4-[(2-hydroxynaphthalen-1-ylmethylene)amino]benzenesulfonamide | 39902-56-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[(2-hydroxynaphthalen-1-ylmethylene)amino]benzenesulfonamide
• 英文别名: Benzenesulfonamide, 4-[[(2-hydroxy-1-naphthalenyl)methylene]amino]-；4-[(2-hydroxynaphthalen-1-yl)methylideneamino]benzenesulfonamide
• CAS: 39902-56-2
• 化学式: C₁₇H₁₄N₂O₃S
• 分子量: 326.376
• InChiKey: KTTRXPZAPZPZER-UHFFFAOYSA-N

物化性质

• 熔点：
  240 °C (decomp)
• 沸点：
  597.7±60.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  neodymium(III) nitrate hexahydrate 、 4-[(2-hydroxynaphthalen-1-ylmethylene)amino]benzenesulfonamide 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 24.0h， 以69%的产率得到
  参考文献：
  名称：

  An experimental and theoretical investigation of lanthanide complexes [Ln = Nd, Yb, Eu, Dy and tb] with 4-((2-hydroxy-naphthalen-1-yl)methylene amino)benzenesulfonamide ligand

  摘要：

  Reaction of lanthanide(III) salts with N, O donors 4-((2-hydroxynaphthalen-1-yl) methyleneamino)benzenesulfonamide (L) Schiff base ligand afforded five new mononuclear lanthanide complexes of type [Ln(NO3)(2)(L) (H2O)(2)](H2O) x {where Ln = Nd (1), x = 2, Yb (2), x = 1, Eu (3), x = 2, Dy (4), x = 1, Tb (5), x = 2}. These newly synthesized complexes were characterized by elemental analysis, molar conductance, FT-IR, UV-Vis spectroscopy and mass spectrometry. The thermal behavior of complexes was studied by TGA technique. The computational calculations using density functional theory (DFT) of ligand and their lanthanide complexes were performed to obtain optimized molecular geometry, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and other parameters. The fluorescence studies reveal that emission spectra of lanthanide complexes show the characteristic luminescence due to lanthanide ions which indicates that Schiff base ligand can sensitize the Ln(III) ions. The Schiff base and their lanthanide complexes were screened for their in vitro antibacterial studies against Escherichia coli (ATCC 25922), Staphylococcus aureus (ATCC 29213), Klebsiella pneumoniae (BAA 1705), Acinetobacterr baumannii (BAA 1605) and Pseudomonas aeruginosa (ATCC 27853). The results exhibit that the antibacterial activity of Ln(III) complexes was greater than the free Schiff base ligand.

  DOI：

  10.1016/j.ica.2020.119955
• 作为产物：
  描述：

  磺胺 、 2-羟基-1-萘甲醛 在 溶剂黄146 作用下， 以 甲醇 为溶剂， 以80 %的产率得到4-[(2-hydroxynaphthalen-1-ylmethylene)amino]benzenesulfonamide
  参考文献：
  名称：

  磺胺席夫碱金属螯合物的合成、表征、抗糖化和抗氧化活性。

  摘要：

  目前的研究报告了配体 4-[(2-hydroxynaphthalene-1-ylmethylene)-amino]-benzenesulfonamide (L) 及其与 Mn(II) 的配位化合物的合成、结构建立、抗糖化和抗氧化活性， Co(II)、Ni(II)、Cu(II) 和 Zn(II) 金属离子。使用的分析技术（UV-Vis、FT-IR、CHN/S）证实了配体的双齿性质，通过 O 和 N 原子以 2:1 配体与金属的比例配位。TG/DTA 分析显示这些化合物是热稳定的。此外，还评估了合成化合物的抗糖化和抗氧化潜力，并显示出显着的活性，IC50 值范围分别为 184.11-386.34 µM 和 37.05-126.27 µM。Mn (IC50 = 184.11 ± 2.11 µM)、Ni (IC50 = 211.26 ± 1.46 µM)、Cu (IC50 = 254.56 ± 1

  DOI：

  10.17344/acsi.2022.7422

文献信息

• Efficacy of Novel Schiff base Derivatives as Antifungal Compounds in Combination with Approved Drugs Against Candida Albicans
  作者：Manzoor Ahmad Malik、Shabir Ahmad Lone、Parveez Gull、Ovas Ahmad Dar、Mohmmad Younus Wani、Aijaz Ahmad、Athar Adil Hashmi

  DOI：10.2174/1573406415666181203115957

  日期：2019.8.26

  The increasing incidence of fungal infections, especially caused by Candida albicans, and their increasing drug resistance has drastically increased in recent years. Therefore, not only new drugs but also alternative treatment strategies are promptly required.

