N^4'-chloroacetylsulphamethazine | 116488-93-8

• 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: N^4'-chloroacetylsulphamethazine
• 英文别名: 4-(2-chloro-acetylamino)-N-(4,6-dimethyl-pyrimidin-2-yl)-benzenesulfonamide；2-Chloro-N-(4-(N-(4,6-dimethylpyrimidin-2-yl)sulfamoyl)phenyl)acetamide；2-chloro-N-[4-[(4,6-dimethylpyrimidin-2-yl)sulfamoyl]phenyl]acetamide
• CAS: 116488-93-8
• 化学式: C₁₄H₁₅ClN₄O₃S
• mdl: MFCD01180900
• 分子量: 354.817
• InChiKey: KELBEZWMFXZILY-UHFFFAOYSA-N

物化性质

• 熔点：
  170 °C
• 密度：
  1.466±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N^4'-chloroacetylsulphamethazine 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 24.0h， 生成 N-(4,6-dimethylpyrimidin-2-yl)-4-((4-oxo-5-((4-oxo-4H-chromen-3-yl)methylene)-4,5-dihydrothiazol-2-yl)amino)benzene sulfonamide
  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：

  磺胺二甲嘧啶 、 氯乙酰氯 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 N^4'-chloroacetylsulphamethazine
  参考文献：
  名称：

  设计，合成，分子建模，体内研究和喹唑啉-4（3H）-一衍生物作为潜在的VEGFR-2抑制剂和细胞凋亡诱导剂的体内抗癌评估。

  摘要：

  已经建立了抑制VEGFR-2作为治疗癌症的治疗策略。因此，设计并合成了具有VEGFR-2抑制剂的结构特征的新的基于喹唑啉的衍生物。使用MTT分析方法评估了针对三种人类癌细胞系（HepG-2，MCF-7和HCT-116）的抗增殖活性。阿霉素和索拉非尼用作阳性对照。化合物26b，29a，29b和30对所有细胞系均表现出优异的抗癌活性。此外，化合物31的活性最高，IC 50值分别为3.97±0.2、4.83±0.2和4.58±0.3 µM。进一步评估了最具活性的细胞毒剂的VEGFR-2抑制活性，化合物31对VEGFR-2表现出高活性，IC50值为2.5±0.04 µM，几乎等于索拉非尼（IC50 = 2.4±0.05 µM）。进一步的研究揭示了这种有前途的喹唑啉衍生物31诱导细胞凋亡并阻止G2 / M期细胞周期生长的能力。合成化合物的体内抗肿瘤活性表明化合物30和31具有显着的肿瘤生长抑制作用。

  DOI：

  10.1016/j.bioorg.2019.103422

文献信息

• Design, synthesis, and anti-proliferative evaluation of new quinazolin-4(3H)-ones as potential VEGFR-2 inhibitors
  作者：Khaled El-Adl、Abdel-Ghany A. El-Helby、Rezk R. Ayyad、Hazem A. Mahdy、Mohamed M. Khalifa、Hamdy A. Elnagar、Ahmed B.M. Mehany、Ahmed M. Metwaly、Mostafa A. Elhendawy、Mohamed M. Radwan、Mahmoud A. ElSohly、Ibrahim H. Eissa

  DOI：10.1016/j.bmc.2020.115872

  日期：2021.1

  Inhibiting VEGFR-2 has been set up as a therapeutic strategy for treatment of cancer. Thus, nineteen new quinazoline-4(3H)-one derivatives were designed and synthesized. Preliminary cytotoxicity studies of the synthesized compounds were evaluated against three human cancer cell lines (HepG-2, MCF-7 and HCT-116) using MTT assay method. Doxorubicin and sorafenib were used as positive controls. Five compounds

