4-((1H-indol-3-yl)methyleneamino)-N-(pyridin-2-yl)benzenesulfonamide | 1214992-18-3

• 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: 4-((1H-indol-3-yl)methyleneamino)-N-(pyridin-2-yl)benzenesulfonamide
• 英文别名: 4-(1H-indol-3-ylmethylideneamino)-N-pyridin-2-ylbenzenesulfonamide
• CAS: 1214992-18-3
• 化学式: C₂₀H₁₆N₄O₂S
• 分子量: 376.439
• InChiKey: SYBCKAPBTDRLAB-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：
  0.0
• 拓扑面积：
  95.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-((1H-indol-3-yl)methyleneamino)-N-(pyridin-2-yl)benzenesulfonamide 、 硫代水杨酸 以 1,4-二氧六环 为溶剂， 反应 48.0h， 以70%的产率得到2-(3-indolyl)-3-[4-[(pyridin-2-yl)aminosulfonyl]phenyl]-2,4-dihydrobenzo[e][1,3]thiazin-4-one
  参考文献：
  名称：

  Synthesis, antitumor activity and molecular docking study of novel Sulfonamide-Schiff's bases, thiazolidinones, benzothiazinones and their C-nucleoside derivatives

  摘要：

  A series of sulfapyridine-polyhydroxyalkylidene (or arylidene)-imino derivatives (Schiff's bases) 2a-c and 4a-e were prepared by condensation of 4-amino-N-pyridin-2-ylbenzenesulfonamide (1) with different monosaccharides or with aromatic aldehydes. Treatment of 2a-c with thioglycolic acid led to the formation of the C-nucleosides (3a-c), while treatment of 4a-e with thioglycolic and/or thiosalicylic acids afforded the corresponding 2-arylthiazolidin-4-one or 2-arylbenzothiazin-4-one derivatives 5a-e and/or 6a-e, respectively. Some representative examples of the newly prepared compounds showed considerable cytotoxic effect against breast carcinoma cell line MCF7 and cervix carcinoma cell line HEIA in comparison with 5-flurouracil and doxorubicin. AutoDock molecular docking into PTK has been done for lead optimization of the compounds in study as potential PTK inhibitors. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.044
• 作为产物：
  描述：

  吲哚 在 溶剂黄146 、 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 生成 4-((1H-indol-3-yl)methyleneamino)-N-(pyridin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Inhibition studies on a panel of human carbonic anhydrases withN1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails

  摘要：

  Being the primary sulfonamide among the most efficient zinc binding group (ZBG) to design inhibitors for the metallo-enzymes carbonic anhydrases (CA, EC 4.2.1.1), herein, we propose an investigation on four physiologically important human (h) CAs (hCA I, II, IV, and IX) with N-1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails. The effect of the functionalisation of the sulfonamide group with five different substitution patterns, namely acetyl, pyridine, thiazole, pyrimidine, and carbamimidoyl, was evaluated in relation to the inhibition profile of the corresponding primary sulfonamide analogues. With most of these latter being nanomolar inhibitors of all four considered isoforms, a totally counterproductive effect on the inhibition potency can be ascribed to N-1-functionalisations of the ZBG primary sulfonamide structure with pyridine, thiazole, and pyrimidine moieties. On the other hand, incorporation of less hindered groups, such as sulfonylacetamides and sulfonylguanidines, maintained a certain degree of activity dependent on the tailing moiety, with K(I)s spanning in the low micromolar range.

  DOI：

  10.1080/14756366.2018.1446432

文献信息

• Biological function of sulfapyridine derivatives and their manganese(II) complexes
  作者：A. Nihath Nazleen、M. Umadevi

  DOI：10.1080/00958972.2023.2232927

  日期：2023.5.19

  Abstract Three derivatives of Schiff bases, 6-chloro-chromensulfapyridine (CCSP), indol-3-sulfapyridine (ISP), and 5-chlorothiophen-2-sulfapyridine (CTSP), were synthesized and characterized by analytical, spectroscopic (IR, UV-Vis., 1H and 13C NMR, Mass, EPR), and electrochemical techniques. Antioxidant capabilities were recorded for both ligands and their Mn(II) complexes using DPPH scavenger and

  摘要 合成了三种席夫碱衍生物，6-氯-苯磺吡啶 (CCSP)、吲哚-3-磺胺吡啶 (ISP) 和 5-氯噻吩-2-磺胺吡啶 (CTSP)，并通过分析、光谱（IR、UV-Vis）进行表征。 ., 1 H 和13 C NMR, Mass, EPR) 和电化学技术。使用 DPPH 清除剂和抗坏血酸作为参考，记录了两种配体及其 Mn(II) 配合物的抗氧化能力。与游离配体相比，Mn(II)配合物表现出更强的抗氧化活性。通过良好扩散技术进行体外抗菌和抗真菌研究。从IC 50值获得的结果表明 (CTCSP) 2 Mn ( IC 50 = 210.8 μg/mL) 具有有效的抗菌剂。此外，还对配体和复合物的计算机药物相似性、吸收、分布、代谢和排泄 (ADME) 特性进行了检查。
• 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.