2-methyl-2H-benzotriazol-5-amine | 89852-83-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并三唑类
• 英文名称: 2-methyl-2H-benzotriazol-5-amine
• 英文别名: 2-methyl-2H-benzo[d][1,2,3]triazol-5-amine；2-Methyl-5-amino-benzotriazol；2-methyl-2H-1,2,3-benzotriazol-5-amine；2-methylbenzotriazol-5-amine
• CAS: 89852-83-5
• 化学式: C₇H₈N₄
• mdl: MFCD19203480
• 分子量: 148.167
• InChiKey: MBOVZBKVDAMSEZ-UHFFFAOYSA-N

物化性质

• 熔点：
  101 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  346.6±34.0 °C(Predicted)
• 密度：
  1.42±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  56.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-methyl-2H-benzotriazol-5-amine 在 palladium on activated charcoal arsenic pentoxide hydrate 、 硫酸 、 氢气 、 potassium nitrate 作用下， 以 四氢呋喃 为溶剂， 25.0~160.0 ℃ 、303.98 kPa 条件下， 反应 18.0h， 生成 5-amino-2-methyl-2H-triazolo<4,5-f>quinoline
  参考文献：
  名称：

  Synthesis of Triazolo[4,5-f]quinolines. An Unusual Case of Displacement of Nitro Group in the Reaction of 8-Acetylamino-6-chloro-5-nitroquinoline with Hydrazine and Methylhydrazine

  摘要：

  Nitration of 1H-, 3-methyl- and 2-methyltriazolo[4,5-f]quinolines (6a-c) as a way to obtain the desired 4-aminotriazolo[4,5-f]quinolines (4) for a medicinal chemistry project was successful only in the case of 6c. Attempted building up of the triazole ring starting from 8-acetylamino-6-chloro-5-nitroquinoline (8) with ammonia, hydrazine and methylhydrazine at 150 degrees C in ethanol failed, However, the results obtained from these reactions allowed us to observe that, during nucleophilic aromatic substitution of chlorine by these bases an unusual displacement of the nitro group by hydrogen occurred. Comparison of these results with those obtained using different substrates allowed us to evaluate the influence of both para-acetylamino group and pyridine ring in this type of nucleophilic aromatic substitution.

  DOI：

  10.3987/com-98-s(h)34
• 作为产物：
  描述：

  5-硝基苯并三唑 在 palladium on activated charcoal 氢气 、 sodium ethanolate 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 24.0h， 生成 2-methyl-2H-benzotriazol-5-amine
  参考文献：
  名称：

  Synthesis, antimicrobial data and correlation analysis in a set of 2-alkyl-5-amidobenzotriazoles

  摘要：

  A set of 2-alkyl-5-amidobenzotriazoles has been prepared and characterized. Shake-flask partition coefficients (log P) and capacity factors (log k') have been experimentally determined. The in vitro antimicrobial activity against Gram-positive, Gram-negative and Candida albicans have been correlated, through regression analysis, with the corresponding partition coefficients.

  DOI：

  10.1016/0223-5234(92)90105-a

文献信息

• [EN] SUBSTITUTED OXOPYRIDINE DERIVATIVES<br/>[FR] DÉRIVÉS D'OXOPYRIDINE SUBSTITUÉS
  申请人：BAYER PHARMA AG

  公开号：WO2017005725A1

  公开（公告）日：2017-01-12

  The invention relates to substituted oxopyridine derivatives and to processes for their preparation, and also to their use for preparing medicaments for the treatment and/or prophylaxis of diseases, in particular cardiovascular disorders, preferably thrombotic or thromboembolic disorders, and o edemas, and also ophthalmic disorders.

  这项发明涉及替代氧吡啶衍生物及其制备方法，以及它们用于制备治疗和/或预防疾病的药物，特别是心血管疾病，最好是血栓性或血栓栓塞性疾病，以及水肿和眼科疾病。
• Pyrazole compounds
  申请人：——

  公开号：US20030060453A1

  公开（公告）日：2003-03-27

  Pharmaceutical compositions and compounds are provided. The compounds of the invention demonstrate anti-proliferative activity, and may promote apoptosis in cells lacking normal regulation of cell cycle and death. In one embodiment of the invention, pharmaceutical compositions of the compounds in combination with a physiologically acceptable carrier are provided. The pharmaceutical compositions are useful in the treatment of hyperproliferative disorders, which disorders include tumor growth, lymphoproliferative diseases, angiogenesis. The compounds of the invention are substituted pyrazoles and pyrazolines.

