5-Hydroxy-3-(o-nitrobenzyl)-1,2,4-triazole | 95614-38-3

• 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: 5-Hydroxy-3-(o-nitrobenzyl)-1,2,4-triazole
• 英文别名: 3-[(2-nitrophenyl)methyl]-1,4-dihydro-1,2,4-triazol-5-one
• CAS: 95614-38-3
• 化学式: C₉H₈N₄O₃
• 分子量: 220.188
• InChiKey: RWALGXNMKVIWJC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  99.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-Hydroxy-3-(o-nitrobenzyl)-1,2,4-triazole 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 以100%的产率得到3-[(2-Aminophenyl)methyl]-1,4-dihydro-1,2,4-triazol-5-one
  参考文献：
  名称：

  Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  We have discovered selective and potent inhibitors of TACE that replace the common hydroxamate zinc binding group with a hydantoin, triazolone, and imidazolone heterocycle. These novel heterocyclic inhibitors of a zinc metalloprotease were designed using a pharmacophore model that we previously described while developing hydantoin and pyrimidinetrione (barbiturate) inhibitors of TACE. The potency and binding orientation of these inhibitors is discussed and they are modeled into the X-ray crystal structure of TACE and compared to hydroxamate and earlier hydantoin TACE inhibitors which share the same 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl Pl' group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.076
• 作为产物：
  描述：

  邻硝基苯乙腈 在 N-甲基吗啉 、 盐酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 5-Hydroxy-3-(o-nitrobenzyl)-1,2,4-triazole
  参考文献：
  名称：

  Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)

  摘要：

  We have discovered selective and potent inhibitors of TACE that replace the common hydroxamate zinc binding group with a hydantoin, triazolone, and imidazolone heterocycle. These novel heterocyclic inhibitors of a zinc metalloprotease were designed using a pharmacophore model that we previously described while developing hydantoin and pyrimidinetrione (barbiturate) inhibitors of TACE. The potency and binding orientation of these inhibitors is discussed and they are modeled into the X-ray crystal structure of TACE and compared to hydroxamate and earlier hydantoin TACE inhibitors which share the same 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl Pl' group. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2007.02.076

文献信息

• Diazacycloalkyl-1,2,4-triazolo[2,3-c][1,3]benzodiazepines useful as
  申请人：Ciba-Geigy Corporation

  公开号：US04595535A1

  公开（公告）日：1986-06-17

  Described are 5-diazacycloalkyltriazolo[2,3-c][1,3]benzodiazepines, for example compounds of the formula ##STR1## wherein R.sub.1 represents hydrogen, halogen, trifluoromethyl, lower alkylthio, lower alkoxy or lower alkyl; R.sub.2 represents hydrogen, lower alkyl or hydroxy-C.sub.2 -C.sub.7 alkyl wherein the hydroxy group is separated from the nitrogen atom by at least 2 carbon atoms; R.sub.3 represents hydrogen, lower alkyl, lower alkoxy, lower alkylthio, halogen or trifluoromethyl; and C.sub.n H.sub.2n represents ethylene. The synthesis, pharmaceutical compositions and methods of use as neuroleptic and/or antihistaminic agents are given.

  本文描述了5-二氮杂环己基三唑并[2,3-c][1,3]苯二氮平类化合物，例如式中的化合物：##STR1## 其中R.sub.1代表氢、卤素、三氟甲基、较低的烷基硫、较低的烷氧基或较低的烷基；R.sub.2代表氢、较低的烷基或羟基-C.sub.2-C.sub.7烷基，其中羟基与氮原子至少相隔2个碳原子；R.sub.3代表氢、较低的烷基、较低的烷氧基、较低的烷基硫、卤素或三氟甲基；C.sub.n H.sub.2n代表乙烯基。给出了制备方法、制药组合物和作为神经精神药和/或抗组胺药使用的方法。
• Triazol(2,3-c)(1,3)benzodiazepine, Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend diese Verbindungen, sowie ihre therapeutische Verwendung
  申请人：CIBA-GEIGY AG

