3-(3,4,5-trimethoxyphenyl)propanoylhydrazine | 257284-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 3-(3,4,5-trimethoxyphenyl)propanoylhydrazine
• 英文别名: 3-(3,4,5-trimethoxyphenyl)propanohydrazide；3-(3,4,5-trimethoxyphenyl)propionylhydrazide；3-(3,4,5-Trimethoxyphenyl)propanehydrazide
• CAS: 257284-96-1
• 化学式: C₁₂H₁₈N₂O₄
• mdl: MFCD00126654
• 分子量: 254.286
• InChiKey: BLDQAECFPICFAM-UHFFFAOYSA-N

物化性质

• 熔点：
  122-125 °C(Solv: ethanol (64-17-5))
• 沸点：
  454.3±45.0 °C(Predicted)
• 密度：
  1.153±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 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：
  82.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(3,4,5-trimethoxyphenyl)propanoylhydrazine 在 Celite 、 碳酸氢钠 、 silver carbonate 作用下， 以 二氯甲烷 、 苯 为溶剂， 生成 methyl (7,9-dimethoxy-2,8-dioxo-1-azaspiro[4.5]deca-6,9-dien-1-yl)carbamate
  参考文献：
  名称：

  Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

  摘要：

  适当的芳基取代的不对称二羧肼化合物通过氧化从双肼酰胺生成，发生分子内环化，生成各种有用的杂环化合物，如N-取代的氧杂吲哚、羧基醇、苯并氮杂哌啶、苯并氮杂呋喃、苯并咪唑酮、苯并氧杂噁唑和吡唑酮，效率各不相同。文中描述了去除杂芳香化合物中N-酰基基团的方法。在弱酸性条件下，当存在相等机会进行ipso或正常环化时，前者过程优先发生。证据支持在ipso产物中发生C到C的迁移，用于形成甲氧基取代的羧基醇衍生物。显示出某个螺旋物质参与二烯酮–酚重排，以高产率生成相应的喹啉–酚。

  DOI：

  10.1039/b110414d
• 作为产物：
  描述：

  methyl 3-(3,4,5-trimethoxyphenyl)propionate 在 一水合肼 作用下， 以85%的产率得到3-(3,4,5-trimethoxyphenyl)propanoylhydrazine
  参考文献：
  名称：

  Intramolecular addition of acyldiazenecarboxylates onto double bonds in the synthesis of heterocycles

  摘要：

  适当的芳基取代的不对称二羧肼化合物通过氧化从双肼酰胺生成，发生分子内环化，生成各种有用的杂环化合物，如N-取代的氧杂吲哚、羧基醇、苯并氮杂哌啶、苯并氮杂呋喃、苯并咪唑酮、苯并氧杂噁唑和吡唑酮，效率各不相同。文中描述了去除杂芳香化合物中N-酰基基团的方法。在弱酸性条件下，当存在相等机会进行ipso或正常环化时，前者过程优先发生。证据支持在ipso产物中发生C到C的迁移，用于形成甲氧基取代的羧基醇衍生物。显示出某个螺旋物质参与二烯酮–酚重排，以高产率生成相应的喹啉–酚。

  DOI：

  10.1039/b110414d

文献信息

• Neurotrophic pyrrolidines and piperidines, and related compositions and methods
  申请人：Ortho-McNeil Pharmaceutical, Inc.

  公开号：US06809107B1

  公开（公告）日：2004-10-26

  This invention provides compounds having the following general structures: This invention also provides pharmaceutical compositions comprising same and methods of using these compositions to treat and prevent disorders characterized by neuronal damage.

  这项发明提供具有以下一般结构的化合物：这项发明还提供包含相同化合物的药物组合物，以及使用这些组合物治疗和预防由神经元损伤所特征化的疾病的方法。
• Synthesis, Acetylcholinesterase and Alkaline Phosphatase Inhibition of Some New 1,2,4-Triazole and 1,3,4-Thiadiazole Derivatives
  作者：Imtiaz Khan、Muhammad Hanif、Muhammad Tahir Hussain、Aftab Ahmed Khan、Muhammad Adil S. Aslam、Nasim Hasan Rama、Jamshed Iqbal

  DOI：10.1071/ch12134

  日期：——

  and alkaline phosphatase inhibition studies. Most of the tested compounds showed promising activities, amongst them (6k) and (6q) showed excellent acetylcholinesterase inhibitory activity with IC50 0.241 ± 0.012 and 0.260 ± 0.013 µM, respectively, as compared with those of standard drug whereas the compound (6p), with IC50 0.044 ± 0.001 µM, was found to be the most potent inhibitor of alkaline phosphatase

