4-[((1H-indol-3-yl)methylene)amino]-N-(thiazol-2-yl)benzenesulfonamide | 905241-47-6

• 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: 4-[((1H-indol-3-yl)methylene)amino]-N-(thiazol-2-yl)benzenesulfonamide
• 英文别名: N-(thiazol-2-yl)-4-[(1H-indol-3-ylmethylene)amino]benzenesulfonamide；4-[(E)-1H-indol-3-ylmethyleneamino]-N-thiazol-2-yl-benzenesulfonamide；4-(1H-indol-3-ylmethylideneamino)-N-(1,3-thiazol-2-yl)benzenesulfonamide
• CAS: 905241-47-6
• 化学式: C₁₈H₁₄N₄O₂S₂
• 分子量: 382.467
• InChiKey: NTOLWOIOCZZKKZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  26
• 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：
  124
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 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)methylene)amino]-N-(thiazol-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

• 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.