4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide | 81059-98-5

• 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-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide
• 英文别名: 4-[(4-Oxo-4,5-dihydro-1,3-thiazol-2-yl)amino]benzenesulfonamide；4-[(4-oxo-1,3-thiazolidin-2-ylidene)amino]benzenesulfonamide
• CAS: 81059-98-5
• 化学式: C₉H₉N₃O₃S₂
• 分子量: 271.321
• InChiKey: RWMDQWYQDKEGBG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  135
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide 在 sodium acetate 、 溶剂黄146 、 potassium hydroxide 作用下， 以 乙醇 为溶剂， 反应 18.0h， 生成 4-((7-(4-methoxyphenyl)-5-thioxo-5,6-dihydrothiazolo[4,5-d]pyrimidin-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  一些新型磺酰胺衍生物作为细胞凋亡诱导剂的设计，合成及生物学评价

  摘要：

  合成了几种带有苯磺酰胺部分的新型噻唑烷酮和稠合的噻唑烷酮衍生物，并通过光谱和元素分析对其进行了确认。评价新合成的化合物对结肠直肠癌细胞系（Caco-2）的细胞毒性活性。所有合成的化合物均显示出比参考标准品（阿霉素和5-FU）更好的活性。对最具活性的化合物的凋亡活性的研究表明，化合物3a，5a，5c和6c激活Caco-2细胞系中的caspase-3和Fas-配体。在处理过的Caco-2细胞中，化合物3a是活性最高的化合物，其caspase-3浓度为0.43 nmol / mL，Fas配体浓度为775.2 pg / mL。化合物3a用99m Tc进行放射性标记，并使用正常的瑞士Albino小鼠体内评估其生物分布模式。99m Tc-化合物3a复合物除了在结肠中积累外，在任何人体器官中均未显示出任何积累。目标器官 在pi的15min处显示8.97±1.35％ID / g，在pi的120min处升高至16

  DOI：

  10.1016/j.ejmech.2017.04.069
• 作为产物：
  描述：

  在 sodium acetate 作用下， 以 乙醇 为溶剂， 以68%的产率得到4-((4-oxo-4,5-dihydrothiazol-2-yl)amino)benzenesulfonamide
  参考文献：
  名称：

  New benzenesulfonamide scaffold-based cytotoxic agents: Design, synthesis, cell viability, apoptotic activity and radioactive tracing studies

  摘要：

  A new series of thiazolidinone (5a-g), thiazinone (9a-g) and dithiazepinone (9a-g) heterocycles bearing a benzenesulfonamide scaffold was synthesized. Cytotoxicity of these derivatives was assessed against MCF-7, HepG2, HCT-116 and A549 cancer cell lines and activity was compared to the known cytotoxic agents doxorubicin and 5-FU where the most active compounds displayed better to nearly similar IC50 values to the reference compounds. For assessing selectivity, the most active derivatives against MCF-7, 5b, 5c and 5e, were also assessed against the normal breast cell line MCF-10 A where they demonstrated high selective cytotoxicity to cancerous cells over that to normal cells. Further, the effect of the most active compounds 5b-e on MCF-7 and HepG2 cell cycle phase distribution was assessed and the tested sulfonamide derivatives were found to induce accumulation of cells in the < 2n phase. To further confirm apoptosis induction, caspase 8 and 9 levels in MCF-7 and HepG2 were evaluated before and after treatment with compounds 5b-e and were found to be significantly higher after exposure to the test agents. Since 5c was the most active, its effect on the cell cycle regulation was confirmed where it showed inhibition of the CDK2/cyclin E1. Finally, in vivo biodistribution study using radioiodinated-5c revealed a significant uptake and targeting ability into solid tumor in a xenograft mouse model.

