4-(3-nitrophenyl)-1H-imidazol-2-amine | 76507-17-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(3-nitrophenyl)-1H-imidazol-2-amine
• 英文别名: 5-(3-nitrophenyl)-1H-imidazol-2-amine
• CAS: 76507-17-0
• 化学式: C₉H₈N₄O₂
• 分子量: 204.188
• InChiKey: VMJSWJARYYJDPV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(3-nitrophenyl)-1H-imidazol-2-amine 在 N-甲基吗啉 、 盐酸 、 palladium on activated charcoal 、 氢气 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 为溶剂， 反应 37.5h， 生成 (R)-2-amino-4-(3-(pyrrolidin-1-ium-2-carboxamido)phenyl)-1H-imidazol-3-ium chloride
  参考文献：
  名称：

  Substituted 4-phenyl-2-aminoimidazoles and 4-phenyl-4,5-dihydro-2-aminoimidazoles as voltage-gated sodium channel modulators

  摘要：

  Voltage-gated sodium channels play an integral part in neurotransmission and their dysfunction is frequently a cause of various neurological disorders. On the basis of the structure of marine alkaloid clathrodin, twenty eight new analogs were designed, synthesized and tested for their ability to block human Na(v)1.3, Na(v)1.4 and Na(v)1.7 channels, as well as for their selectivity against human cardiac isoform Na(v)1.5, using automated patch clamp electrophysiological assay. Several compounds exhibited promising activities on different Na-v channel isoforms in the medium micromolar range and some of the compounds showed also moderate isoform selectivities. The most promising results were obtained for the Na(v)1.3 channel, for which four compounds were found to possess IC50 values lower than 15 mu M. All of the active compounds bind to the open-inactivated states of the channels and therefore act as state-dependent modulators. The obtained results validate the approach of using natural products driven chemistry for drug discovery starting points and represent a good foundation for future design of selective Na-v modulators. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.12.034
• 作为产物：
  描述：

  间硝基苯乙酮 生成 4-(3-nitrophenyl)-1H-imidazol-2-amine
  参考文献：
  名称：

  NATH, J. P.;MAHAPATRA, G. N., INDIAN J. CHEM., 1980, 19, N 6, 526-528

  摘要：

  DOI：

文献信息

• Antimicrobial Activity of the Marine Alkaloids, Clathrodin and Oroidin, and Their Synthetic Analogues
  作者：Nace Zidar、Sofia Montalvão、Žiga Hodnik、Dorota Nawrot、Aleš Žula、Janez Ilaš、Danijel Kikelj、Päivi Tammela、Lucija Mašič

  DOI：10.3390/md12020940

  日期：——

  fungal strain (Candida albicans), and oroidin was found to possess promising Gram-positive antibacterial activity. Using oroidin as a scaffold, 34 new analogues were designed, prepared and screened for their antimicrobial properties. Of these compounds, 12 exhibited >80% inhibition of the growth of at least one microorganism at a concentration of 50 µM. The most active derivative was found to be 4-phenyl-2-aminoimidazole

  海洋生物产生的次级代谢物可能对开发新的药物先导物很有价值，也可以为设计和合成新的生物活性化合物提供结构支架。海洋生物碱、clathrodin 和 oroidin 最初是从 Agelas 属的海绵中分离出来的，它们被制备并评估了它们对三种细菌菌株（粪肠球菌、金黄色葡萄球菌和大肠杆菌）和一种真菌菌株（白色念珠菌）的抗菌活性，并且发现 oroidin 具有有希望的革兰氏阳性抗菌活性。使用 oroidin 作为支架，设计、制备了 34 种新类似物并筛选了它们的抗菌特性。在这些化合物中，12 种在 50 µM 的浓度下表现出对至少一种微生物生长的抑制 > 80%。发现活性最强的衍生物是 4-苯基-2-氨基咪唑 6 小时，其对革兰氏阳性菌的 MIC₉₀（最低抑制浓度）值为 12.5 µM，对大肠杆菌为 50 µM。发现金黄色葡萄球菌和哺乳动物细胞之间的选择性指数对于化合物 6h 为 2.9，这在评估化合物作为抗菌先导物的潜力时很重要。
• THERAPEUTIC TARGETING OF INTERLEUKIN-1 RECEPTOR-ASSOCIATED KINASE 4 (IRAK4) IN CANCERS CHARACTERIZED BY REARRANGEMENTS IN THE MIXED LINEAGE LEUKEMIA GENE (MLL-r)
  申请人：Northwestern University

