N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester | 57699-48-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester
• 英文别名: (4-Hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester；N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid t-butyl ester；N-(4-Hydroxybenzyliden)hydrazincarboxylic acid-tert.-butylester；3-(4-Hydroxybenzyliden)-carbazinsaeure-tert-butylester；Tert-butyl-2-(4-hydroxybenzylidene)hydrazinecarboxylate；tert-butyl N-[(E)-(4-hydroxyphenyl)methylideneamino]carbamate
• CAS: 57699-48-6
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: QMJJNDMTFBIPCW-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  70.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester 在 palladium on activated charcoal 氢气 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以78%的产率得到N-t-butoxycarbonyl-N'-4-hydroxybenzyl hydrazine
  参考文献：
  名称：

  Aza-Peptide Analogs as Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors with Oral Bioavailability

  摘要：

  A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition-state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P-2'P-3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P-3 and an ethyl carbamate in P-3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED(50) values 150-fold following oral application in mice.

  DOI：

  10.1021/jm960022p
• 作为产物：
  描述：

  肼基甲酸叔丁酯 、 对羟基苯甲醛 以 乙醇 为溶剂， 反应 3.0h， 以80%的产率得到N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester
  参考文献：
  名称：

  Aza-Peptide Analogs as Potent Human Immunodeficiency Virus Type-1 Protease Inhibitors with Oral Bioavailability

  摘要：

  A series of aza-peptide analogs with a (hydroxyethyl)hydrazine isostere has been synthesized as HIV-1 protease inhibitors using a simple synthetic scheme. Structure-activity studies based on the X-ray of a previously described inhibitor-enzyme complex led to potent inhibitors with antiviral activity in the low-nanomolar range. The S-configuration of the transition-state hydroxyl group was preferred in this series. Small modifications of the P2P3 and P-2'P-3' substituents had little effect on enzyme inhibition but greatly influenced the pharmacokinetic profile. As a result of these studies, the symmetrically acylated compound 8a and its close analog 24a bearing a methyl carbamate in P-3 and an ethyl carbamate in P-3' position were identified as potent inhibitors with plasma concentrations exceeding antiviral ED(50) values 150-fold following oral application in mice.

  DOI：

  10.1021/jm960022p

文献信息

• Compounds and methods for the treatment of pain
  申请人：——

  公开号：US20030176435A1

  公开（公告）日：2003-09-18

  Compounds useful for the treatment of pain in accord with structural diagram I, 1 or tautomers or pharmaceutically-acceptable salts of such compounds, wherein A, D and R 1 are as disclosed in the specification. Also disclosed are methods for the treatment of pain using compounds according to structural diagram I and pharmaceutical compositions comprising compounds according to structural diagram I.

  本发明涉及用于治疗疼痛的化合物，符合结构图I，1或其互变异构体或药学上可接受的盐，其中A、D和R1如规范中所披露。还披露了使用结构图I中的化合物治疗疼痛的方法以及包含符合结构图I的化合物的制药组合物。
• Methods of treating alzheimer's disease
  申请人：Schostarez Heinrich

  公开号：US20050130941A1

  公开（公告）日：2005-06-16

  Disclosed are methods for treating Alzheimer's disease, and other diseases, and/or inhibiting beta-secretase enzyme, and/or inhibiting deposition of A beta peptide in a mammal, by use of hydrazine compounds of formula (I) wherein the variables R 1 -R 9 are defined herein.

  本发明涉及使用式(I)中变量R1-R9所定义的肼化合物治疗阿尔茨海默病和其他疾病，抑制β-分泌酶酶活性，抑制A beta肽在哺乳动物体内的沉积。
• Substituted 1,2,5,10-tetrahydropyridazino [4,5-b]quinoline-1,10-dione compounds and methods for the treatment of pain
  申请人：Brown Gordon Dean

  公开号：US20050227977A1

  公开（公告）日：2005-10-13

  Compounds useful for the treatment of pain in accord with structural diagram I, or tautomers or pharmaceutically-acceptable salts of such compounds, wherein A, D and R 1 are as disclosed in the specification. Also disclosed are methods for the treatment of pain using compounds according to structural diagram I and pharmaceutical compositions comprising compounds according to structural diagram I.

  本发明涉及一种用于治疗疼痛的化合物，符合结构图I，或其互变异构体或药学上可接受的盐，其中A、D和R1如规范中所披露。还披露了使用符合结构图I的化合物治疗疼痛的方法和包含符合结构图I的化合物的药物组合物。
• Antiretrovirale hydrazinderivate
  申请人：CIBA-GEIGY AG

  公开号：EP0604368A1

  公开（公告）日：1994-06-29

  Beschrieben werden Verbindungen der Formel worin R₁ und R₉ unabhängig voneinander Wasserstoff, Acyl, unsubstituiertes oder substituiertes Alkyl; Sulfo; oder durch unsubstituiertes oder substituiertes Alkyl, Aryl oder Heterocyclyl substituiertes Sulfonyl bedeuten, mit der Massgabe, dass höchstens einer der Reste R₁ und R₉ Wasserstoff bedeutet; und R₂ und R₈ jeweils unabhängig voneinander Wasserstoff oder unsubstituiertes oder substituiertes Alkyl bedeuten; R₃ und R₄ unabhängig voneinander Wasserstoff, unsubstituiertes oder substituiertes Alkyl, unsubstituiertes oder substituiertes Cycloalkyl oder Aryl bedeuten; R₅ Acyloxy bedeutet; R₆ Wasserstoff bedeutet; und R₇ unsubstituiertes oder substituiertes Alkyl, unsubstituiertes oder substituiertes Cycloalkyl oder Aryl bedeutet; sowie Salze der genannten Verbindungen, sofern salzbildende Gruppen vorliegen; diese Verbindungen zeigen antiretrovirale Wirksamkeit.

  式中的化合物 其中 R₁ 和 R𠢙 相互独立地为氢、酰基、未取代或取代的烷基；磺酰基；或被未取代或取代的烷基、芳基或杂环基取代的磺酰基，但 R₁ 和 R𠢙 自由基中最多有一个是氢；R₂ 和 R₈ 相互独立地为氢或未取代或取代的烷基； R₃ 和 R₄ 各自独立地为氢、未取代或取代的烷基、未取代或取代的环烷基或芳基； R₅ 表示酰氧基； R₆ 表示氢； R₇ 表示未取代或取代的烷基、未取代或取代的环烷基或芳基； 以及上述化合物的盐类，只要存在成盐基团；这些化合物具有抗逆转录病毒活性。
• Piperidine derivatives as LTD4 and H1 antagonists
  申请人：KOWA COMPANY, LTD.

  公开号：EP0905134B1

  公开（公告）日：2002-01-16