  DOI：

  10.1016/j.bioorg.2020.103577

文献信息

• Synthesis of 4-(thiazol-2-ylamino)-benzenesulfonamides with carbonic anhydrase I, II and IX inhibitory activity and cytotoxic effects against breast cancer cell lines
  作者：Nagwa M. Abdel Gawad、Noha H. Amin、Mohammed T. Elsaadi、Fatma M.M. Mohamed、Andrea Angeli、Viviana De Luca、Clemente Capasso、Claudiu T. Supuran

  DOI：10.1016/j.bmc.2016.05.016

  日期：2016.7

  activity on human breast cancer cell line MCF-7. Human (h) CA isoforms I, II and IX were included in the study. The new sulfonamides showed excellent inhibition of all three isoforms, with KIs in the range of 0.84–702 nM against hCA I, of 0.41–288 nM against hCA II and of 5.6–29.2 against the tumor-associated hCA IX, a validated anti-tumor target, with a sulfonamide (SLC-0111) in Phase I clinical trials

  合成了一系列的4-（噻唑-2-基氨基）-苯磺酰胺，并筛选了它们的碳酸酐酶（CA，EC 4.2.1.1）对人乳腺癌细胞系MCF-7的抑制和细胞毒活性。研究中包括人（h）CA同工型I，II和IX。新的磺酰胺类药物对所有三种同工型均表现出优异的抑制作用，对hCA I的K I范围为0.84–702 nM，对hCA II的K I范围为0.41–288 nM，对与肿瘤相关的hCA IX的K I范围为5.6–29.2。在I期临床试验中使用磺酰胺（SLC-0111）作为抗肿瘤靶标，用于治疗过表达CA IX的低氧，转移性实体瘤。新化合物显示出微摩尔抑制对乳腺癌MCF-7细胞系生长功效的抑制作用。
• 一种5-(1H-吲哚-3-亚甲基)-1,3-噻唑烷-4- 酮类衍生物及其合成方法和应用
  申请人：西安交通大学

  公开号：CN104059060B

  公开（公告）日：2017-08-01

  一种5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物及其合成方法和应用，以乙醇和或水为溶剂，将取代2‑取代亚氨基‑1,3‑噻唑烷‑4‑酮与1H‑吲哚‑3‑甲醛在哌啶催化条件下，回流反应，通过分子间脱水缩合反应形成亚甲基连接基，得到5‑(1H‑吲哚‑3‑亚甲基)‑1,3‑噻唑烷‑4‑酮类衍生物。其中所涉及的中间体2‑取代亚氨基噻唑烷‑4‑酮是由各种单取代的硫脲氯乙酸乙酯或氯乙酸在低沸点溶剂中经回流条件下的环合反应制备而得，中间体2‑取代亚氨基‑3‑取代‑1,3,‑噻唑烷‑4‑酮由各种双取代的对称硫脲和氯乙酸通过绿色环保合成工艺制备。对所有目标化合物在酶分子水平上的生物活性初步筛选实验结果显示，目标产物对PTP1B和CDC25B在不同程度上显示一定的抑制活性。
• Novel 4/3-((4-oxo-5-(2-oxoindolin-3-ylidene)thiazolidin-2-ylidene)amino) benzenesulfonamides: Synthesis, carbonic anhydrase inhibitory activity, anticancer activity and molecular modelling studies
  作者：Wagdy M. Eldehna、Mahmoud F. Abo-Ashour、Alessio Nocentini、Paola Gratteri、Ibrahim H. Eissa、Mohamed Fares、Omnia E. Ismael、Hazem A. Ghabbour、Mahmoud M. Elaasser、Hatem A. Abdel-Aziz、Claudiu T. Supuran

  DOI：10.1016/j.ejmech.2017.07.073

  日期：2017.10

  their anti-proliferative activity against breast cancer MCF-7 and colorectal cancer Caco-2 cell lines. Compound 4c was found to be the most potent derivative against MCF-7 (IC50 = 3.96 ± 0.21 μM), while 4j was the most active member against Caco-2 cells (IC50 = 5.87 ± 0.37 μM). Compound 4c induced the intrinsic apoptotic mitochondrial pathway in MCF-7 cells; evidenced by the enhanced expression of the

