3-hydroxy-4-methoxy-benzaldehyde-semicarbazone | 115213-68-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 3-hydroxy-4-methoxy-benzaldehyde-semicarbazone
• 英文别名: 3-Hydroxy-4-methoxy-benzaldehyd-semicarbazon；[(3-Hydroxy-4-methoxyphenyl)methylideneamino]urea
• CAS: 115213-68-8
• 化学式: C₉H₁₁N₃O₃
• mdl: MFCD04070197
• 分子量: 209.205
• InChiKey: FBAOWSXIQQAPRP-UHFFFAOYSA-N

物化性质

• 熔点：
  212 °C (decomp)
• 密度：
  1.34±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.111
• 拓扑面积：
  96.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-hydroxy-4-methoxy-benzaldehyde-semicarbazone 在 磷酸 作用下， 反应 0.01h， 以56%的产率得到异香兰素
  参考文献：
  名称：

  Banerjee, Krishna; Mitra, Alok Kumar; Patra, Amarendra, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2006, vol. 45, # 2, p. 537 - 539

  摘要：

  DOI：
• 作为产物：
  描述：

  异香兰素 生成 3-hydroxy-4-methoxy-benzaldehyde-semicarbazone
  参考文献：
  名称：

  Aiding chronic written language expression difficulties: A case study

  摘要：

  This paper describes some progress made in helping a young aphasic man (MD) to overcome what had appeared to be intractable written language expression difficulties, which continued to be significant for him. Traditional therapy methods based on cognitive neuropsychological assessment had failed to help MD to generalize improvement in his spelling particularly, but not exclusively, of longer and irregular words. Both a splint which allowed him to use his dominant hand for writing directly onto a computer screen and a simple word-processing programme with synthesized auditory feedback and lexical and grammatical prediction (Write:OutLoud(R) and Co:Writer(R)) enabled him to produce more normal written output (increased quantity and more normal quality). The discussion also focuses on how effectiveness of language therapy can be measured in this man with chronic aphasia.

  DOI：

  10.1080/026870300401612

文献信息

• Spectroscopic Elucidation of Some Complexes of Vanillin Semicarbazone
  作者：Navneet Sinha、Rajnish Kumar、Vijay Pratap Singh、Deepak KUMAR、Shivadhar Sharma

  DOI：10.13005/ojc/370409

  日期：2021.8.30

  3-Phenyl-4-methoxybenzaldehyde undergoes condensation with semicarbazide hydrochloride to form a Schiff-base i.e. 3-phenyl-4-methoxybenzaldehyde semicarbazone (abbreviated as MBS). It undergoes complexation with Vanadium(II), Manganese(II), and Copper(II). The comparison of FTIR-spectra of complexes with that of free ligand helps ascertain the coordination points of ligand through the nitrogen of –CH=N– group and oxygen of group. The axial ligands have been varied by chloride, acetate and nitrate ions. The UV/Visible and ESR spectra of complexes predicts their tetragonally distorted octahedral (D4h) symmetry. The tetragonal distortion parameter (Dt) is observed maximum for chloride while it is minimum for nitrate along z-axis. Both vanillin and semicarbazide are established biologically active compounds and hence their biological activities may be enhanced by their complexation and than a versatile field may be developed for further exploration.

  3-苯基-4-甲氧基苯甲醛与盐酸异半胱氨酸甲酯发生缩合反应，形成一种席夫碱，即3-苯基-4-甲氧基苯甲醛异半胱氨酸脲（简称MBS）。它与钒（II）、锰（II）和铜（II）发生络合反应。通过比较络合物的傅立叶变换红外光谱与游离配体的光谱，可以确定通过-CH=N-基团的氮原子和氧原子的配位点。轴向配体通过氯离子、乙酸根离子和硝酸根离子进行变化。络合物的紫外/可见光谱和电子自旋共振谱预测其具有四方畸变八面体（D4h）对称性。四方畸变参数（Dt）在氯离子的情况下观察到最大值，而在沿z轴的硝酸根离子的情况下观察到最小值。香草醛和异半胱氨酸脲均为已知的生物活性化合物，因此它们的生物活性可能通过它们的络合作用而得到增强，从而为进一步探索开发一个多功能领域奠定基础。
• Synthesis, SAR elucidations and molecular docking study of newly designed isatin based oxadiazole analogs as potent inhibitors of thymidine phosphorylase
  作者：Muhammad Tariq Javid、Fazal Rahim、Muhammad Taha、Mohsan Nawaz、Abdul Wadood、Muhammad Ali、Ashik Mosaddik、Syed Adnan Ali Shah、Rai Khalid Farooq

