4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide | 681235-15-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide
• 英文别名: 4-isothiocyanato-N-quinoxaline-2-yl-benzenesulfonamide；4-Isothiocyanato-N-(quinoxalin-2-yl)benzene-1-sulfonamide；4-isothiocyanato-N-quinoxalin-2-ylbenzenesulfonamide
• CAS: 681235-15-4
• 化学式: C₁₅H₁₀N₄O₂S₂
• 分子量: 342.402
• InChiKey: VKGAYTSLUKDQGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-羟基吡啶 、 4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 8.0h， 以95%的产率得到4-(O-pyridin-3-yl-carbamothioate)-N-(quinoxalin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, in-vitro Anticancer Screening and Radiosensitizing Evaluation of some New N-(quinoxalin-2-yl)benzenesulfonamide Derivatives

  摘要：

  这项工作的目的是通过加入生物活性分子（硫醚、噻唑、咪唑、咪唑嘧啶、咪唑嘧啶基嘧啶、噻吩基嘧啶、苯并嘧啶酮、苯并噻唑、噻唑和吡啶分子），合成并研究一系列新的磺胺喹喔啉衍生物的抗癌活性。对所有新合成的化合物进行了体外抗癌活性评估，以检测它们对人肝细胞系（HEPG2）的抗癌活性。所有测试化合物都显示出与参考药物 5-氟尿嘧啶相当的活性（IC50=40 µM），其中最强效的化合物是化合物 4 和 17（IC50 分别为 4.29 µM 和 11.27 µM）。另一方面，最有效的化合物 4 和 17 被评估为放射增敏剂。

  DOI：

  10.1055/s-0031-1295496
• 作为产物：
  描述：

  硫光气 、 磺胺喹噁啉 以 水 为溶剂， 反应 1.0h， 以86%的产率得到4-isothiocyanato-N-(quinoxalin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, in-vitro Anticancer Screening and Radiosensitizing Evaluation of some New N-(quinoxalin-2-yl)benzenesulfonamide Derivatives

  摘要：

  这项工作的目的是通过加入生物活性分子（硫醚、噻唑、咪唑、咪唑嘧啶、咪唑嘧啶基嘧啶、噻吩基嘧啶、苯并嘧啶酮、苯并噻唑、噻唑和吡啶分子），合成并研究一系列新的磺胺喹喔啉衍生物的抗癌活性。对所有新合成的化合物进行了体外抗癌活性评估，以检测它们对人肝细胞系（HEPG2）的抗癌活性。所有测试化合物都显示出与参考药物 5-氟尿嘧啶相当的活性（IC50=40 µM），其中最强效的化合物是化合物 4 和 17（IC50 分别为 4.29 µM 和 11.27 µM）。另一方面，最有效的化合物 4 和 17 被评估为放射增敏剂。

  DOI：

  10.1055/s-0031-1295496

文献信息

• Carbonic anhydrase inhibition with a series of novel benzenesulfonamide-triazole conjugates
  作者：Marwa G. El-Gazzar、Nessma H. Nafie、Alessio Nocentini、Mostafa M. Ghorab、Helmi I. Heiba、Claudiu T. Supuran

  DOI：10.1080/14756366.2018.1513927

  日期：2018.1.1

  We report the synthesis and characterisation of a novel series of triazole benzenesulfonamide derivatives, which incorporate the general pharmacophore associated with carbonic anhydrase (CA, EC 4.2.1.1) inhibitors. The synthesised compounds were tested in vitro against four human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes, hCA I, hCA II, hCA IV and hCA IX. The obtained results showed that the tumour-associated

  我们报告了一系列新型三唑苯磺酰胺衍生物的合成和表征，其中包含与碳酸酐酶（CA，EC 4.2.1.1）抑制剂相关的一般药效团。合成的化合物针对四种人碳酸酐酶（hCA、EC 4.2.1.1）同工酶（hCA I、hCA II、hCA IV 和 hCA IX）进行了体外测试。所得结果表明，肿瘤相关的hCA IX对合成衍生物的抑制最敏感，其中三唑并吡啶苯磺酰胺14、16和17是最有效的抑制剂。选择一些选定的化合物对一组 57 种人类肿瘤细胞系进行单剂量抗增殖活性测试，并显示出一些离体抗增殖活性。
• 2‐Thioxo‐3,4‐dihydropyrimidine and thiourea endowed with sulfonamide moieties as dual EGFR^T790M and VEGFR‐2 inhibitors: Design, synthesis, docking, and anticancer evaluations
  作者：Mohamed S. A. El‐Gaby、Mohamed A. M. Abdel Reheim、Zuhir S. M. Akrim、Bassem H. Naguib、Nashwa M. Saleh、Abu Bakr A. A. M. El‐Adasy、Khaled El‐Adl、Samy Mohamady

  DOI：10.1002/ddr.22143

  日期：2024.2

  assessed for dual VEGFR-2 and EGFRT790M inhibition effects. Compounds 8f and 8g were the most potent derivatives inhibited VEGFR-2 at IC50 value of 0.88 and 0.90 µM, correspondingly. As well, derivatives 8f and 8g could inhibit EGFRT790M demonstrating strongest effects with IC50 = 0.32 and 0.33 µM sequentially. Additionally, the greatest active derivatives ADMET profile was evaluated in relationship