  公开号：US20170305901A1

  公开（公告）日：2017-10-26

  Disclosed are methods for treating cancers associated with rearrangements in the mixed lineage leukemia gene (MLL-r), including MLL-r leukemia. The methods typically include administering a therapeutic amount of one or more therapeutic agents that inhibit the biological activity of one or more members of the interleukin-1 signaling pathway such inhibitors of interleukin-1 receptor-associated kinase 4 (IRAK4).

  揭示了治疗与混合系谱白血病基因（MLL-r）重排相关的癌症的方法，包括MLL-r白血病。这些方法通常包括给予治疗量的一个或多个治疗剂，其抑制白介素-1信号通路的一个或多个成员的生物活性，例如白介素-1受体相关激酶4（IRAK4）的抑制剂。
• A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7-deaza-adenines
  作者：Felicia Phei Lin Lim、Szy Teng Low、Elvina Lee King Ho、Nathan R. Halcovitch、Edward R. T. Tiekink、Anton V. Dolzhenko

  DOI：10.1039/c7ra11305f

  日期：——

  An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5]triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated

  开发了一种高效，高选择性的4-氨基咪唑并[1,2- a ] [1,3,5]三嗪的多组分合成方法，该化合物是腺嘌呤的5-aza-7-deaza-isosteres。2-氨基咪唑，原甲酸三乙酯和氰酰胺在微波辐射下的反应选择性进行，从而以良好的收率和纯度提供了新型5-氮杂-7-脱氮杂戊烯的文库。事实证明，所开发的方法在三种不同的单模微波反应堆中具有可扩展性和高度可重复性。提出了重排以解释反应的高选择性。
• Therapeutic targeting of the interleukin 1 receptor-associated kinase 4 (IRAK4) in leukemias characterized by rearrangements in the mixed lineage leukemia gene (MLL-r)
  申请人：Northwestern University

  公开号：US10059708B2

  公开（公告）日：2018-08-28

  Disclosed are methods for treating cancers associated with rearrangements in the mixed lineage leukemia gene (MLL-r), including MLL-r leukemia. The methods typically include administering a therapeutic amount of one or more therapeutic agents that inhibit the biological activity of one or more members of the interleukin-1 signaling pathway such inhibitors of interleukin-1 receptor-associated kinase 4 (IRAK4).

  所公开的是治疗与混合系白血病基因（MLL-r）重排相关的癌症（包括 MLL-r 白血病）的方法。这些方法通常包括施用治疗量的一种或多种治疗剂，这些治疗剂可抑制白细胞介素-1 信号通路的一个或多个成员的生物活性，如白细胞介素-1 受体相关激酶 4（IRAK4）的抑制剂。
• Therapeutic targeting of interleukin-1 receptor-associated kinase 4 (IRAK4) in cancers characterized by rearrangements in the mixed lineage leukemia gene (MLL-r)
  申请人：Northwestern University

  公开号：US10640502B2

  公开（公告）日：2020-05-05

  Disclosed are methods for treating cancers associated with rearrangements in the mixed lineage leukemia gene (MLL-r), including MLL-r leukemia. The methods typically include administering a therapeutic amount of one or more therapeutic agents that inhibit the biological activity of one or more members of the interleukin-1 signaling pathway such inhibitors of interleukin-1 receptor-associated kinase 4 (IRAK4).

  所公开的是治疗与混合系白血病基因（MLL-r）重排相关的癌症（包括 MLL-r 白血病）的方法。这些方法通常包括施用治疗量的一种或多种治疗剂，这些治疗剂可抑制白细胞介素-1 信号通路的一个或多个成员的生物活性，如白细胞介素-1 受体相关激酶 4（IRAK4）的抑制剂。