N-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone | 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-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone
• 英文别名: 4-hydroxybenzaldehyde-tert-butoxycarbonylhydrazone；3-(4-Hydroxybenzyliden)-carbazinsaeure-tert-butylester；N'-(4-hydroxy-benzylidene)-hydrazinecarboxylic acid tert-butyl ester；tert-butyl N-[(4-hydroxyphenyl)methylideneamino]carbamate
• CAS: 57699-48-6
• 化学式: C₁₂H₁₆N₂O₃
• 分子量: 236.271
• InChiKey: QMJJNDMTFBIPCW-UHFFFAOYSA-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-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone 在 palladium on activated charcoal ammonium formate 、 三乙胺 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 1.5h， 生成 N-t-butoxycarbonyl-azatyrosine ethyl ester
  参考文献：
  名称：

  Wieczerzak; Kozlowska; Lankiewicz, Polish Journal of Chemistry, 2002, vol. 76, # 12, p. 1693 - 1697

  摘要：

  DOI：
• 作为产物：
  描述：

  对羟基苯甲醛 以 乙醇 为溶剂， 生成 N-t-butoxycarbonyl-N'-4-hydroxybenzaldehyde hydrazone
  参考文献：
  名称：

  Antiretroviral hydrazine derivatives

  摘要：

  本发明涉及具有公式##STR1##的化合物及其盐、药物组合物、中间体及其制备方法。

  公开号：

  US05753652A1

文献信息

• Synthesis and Biological Evaluation of Hydrazone Derivatives as Antifungal Agents
  作者：Bruna Casanova、Mauro Muniz、Thayse de Oliveira、Luís de Oliveira、Michel Machado、Alexandre Fuentefria、Grace Gosmann、Simone Gnoatto

  DOI：10.3390/molecules20059229

  日期：——

  Emerging yeasts are among the most prevalent causes of systemic infections with high mortality rates and there is an urgent need to develop specific, effective and non-toxic antifungal agents to respond to this issue. In this study 35 aldehydes, hydrazones and hydrazines were obtained and their antifungal activity was evaluated against Candida species (C. parapsilosis, C. tropicalis, C. krusei, C. albicans, C. glabrata and C. lusitaneae) and Trichosporon asahii, in an in vitro screening. The minimum inhibitory concentrations (MICs) of the active compounds in the screening was determined against 10 clinical isolates of C. parapsilosis and 10 of T. asahii. The compounds 4-pyridin-2-ylbenzaldehyde] (13a) and tert-butyl-(2Z)-2-(3,4,5-trihydroxybenzylidine)hydrazine carboxylate (7b) showed the most promising MIC values in the range of 16–32 μg/mL and 8–16 μg/mL, respectively. The compounds’ action on the stability of the cell membrane and cell wall was evaluated, which suggested the action of the compounds on the fungal cell membrane. Cell viability of leukocytes and an alkaline comet assay were performed to evaluate the cytotoxicity. Compound 13a was not cytotoxic at the active concentrations. These results support the discovery of promising candidates for the development of new antifungal agents.

  新兴酵母菌是系统性感染中最常见的病原体之一，死亡率极高，因此迫切需要开发具有特异性、有效且无毒的抗真菌药物来应对这一问题。本研究中，我们获得了35种醛类、肼类和酰肼类化合物，并在体外筛选中评估了它们对Candida属（C. parapsilosis、C. tropicalis、C. krusei、C. albicans、C. glabrata和C. lusitaneae）和Trichosporon asahii的抗真菌活性。我们对筛选出的活性化合物对10株临床分离的C. parapsilosis和10株T. asahii的最低抑菌浓度（MICs）进行了测定。化合物4-吡啶-2-基苯甲醛（13a）和叔丁基-(2Z)-2-(3,4,5-三羟基苄脒)酰肼羧酸酯（7b）分别在16-32 μg/mL和8-16 μg/mL的范围内显示出最有希望的MIC值。我们评估了这些化合物对细胞膜和细胞壁稳定性的影响，结果表明这些化合物作用于真菌细胞膜。通过细胞活力测定和碱性彗星试验评价了其细胞毒性。化合物13a在活性浓度下不具有细胞毒性。这些结果支持了发现有希望的候选药物用于开发新型抗真菌药物。
• Phenolic Hydrazones Are Potent Inhibitors of Macrophage Migration Inhibitory Factor Proinflammatory Activity and Survival Improving Agents in Sepsis
  作者：Darrin R. Dabideen、Kai Fan Cheng、Bayan Aljabari、Edmund J. Miller、Valentin A. Pavlov、Yousef Al-Abed

  DOI：10.1021/jm061477+

  日期：2007.4.1

  A series of phenolic hydrazones were synthesized and evaluated for their inhibition of macrophage migration inhibitory factor (MIF) tautomerase activity. Compound 7 emerged as a potent inhibitor of MIF with an IC50 of 130 nM. Compound 7 dose-dependently suppressed TNFalpha secretion from lipopolysaccharide stimulated macrophages. The therapeutic importance of the MIF inhibition by 7 is demonstrated

  合成了一系列酚，并评估了它们对巨噬细胞迁移抑制因子（MIF）互变异构酶活性的抑制作用。化合物7作为MIF的有效抑制剂出现，IC50为130 nM。化合物7剂量依赖性地抑制了脂多糖刺激的巨噬细胞的TNFα分泌。当在临床相关的时间范围内开始施用该化合物时，通过显着保护免受败血症致死性的作用证明了MIF抑制7的治疗重要性。
• 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。