4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)-N-(thiazol-2-yl)benzenesulfonamide

• 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-((4-oxo-4,5-dihydrothiazol-2-yl)amino)-N-(thiazol-2-yl)benzenesulfonamide
• 英文别名: 4-((4-oxothiazolidin-2-ylidene)amino)-N-(thiazol-2-yl)benzenesulfonamide；4-[(4-oxo-1,3-thiazolidin-2-ylidene)amino]-N-(1,3-thiazol-2-yl)benzenesulfonamide
• 化学式: C₁₂H₁₀N₄O₃S₃
• 分子量: 354.434
• InChiKey: DKCUCBAMRIOUKT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  162
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)-N-(thiazol-2-yl)benzenesulfonamide 、 色酮-3-甲醛 在 sodium acetate 、 溶剂黄146 作用下， 反应 8.0h， 以65%的产率得到4-((4-oxo-5-((4-oxo-4H-chromen-3-yl)methylene)-4,5-dihydrothiazol-2-yl)amino)-N-(thiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives

  摘要：

  Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 mu M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.04.033
• 作为产物：
  描述：

  磺胺噻唑 在 盐酸 、 乙醇 作用下， 以 水 为溶剂， 反应 10.0h， 生成 4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)-N-(thiazol-2-yl)benzenesulfonamide
  参考文献：
  名称：

  明显改性的磺胺噻唑衍生物的合成，抗菌和对接研究。

  摘要：

  合成了一些新的磺胺噻唑衍生物。使巯基噻唑起始原料与溴乙酸乙酯反应并意外地产生酯产物2。取代选择性地发生在NH噻唑基氮的互变异构质子而不是芳族NH 2质子上。将该酯进一步肼解，然后与几种醛缩合以形成（4a-h）。Hantzesch噻唑合成还用于构建包含多噻唑部分的抗菌剂。合成的化合物的结构通过1 H，13 C，2 D 1 H NMR，MS和微量分析证实。测试合成的化合物对革兰氏阳性和革兰氏阴性细菌以及真菌菌株的抗菌活性。一些被研究的化合物显示出显着的高效力。

  DOI：

  10.21608/ejchem.2019.13909.1862

文献信息

• Design, synthesis, and molecular docking of novel indole scaffold-based VEGFR-2 inhibitors as targeted anticancer agents
  作者：Hanaa M. Roaiah、Iman A. Y. Ghannam、Islam H. Ali、Ahmed M. El Kerdawy、Mamdouh M. Ali、Safinaz E-S. Abbas、Sally S. El-Nakkady

  DOI：10.1002/ardp.201700299

  日期：2018.2

  on a panel of 60 tumor cell lines. Additionally, molecular docking was carried out to study their binding pattern and binding affinity in the VEGFR‐2 active site using sorafenib as a reference VEGFR‐2 inhibitor. Based on the molecular docking results, compounds 5a, 5b, 6, 7, 14b, 18b, and 18c were selected to be evaluated for their VEGFR‐2 inhibitory activity. Compound 18b exhibited a broad‐spectrum

  合成了一系列新的吲哚衍生物 1-18，并测试了它们对 60 个肿瘤细胞系的细胞毒活性。此外，使用索拉非尼作为参考 VEGFR-2 抑制剂，进行分子对接以研究它们在 VEGFR-2 活性位点的结合模式和结合亲和力。根据分子对接结果，选择化合物5a、5b、6、7、14b、18b和18c评估其VEGFR-2抑制活性。化合物 18b 对 47 个细胞系表现出广谱抗增殖活性，GI % 范围为 31% 至 82.5%。此外，化合物 18b 是最有效的 VEGFR-2 抑制剂，IC50 值为 0.07 μM，比索拉非尼 (0.09 μM) 更有效。
• Inhibition studies on a panel of human carbonic anhydrases with<i>N</i>1-substituted secondary sulfonamides incorporating thiazolinone or imidazolone-indole tails
  作者：Fadi M. Awadallah、Silvia Bua、Walaa R. Mahmoud、Hossam H. Nada、Alessio Nocentini、Claudiu T. Supuran

  DOI：10.1080/14756366.2018.1446432

  日期：2018.1.1

  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.
• Synthesis, carbonic anhydrase inhibition and cytotoxic activity of novel chromone-based sulfonamide derivatives
  作者：Fadi M. Awadallah、Tamer A. El-Waei、Mona M. Hanna、Safinaz E. Abbas、Mariangela Ceruso、Beyza Ecem Oz、Ozen Ozensoy Guler、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2015.04.033

  日期：2015.5

  Four series of sulfonamides incorporating chromone moieties were synthesized and assessed for their cytotoxic activity against MCF-7 and A-549 cell lines, considering the fact that some of these tumors overexpress isoforms of carbonic anhydrase (CA, EC 4.2.1.1) which is inhibited by sulfonamides. Most new sulfonamides showed weak inhibitory activity against the offtarget, cytosolic isoforms hCA I, II but effectively inhibited the tumor-associated hCA IX and XII. The most active compounds featured a primary SO2NH2 group and were active in the low micromolar range against MCF-7 and A-549 cell lines. Compound 4a showed IC50 of 0.72 and 0.50 mu M against MCF-7 and A-549 cell lines, respectively, and was further evaluated for its proapoptotic activity which proved enhanced in both tumor types. (C) 2015 Elsevier Masson SAS. All rights reserved.
• Synthesis, Antimicrobial, and Docking Investigations of Remarkably Modified Sulfathiazole Derivatives
  作者：Samir Gaballah、H. Amer、A. Hofinger-Horvath、M. Al-Moghazy、M. I. Hemida

  DOI：10.21608/ejchem.2019.13909.1862

  日期：2020.1.1

  Some new sulfathiazole derivatives were synthesized. The sulfathiazole starting material was reacted with ethyl bromoacetate and gave unpredictably an ester product 2. The substitution occurred selectively at the tautomeric proton of the NH thiazolyl nitrogen rather than the aromatic NH2 protons. The ester was further hydrazinolysed followed by condensation with several aldehydes to establish hydrazones

  合成了一些新的磺胺噻唑衍生物。使巯基噻唑起始原料与溴乙酸乙酯反应并意外地产生酯产物2。取代选择性地发生在NH噻唑基氮的互变异构质子而不是芳族NH 2质子上。将该酯进一步肼解，然后与几种醛缩合以形成（4a-h）。Hantzesch噻唑合成还用于构建包含多噻唑部分的抗菌剂。合成的化合物的结构通过1 H，13 C，2 D 1 H NMR，MS和微量分析证实。测试合成的化合物对革兰氏阳性和革兰氏阴性细菌以及真菌菌株的抗菌活性。一些被研究的化合物显示出显着的高效力。