2-chloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide

• 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: 2-chloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide
• 英文别名: 2-chloro-N-{4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl}acetamide；2-chloro-N-[4-[(5-methyl-1,2-oxazol-3-yl)sulfamoyl]phenyl]acetamide
• 化学式: C₁₂H₁₂ClN₃O₄S
• 分子量: 329.764
• InChiKey: KOSZDYWVAWNFNA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  110
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide 在 sodium acetate 、 溶剂黄146 作用下， 以 乙醇 为溶剂， 反应 16.0h， 生成 N-(5-methylisoxazol-3-yl)-4-((4-oxo-5-((4-oxo-4H-chromen-3-yl)methylene)-4,5-dihydrothiazol-2-yl)amino)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：

  磺胺甲恶唑 、 氯乙酰氯 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 生成 2-chloro-N-(4-(N-(5-methylisoxazol-3-yl)sulfamoyl)phenyl)acetamide
  参考文献：
  名称：

  用于伤口敷料的新型抗菌壳聚糖衍生物。

  摘要：

  壳聚糖是一种无毒，生物相容，可生物降解的天然阳离子聚合物，以其低免疫原性，抗菌，抗氧化作用和伤口愈合活性而著称。为了提高其治疗潜力，已经设计了新的壳聚糖-磺酰胺衍生物来开发新的伤口敷料生物材料。通过FT-IR，（1）H NMR光谱，扫描电子显微镜，溶胀能力和孔隙率分析了合成的壳聚糖衍生物的结构，形态和理化性质。还进行了抗微生物，体内测试和生物降解行为。壳聚糖衍生物膜显示出改善的溶胀和生物降解速率，这是伤口愈合过程所需的重要特征。抗菌测定表明，壳聚糖基磺胺嘧啶，磺胺二甲嘧啶和磺胺甲恶唑衍生物活性最高。MTT分析表明，一些壳聚糖衍生物是无毒的。此外，在Wistar大鼠中诱导的烧伤创面模型的体内研究表明，与纯壳聚糖相比，壳聚糖-磺酰胺衍生物的愈合效果更高，上皮化程度更高。获得的结果强烈建议使用一些新开发的壳聚糖衍生物作为抗菌伤口敷料生物材料。

  DOI：

  10.1016/j.carbpol.2015.12.078

文献信息

• A facile and efficient method for the selective deacylation of N-arylacetamides and 2-chloro-N-arylacetamides catalyzed by SOCl2
  作者：Gong-Bao Wang、Lin-Fa Wang、Chao-Zhang Li、Jing Sun、Guang-Ming Zhou、Da-Cheng Yang

  DOI：10.1007/s11164-011-0327-6

  日期：2012.1

  Thionyl chloride efficiently and selectively promoted the deacylation of N-arylacetamides and 2-chloro-N-arylacetamides, under anhydrous conditions, without effecting the ester group, aminosulfonyl group, or benzyloxyamide group. This method, which has been successfully applied to a variety of substrates including different N-arylacetamides and 2-chloro-N-arylacetamides, has the attractive advantages of inexpensive reagents, satisfactory selectivity, excellent yields, short reaction time, and convenient workup. This new method can probably be used to selectively deacylate between aromatic amides and alkyl amides.

  亚硫酰氯在无水条件下高效且选择性地促进了N-芳基乙酰胺和2-氯-N-芳基乙酰胺的去酰化反应，且不影响酯基、氨基磺酰基或苄氧酰胺基。这种方法已成功应用于多种底物，包括不同的N-芳基乙酰胺和2-氯-N-芳基乙酰胺，具有试剂成本低、选择性好、产率高、反应时间短和操作简便等吸引人的优点。这种新方法可能被用于选择性地在芳香族酰胺和烷基酰胺之间进行去酰化反应。
• 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。
• 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。
• New Sulfamethoxazole Derivatives as Selective Carbonic Anhydrase IX and XII Inhibitors: Design, Synthesis, Cytotoxic Activity and Molecular Modeling
  作者：Mohamed A. Abdelgawad、Syed N. A. Bukhari、Arafa Musa、Mohammed Elmowafy、Mohammed H. Elkomy、AbdElAziz. A. Nayl、Ahmed H. El-Ghorab、Ibrahim Hotan Alsohaimi、Mohamed Sadek Abdel-Bakky、Ibrahim O. Althobaiti、Hamud A. Altaleb、Hany A. Omar、Ahmed H. Abdelazeem、Mohamed A. Zaki、Mohamed E. Shaker、Heba A. H. Elshemy

  DOI：10.3390/ph15091134

  日期：——

  In this study new sulphamethoxazole derivatives (S1–S4, S6–S12, and S14–S22) were designed and synthesized and their structures were fully characterized and validated using NMR, mass, and IR spectroscopy, as well as elemental analyses. All new derivatives (S1–S22) were assayed against human carbonic anhydrase (hCAs IX and XII) for their inhibitory activities. hCAs IX and XII were chosen due to the

  在这项研究中，设计和合成了新的磺胺甲恶唑衍生物（S1 - S4、S6 - S12和S14 - S22），并使用 NMR、质谱和 IR 光谱以及元素分析对其结构进行了全面表征和验证。所有新衍生物 ( S1 – S22 ) 均针对人碳酸酐酶 (hCAs IX 和 XII) 进行了抑制活性测定。选择 hCA IX 和 XII 是因为 CAIX 表达被认为是乳腺癌预后不良的缺氧标志物。当与作为标准参考的 Dorzolamide HCl 进行比较时，衍生物S2、S3、S8、S9和S15具有最有效的抑制作用，IC 50值低。进一步评估活性化合物对 hCAs I 和 II 的抑制活性，与参考标准乙酰唑胺相比，化合物S8、S9和S15的抑制作用最小，表明它们在正常细胞中的作用是最低的。所选化合物的细胞活力测试在 MCF7（常氧和缺氧）和正常乳腺细胞系 (MCF10a) 上以星形孢菌素为标准进行。结果表明，