙酯 | 865998-46-5

• 物质功能分类: 化学试剂 - 有机试剂 - 酯类
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 4-硝基-1H-咪唑-2-甲酸乙酯
• 中文别名: 4-硝基-1H-咪唑-2-羧酸乙酯；1H-咪唑-2-羧基LICACID,5-硝基-,乙基酯；5-硝基-1H-咪唑-2-羧酸乙酯
• 英文名称: ethyl 4-nitro-1H-imidazole-2-carboxylate
• CAS: 865998-46-5
• 化学式: C₆H₇N₃O₄
• mdl: MFCD08275005
• 分子量: 185.139
• InChiKey: YSVPLWXCZZORIO-UHFFFAOYSA-N

物化性质

• 沸点：
  374.2±34.0 °C(Predicted)
• 密度：
  1.455

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  5

安全信息

• 海关编码：
  2933290090
• 危险性防范说明：
  P261,P280,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H332,H335

反应信息

• 作为反应物：
  描述：

  4-硝基-1H-咪唑-2-甲酸乙酯 在 吡啶 、 palladium 10% on activated carbon 、 氢气 、 caesium carbonate 、 potassium iodide 作用下， 以 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 20.0~135.0 ℃ 、101.33 kPa 条件下， 反应 0.75h， 生成 ethyl 4-((5-bromo-3-chloro-2-hydroxyphenyl)sulfonamido)-1-cyclopentyl-1H-imidazole-2-carboxylate
  参考文献：
  名称：

  Discovery of WD Repeat-Containing Protein 5 (WDR5)–MYC Inhibitors Using Fragment-Based Methods and Structure-Based Design

  摘要：

  The frequent deregulation of MYC and its elevated expression via multiple mechanisms drives cells to a tumorigenic state. Indeed, MYC is overexpressed in up to similar to 50% of human cancers and is considered a highly validated anticancer target. Recently, we discovered that WD repeat-containing protein 5 (WDR5) binds to MYC and is a critical cofactor required for the recruitment of MYC to its target genes and reported the first small molecule inhibitors of the WDR5-MYC interaction using structure-based design. These compounds display high binding affinity, but have poor physicochemical properties and are hence not suitable for in vivo studies. Herein, we conducted an NMR-based fragment screening to identify additional chemical matter and, using a structure-based approach, we merged a fragment hit with the previously reported sulfonamide series. Compounds in this series can disrupt the WDR5-MYC interaction in cells, and as a consequence, we observed a reduction of MYC localization to chromatin.

  DOI：

  10.1021/acs.jmedchem.0c00224
• 作为产物：
  描述：

  1-苄基咪唑-2-羧酸乙酯 在 硫酸 、 palladium 10% on activated carbon 、 氢气 、 硝酸 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 4-硝基-1H-咪唑-2-甲酸乙酯
  参考文献：
  名称：

  Orthogonally Positioned Diamino Pyrrole- and Imidazole-Containing Polyamides: Synthesis of 1-(3-Substituted-propyl)-4-nitropyrrole-2-carboxylic Acid and 1-(3-Chloropropyl)-4-nitroimidazole-2-carboxylic Acid

  摘要：

  Pyrrole- and imidazole-containing polyamides can be tailored to recognize the DNA 6-8 base pair sequence. We found that adding a second amino group via the N1-position of pyrrole or imidazole in polyamides could enhance their DNA binding affinity and water solubility while retaining sequence specificity. Synthesis of the key 1-substituted-4-nitropyrrole (and imidazole)-2-carboxylic acid building blocks are described. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications (R) for the following free supplemental resource(s): Full experimental and spectral details.]

  DOI：

  10.1080/00397911.2013.839795

文献信息

• BISARYL-BONDED ARYLTRIAZOLONES AND USE THEREOF
  申请人：Furstner Chantal

  公开号：US20130190330A1

  公开（公告）日：2013-07-25

  The present application relates to novel bisaryl-linked 5-aryl-1,2,4-triazolone derivatives, to processes for preparing them, to their use alone or in combinations for the treatment and/or prevention of diseases and also to their use for the production of medicaments for the treatment and/or prevention of diseases, more particularly for the treatment and/or prevention of cardiovascular disorders.