  在这里，我们报告了两个系列的新型4/3-（（4-氧代-5-（2-氧吲哚-3-基）噻唑烷二-2-亚基）氨基）苯磺酰胺的合成（4a-m和7a-g）。所有的新制备的磺酰胺都在体外进行了研究，作为金属酶碳酸酐酶（CA，EC 4.2.1.1）同工型hCA I，II，IV和IX的抑制剂，采用了限流CO 2氢化酶测定法。特别是，hCA同工型II和IX（与肿瘤相关）更容易受到合成衍生物的抑制，hCA II的K I范围为2.6–598.2 nM，hCA IX的K I范围为16.1–321 nM。所有化合物（4a-m和7a-g评估了它们对乳腺癌MCF-7和结肠直肠癌Caco-2细胞系的抗增殖活性。化合物4c中被发现是抗MCF-7的最有效的衍生物（IC 50  = 3.96±0.21μM），而图4j是反对的Caco-2细胞中最活跃的成员（IC 50  = 5.87±0.37μM）。化合物4c诱导MCF-7细胞内
• Toward a treatment of antibacterial and antifungal infections: Design, synthesis and in vitro activity of novel arylhydrazothiazolylsulfonamides analogues and their insight of DFT, docking and molecular dynamic simulations
  作者：Ismail M.M. Othman、Mahmoud H. Mahross、Mohamed A.M. Gad-Elkareem、Mithun Rudrapal、Neelutpal Gogoi、Dipak Chetia、Kaïss Aouadi、Mejdi Snoussi、Adel Kadri

  DOI：10.1016/j.molstruc.2021.130862

  日期：2021.11

  To find out effective new antibacterial agents, a series of novel aryl-hydrazothiazolyl-sulfonamide derivatives 3a-e were synthesized and well characterized by analytical and spectroscopic techniques. All the compounds were evaluated for their antibacterial and antifungal potential and the results showed excellent antimicrobial activity of 3d against all strains, especially B. cereus (MIC = 5.54 μM

  为了寻找有效的新型抗菌剂，我们合成了一系列新型芳基-肼基噻唑基-磺酰胺衍生物3a-e，并通过分析和光谱技术对其进行了表征。对所有化合物的抗菌和抗真菌潜力进行了评估，结果显示3d对所有菌株都有出色的抗菌活性，尤其是蜡状芽孢杆菌（MIC = 5.54 μM 对 17.6 μM）、铜绿假单胞菌（MIC = 7.3 μM 对 12.8 μM)、大肠杆菌（MIC = 6.4 μM 与 21.3 μM）和 C 。白化病患者（MIC = 6.8 μM 与 26.4 μM）分别与商业抗生素四环素和两性霉素 B 相比。其他类似物显示出强效至中等的抗菌活性。构效关系 (SAR) 特别表明，在对苯基位置 ( 3d )处掺入嘧啶-2-基氨磺酰基是提高抗菌活性的良好贡献者。此外，3d上的密度泛函理论 (DFT)揭示了其高稳定性和最强的给电子能力。S. aureus tyrosyl-tRNA 合成酶 (PDB ID:
• Synthesis of some new thiazolopyrane and thiazolopyranopyrimidine derivatives bearing a sulfonamide moiety for evaluation as anticancer and radiosensitizing agents
  作者：Dalal A. Abou El Ella、Mostafa M. Ghorab、Helmy I. Heiba、Aiten M. Soliman

  DOI：10.1007/s00044-011-9751-9

  日期：2012.9

  11–13 and thiazolopyranopyrimidine 6–10, 7b, 8b, and 14 derivatives bearing a sulfonamide moiety were designed and synthesized. The molecular design was performed using molecular operating environment software to predict the binding mode of the proposed compounds on hCAII. All the newly synthesized compounds were evaluated for their in vitro anticancer activity against human liver cancer cell line in which

  一系列新thiazolopyrane的图5a-d ，11-13和thiazolopyranopyrimidine 6-10，图7B，图8B，和14个衍生物带有磺酰胺部分，设计并合成。使用分子操作环境软件进行分子设计，以预测拟议化合物在hCAII上的结合模式。评价所有新合成的化合物对其中hCAII过表达的人肝癌细胞系的体外抗癌活性。与作为阳性对照的阿霉素相比，化合物8b和14显示出更高的活性。有前途的化合物的放射增敏能力3研究了7a，8b，12和14，它们与γ-射线组合后对细胞的杀伤作用增强。