  公开号：EP0129509A2

  公开（公告）日：1984-12-27

  Die Erfindung betrifft psychoaktive und antiallergische Verbindungen der Formal worin R, Wasserstoff, Niederalkylthio, Amino, (Acyl, Mono-oder Diniederalkyl)-amino, Niederalkoxy, Acyloxy, Niederalkyl, Niederalkanoyl, Hydroxy, Halogen, Trifluormethyl, Cyano, Carboxy, Niederalkoxycarbonyl, Carbamoyl, Mono-oder Diniederalkylcarbamoyl, Hydroxyniederalkyl oder Diniederalkylamino-niederalkyl bedeutet; CnH2n für Niederalkylen steht, welches die zwei Stickstoffatome durch 2 oder 3 Kohlenstoffatome trennt; R2 für Wasserstoff, Niederalkyl, Niederalkenyl, Niederalkinyl, Niederalkanoyl, Arylniederalkyl, Niederalkoxycarbonyl, Phenylniederalkoxycarbonyl oder (Hydroxy, Niederalkanoyloxy, Aryloxy oder Niederalkyloxy) -nieder -alkyl steht, worin der Niederalkylrest mindestens zwei Kohlenstoffatome enthält; R3 und R. unabhängig voneinander Wasserstoff, Niederalkyl, Niederalkoxy, Niederalkylthio, Halogen, Trifluormethyl, Hydroxy, Niederalkanoyloxy, Sulfamoyl, Mono- oder Diniederalkylsulfamoyl; und Rs und R6 Wasserstoff oder Niederalkyl bedeuten; ihre N-Oxide, und Salze, insbesondere therapeutisch verwendbaren Salze mit Säuren oder Basen, von all diesen Verbindungen, sowie Verfahren zu ihrer Herstellung, pharmazeutische Präparate enthaltend, diese Verbindungen, sowie ihre therapeutische Verwendung.

  本发明涉及以下形式的精神活性和抗过敏化合物 其中 R 是氢、低级烷硫基、氨基、（酰基、单或双低级烷基）-氨基、低级烷氧基、酰氧基、低级烷基、低级烷酰基、羟基、卤素、三氟甲基、氰基、羧基、低级烷氧基羰基、氨基甲酰基、单或双低级烷基氨基甲酰基、羟基-低级烷基或双低级烷基氨基-低级烷基；R2 是氢、低级烷基、低级烯基、低级炔基、低级烷酰基、芳基低级烷基、低级烷氧基羰基、苯基低级烷氧基羰基或（羟基、低级烷酰氧基、芳氧基或低级烷氧基）低级烷基，其中低级烷基分子至少含有两个碳原子；R3 和 R.A 相互独立地代表氢、低级烯基、低级炔基、低级烷酰基、芳基低级烷基、低级烷氧基羰基、苯基低级烷氧基羰基或（羟基、低级烷酰氧基、芳氧基或低级烷氧基）低级烷基。分别代表氢、低级烷基、低级烷氧基、低级烷硫基、卤素、三氟甲基、羟基、低级烷酰氧基、氨基磺酰基、单或双低级烷基氨基磺酰基；Rs 和 R6 代表氢或低级烷基；所有这些化合物的 N-氧化物和盐，特别是可用于治疗的酸或碱盐，以及它们的制备工艺、含有这些化合物的药物组合物及其治疗用途。
• US4595535A
  申请人：——

  公开号：US4595535A

  公开（公告）日：1986-06-17
• Hydantoins, triazolones, and imidazolones as selective non-hydroxamate inhibitors of tumor necrosis factor-α converting enzyme (TACE)
  作者：James E. Sheppeck、John L. Gilmore、Andrew Tebben、Chu-Biao Xue、Rui-Qin Liu、Carl P. Decicco、James J.-W. Duan

  DOI：10.1016/j.bmcl.2007.02.076

  日期：2007.5

  We have discovered selective and potent inhibitors of TACE that replace the common hydroxamate zinc binding group with a hydantoin, triazolone, and imidazolone heterocycle. These novel heterocyclic inhibitors of a zinc metalloprotease were designed using a pharmacophore model that we previously described while developing hydantoin and pyrimidinetrione (barbiturate) inhibitors of TACE. The potency and binding orientation of these inhibitors is discussed and they are modeled into the X-ray crystal structure of TACE and compared to hydroxamate and earlier hydantoin TACE inhibitors which share the same 4-[(2-methyl-4-quinolinyl)methoxy]benzoyl Pl' group. (c) 2007 Elsevier Ltd. All rights reserved.