3-(n-丁氧基)-4-甲氧基苯甲酸酰肼 | 133074-65-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 3-(n-丁氧基)-4-甲氧基苯甲酸酰肼
• 英文名称: 3-(n-butoxy)-4-methoxybenzoic acid hydrazide
• 英文别名: 3-Butoxy-4-methoxybenzohydrazide
• CAS: 133074-65-4
• 化学式: C₁₂H₁₈N₂O₃
• 分子量: 238.287
• InChiKey: UIAUIVWRJZOUCO-UHFFFAOYSA-N

物化性质

• 熔点：
  124-125 °C(Solv: ethanol (64-17-5))
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  73.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(n-丁氧基)-4-甲氧基苯甲酸酰肼 在 sodium hydroxide 作用下， 以 四氢呋喃 为溶剂， 反应 40.0h， 生成 3-(3-丁氧基-4-甲氧基苯基)-4-甲基-1H-1,2,4-三唑-5-酮
  参考文献：
  名称：

  2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents

  摘要：

  A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline cyclization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-triazol-3-ones were then alkylated, yielding 2,4-dialkyl-3H-1,2,4-triazol-3-ones. Approximately one-third of the compounds examined exhibited activity against both maximal electroshock- and pentylenetetrazole-induced seizures in mice. Receptor-binding studies suggest that this activity was not a consequence of activity at either benzodiazepine or NMDA-type glutamate receptors. From this series, compound 45 was selected for further evaluation where it was also found to be active against 3-mercaptopropionic acid, bicuculline, and quinolinic acid induced seizures in mice. In addition, 45 also protected gerbils from hippocampal neuronal degeneration produced by either hypoxia or intrastriatal quinolinic acid injection.

  DOI：

  10.1021/jm00172a015
• 作为产物：
  描述：

  3-羟基-4-甲氧基苯甲酸甲酯 在 potassium carbonate 、 一水合肼 作用下， 以 乙醇 、 丙酮 为溶剂， 反应 10.0h， 生成 3-(n-丁氧基)-4-甲氧基苯甲酸酰肼
  参考文献：
  名称：

  新型 Combretastatin A-4 类似物作为抗有丝分裂抗肿瘤药物的设计、合成、计算机模拟和体外评价

  摘要：

  背景：康布他汀 A-4 (CA-4) 在秋水仙碱结合位点结合 β-微管蛋白，防止微管蛋白聚合成微管。CA-4 和顺式考布他汀类似物异构化为反式，导致细胞毒性和抗微管蛋白活性降低。然而，CA-4优异的抗癌潜力和相对简单的分子结构为开发新的、更稳定和更有效的抗微管蛋白化合物提供了令人鼓舞的起点。目的：本研究旨在合成一系列新的衍生自4-(3,4,5-三甲氧基苯基)-2,4-二氢-3H-1,2,4-三唑-3-硫酮衍生物的化合物(化合物10- 12)在三唑环(B-环)的C5处具有取代的苯基，作为CA-4的类似物，在三唑部分具有不同的烷基和芳基侧链取代基，导致两个苯环的永久顺式构型。此外，还评估了新化合物的抗癌活性。方法：采用常规有机方法进行化学合成。新合成的CA-4类似物通过FT-IR、1HNMR、13CNMR和HR-MS(ESI)技术进行了表征。进行了分子对接研究，包括对接评分 (ΔG)、ADMET、DFT

  DOI：

  10.2174/1573406419666230530155741

文献信息

• 2,4-Dihydro-3H-1,2,4-triazol-3-ones as anticonvulsant agents
  作者：John M. Kane、Bruce M. Baron、Mark W. Dudley、Stephen M. Sorensen、Michael A. Staeger、Francis P. Miller

  DOI：10.1021/jm00172a015

  日期：1990.10

  A series of 5-aryl-2,4-dihydro-3H-1,2,4-triazol-3-ones was evaluated for anticonvulsant activity. In general the members of this series were prepared by the alkaline cyclization of 1-aroyl-4-alkylsemicarbazides. The resulting 2-unsubstituted 3H-1,2,4-triazol-3-ones were then alkylated, yielding 2,4-dialkyl-3H-1,2,4-triazol-3-ones. Approximately one-third of the compounds examined exhibited activity against both maximal electroshock- and pentylenetetrazole-induced seizures in mice. Receptor-binding studies suggest that this activity was not a consequence of activity at either benzodiazepine or NMDA-type glutamate receptors. From this series, compound 45 was selected for further evaluation where it was also found to be active against 3-mercaptopropionic acid, bicuculline, and quinolinic acid induced seizures in mice. In addition, 45 also protected gerbils from hippocampal neuronal degeneration produced by either hypoxia or intrastriatal quinolinic acid injection.
• KANE, JOHN M.;BARON, BRUCE M.;DUDLEY, MARK W.;SORENSEN, STEPHEN M.;STAEGE+, J. MED. CHEM., 33,(1990) N0, C. 2772-2777
  作者：KANE, JOHN M.、BARON, BRUCE M.、DUDLEY, MARK W.、SORENSEN, STEPHEN M.、STAEGE+

  DOI：——

  日期：——
• HUBER, EDWARD W.;KANE, JOHN M., J. HETEROCYCL. CHEM., 27,(1990) N, C. 1957-1961
  作者：HUBER, EDWARD W.、KANE, JOHN M.

  DOI：——

  日期：——
• Huber, Edward W.; Kane, John M., Journal of Heterocyclic Chemistry, 1990, vol. 27, # 7, p. 1957 - 1961
  作者：Huber, Edward W.、Kane, John M.

  DOI：——

  日期：——
• Design, Synthesis, in silico and in vitro Evaluation of New Combretastatin A-4 Analogs as Antimitotic Antitumor Agents
  作者：Shaker A. Abdul Hussein、Ammar Kubba、Asim A. Balakit、Lubna H. Tahtamouni、Ali H. Abbas

  DOI：10.2174/1573406419666230530155741

  日期：2023.12

  triazole ring (B-ring) as analogs of CA-4, with different alkyl and aryl side chain substituents at the triazole moiety, resulting in the permanent cis configuration of the two phenyl rings. Moreover, the anti-cancer activities of the new compounds were assessed. Methods: Chemical synthesis was carried out by conventional organic methods. The newly synthesized CA-4 analogs were characterized by FT-IR

  背景：康布他汀 A-4 (CA-4) 在秋水仙碱结合位点结合 β-微管蛋白，防止微管蛋白聚合成微管。CA-4 和顺式考布他汀类似物异构化为反式，导致细胞毒性和抗微管蛋白活性降低。然而，CA-4优异的抗癌潜力和相对简单的分子结构为开发新的、更稳定和更有效的抗微管蛋白化合物提供了令人鼓舞的起点。目的：本研究旨在合成一系列新的衍生自4-(3,4,5-三甲氧基苯基)-2,4-二氢-3H-1,2,4-三唑-3-硫酮衍生物的化合物(化合物10- 12)在三唑环(B-环)的C5处具有取代的苯基，作为CA-4的类似物，在三唑部分具有不同的烷基和芳基侧链取代基，导致两个苯环的永久顺式构型。此外，还评估了新化合物的抗癌活性。方法：采用常规有机方法进行化学合成。新合成的CA-4类似物通过FT-IR、1HNMR、13CNMR和HR-MS(ESI)技术进行了表征。进行了分子对接研究，包括对接评分 (ΔG)、ADMET、DFT