N-(5-methylisoxazol-3-yl)-4-[(1H-indol-3-ylmethylene)amino]benzenesulfonamide | 903843-35-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-(5-methylisoxazol-3-yl)-4-[(1H-indol-3-ylmethylene)amino]benzenesulfonamide
• 英文别名: 4-(1H-indol-3-ylmethylideneamino)-N-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide
• CAS: 903843-35-6
• 化学式: C₁₉H₁₆N₄O₃S
• 分子量: 380.427
• InChiKey: VJVCWTPYLCRQIB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 、 磺胺甲恶唑 以 乙醇 为溶剂， 以30 %的产率得到N-(5-methylisoxazol-3-yl)-4-[(1H-indol-3-ylmethylene)amino]benzenesulfonamide
  参考文献：
  名称：

  磺胺甲恶唑衍生希夫碱：合成、表征、生物活性、分子对接、DFT 和 ADME 研究

  摘要：

  在此，我们报道了使用芳香醛合成磺胺甲恶唑衍生的希夫碱（SB）用于体外生物应用（抗菌、抗氧化剂、抗糖尿病和抗炎）。经过彻底表征（UV/可见光、FT-IR、1HNMR 和 13CNMR）的 SB 比磺胺甲恶唑具有更好的抗菌活性，其中 4d 对肺炎克雷伯菌、金黄色葡萄球菌和无乳链球菌具有出色的细菌生长抑制作用。 DPPH 测定显示 3d 具有最有效的自由基清除潜力，甚至优于抗坏血酸。使用针对 α-淀粉酶和 α-酶的餐后葡萄糖吸收抑制评估的 SB 的体外抗糖尿病潜力显示出良好的潜力，7d 对这两种酶均有效。使用双氯芬酸钠作为阳性对照的蛋白质变性测定的体外抗炎潜力不显着，除了 5d 外，显示出相当大的潜力（p 值 < 0.0001）。分子对接表明，合成的SB对不同受体蛋白具有良好的结合亲和力，支持了实验结果。使用 DFT 计算的电子特性显示出 1d 的低能隙 (3.61 eV)，这表明其与其他 SB

  DOI：

  10.1016/j.molstruc.2024.138640

文献信息

• A new series of Schiff bases derived from sulfa drugs and indole-3-carboxaldehyde: Synthesis, characterization, spectral and DFT computational studies
  作者：H. Ebrahimi、J.S. Hadi、H.S. Al-Ansari

  DOI：10.1016/j.molstruc.2013.01.063

  日期：2013.5

  A new series of Schiff bases were synthesized for the first time by the condensation of indole-3-carboxaldehyde with various sulfa drugs including sulfanilamide, sulfapyridine, sulfadiazine, sulfamerazine, sulfamethoxazole, sulfamethoxypyridazine and sulfacetamide sodium in ethanol (1:1). The structure of Schiff bases were experimentally characterized by using IR, H-1 NMR, C-13 NMR and mass spectroscopic methods. The structural and electronic properties of the studied molecules were investigated theoretically by performing density functional theory (DFT) to access reliable results to the experimental values. The molecular geometry, the highest occupied molecular orbital (HOMO), the lowest unoccupied molecular orbital (LUMO) and Mulliken atomic charges of the studied molecules have been calculated at the B3LYP method and standard 6-31 + G(d,p) basis set starting from optimized geometry. The theoretical C-13 chemical shift results were also calculated using the gauge independent atomic orbital (GIAO) approach and their respective linear correlations were obtained. The comparison of the results indicates that B3LYP/6-31 + G(d,p) yields good agreement with the observed chemical shifts. (C) 2013 Elsevier B.V. All rights reserved.
• Identification of antibacterial and antifungal pharmacophore sites for potent bacteria and fungi inhibition: Indolenyl sulfonamide derivatives
  作者：Zahid H. Chohan、Moulay H. Youssoufi、Aliasghar Jarrahpour、Taibi Ben Hadda

  DOI：10.1016/j.ejmech.2009.11.029

  日期：2010.3

  Synthesis of seven new indolenyl sulfonamides, have been prepared by the condensation reaction of indole-3-carboxaldehyde with different sulfonamides such as, sulphanilamide, sulfaguanidine, sulfathiazole, sulfamethoxazole, sulfisoxazole, sulfadiazine and sulfamethazine. These synthesized compounds have been used as potential ligands for complexation with some selective divalent transition metal ions (cobalt, copper, nickel & zinc). Structure of the synthesized ligands has been deduced from their physical, analytical (elemental analyses) and spectral (IR, H-1 NMR and C-13 NMR & UV-vis) data. All the compounds have also been assayed for their in vitro antibacterial and antifungal activities examining six species of pathogenic bacteria (Escherichia coli, Shigella flexneri, Pseudomonas aeruginosa, Salmonella typhi, Staphylococcus aureus and Bacillus subtilis) and six of fungi (Trichophyton longifusus, Candida albicans, Aspergillus flavus, Microsporum canis, Fusarium soloni and Candida glabrata). Antibacterial and antifungal results showed that all the compounds showed significant antibacterial activity whereas most of the Compounds displayed good antifungal activity. Brine shrimp bioassay was also carried out for in vitro cytotoxic properties against Artemia salina. Crown Copyright (C) 2009 Published by Elsevier Masson SAS. All rights reserved.