  在 HCT-116、MCF-7、HepG2 和 A549 上测试了一系列新的含有磺酰胺部分的硫代嘧啶和硫脲的有效性。 HepG2 细胞系是所有新衍生物中受影响最大的细胞系。针对四种 HepG2、HCT116、MCF-7 和 A549 细胞系最有效的化合物为8f和8g ，IC 50分别为 4.13、6.64、5.74、6.85 µM 和 4.09、4.36、4.22、7.25 µM。化合物8g对HCT116和MCF-7表现出比索拉非尼更高的活性，但对HepG2和A549表现出较低的活性。此外，化合物8f和8g对HepG2、HCT116和MCF-7表现出比厄洛替尼更高的活性，但对A549表现出较低的活性。在正常 VERO 细胞系上检查了最有效的细胞毒性衍生物6f 、 6g 、 8c 、 8d 、 8e 、 8f和8g 。我们的衍生物对 VERO 细胞具有低毒性，IC 50值范围为 32.05 至
• Anti-inflammatory, analgesic and COX-2 inhibitory activity of novel thiadiazoles in irradiated rats
  作者：Fatma A. Ragab、Helmi I. Heiba、Marwa G. El-Gazzar、Sahar M. Abou-Seri、Walaa A. El-Sabbagh、Reham M. El-Hazek

  DOI：10.1016/j.jphotobiol.2016.12.007

  日期：2017.1

  In this work, novel series of pyran, thiophene and thienopyrimidine derivatives based on 2-acetamide-thiadiazole scaffold were designed and synthesized for evaluation as selective COX-2 inhibitors in-vitro and investigated in-vivo as anti-inflammatory and analgesic agents against carrageenan-induced rat paw oedema model in irradiated rats, since its well-known that ionizing radiation plays an important role in exaggerating the inflammatory responses and in enhancing the release of inflammatory mediators in experimental animals. Toxicological studies were carried out to evaluate the ulcerogenic activity, acute toxicity and kidney and liver functions for the most potent compounds. In order to understand the binding mode of the synthesized compounds into the active site of COX-2, docking study was performed. Most of the tested compounds showed high inhibitory ability to COX-2. Among them, thiadiazole derivatives bearing thiophene and thienopyrimidine moieties were the most active derivatives, compound 26 showed extremely high selectivity index (SI) of >555.5 pM which is nearly two folds better than celecoxib (>277.7 mu M), in addition to compounds 3, 16, 17, 21 and 26 with SI in the range of >308.6->384.6 M. The 4-chlorothieno[2.3-d]pyrimidine derivative of thiadiazole 21 showed the highest anti-inflammatory activity in this study having 24.49% of oedema compared to celecoxib (18.61%) in addition to compounds 17 and 26 with 24.70 and 25.40% of oedema, respectively, while the thiadiazol-2-acetamide derivative 2 was the most potent analgesic compound with the highest nociceptive threshold (85.72 g) very close to that of celecoxib (9023 g). These compounds showed high safety margin on gastric mucosa with no ulceration effect. Also the most active in-vivo anti-inflammatory compounds 17, 21 and 26 were found to be non-toxic in experimental rats with normal kidney and liver functions. Docking study of the synthesized compounds showed similar orientation as celecoxib within the active site of COX-2 enzyme and similar ability to emerge deeply in the additional pocket and binding with Arg513 and His90 the key amino acids responsible for selectivity. (C) 2016 Elsevier B.V. All rights reserved.
• Synthesis, in-vitro Anticancer Screening and Radiosensitizing Evaluation of some New N-(quinoxalin-2-yl)benzenesulfonamide Derivatives
  作者：M. Ghorab、F. Ragab、H. Heiba、M. El-Gazzar、M. El-Gazzar

  DOI：10.1055/s-0031-1295496

  日期：2012.1

  The objective of this work is to synthesize and investigate the anticancer activity of a new series of sulfaquinoxaline derivatives by incorporating biologically active moieties (thiourethane, thiazole, imidazole, imidazopyrimidine, imidazopyrimido-pyrimidine, thienopyrimidine, benzopyrimidinone, benzothiazole, thiazole and pyridine moieties). All the newly synthesized compounds were evaluated for their in-vitro anticancer activity against human liver cell line (HEPG2). All the tested compounds showed comparable activity to that of the reference drug 5-fluorouracil (IC50=40 µM), and the most potent compounds were found to be compounds 4 and 17 (IC50=4.29 and 11.27 µM, respectively). On the other hand, the most potent compounds 4 and 17 were evaluated as radiosensitizing agents.

  这项工作的目的是通过加入生物活性分子（硫醚、噻唑、咪唑、咪唑嘧啶、咪唑嘧啶基嘧啶、噻吩基嘧啶、苯并嘧啶酮、苯并噻唑、噻唑和吡啶分子），合成并研究一系列新的磺胺喹喔啉衍生物的抗癌活性。对所有新合成的化合物进行了体外抗癌活性评估，以检测它们对人肝细胞系（HEPG2）的抗癌活性。所有测试化合物都显示出与参考药物 5-氟尿嘧啶相当的活性（IC50=40 µM），其中最强效的化合物是化合物 4 和 17（IC50 分别为 4.29 µM 和 11.27 µM）。另一方面，最有效的化合物 4 和 17 被评估为放射增敏剂。