  提供药物组合物和化合物。发明的化合物显示出抗增殖活性，并且可能促进缺乏正常细胞周期和死亡调控的细胞的凋亡。发明的一个实施例提供了化合物与生理可接受载体组合的药物组合物。该药物组合物可用于治疗过度增殖障碍，包括肿瘤生长、淋巴增殖性疾病、血管生成。发明的化合物是取代吡唑和吡唑啉。
• [EN] COMPOUNDS<br/>[FR] COMPOSÉS
  申请人：JANSSEN PHARMACEUTICA NV

  公开号：WO2021239885A1

  公开（公告）日：2021-12-02

  The invention relates to novel compounds for use as inhibitors of NLRP3 inflammasone production, wherein such compounds are as defined by compounds of formula (I) and wherein the integers R1, R2 and R3 are defined in the description, and where the compounds may be useful as medicaments, for instance for use in the treatment of a disease or disorder that is associated with NLRP3 inflammasome activity.

  本发明涉及用于抑制NLRP3炎症体产生的新化合物，其中所述化合物由公式（I）定义，其中整数R1、R2和R3在描述中定义，且所述化合物可用作药物，例如用于治疗与NLRP3炎症体活性相关的一种疾病或失调。
• Discovery of 2-phenoxyacetamides as inhibitors of the Wnt-depalmitoleating enzyme NOTUM from an X-ray fragment screen
  作者：Benjamin N. Atkinson、David Steadman、Yuguang Zhao、James Sipthorp、Luca Vecchia、Reinis R. Ruza、Fiona Jeganathan、Georgie Lines、Sarah Frew、Amy Monaghan、Svend Kjær、Magda Bictash、E. Yvonne Jones、Paul V. Fish

  DOI：10.1039/c9md00096h

  日期：——

  (IC50 33 μM). Optimization of hit 3 by SAR studies guided by SBDD identified indazole 38 (IC50 0.032 μM) and isoquinoline 45 (IC50 0.085 μM) as potent inhibitors of NOTUM. The binding of 45 to NOTUM was rationalized through an X-ray co-crystal structure determination which showed a flipped binding orientation compared to 3. However, it was not possible to combine NOTUM inhibition activity with metabolic

  NOTUM 是一种羧酸酯酶，已被证明通过介导 Wnt 蛋白的O-去棕榈油酰化而发挥作用，从而抑制 Wnt 信号传导。在这里，我们描述了 NOTUM 抑制剂的开发，该抑制剂可恢复 Wnt 信号传导，用于在NOTUM 过度活动是潜在原因的体外疾病模型中。用 NOTUM 进行的晶体片段筛选确定 2-苯氧基乙酰胺3与棕榈油酸袋结合，具有适度的抑制活性 (IC 50 33 μM)。由 SBDD 指导的 SAR 研究优化命中3确定了吲唑38 (IC 50 0.032 μM) 和异喹啉45 (IC 500.085 μM) 作为 NOTUM 的有效抑制剂。通过 X 射线共晶体结构测定使45与 NOTUM的结合合理化，该测定显示与3相比翻转的结合方向。然而，不可能将 NOTUM 抑制活性与代谢稳定性结合起来，因为大多数测试的化合物以 NADPH 非依赖性方式快速代谢。
• Novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors
  申请人：Schering Aktiengesellschaft

  公开号：EP1657241A1

  公开（公告）日：2006-05-17

  The invention relates to novel anthranilamide pyridinureas as VEGF receptor kinase inhibitors, their production and use as pharmaceutical agents for treating diseases that are triggered by persistent angiogenesis.

  这项发明涉及新型蒽酰胺吡啶脲作为VEGF受体激酶抑制剂，它们的生产和用作治疗由持续血管生成引发的疾病的药物代理。