  一个新的4,5-二取代-2,4-二氢-3 H -1,2,4-三唑-3-硫酮（6a – s）和2,5-二取代-1,3,4-噻二唑（通过在4 N氢氧化钠水溶液中回流和分别与多磷酸搅拌过夜，将各种1,4-二取代的硫代氨基脲衍生物（5a - s）进行分子内脱氢环化反应，合成7a - h）。这些化合物的结构由IR，1 H和13表征13 C NMR，元素分析和质谱研究。筛选所有合成的化合物的乙酰胆碱酯酶和碱性磷酸酶抑制研究。大多数所测试的化合物显示有希望的活动，在他们之中（6K）和（6Q）表现出优异的乙酰胆碱酯酶抑制活性用IC 50 0.241±0.012和0.260±0.013μM，分别作为与标准药物的，而化合物（比较6P） IC 50为0.044±0.001 µM，是最有效的碱性磷酸酶抑制剂。
• Synthesis, Urease and Acetylcholine Esterase Inhibition Activities of Some 1,4-Disubstituted Thiosemicarbazides and their 2,5-Disubstituted Thiadiazoles
  作者：Muhammad Saleem、Muhammad Rafiq、Muhammad Hanif、Nasim Hasan Rama、Sung-Yum Seo、Ki-Hwan Lee

  DOI：10.5012/bkcs.2012.33.8.2741

  日期：2012.8.20

  A new series of 2,5-disubstituted-1,3,4-thiadiazoles 6a-i was synthesized by overnight stirring various 1,4-disubstituted thiosemicarbazides 5a-i in polyphosphoric acid followed by neutralization. The structures of newly synthesized compounds 5a-i and 6a-i were characterized by IR, $^1H$ and $^13}C$ NMR, elemental analysis and mass spectrometric studies. All the synthesized compounds were evaluated for their urease and acetylcholine esterase inhibition activities. Thiosemicarbazides 5a-i are found to possess excellent potential for urease inhibition, more than the standard drug. Thiosemicarbazides 5a-i are more potent urease inhibitor than their cyclic analogues thiadiazoles 6a-i. Almost all of the compounds are excellent inhibitors of acetylcholine esterase. The inhibition of acetylcholine esterase of compounds 5a, 5c, 5d, 5g, 5i, 6e, 6f, 6g, and 6i is much more than that of standard drug.

  通过将各种 1,4-二取代的硫代氨基甲酸 5a-i 在多磷酸中搅拌过夜并中和，合成了一系列新的 2,5-二取代-1,3,4-噻二唑 6a-i。通过红外光谱、$^1H$和$^13}C$核磁共振、元素分析和质谱研究对新合成的化合物 5a-i 和 6a-i 的结构进行了表征。对所有合成化合物的脲酶和乙酰胆碱酯酶抑制活性进行了评估。研究发现，硫代氨基脲 5a-i 具有比标准药物更强的抑制脲酶的潜力。与环状类似物噻二唑 6a-i 相比，硫代氨基脲 5a-i 是更有效的尿素酶抑制剂。几乎所有化合物都是乙酰胆碱酯酶的出色抑制剂。化合物 5a、5c、5d、5g、5i、6e、6f、6g 和 6i 对乙酰胆碱酯酶的抑制作用远高于标准药物。
• Structure–activity study on a series of α-glutamic acid scaffold based compounds as new ADAMTS inhibitors
  作者：Lijie Peng、Lei Duan、Xiaofeng Liu、Mengjie Shen、Yingjun Li、Jiajie Yan、Honglin Li、Ke Ding

  DOI：10.1016/j.bmcl.2011.06.009

  日期：2011.8

  A series of alpha-glutamic acid scaffold based 4-(benzamido)-4-(1,3,4-oxadiazol-2-yl) butanoic acids were designed and synthesized as new ADAMTS inhibitors. The compounds dose-dependently inhibited the enzymatic activities of ADAMTS-4 and ADAMTS-5. One of the most active compound 2h potently inhibited ADAMTS-4 and ADAMTS-5 with IC(50) values of 1.2 and 0.8 mu M, respectively. These inhibitors may serve as new lead compounds for further development of therapeutics to treat osteoarthritis. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel Heterobivalent Tacrine Derivatives as Cholinesterase Inhibitors with Notable Selectivity Toward Butyrylcholinesterase
  作者：Paul W. Elsinghorst、Camino M. González Tanarro、Michael Gütschow

  DOI：10.1021/jm060742o

  日期：2006.12.1

  Two series of novel heterobivalent tacrine derivatives were synthesized. A trimethoxy substituted benzene was linked to the tacrine moiety by a hydrazide-based linker. The compounds were evaluated as cholinesterase inhibitors, and trimethoxybenzoic acid derivatives with 11- or 12-atom spacers were the most potent inhibitors of human acetylcholinesterase. The inhibitors showed a surprising selectivity toward human butyrylcholinesterase, where several trimethoxyphenylpropionic acid derivatives had IC50 values less than 250 mu M.