  抑制 VEGFR-2 已被确立为治疗癌症的治疗策略。因此，设计并合成了19 种新的喹唑啉-4(3 H )-one 衍生物。使用 MTT 分析方法对合成的化合物对三种人类癌细胞系（HepG-2、MCF-7 和 HCT-116）的初步细胞毒性研究进行了评估。多柔比星和索拉非尼用作阳性对照。发现五种化合物对所有细胞系都具有良好的细胞毒活性。化合物16 f含有一个 2-氯-5-硝基苯基，已成为最活跃的成员。它对 HepG2、HCT-116 和 MCF-7 细胞的活性分别比阿霉素高约 4.39、5.73 和 1.96 倍，比索拉非尼高 3.88、5.59 和 1.84 倍。最活跃的细胞毒性剂在体外进一步评估了它们的 VEGFR-2 抑制活性。体外VEGFR-2 抑制的结果与细胞毒性数据的结果一致。此外，这些化合物与激酶结构域的分子对接支持了结果。
• Design, Synthesis and Biological Evaluation of Some Novel Chalcones-sulphonamide Hybrids
  作者：Khanusiya, Mahammadali、Gadhawala, Zakirhusen

  DOI：10.5012/jkcs.2018.62.5.377

  日期：——

  A new class of Chalcone-Sulphonamide hybrids has been designed by condensing appropriate sulphonamide scaffold with substituted chalcones tethered by chloroacetyl chloride as a multi-target drug for therapeutic treatment. Chalcones were prepared by Claisen-Schmidt condensation of a substituted aldehyde with para aminoacetophenone. These Chalcone-Sulphonamide hybrids were screened by means of their antibacterial activity by NCCLS method. Among all these compounds, 5e and 5c displayed more potent growth inhibitory activity against Staphylococcus epidermidis and Pseudomonas aeruginosa bacteria respectively. Further, these hybrids were evaluated for their antifungal activity, among all hybrid 5a exhibited potent antifungal activity. The synthesized compounds were characterized by FT-IR, $^1HNMR$, $^13}CNMR$ and HR-LCMS and spectral study supports the structures of synthesized Chalcone-Sulphonamide hybrids.

  通过将适当的磺酰胺支架与氯乙酰氯拴住的取代查耳酮缩合，设计出了一类新的查耳酮-磺酰胺杂交化合物，作为多靶点治疗药物。查耳酮是通过取代醛与对氨基苯乙酮的克莱森-施密特缩合反应制备的。通过 NCCLS 方法对这些查耳酮-磺酰胺杂化物的抗菌活性进行了筛选。在所有这些化合物中，5e 和 5c 分别对表皮葡萄球菌和绿脓杆菌具有更强的生长抑制活性。此外，还对这些杂交化合物的抗真菌活性进行了评估，其中杂交化合物 5a 具有很强的抗真菌活性。通过傅立叶变换红外光谱（FT-IR）、$^1HNMR$、$^13}CNMR$和 HR-LCMS，对合成的化合物进行了表征。
• Synthesis of Some New Biologically Active Sulfur Compounds Containing Pyrazolo[3,4-d] pyrimidine Moiety
  作者：Zeinab H. Ismail、Soad M. Abdel-Gawad、Anhar Abdel-Aziem、M. M. Ghorab

  DOI：10.1080/10426500307825

  日期：2003.8.1

  A novel series of the pyrazolo[3,4-d]pyrimidines having biologically active sulfur moieties 3-20 were prepared via reaction of 4-mercapto-1-phenyl-1 H -pyrazolo[3,4-d]pyrimidine 3 with different reagents. Identification of the new compounds was established by elemental analyses, IR, 1 H-NMR, and mass spectral data. Some of the obtained compounds showed the interesting antimicrobial activity comparable

  通过 4-mercapto-1-phenyl-1 H-pyrazolo[3,4-d]pyrimidine 3 与不同的生物活性硫部分 3-20 的反应制备了一系列具有生物活性硫部分的新型吡唑并[3,4-d]嘧啶。试剂。新化合物的鉴定是通过元素分析、IR、1 H-NMR 和质谱数据确定的。一些获得的化合物显示出与作为标准抗菌剂的抗生素氯霉素和作为标准抗真菌剂的特比萘芬相当的有趣的抗菌活性。
• Sharma, Pratibha; Mandloi, Anupam; Pritmani, Shreeya, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1999, vol. 38, # 11, p. 1289 - 1294
  作者：Sharma, Pratibha、Mandloi, Anupam、Pritmani, Shreeya

  DOI：——

  日期：——
• El-Helby, Pakistan Journal of Scientific and Industrial Research, 2001, vol. 44, # 3, p. 121 - 126
  作者：El-Helby

  DOI：——

  日期：——