  DOI：10.1016/j.bioorg.2018.05.011

  日期：2018.9

  cell survival. Thus TP is identified as a prime target for developing novel anticancer therapies. A new class of exceptionally potent isatin based oxadiazole (1–30) has been synthesized and evaluated for thymidine phosphorylase inhibitory potential. All analogs showed potent thymidine phosphorylase inhibition when compared with standard 7-Deazaxanthine, 7DX (IC50 = 38.68 ± 1.12 µM). Molecular docking study

  胸苷磷酸化酶是参与嘧啶挽救途径的酶，与血小板衍生的内皮细胞生长因子（PD-ECGF）和gliostatin相同。它在各种实体瘤中都被极大地上调。此外，超过TP水平可保护肿瘤细胞免于凋亡并帮助细胞存活。因此，TP被确定为开发新型抗癌疗法的主要靶标。一类新的特别有效的靛红基于恶二唑（的1 - 30）已被合成并评价了胸苷磷酸化酶抑制潜力。与标准7-地塞黄嘌呤7DX（IC 50）相比，所有类似物均显示有效的胸苷磷酸化酶抑制作用 = 38.68±1.12 µM）。进行分子对接研究以确定这些新合成的化合物的结合相互作用，这表明与标准化合物7DX相比，这些合成的化合物建立了更强的氢键网络，具有残基的活性位点。
• Synthesis, In vitro α-Glucosidase Inhibitory Potential and Molecular Docking Studies of 2-Amino-1,3,4-Oxadiazole Derivatives
  作者：Hayat Ullah、Fazal Rahim、Muhammad Taha、Raffaqat Hussain、Abdul Wadood、Mohsan Nawaz、Zainul Wahab、Kanwal、Khalid M. Khan

  DOI：10.2174/1573406415666190612150447

  日期：2020.9.7

  In the recent past, we have synthesized and reported different derivatives of oxadiazoles as potential α-glucosidase inhibitors, keeping in mind, the pharmacological aspects of oxadiazole moiety and in continuation of our ongoing research on the chemistry and bioactivity of new heterocyclic compounds.

  1,3,4-Oxadiazole derivatives (1-14) have been synthesized and characterized by different spectroscopic techniques such as 1H-, 13C-NMR and HREI-MS.

  The synthetic derivatives were screened for α-glucosidase inhibitory potential. All compounds exhibited good inhibitory activity with IC50 values ranging between 0.80 ± 0.1 to 45.1 ± 1.7 μM in comparison with the standard acarbose having IC50 value 38.45 ± 0.80 μM.

  Thirteen compounds 1-6 and 8-14 showed potential inhibitory activity as compared to the standard acarbose having IC50 value 38.45 ± 0.80 μM, however, only one compound 7 (IC50 = 45.1 ± 1.7 μM) was found to be less active. Compound 14 (IC50 = 0.80 ± 0.1 μM) showed promising inhibitory activity among all synthetic derivatives. Molecular docking studies were also conducted for the active compounds to understand the ligand-enzyme binding interactions.

  背景：最近，我们合成并报告了不同的氧代二唑衍生物作为潜在的α-葡萄糖苷酶抑制剂，考虑到氧代二唑基团的药理学方面，并延续我们对新异环化合物的化学和生物活性研究。 方法：合成和表征了1,3,4-氧代二唑衍生物（1-14），并通过不同的光谱技术如1H-、13C-NMR和HREI-MS进行了表征。 结果：合成的衍生物被筛选用于α-葡萄糖苷酶抑制潜力。所有化合物在抑制活性方面表现出良好的活性，IC50值在0.80±0.1至45.1±1.7μM之间，与标准药物阿卡波糖的IC50值38.45±0.80μM相比。 结论：化合物1-6和8-14中的十三种化合物显示出潜在的抑制活性，与具有IC50值38.45±0.80μM的标准药物阿卡波糖相比，然而，只有一种化合物7（IC50=45.1±1.7μM）显示出较低的活性。化合物14（IC50=0.80±0.1μM）在所有合成衍生物中表现出有希望的抑制活性。还进行了活性化合物的分子对接研究，以了解配体-酶结合相互作用。
• Karchaudhuri, Nilay; De, Aparna; Mitra, Alok Kumar, Journal of the Indian Chemical Society, 2004, vol. 81, # 1, p. 79 - 81
  作者：Karchaudhuri, Nilay、De, Aparna、Mitra, Alok Kumar

  DOI：——

  日期：——
• Banerjee, Krishna; Mitra, Alok Kumar, Journal of the Indian Chemical Society, 2003, vol. 80, # 3, p. 184 - 186
  作者：Banerjee, Krishna、Mitra, Alok Kumar

  DOI：——

  日期：——