  本申请涉及新型的双芳基连接的5-芳基-1,2,4-三唑啉酮衍生物，涉及制备它们的方法，涉及它们单独或组合用于治疗和/或预防疾病，以及涉及它们用于生产用于治疗和/或预防疾病的药物，尤其是用于治疗和/或预防心血管疾病的药物。
• [DE] 4-AMINOCARBONYLAMINO-SUBSTITUIERTE IMIDAZOLVERBINDUNGEN MIT ANTIVIRALERWIRKUNG<br/>[EN] ANTIVIRAL 4-AMINOCARBONYLAMINO-SUBSTITUTED IMIDAZOLE COMPOUND<br/>[FR] COMPOSES IMIDAZOLE A SUBSTITUTION 4-AMINOCARBONYLAMINO A ACTIVITE ANTIVIRALE
  申请人：BAYER HEALTHCARE AG

  公开号：WO2005092865A1

  公开（公告）日：2005-10-06

  Die Erfindung betrifft substituierte Imidazole der Formel (I) und Verfahren zu ihrer Herstellung, ihre Verwendung zur Behandlung und/oder Prophylaxe von Krankheiten sowie ihre Verwendung zur Herstellung von Arzneimitteln zur Behandlung und/oder Prophylaxe von Krankheiten, insbesondere zur Verwendung als antivirale Mittel, insbesondere gegen Cytomegaloviren.

  这项发明涉及公式（I）的取代咪唑化合物，以及其制备方法，其用于治疗和/或预防疾病的用途，以及其用于制备用于治疗和/或预防疾病的药物的用途，特别是用作抗病毒剂，特别是针对巨细胞病毒的用途。
• Nitroimidazole carboxamides as antiparasitic agents targeting Giardia lamblia, Entamoeba histolytica and Trichomonas vaginalis
  作者：A.M. Jarrad、A. Debnath、Y. Miyamoto、K.A. Hansford、R. Pelingon、M.S. Butler、T. Bains、T. Karoli、M.A.T. Blaskovich、L. Eckmann、M.A. Cooper

  DOI：10.1016/j.ejmech.2016.04.064

  日期：2016.9

  showed improved activity against E. histolytica (EC50 = 1.7-5.1 muM cf. metronidazole EC50 = 5.0 muM), potent activity against Trichomonas vaginalis (EC50 = 0.6-1.4 muM cf. metronidazole EC50 = 0.8 muM) and moderate activity against the intestinal bacterial pathogen Clostridium difficile (0.5-2 mug/mL, cf. metronidazole = 0.5 mug/mL). The new compounds had low toxicity against mammalian kidney and liver

  由肠道寄生虫贾第鞭毛虫和溶组织性变形杆菌引起的腹泻疾病构成了主要的全球健康负担。硝基咪唑是治疗贾第鞭毛虫病和阿米巴病的一线药物，其中甲硝唑1是全球最常用的药物。但是，贾第鞭毛虫病的治疗失败率高达20％，因此人们对甲硝唑耐药性的发展值得关注。我们已经重新检查了“旧的”硝基咪唑，作为系统开发下一代衍生物的基础。使用这种方法，硝基咪唑羧酰胺支架的衍生化提供了改进的抗寄生虫剂。合成了33种新颖的硝基咪唑羧酰胺，并评估了其对兰伯氏菌和组织溶大肠杆菌的活性。几种新化合物对兰氏芽孢杆菌菌株表现出有效的活性，包括兰氏芽孢杆菌对甲硝唑的抗性菌株（EC50 = 0.1-2.5μM，而甲硝唑EC50 = 6.1-18μM）。其他化合物显示出对溶组织性大肠杆菌的增强活性（EC50 = 1.7-5.1μM，对甲硝唑EC50 = 5.0μM），对阴道毛滴虫的有效活性（EC50 = 0.6-1.4μM，对甲硝唑EC50
• [EN] WDR5-MYC INHIBITORS<br/>[FR] INHIBITEURS DE WDR5-MYC
  申请人：UNIV VANDERBILT

  公开号：WO2021101927A1

  公开（公告）日：2021-05-27

  Substituted N-heteroaryl sulfonamide compounds inhibit WDR5-MYC interactions, and the compounds and their pharmaceutical compositions are useful for treating disorders and conditions in a subject such as cancer cell proliferation.

  N-杂环磺胺化合物替代物抑制WDR5-MYC相互作用，这些化合物及其药物组合物适用于治疗主体中的疾病和状况，如癌细胞增殖。
• SULFONIC ACID SALTS OF HETEROCYCLYLAMIDE-SUBSTITUTED IMIDAZOLES
  申请人：Schwab Wilfried

  公开号：US20140315924A1

  公开（公告）日：2014-10-23

  The invention relates to sulfonic acid salts of heterocyclylamide-substituted imidazoles, and to solvates and hydrates thereof, to the use thereof for treating and/or preventing diseases, and to use thereof for producing drugs for treating and/or preventing diseases, in particular for use as antiviral agents, in particular against cytomegaloviruses.

  本发明涉及杂环酰胺取代咪唑的磺酸盐，以及其溶剂化物和水合物，用于治疗和/或预防疾病的用途，以及用于制造用于治疗和/或预防疾病的药物的用途，特别是用作抗病毒剂，特别是针对巨细胞病毒的抗病毒剂。