4-isothiocyanato-N-(pyridin-2-yl)benzenesulfonamide | 7403-88-5

• 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-isothiocyanato-N-(pyridin-2-yl)benzenesulfonamide
• 英文别名: 4-isothiocyanato-benzenesulfonic acid-[2]pyridylamide；4-Isothiocyanato-benzolsulfonsaeure-[2]pyridylamid；4-Isothiocyanato-N-(pyridin-2-yl)benzene-1-sulfonamide；4-isothiocyanato-N-pyridin-2-ylbenzenesulfonamide
• CAS: 7403-88-5
• 化学式: C₁₂H₉N₃O₂S₂
• 分子量: 291.354
• InChiKey: ZVMCJLUDHSKSPH-UHFFFAOYSA-N

物化性质

• 沸点：
  493.8±51.0 °C(Predicted)
• 密度：
  1.37±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-isothiocyanato-N-(pyridin-2-yl)benzenesulfonamide 在 吡啶 、 溶剂黄146 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 、 乙醇 为溶剂， 反应 31.0h， 生成 (E)-4-(3-(3-(3-(phenylamino)acryloyl)phenyl)thioureido)-N-(pyridin-2-yl)-benzenesulfonamide
  参考文献：
  名称：

  Novel thioureido-benzenesulfonamide derivatives with enaminone linker as potent anticancer, radiosensitizers and VEGFR2 inhibitors

  摘要：

  In this study, novel series of thioureido-benzenesulfonamide derivatives bearing an enaminone linker either meta or para oriented and having terminal linear or substituted aromatic or heteroaromatic ring system 5-16a, b were designed and synthesized based on the general pharmacophoric features of type II VEGFR2 inhibitors. Evaluation of the synthesized compounds against HEPG2 hepatocellular carcinoma cells in vitro identified compounds 5b, 6b and 10-13b as most active anticancer agents with IC50 equal to 0.12, 0.29, 0.58, 0.44, 0.42 and 0.66 mu M, respectively. These compounds were evaluated for their ability to in vitro inhibit VEGFR2 kinase enzyme. The results demonstrated highly potent dose-related VEGFR2 inhibition with IC50 values in nanomolar range (33, 57, 210, 37, 37 and 220 nM, respectively). The radiosen sitizing ability of the most promising compounds was studied which showed an increase in the cell killing effect of radiation after combination with the synthesized compounds which revealed lowered IC50 by nearly 50%. Molecular docking for the most potent compounds was performed to predict their possible binding mode within VEGFR2 active site and they showed binding affinity in a similar way to sorafenib. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.089
• 作为产物：
  描述：

  硫光气 、 磺胺吡啶 在 盐酸 作用下， 以 水 为溶剂， 以86%的产率得到4-isothiocyanato-N-(pyridin-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Novel thioureido-benzenesulfonamide derivatives with enaminone linker as potent anticancer, radiosensitizers and VEGFR2 inhibitors

  摘要：

  In this study, novel series of thioureido-benzenesulfonamide derivatives bearing an enaminone linker either meta or para oriented and having terminal linear or substituted aromatic or heteroaromatic ring system 5-16a, b were designed and synthesized based on the general pharmacophoric features of type II VEGFR2 inhibitors. Evaluation of the synthesized compounds against HEPG2 hepatocellular carcinoma cells in vitro identified compounds 5b, 6b and 10-13b as most active anticancer agents with IC50 equal to 0.12, 0.29, 0.58, 0.44, 0.42 and 0.66 mu M, respectively. These compounds were evaluated for their ability to in vitro inhibit VEGFR2 kinase enzyme. The results demonstrated highly potent dose-related VEGFR2 inhibition with IC50 values in nanomolar range (33, 57, 210, 37, 37 and 220 nM, respectively). The radiosen sitizing ability of the most promising compounds was studied which showed an increase in the cell killing effect of radiation after combination with the synthesized compounds which revealed lowered IC50 by nearly 50%. Molecular docking for the most potent compounds was performed to predict their possible binding mode within VEGFR2 active site and they showed binding affinity in a similar way to sorafenib. (C) 2018 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2018.03.089

文献信息

• Synthesis of Some Novel Sulfonamide Derivatives
  作者：M. M. Aly

  DOI：10.1080/10426500701242954

  日期：2007.6.1

  Sulfapyridine (1) was selected as the starting material for the synthesis of some novel thiazolidine, thiosemicarbazide, and quinazoline derivatives. The structures of synthesized compounds were elucidated by elemental analyses and spectral data.

  磺胺吡啶 (1) 被选为合成一些新型噻唑烷、氨基硫脲和喹唑啉衍生物的原料。通过元素分析和光谱数据阐明了合成化合物的结构。
• Induction of apoptosis, cytotoxicity and radiosensitization by novel 3,4-dihydroquinazolinone derivatives
  作者：Aiten M. Soliman、Amira Khalil、Eman Ramadan、Mostafa M. Ghorab

  DOI：10.1016/j.bmcl.2021.128308

  日期：2021.10
• 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.
• p-Substituted Phenyl Isothiocyanates and Some Related Thioureas
  作者：R. L. McKee、R. W. Bost

  DOI：10.1021/ja01216a022

  日期：1946.12
• Novel thioureido-benzenesulfonamide derivatives with enaminone linker as potent anticancer, radiosensitizers and VEGFR2 inhibitors
  作者：Mostafa M. Ghorab、Fatma A. Ragab、Helmy I. Heiba、Marwa G. El-Gazzar、Mostafa G.M. El-Gazzar

  DOI：10.1016/j.bmcl.2018.03.089

  日期：2018.5

  In this study, novel series of thioureido-benzenesulfonamide derivatives bearing an enaminone linker either meta or para oriented and having terminal linear or substituted aromatic or heteroaromatic ring system 5-16a, b were designed and synthesized based on the general pharmacophoric features of type II VEGFR2 inhibitors. Evaluation of the synthesized compounds against HEPG2 hepatocellular carcinoma cells in vitro identified compounds 5b, 6b and 10-13b as most active anticancer agents with IC50 equal to 0.12, 0.29, 0.58, 0.44, 0.42 and 0.66 mu M, respectively. These compounds were evaluated for their ability to in vitro inhibit VEGFR2 kinase enzyme. The results demonstrated highly potent dose-related VEGFR2 inhibition with IC50 values in nanomolar range (33, 57, 210, 37, 37 and 220 nM, respectively). The radiosen sitizing ability of the most promising compounds was studied which showed an increase in the cell killing effect of radiation after combination with the synthesized compounds which revealed lowered IC50 by nearly 50%. Molecular docking for the most potent compounds was performed to predict their possible binding mode within VEGFR2 active site and they showed binding affinity in a similar way to sorafenib. (C) 2018 Elsevier Ltd. All rights reserved.