(E)-3-((4-hydroxy-3-methoxybenzylidene)amino)-2-thioxothiazolidin-4-one | 99985-12-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: (E)-3-((4-hydroxy-3-methoxybenzylidene)amino)-2-thioxothiazolidin-4-one
• 英文别名: 3-[(4-Hydroxy-3-methoxybenzylidene)amino]-2-thioxo-1,3-thiazolidin-4-one；3-[(E)-(4-hydroxy-3-methoxyphenyl)methylideneamino]-2-sulfanylidene-1,3-thiazolidin-4-one
• CAS: 99985-12-3
• 化学式: C₁₁H₁₀N₂O₃S₂
• 分子量: 282.344
• InChiKey: PAGIJQUQUHPMBS-LFYBBSHMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  120
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  N-氨基绕丹宁 、 香草醛 以 乙醇 为溶剂， 以76%的产率得到(E)-3-((4-hydroxy-3-methoxybenzylidene)amino)-2-thioxothiazolidin-4-one
  参考文献：
  名称：

  绿色合成和新型N-取代的罗丹宁类分子的对接，可作为碳酸酐酶和乙酰胆碱酯酶的有效抑制剂。

  摘要：

  近来，诸如乙酰胆碱酯酶（AChE）和碳酸酐酶（CA）之类的酶的抑制作用已显示出是对多种疾病例如癫痫，阿尔茨海默氏病和肥胖症进行药理学干预的有前途的方法。为此目的，通过绿色合成方法在一锅反应中合成了新颖的N-取代的罗丹宁衍生物（RhAs）。合成新化合物后，对RhAs衍生物针对AChE和胞质碳酸酐酶I和II（hCA I和II）同工型进行了测试。这项研究的结果是，对AChE的抑制常数（Ki）为66.35±8.35至141.92±12.63 nM，对于hCA I为43.55±14.20至89.44±24.77 nM，而16.97±1.42至64.57±13.27 nM分别用于hCA II。通过对接研究计算结合能为-5.969，-5.981和-9。

  DOI：

  10.1016/j.bioorg.2019.103096

文献信息

• Syntheses, in vitro, and in silico studies of rhodanine-based schiff bases as potential α-amylase inhibitors and radicals (DPPH and ABTS) scavengers
  作者：Samuel Attah Egu、Irfan Ali、Khalid Mohammed Khan、Sridevi Chigurupati、Urooj Qureshi、Uzma Salar、Muhammad Taha、Shatha Ghazi Felemban、Vijayan Venugopal、Zaheer Ul-Haq

  DOI：10.1007/s11030-022-10454-0

  日期：——

  A two-step reaction method was used to synthesize a series of rhodanine-based Schiff bases (2–33) that were characterized using spectroscopic techniques. All compounds were assessed for α-amylase inhibitory and radical scavenging (DPPH and ABTS) activities. In comparison to the standard acarbose (IC50 = 9.08 ± 0.07 µM), all compounds demonstrated good to moderate α-amylase inhibitory activity (IC50 = 10.91 ± 0.08–61.89 ± 0.102 µM). Compounds also demonstrated significantly higher DPPH (IC50 = 10.33 ± 0.02–96.65 ± 0.03 µM) and ABTS (IC50 = 12.01 ± 0.12–97.47 ± 0.13 µM) radical scavenging activities than ascorbic acid (DPPH, IC50 = 15.08 ± 0.03 µM; ABTS, IC50 = 16.09 ± 0.17 µM). The limited structure-activity relationship (SAR) suggests that the position and nature of the substituted groups on the phenyl ring have a vital role in varying inhibitory potential. Among the series, compounds with an electron-withdrawing group at the para position showed the highest potency. Kinetic studies revealed that the compounds followed a competitive mode of inhibition. Molecular docking results are found to agree with experimental findings, showing that compounds reside in the active pocket due to the main rhodanine moiety.

  采用两步反应法合成了一系列基于罗丹宁的席夫碱（2-33），并利用光谱技术对其进行了表征。对所有化合物进行了α-淀粉酶抑制和自由基清除（DPPH和ABTS）活性评估。与标准药物阿卡波糖（IC50=9.08±0.07µM）相比，所有化合物均表现出良好至中等的α-淀粉酶抑制活性（IC50=10.91±0.08-61.89±0.102µM）。与抗坏血酸（DPPH，IC50=15.08±0.03µM；ABTS，IC50=16.09±0.17µM）相比，这些化合物还表现出显著更高的DPPH（IC50=10.33±0.02-96.65±0.03µM）和ABTS（IC50=12.01±0.12-97.47±0.13µM）自由基清除活性。有限的构效关系（SAR）表明，苯环上取代基的位置和性质对抑制潜力的变化起着至关重要的作用。在该系列化合物中，对位具有吸电子基团的化合物表现出最强的效力。动力学研究表明，这些化合物遵循竞争抑制模式。分子对接
• Sandstroem, Arkiv foer Kemi, 1956, vol. 8, p. 487,502
  作者：Sandstroem

  DOI：——

  日期：——
• Lapiere, Journal de Pharmacie de Belgique, <NS> 14 <1959> 126, 137
  作者：Lapiere

  DOI：——

  日期：——
• Synthesis, antioxidant and cytoprotective evaluation of potential antiatherogenic phenolic hydrazones. A structure–activity relationship insight
  作者：Corinne Vanucci-Bacqué、Chantal Carayon、Corinne Bernis、Caroline Camare、Anne Nègre-Salvayre、Florence Bedos-Belval、Michel Baltas

  DOI：10.1016/j.bmc.2014.05.034

  日期：2014.8

  A novel series of hydrazones derived from substituted benzaldehydes have been synthesized as potential antiatherogenic agents. Several methods were used for exploring their antioxidant and cytoprotective properties, such as their scavenging effect on 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical, the inhibition of superoxide anion (O₂(·-)) generation and the measurement of cell-induced low-density lipoprotein oxidation (monitored by the formation of TBARS). The cytoprotective efficacy was also evaluated by measuring the cell viability (monitored by the MTT assay) in the presence of cytotoxic oxidized LDL. In this report, we discuss the relationship between the chemical structure of phenolic hydrazones and their antioxidant and cytoprotective activities, for subsequent application as antiatherogenic agents. This SAR study confirms that the phenolic frame is not the only prerequisite for antioxidant activity and N-methylbenzothiazole hydrazone moiety magnifies the dual required properties in two most interesting derivatives.