  We previously reported on the synergistic interaction of some azole and non-azole compounds with fluconazole for combination antifungal therapy. In this study, we synthesized some non-azole Schiff-base derivatives and evaluated their antifungal activity profile alone and in combination with the most commonly used antifungal drugs- fluconazole (FLC) and amphotericin B (AmB) against four drug susceptible, three FLC resistant and three AmB resistant clinically isolated Candida albicans strains. To further analyze the mechanism of antifungal action of these compounds, we quantified total sterol contents in FLC-susceptible and resistant C. albicans isolates.

  A pyrimidine ring-containing derivative SB5 showed the most potent antifungal activity against all the tested strains. After combining these compounds with FLC and AmB, 76% combinations were either synergistic or additive while as the rest of the combinations were indifferent. Interestingly, none of the combinations was antagonistic, either with FLC or AmB. Results interpreted from fractional inhibitory concentration index (FICI) and isobolograms revealed 4-10-fold reduction in MIC values for synergistic combinations. These compounds also inhibit ergosterol biosynthesis in a concentration-dependent manner, supported by the results from docking studies.

  The results of the studies conducted advocate the potential of these compounds as new antifungal drugs. However, further studies are required to understand the other mechanisms and in vivo efficacy and toxicity of these compounds.

  背景：近年来，真菌感染的发病率不断增加，尤其是由白念珠菌引起的感染及其对药物的抗药性不断增加。因此，不仅需要新药物，还迫切需要替代性治疗策略。 方法：我们先前报道了一些咪唑和非咪唑化合物与氟康唑的协同作用，用于联合抗真菌治疗。在本研究中，我们合成了一些非咪唑席夫碱衍生物，并评估了它们与最常用的抗真菌药物氟康唑（FLC）和两性霉素B（AmB）在四种药物敏感、三种FLC耐药和三种AmB耐药的临床分离的白念珠菌菌株中的抗真菌活性谱。为进一步分析这些化合物的抗真菌作用机制，我们对FLC敏感和耐药的C. albicans分离物中的总固醇含量进行了定量。 结果：含有嘧啶环的衍生物SB5对所有测试菌株表现出最强的抗真菌活性。将这些化合物与FLC和AmB结合后，76%的组合是协同作用或加成作用，其余组合是无关的。有趣的是，无论是与FLC还是AmB结合，都没有发现任何拮抗作用。从分数抑制浓度指数（FICI）和等效图中解释的结果显示，协同作用组合的MIC值降低了4-10倍。这些化合物还以浓度依赖的方式抑制麦角固醇的生物合成，这一结果得到了对接研究的支持。 结论：所进行的研究结果证明了这些化合物作为新型抗真菌药物的潜力。然而，需要进一步研究来了解这些化合物的其他机制以及其在体内的功效和毒性。
• Design, synthesis, molecular modeling, and biological evaluation of sulfanilamide-imines derivatives as potential anticancer agents
  作者：Sofian S. Mohamed、Abdalkarem R. Tamer、Salah M. Bensaber、Mousa I. Jaeda、Nouri B. Ermeli、Aemen Ali Allafi、Ibrahim A. Mrema、Mabrouk Erhuma、Anton Hermann、Abdul M. Gbaj

  DOI：10.1007/s00210-013-0883-y

  日期：2013.9

  A series of sulfanilamide Schiff base derivatives (1 to 15) have been designed as potential antitubulin agents depending on the chemical structures of combretastatine A-4 and isoquinoline sulfamate (antimitotic agents under investigation). The designed compounds were synthesized by microwave chemical synthesis, their purity was confirmed by melting point and HPLC and chemical structures were determined

  根据考布他汀 A-4 和异喹啉氨基磺酸盐（正在研究的抗有丝分裂剂）的化学结构，一系列磺胺席夫碱衍生物（1 至 15）已被设计为潜在的抗微管蛋白药物。设计的化合物通过微波化学合成合成，其纯度通过熔点和 HPLC 确定，化学结构通过 FT-IR、UV、1H 和 13C-NMR 光谱技术确定。使用分子建模程序将合成的化合物对接在 β-微管蛋白的秋水仙碱结合位点，并通过细胞计数法筛选了对人乳腺癌和肺癌细胞的抗肿瘤活性。一些测试化合物显示出针对乳腺癌 (MCF-7) 的有效和选择性活性，IC50 范围为 90 至 166 μM。关于广谱活动，化合物 4、8 和 13 对人乳腺和人肺细胞显示出有效的抗肿瘤活性，IC50 范围为 96 至 140 μM。所得结果表明磺胺席夫碱衍生物可能构成一类有趣的新型抗癌剂，值得进一步研究。
• Mukherjee; Ray, Journal of the Indian Chemical Society, 1955, vol. 32, p. 604,607
  作者：Mukherjee、Ray

  DOI：——

  日期：——